Psychonauts• psychedelics: A

systematic, multilingual, web-crawling

exercise Valeria Catalani & John Martin
Corkery & Amira Guirguis & Flavia
Napoletano & Davide Arillotta &
Caroline Zangani & Alessandro Vento &
Fabrizio Schifano
Visit to download the full and correct content document:
https://ebookmass.com/product/psychonauts-psychedelics-a-systematic-multilingual-
web-crawling-exercise-valeria-catalani-john-martin-corkery-amira-guirguis-flavia-napo
letano-davide-arillotta-caroline-zangani/
 European Neuropsychopharmacology 49 (2021) 69–92

www.elsevier.com/locate/euroneuro

Psychonauts’ psychedelics: A systematic,

multilingual, web-crawling exercise
Valeria Catalani a, John Martin Corkery a, Amira Guirguis a,b,
Flavia Napoletano c, Davide Arillotta a, Caroline Zangani d,
Alessandro Vento e,f,g,∗, Fabrizio Schifano a

a
Psychopharmacology, Drug Misuse & Novel Psychoactive Substances Research Unit, School of Life &
Medical Sciences, University of Hertfordshire, United Kingdom
b
Swansea University Medical School, Institute of Life Sciences 2, Swansea University, Singleton Park,
Swansea, United Kingdom
c
Homerton University Hospital, London, United Kingdom
d
Department of Health Sciences, University of Milan, Milan, Italy
e
Addictions’ Observatory (ODDPSS), Rome, Italy
f
Department of Psychology, Guglielmo Marconi University, Rome, Italy
g
Department of Mental Health, ASL Roma 2, Rome, Italy

Received 25 August 2020; received in revised form 3 February 2021; accepted 8 March 2021

KEYWORDS Abstract
New Psychoactive Psychedelics alter the perception of reality through agonist or partial agonist interaction with
Substances; the 2A serotoninergic receptor. They are classified as phenethylamines, tryptamines and ly-
psychedelics; sergamides. These classes, according to the United Nations Office on Drugs and Crime (UNODC)
Psychonauts; and European Monitoring Centre for Drugs and Drug Addiction (EMCDDA), account for an impor-
Web Crawler; tant percentage of the new psychoactive substances (NPS) current scenario.The paper aimed
NPSfinder R at: a) identifying and categorising psychedelic molecules from a list of psychonaut websites
and NPS online resources; and b) comparing the NPSfinder R
results with those from the Eu-
ropean and United Nations databases. A crawling software (i.e. ‘NPSfinder R
’) was created to
automatically scan, 24/7, a list of URLs and to extract a range of information (chemical/street
names, chemical formulae, etc.) to facilitate NPS identification. Data collected were manu-
ally analysed and compared with the EMCDDA and UNODC databases.The overall number of
psychedelic NPS detected by NPSfinder R
(November 2017-February 2020) was 1344, almost

∗ Corresponding
author at: Department of Psychology, Guglielmo Marconi University, Rome, Italy.
E-mail addresses: v.catalani@herts.ac.uk (V. Catalani), j.corkery@herts.ac.uk (J.M. Corkery), amira.guirguis@swansea.ac.uk (A. Guir-
guis), flavia.napoletano@gmail.com (F. Napoletano), davide.arillotta@yahoo.it (D. Arillotta), caroline.zangani@unimi.it (C. Zangani),
alessandro.vento@aslroma2.it (A. Vento), f.schifano@herts.ac.uk (F. Schifano).

https://doi.org/10.1016/j.euroneuro.2021.03.006
0924-977X/© 2021 Elsevier B.V. and ECNP. All rights reserved.
 V. Catalani, J.M. Corkery, A. Guirguis et al.

ten-times higher than that reported by the UNODC and EMCDDA combined. Of these, 994 previ-
ously unknown molecules were identified as (potential) novel psychedelics, suggesting a strong
discrepancy between online and real-world NPS scenarios. The results show the interest of
psychonauts, and maybe of the much larger community of ‘recreational’ drug users, towards
psychedelics. Moreover, examining online scenario may help in assessing the availability in the
real world of psychedelic NPS; understanding drug trends; and in possibly predicting future drug
scenarios
© 2021 Elsevier B.V. and ECNP. All rights reserved.

1. Introduction chiatry, psychology, sociology, and others (Nichols, 2016);

Psychedelics are “substances that have a mind-manifesting
capability, revealing useful or beneficial properties of the
mind” (Osmond, 1957). These molecules are often termed
hallucinogens (Abdulrahim and Bowden-Jones, 2015), a
word that remains the favourite definition and is still
widely used across a high number of scientific disciplines
(Green, 2008; Griffiths and Grob, 2010; Passie et al., 2008;
Winter, 2009). The United Nations Office on Drugs and
Crime (UNODC) defines hallucinogens as “a diverse group
of naturally occurring and synthetic drugs that induce dis-
torted states of consciousness, perception, thinking and
feeling, accompanied by different degrees of auditory or vi-
sual hallucinations (UNODC, 2016).They are also referred to
as “psychedelics”, which ultimately produce “synaesthesia
and altered perceptions of reality” (UNODC, 2016).
While the term ‘hallucinogen’ is used to describe a wide
range of different types of psychoactive molecules (Bey and
Patel, 2007; Martinotti et al., 2015; Teitler et al., 1990),
psychedelics referred here specifically to tryptamines
(e.g. psilocin, 5-Meo-DALT; Nichols et al., 2015;
Sakashita et al., 2015); LSD; lysergamides/rigidified
tryptamines (Seidler, 2001); and phenethylamines
(e.g. mescaline and 2C-B) (Dinis-Oliveira et al., 2018;
Papaseit et al., 2018). This is due to their action as spe-
cific agonists or partial agonists on the brain’s serotonin
(5-HT)-2A subtype receptors (López-Giménez and González-
Maeso, 2018). This agonist activity has been proven vital for
the psychedelic effect (Halberstadt and Geyer, 2011) with
the serotonin subtype receptor 2A indicated and widely
accepted as responsible for the distinct hallucinations of
psychedelic trips (Fiorella et al., 1995; Kometer et al.,
2013; López-Giménez and González-Maeso, 2018). In this
paper, the definition of psychedelics will be adopted.
While all psychoactive tryptamine and lysergamide NPS
can be classified as psychedelics, phenethylamines rep-
resent a wider chemical class, that comprises molecules
with diverse activity, including: stimulants, entactogens and
psychedelics (Abdulrahim and Bowden-Jones, 2015). Very
often one molecule can exhibit several of these effects
(Carroll et al., 2012). For the purpose of this paper only
the psychedelics subclass was considered.
Psychedelics may be considered one of the most ancient
class of psychopharmacological agents. Known to a wide
public from the discovery of the psychoactive effects of LSD
in 1943 (Hofmann, 1959), they are of high interest mostly
for two reasons: the nature of their phenomenon, spread
across diverse research fields including anthropology, psy-
and their ability to produce unique and dramatic conscious-
ness alterations (Freedman, 1968; Nichols, 2018).
The psychedelics’ market started to change in the early
2000s with the introduction of a considerable number of
synthetic derivatives of LSD, tryptamine and phenethy-
lamines described as Novel Psychoactive Substances (NPS)
(Schifano et al., 2006, 2015). NPS are defined as “sub-
stances of abuse, either in a pure form or a prepara-
tion, that are not controlled by the 1961 Single Conven-
tion on Narcotic Drugs or the 1971 Convention on Psy-
chotropic Substances, but which may pose a public health
threat” (UNODC, 2019). Synthetic analogues, often way
more potent than their natural counterparts, were offered
for purchase and were spreading on the recreational drug
market, although no knowledge regarding their pharmaco-
logic profiles (dosage, effects and toxicity; Corkery et al.,
2012; Maurer, 2010; Schifano et al., 2017) was avail-
able. Over the last few years, many acute intoxication
and lethal cases, unprecedentedly associated with the use
of psychedelics, have been reported (Dean et al., 2013;
Iwersen-Bergmann et al., 2019; Luethi and Liechti, 2020;
Tang et al., 2014). The polysubstance drug consumption
trend of use/abuse (EMCDDA, 2019a; Hall and Miczek, 2019)
has been a reason of concern as well.
Contextually, alongside the emergence of psychedelic,
‘modern’, NPS there has been a parallel growth in and con-
solidation of a modern form of shamanism, e.g. a new trend
in drug experimentation carried out by NPS enthusiasts, the
so-called e-psychonauts (Deluca et al., 2012; Orsolini et al.,
2016). Psychonauts define themselves as either ‘techno-
shamans’ (Booth, 2000; Labate and Jungaberle, 2011) or
‘sailor of the mind/soul’. They typically explore their in-
ner universe using psychedelic NPS whilst sharing their own
drug experiences online (Orsolini et al., 2015a, 2015b). Psy-
chonauts are typically very attracted to psychedelic NPS
(Móró et al., 2011; Orsolini et al., 2015a, 2015b) and con-
sider these molecules as the best way to investigate the hu-
man mind and address spiritual questions (Carroll and Pe-
ter, 1987).
The NPS diffusion and e-psychonauts phenomena can be
considered strongly interlinked, with the latter allegedly
being a strong influencing voice in defining and feeding the
market for the former (Orsolini et al., 2017; Schifano et al.,
2003). Psychonauts, as ‘psychedelic influencers’, may help
shape and populate online drug scenarios with a huge num-
ber of new substances not yet seized or officially detected
(EMCDDA, 2019b).
Understanding the online psychedelic scenarios, whilst
identifying which substances are being discussed online,

70
 European Neuropsychopharmacology 49 (2021) 69–92
may be of great help in trying to assess the availability
of, and demand for, psychedelic NPS (Corazza et al., 2013;
Schifano et al., 2015). Previous studies have emphasised the
importance of users’ experiences in creating knowledge,
and thus possible NPS trends (Duxbury, 2018; Kataja et al.,
2018).
Concerns have arisen in recent years about certain
psychedelic NPS in respect of their potential to cause seri-
ous acute intoxications, short/long-term mental issues and
fatalities (Luethi and Liechti, 2020; Schifano et al., 2015)
The aims of the current research were: a) use a web
crawler, e.g. the NPSfinder®, to identify and categorise,
from a list of psychonaut websites and NPS online resources,
the number of psychedelic molecules; and b) to compare
the NPSfinder® results with related listings from the Euro-
pean Monitoring Centre for Drugs and Drug Addictions (EM-
CDDA) and UNODC databases.
2. Experimental procedures; methods
2.1. Identification of molecules
A crawling/navigating software (i.e. NPSfinder®; www.npsfinder.
com) was created to facilitate identification of NPS dissemination
on the surface web. This web crawler automatically scans a list of
URLs for new/novel/emerging NPS on a 24/7 basis, whilst extract-
ing information about a large variety of psychoactive molecules
(Schifano et al., 2019a). The scanned URLs were representative
mostly of online psychonaut websites/fora but also of other NPS
online resources (Appendix 1). NPSfinder® was designed by Dami-
com, an IT enterprise based in Rome (Italy), to extract a range of
data regarding NPS including chemical and street names; chemi-
cal formulae; three-dimensional images; and anecdotally reported
clinical/psychoactive effects. These data were then automati-
cally stored in an online, restricted access/password-controlled,
database located within firewall-protected/highly secure and con-
sistently performing proprietary servers. When necessary, the Inter-
national Chemical Identifier Key (InChIKey) was added to the single
entries to facilitate identification of the index NPS and minimise
chances of duplicates. InChIKey is a hashed representation of the
full International Chemical Identifier (InChI) (Heller et al., 2013),
created for the purpose of facilitating online searching of chemical
compounds. The predominant language used in these websites was
English, but other languages were also analysed, including: Span-
ish, German, Russian, Italian, Dutch, French, Swedish and Turkish.
A control panel composed of five professionals trained in medicine;
chemistry; and psychiatry (i.e., FN; DA; CZ; LG and VC) analysed
manually all the data extracted by the web crawler from 26 Novem-
ber 2017 to 24 February 2020. Afterwards, a full assessment and
editing of each NPSfinder® data item was carried out and the range
of unique psychedelic molecules documented was identified.
2.2. Classification of psychedelic molecules
The study focus was here on psychedelic tryptamines, lysergamides
and phenethylamines. All the molecules denominations identi-
fied by the web crawler were searched for in Google®/Google®
Scholar (Google, 2019), PubMed (PubMed-NCBI, 2019) and PubChem
(PubChem, 2019) to classify them according to their chemical de-
scription (e.g. phenethylamines, tryptamines and lysergamides).
No plant-based or natural derived molecules were included in the
study.
71
Phenethylamines were furtherly classified into NBOMes (‘N-
Benzylmethoxy’) (Ninnemann and Stuart, 2013), FLYs and drag-
onFLYs, respectively rigid dihydrofuran or furan rings series
(Trachsel et al., 2013). When available, reported/proven pharma-
cology and effects were added to each entry profile. For phenethy-
lamines, only those showing psychedelic effects were considered
for the scope of this paper; those possessing unsatisfactory lev-
els of pharmacological data were here considered as ‘putative
psychedelics’ (Rickli et al., 2015a).
2.3. Comparison between NPSfinder®, EMCDDA and
UNODC databases
NPSfinder® entries were compared with those from both the EM-
CDDA European Database on New Drugs (EDND, 2019) and the UN-
ODC Early Warning Advisory on NPS (UNODC EWA, 2020) databases;
with authorised access to these restricted resources having here
been provided to JMC. The comparison was conducted using the
International Chemical Identifier Key (InChIKey).
3. Results
3.1. Data from the NPSfinder® web crawler
After more than two years of operation , the overall num-
ber of unique NPS identified by the web crawler activi-
ties was 4368. Phenethylamines were the most popular NPS
class mentioned in psychonaut fora with 1263 (28.9%) en-
tries; including 31 NBOMes and 16 FLYs/ dragonFLYs. Further
phenethylamines with confirmed psychedelic activity were
141, whilst those with stimulant/entactogenic activity to-
talled 109. For the remaining 966 phenethylamines no infor-
mation about pharmacology/effects were found. Because
one cannot assume/predict any pharmacological activity
from the structure itself all 966 were considered as putative
psychedelics. Conversely, tryptamine and lysergamide en-
tries represented a smaller portion of the whole database,
with 65 and 16 molecules, respectively (Fig. 1).
3.2. Data from the EMCDDA and UNODC databases
Across these two databases (EDND, 2019; UNODC EWA, 2020)
a total of 27 NBOMe, 3 FLYS, 50 psychedelics, 58 stimu-
lant/entactogenic and 32 molecules with no reported ef-
fects were identified. The total tryptamines identified were
48 and lysergamides were 11. Overall, across the three
different classes the UNODC database reported more sub-
stances than the EMCDDA.
3.3. Comparison of NPSfinder® vs EMCDDA and
UNODC database entries
NPSfinder® results for psychedelics were compared with
those listed on the EMCDDA and the UNODC databases
(Tables 1–5; Appendix 2). Overall, the NPSfinder® detected
a number of psychedelics that was almost ten times higher
compared to figures from the other 2 databases. More pre-
cisely, the phenethylamine entries in the NPSfinder® were
1263 vs 123 from the EMCDDA and 156 from the UNODC.
 Table 1 NPSfinder® psychedelic phenethylamines and comparisons with EMCDDA and UNODC databases.
N NPSfinder® name Other names IUPAC InChIKey EDND UNODC NPSfinder®
(Feb (July
2020) 2019)
1 1-(1H-Indol-6-yl)-1- N/A 1-(1H-Indol-6-yl)-1-methylethylamine XLWCMUNJQRCUQC-UHFFFAOYSA-N − − Y
methylethylamine
2 1-methylethylamine 2-Amino-propano propan-2-amine JJWLVOIRVHMVIS-UHFFFAOYSA-N − − Y
3 1-phenyl-1-propanamine N/A 1-phenyl-1-propanamine AQFLVLHRZFLDDV-UHFFFAOYSA-N Y − Y
4 2-(1,4-Dimethoxy-2-naphthyl) N/A 2-(1,4-Dimethoxy-2-naphthyl)-1- KWKDBIVLRQTMKR-UHFFFAOYSA-N − − Y
-1-methylethylamine methylethylamine
5 2-(4,7-Dimethoxy-2,3-dihydro- N/A 2-(4,7-Dimethoxy-2,3-dihydro- GLFZOKOHBIKEKN-UHFFFAOYSA-N − − Y
1H-indan-5-yl)-1- 1H-indan-5-yl)-1-methylethylamine
methylethylamine
6 2,3-MDA 2,3-Methylenedioxyamphetamine 1-(1,3-benzodioxol-4-yl)propan- XOOVOZRNDZPGLF-UHFFFAOYSA-N − − Y

V. Catalani, J.M. Corkery, A. Guirguis et al.

2-amine
7 2,4-DMA 2,4-Dimethoxyamphetamine 1-(2,4-Dimethoxyphenyl)propan- DQWOZMUBHQPFFF-UHFFFAOYSA-N Y Y Y
2-amine
8 2,5-Dimethoxy-4-(n)- 2C-T-7 S 2-[2,5-Dimethoxy-4- OLEVEPDJOFPJTF-UHFFFAOYSA-N Y Y Y
propylthiophenenthylamine (propylsulfanyl)phenyl]ethanamine
9 2-BM 2-Bromomescaline 2-(2-Bromo-3,4,5- UXQBKANLBLUVMK-UHFFFAOYSA-N − − Y
trimethoxyphenyl)ethan-1-amine
72

10 2-Br-4,5-MDA 6-Bromo-MDA 1-(6-Bromo-2H-1,3-benzodioxol-5- PHCFFGXVMHXBGD-UHFFFAOYSA-N − − Y

yl)propan-2-amine
11 2C-2-TOET 4-Ethyl-5-methoxy-2- 2-[4-Ethyl-5-methoxy-2- QUBYTLZGKDGHHS-UHFFFAOYSA-N − − Y
methylthiophenethylamine (methylsulfanyl)phenyl]ethan-
1-amine
12 2C-2-TOM 5-Methoxy-4-methyl-2- 2-[5-Methoxy-4-methyl-2- NCCC1=CC(OC)=C(C)C=C1SC − − Y
methylthiophenethylamine (methylsulfanyl)phenyl]ethan-
1-amine
13 2C-3a N/A 2-(4-Methoxy-1,3-benzodioxol-5-yl) AXEJSBWWIHAWJM-UHFFFAOYSA-N − − Y
ethan-1-amine
14 2C-C (4-Chloro-2,5- 2-(4-Chloro-2,5-dimethoxyphenyl) CGKQFIWIPSIVAS-UHFFFAOYSA-N Y Y Y
dimethoxyphenethyl)amine ethan-1-amine
15 2C-D 2,5-Dimethoxy-4- 1-(2,5-Dimethoxy-4-methylphenyl)- UNQQFDCVEMVQHM-UHFFFAOYSA-N Y Y Y
methylphenethylamine 2-aminoethane
16 2C-D-2,5-DIEtO 2,5-Diethoxy-4- 2-(2,5-Diethoxy-4-methylphenyl) ALVWRNQBQUMSMA-UHFFFAOYSA-N − − Y
methylphenethylamine ethan-1-amine
17 2C-D-2-EtO 2CD-2ETO; 2-Ethoxy-5-methoxy- 2-(2-Ethoxy-5-methoxy-4- VYXRROQVSSPCGC-UHFFFAOYSA-N − − Y
4-methylphenethylamine; methylphenyl)ethan-1-amine
2-Tweetio
18 2C-D-5-EtO 5-Ethoxy-2-methoxy-4- 2-(5-Ethoxy-2-methoxy-4- ZMQDQUPRBYFPSO-UHFFFAOYSA-N − − Y
methylphenethylamine methylphenyl)ethan-1-amine
(continued on next page)
 Table 1 (continued)
N NPSfinder® name Other names IUPAC InChIKey EDND UNODC NPSfinder®
(Feb (July
2020) 2019)
19 2C-E 2,5-Dimethoxy-4- 2-(4-Ethyl-2,5- VDRGNAMREYBIHA-UHFFFAOYSA-N Y Y Y
ethylphenethylamine dimethoxyphenyl)ethanamine
20 2C-F 4-Fluoro-2,5- 2-(4-Fluoro-2,5-dimethoxyphenyl)- QAVFEDRVOUKIPM-UHFFFAOYSA-N − Y Y
dimethoxyphenethylamine 1-aminoethane
21 2C-G 2,5-Dimethoxy-3,4- 2-(2,5-Dimethoxy-3,4- NFOHGLKGLZIHJQ-UHFFFAOYSA-N Y Y Y
dimethylphenethylamine dimethylphenyl)ethan-1-amine
22 2C-G-3 2,5-Dimethoxy-3,4- 2-(4,7-Dimethoxy-2,3-dihydro- DUYSKWSFDDDWQI-UHFFFAOYSA-N − − Y
(trimethylene)phenethylamine 1H-inden-5-yl)ethan-1-amine

European Neuropsychopharmacology 49 (2021) 69–92

23 2C-G-5 3,4-Norbornyl-2,5- 2-(5,8-Dimethoxy-1,2,3,4- ASPWVWSIJQTXDB-UHFFFAOYSA-N − − Y
dimethoxyphenethylamine tetrahydro-1,4-methanonaphthalen-
6-yl)ethan-1-amine
24 2C-H 2,5-Dimethoxyphenethylamine 2-(2,5-Dimethoxyphenyl) WNCUVUUEJZEATP-UHFFFAOYSA-N Y Y Y
ethanamine
25 2C-I 2,5-dimethoxy-4- 2-(4-iodo-2,5- PQHQBRJAAZQXHL-UHFFFAOYSA-N Y Y Y
iodophenethylamine dimethoxyphenyl)ethanamine
26 2C-IP Jelena 2-[2,5-Dimethoxy-4-(propan-2- XUGPCRRUMVWELT-UHFFFAOYSA-N − Y Y
yl)phenyl]ethan-1-amine
73

27 2C-N 2,5-dimethoxy-4- 2-(2,5-Dimethoxy-4-nitrophenyl) ZMUSDZGRRJGRAO-UHFFFAOYSA-N Y Y Y

nitrophenethylamine ethan-1-amine
28 2C-O-4 2,5-Dimethoxy-4- 2-(4-Isopropoxy-2,5- KAKXJLWAEMHHTL-UHFFFAOYSA-N − Y Y
isopropoxyphenethylamine dimethoxyphenyl)ethanamine
29 2C-P 2,5-Dimethoxy-4- 2-(2,5-Dimethoxy-4- PZJOKFZGPTVNBF-UHFFFAOYSA-N Y Y Y
propylphenethylamine propylphenyl)ethanamine
30 2C-T 4-methylthio-2,5-DMPEA 2-(2,5-dimethoxy-4- UPZMYCMLLQTYEM-UHFFFAOYSA-N − − Y
(methylthio)phenyl)ethanamine
31 2C-T-13 2,5-dimethoxy-4-(β- 2-[4-(Methoxyethylthio)-2,5- PYJLRNOGMKMRTK-UHFFFAOYSA-N − − Y
methoxyethylthio) dimethoxyphenyl]ethanamine
phenethylamine
32 2C-T-15 4-Cyclopropylthio-2,5- 2-[4-(Cyclopropylsulfanyl)-2,5- HHAPMOUVSYQKLK-UHFFFAOYSA-N − − Y
dimethoxyphenethylamine dimethoxyphenyl]ethan-1-amine
33 2C-T-16 4-Allylthio-2,5- 2-{2,5-Dimethoxy-4-[(prop-2-en-1- BXCMEIZBXNLJKM-UHFFFAOYSA-N − − Y
dimethoxyphenethylamine yl)sulfanyl]phenyl}ethan-1-amine
34 2C-T-17 4-sec-Butylthio-2,5- 2-[4-(but-2-ylthio)-2,5- KSZHVRPGICAZOA-UHFFFAOYSA-N − − Y
dimethoxyphenethylamine dimethoxyphenyl]ethanamine
35 2C-T-19 4-n-Butylthio-2,5- 2-[4-(Butylsulfanyl)-2,5- LGUVDOBGXUFUAJ-UHFFFAOYSA-N − − Y
dimethoxyphenethylamine dimethoxyphenyl]ethan-1-amine
36 2-CT-2 4-Ethylthio-2,5- 2-[4-(Ethylsulfanyl)-2,5- HCWQGDLBIKOJPM-UHFFFAOYSA-N Y Y Y
dimethoxyphenethylamine dimethoxyphenyl]ethan-1-amine
(continued on next page)
 Table 1 (continued)
N NPSfinder® name Other names IUPAC InChIKey EDND UNODC NPSfinder®
(Feb (July
2020) 2019)
37 2C-T-21 4-(2-fluoroethylthio)-2,5- 2-[2,5-Dimethoxy-4-(2- ZBUUUKBTOCTOPW-UHFFFAOYSA-N − − Y
dimethoxyphenethylamine fluoroethylthio)phenyl]
ethanamine
38 2C-T-25 4-Isobutylthio-2,5- 2-{2,5-Dimethoxy-4-[(2- OEPKQBQEDYEXMC-UHFFFAOYSA-N − − Y
dimethoxyphenethylamine methylpropyl)sulfanyl]phenyl}
ethan-1-amine
39 2C-T-8 4-Cyclopropylmethylthio-2,5- 2-{4-[(Cyclopropylmethyl) AHMSSHCYIDBVQB-UHFFFAOYSA-N − Y Y
dimethoxyphenethylamine; sulfanyl]-2,5-dimethoxyphenyl}
ethan-1-amine
40 2C-TFM 2C-CF3 2,5-Dimethoxy-4- LYXGNMLWYONZID-UHFFFAOYSA-N Y Y Y

V. Catalani, J.M. Corkery, A. Guirguis et al.

(trifluoromethyl)phenethylamine
41 2-Me-MDA 2-Methyl-3,4- 1-(4-methyl-1,3-benzodioxol-5- WVACHJAKQMSYSU-UHFFFAOYSA-N − − Y
methylenedioxyamphetamine yl)propan-2-amine
42 3,2,4-DOET N/A 1-(3-Ethyl-2,4-dimethoxyphenyl) YMKTXNPDCOUJMV-UHFFFAOYSA-N − − Y
propan-2-amine
43 3,4-DMA 3,4-Dimethoxyamphetamine 1-(3,4-Dimethoxyphenyl) KAZPHAGSWZTKDW-UHFFFAOYSA-N − Y Y
propan-2-amine
74

44 3,4-methylenedioxy-N, MDMMA (2-Benzo[1,3]dioxol-5-yl-1-methyl- JEJGUIDNYBAPGN-UHFFFAOYSA-N Y Y Y

N-dimethylamphetamine ethyl)-dimethylamine
45 3,5-DMA 3,5-Dimethoxyamphetamine 1-(3,5-Dimethoxyphenyl) PDCLPGSYMZLLDX-UHFFFAOYSA-N − − Y
propan-2-amine
46 3-Bromophenethylamine N/A 2-(3-bromophenyl)ethanamine ORHRHMLEFQBHND-UHFFFAOYSA-N − − Y
47 3C-BZ 4-Benzyloxy-3,5- 1-[4-(Benzyloxy)-3,5- IQKPLBJGFPDASR-UHFFFAOYSA-N − − Y
dimethoxyamphetamine dimethoxyphenyl]propan-2-amine
48 3C-DFE 3C-F2EM 1-[4-(2,2-Difluoroethoxy)-3,5- TYXHBMNQOVLYRX-UHFFFAOYSA-N − − Y
dimethoxyphenyl]propan-2-amine
49 3C-E 3C-Escaline 1-(4-Ethoxy-3,5- AHLXCGRWNKUNTQ-UHFFFAOYSA-N Y Y Y
dimethoxyphenyl)propan-2-amine
50 3C-P alpha-Methyl-4-propoxy-3,5- 3,5-dimethoxy- KKMCHCCXGKYEKJ-UHFFFAOYSA-N Y Y Y
dimethoxyphenethylamine 4-propyloxyamphetamine
51 3-DESMETHYL 3-Demethylmescaline 5-(2-Aminoethyl)−2,3- PDKPJPTZKPCMKR-UHFFFAOYSA-N − − Y
dimethoxyphenol
52 3-TSB 3-Thiosymbescaline 3-ethylthio-4-methoxy-5- BTJFGKUKBHSKHI-UHFFFAOYSA-N − − Y
ethoxyphenethylamine
53 3-T-TRIS 3-Thiotrisescaline 2-[3,4-Diethoxy-5- JSWFZFXPKROBKR-UHFFFAOYSA-N − − Y
(ethylsulfanyl)phenyl]ethanamine
54 4-Bromo-2,5-Dimethoxyphene 2C-B 2-(4-bromo-2,5- YMHOBZXQZVXHBM-UHFFFAOYSA-N − − Y
Thylamine dimethoxyphenyl)ethanamine
(continued on next page)
 Table 1 (continued)
N NPSfinder® name Other names IUPAC InChIKey EDND UNODC NPSfinder®
(Feb (July
2020) 2019)
55 4-Bromo-Beta,2,5- BOB 2-(4-bromo-2,5-dimethoxyphenyl)−2- FYTLQNZPDWLGNU-UHFFFAOYSA-N Y − Y
trimethoxyphenethylamine methoxyethanamine
56 4C-iPrO α-Ethyl-4-isopropoxy-2,5- 1-{2,5-Dimethoxy-4-[(propan-2- KKDGVJJZQGSVHK-UHFFFAOYSA-N − − Y
dimethoxyphenethylamine yl)oxy]phenyl}butan-2-amine
57 4-Isopropylthio-2,5- 2C-T4 2-[4-(Isopropylthio)-2,5- HDYZSVKZKDPLDT-UHFFFAOYSA-N Y Y Y
dimethoxyphenethylamine dimethoxyphenyl]ethanamine
58 4-TSB 4-Thiosymbescaline 4-methylthio-3,5-diethoxy- OMJVPFLTCMALSV-UHFFFAOYSA-N − − Y

European Neuropsychopharmacology 49 (2021) 69–92

phenethylamine
59 4-T-TRIS 4-Thiotrescaline 2-[3,5-Diethoxy-4- VFCYKJRATPCSED-UHFFFAOYSA-N − − Y
(ethylsulfanyl)phenyl]ethan-1-amine
60 5-APDI indanylaminopropane (IAP) (±)-1-(2,3-dihydro-1H-inden-5- QYVNZHBQYJRLEX-UHFFFAOYSA-N Y Y Y
yl)propan-2-amine
61 5-Me-MDA 3-Methyl-4,5- 1-(7-Methyl-2H-1,3-benzodioxol-5- OLENSVFSNAULML-UHFFFAOYSA-N − − Y
methylenedioxyamphetamine; yl)propan-2-amine
1-(7-Methyl-2H-1,3-benzodioxol-
5-yl)propan-2-amine;
75

1-(7-Methyl-1,3-benzodioxol-5-
yl)propan-2-amine
62 5-MeO-DIBF 5-MeO-MiPT 5-Methoxy-N,N- JIUANGKGSPXHML-UHFFFAOYSA-N Y − Y
diisopropylbenzofuranethylamine
63 5-TASB 5-Thioasymbescaline 2-[3,4-Diethoxy-5- WEGXTQPSIDDJRM-UHFFFAOYSA-N − − Y
(methylsulfanyl)phenyl]ethanamine
64 6-APDB 6-(2-Aminopropyl)-2,3- 1-(2,3-Dihydro-1-benzofuran-6- VRNGXHJGMCJRSQ-UHFFFAOYSA-N − − Y
dihydrobenzofuranY yl)propan-2-amine
65 6-EAPB N/A 1-(1-benzofuran-6-yl)-N-ethylpropan-2- MIRNYUKRRZFBOI-UHFFFAOYSA-N − − Y
amine
66 6-MAPB N/A 1-(benzofuran-6-yl)-N-methylpropan-2- QLAAURQYEAEHBO-UHFFFAOYSA-N Y Y −
amine
67 6-Me-MDA 2-Me-4,5-MDA 1-(6-Methyl-1,3-benzodioxol-5- HCFHWXDIZOAUTQ-UHFFFAOYSA-N − − Y
yl)propan-2-amine
68 AAM α-Amylmescaline 1-(3,4,5-Trimethoxyphenyl)heptan-2- QAYOKGOYZRYNSU-UHFFFAOYSA-N − − Y
amine
69 AHM α-Hexylmescaline 1-(3,4,5-Trimethoxyphenyl)octan-2- KMLNVPCGVUWXEK-UHFFFAOYSA-N − − Y
amine
70 ALEPH-2 dot2 1-[4-(Ethylsulfanyl)-2,5- MCYCODJKXUJSAT-UHFFFAOYSA-N − − Y
dimethoxyphenyl]propan-2-amine
(continued on next page)
 Table 1 (continued)
N NPSfinder® name Other names IUPAC InChIKey EDND UNODC NPSfinder®
(Feb (July
2020) 2019)
71 Allylescaline AL 4-Allyloxy-3,5- JNUAYHHGCXYBHX-UHFFFAOYSA-N Y Y Y
dimethoxyphenethylamine
72 Beatrice MDO-D 1-(2,5-Dimethoxy-4-methylphenyl)-N- IWYGVDBZCSCJGT-UHFFFAOYSA-N − − Y
methylpropan-2-amine
73 bH-2C-B beta-hydroxy-2c-b 2-Amino-1-(4-bromo-2,5- HFYJGAIOBIDRPX-UHFFFAOYSA-N − − Y
dimethoxyphenyl)ethan-1-one
74 bk-2C-I beta-keto-2C-I 2-Amino-1-(4-iodo-2,5- SGQREGRMRKZYSF-UHFFFAOYSA-N − − Y
dimethoxyphenyl)ethan-1-one
75 b-Me-2C-2 β-Me-2C-2 2-(6-Methoxy-2H-1,3-benzodioxol-5- MKNWKDHPSQLEJJ-UHFFFAOYSA-N − − Y

V. Catalani, J.M. Corkery, A. Guirguis et al.

yl)propan-1-amine
76 BOHD 4-methyl-2,5-dimethoxy-beta- 2-Amino-1-(2,5-dimethoxy-4- WCURBUJUIMRCCJ-UHFFFAOYSA-N − − Y
hydroxyphenethylamine; methylphenyl)ethanol
2-(4-Methyl-2,5-
dimethoxyphenyl)ethan-beta-
hydroxyamine
77 BOM Beta,3,4,5- 2-methoxy-2-(3,4,5- GAKIJEPUVBHWCK-UHFFFAOYSA-N − − Y
tetramethoxyphenethylamine trimethoxyphenyl)ethanamine
76

78 Cyclopropylmescaline CPM 2-(4-Cyclopropylmethoxy-3,5- LNTBHKZMYJTHTH-UHFFFAOYSA-N − − Y

dimethoxy-phenyl)-ethylamine
79 Dimethoxyamphetamine DOH 1-(2,5-dimethoxyphenyl) LATVFYDIBMDBSY-UHFFFAOYSA-N − − Y
propan-2-amine
80 DMCPA 2-(2,5-Dimethoxy-4- 2-(2,5-Dimethoxy-4- HYVPPECPQRBJEQ-UHFFFAOYSA-N − − Y
methylphenyl)cyclopropylamine methylphenyl)cyclopropan-1-amine
81 DME 3,4-Dimethoxy-beta- 2-Amino-1-(3,4- WIUFFBGZBFVVDL-UHFFFAOYSA-N − − Y
hydroxyphenethylamine dimethoxyphenyl)ethanol
82 DMMDA 2,5-dimethoxy-3,4- 1-(4,7-Dimethoxy-2H-1,3- GRGRGLVMGTVCNZ-UHFFFAOYSA-N − − Y
methylenedioxyamphetamine benzodioxol-5-yl)propan-2-amine
83 DMMDA-2 2,3-Dimethoxy-4,5- 1-(6,7-Dimethoxy-2H-1,3- UQXNREZPUUGSKM-UHFFFAOYSA-N − − Y
methylenedioxyamphetamine benzodioxol-5-yl)propan-2-amine
84 DOB Bromo-DMA 1-(4-Bromo-2,5-dimethoxyphenyl)-2- FXMWUTGUCAKGQL-UHFFFAOYSA-N − − Y
aminopropane
85 DOB-bk N/A 2-Amino-1-(4-bromo-2,5- NFDUSHHXFRLENI-UHFFFAOYSA-N − − Y
dimethoxyphenyl)propan-1-one
86 DOC 2,5-Dimethoxy-4- 1-(4-Chloro-2,5-dimethoxy- ACRITBNCBMTINK-UHFFFAOYSA-N Y Y Y
chloroamphetamine phenyl)propan-2-amine
87 DOET 2,5-dimethoxy-4- 1-(4-Ethyl-2,5-dimethoxyphenyl) HXJKWPGVENNMCC-UHFFFAOYSA-N − − Y
ethylamphetamine propan-2-amine
(continued on next page)
 Table 1 (continued)
N NPSfinder® name Other names IUPAC InChIKey EDND UNODC NPSfinder®
(Feb (July
2020) 2019)
88 DOF 2,5-Dimethoxy-4- 1-(4-Fluoro-2,5- NRANUECGGQVXOT-UHFFFAOYSA-N Y Y Y
fluoroamphetamine dimethoxyphenyl)propan-2-amine
89 DOI 2,5-Dimethoxy-4- 1-(4-Iodo-2,5-dimethoxyphenyl)-2- BGMZUEKZENQUJY-UHFFFAOYSA-N Y Y Y
iodoamphetamine propanamine
90 DOIP 2,5-Dimethoxy-4- 1-[2,5-Dimethoxy-4-(propan-2- SPKSLAUXKHSASF-UHFFFAOYSA-N Y Y Y
isopropylamphetamine yl)phenyl]propan-2-amine
91 DOM 4-Methyl-2,5- 1-(2,5-dimethoxy-4- NTJQREUGJKIARY-UHFFFAOYSA-N Y Y Y
dimethoxyamphetamine methylphenyl)propan-2-amine

European Neuropsychopharmacology 49 (2021) 69–92

92 DOPR 2,5-Dimethoxy-4- 1-(2,5-Dimethoxy-4- UEEAUFJYLUJWQJ-UHFFFAOYSA-N Y Y Y
propylamphetamine propylphenyl)propan-2-amine
93 DOT 2,5-dimethoxy-4- 1-[2,5-Dimethoxy-4- COBYBOVXXDQRAU-UHFFFAOYSA-N Y Y Y
methylthioamphetamine (methylsulfanyl)phenyl]propan-
2-amine
94 DOTFM 2,5-Dimethoxy-4- 1-[2,5-dimethoxy-4- WPGOTSORDNBMHP-UHFFFAOYSA-N − − Y
trifluoromethylamphetamine (trifluoromethyl)phenyl]propan-
2-amine
95 Ephenidine NEDPA N-Ethyl-1,2-diphenylethan-1-amine IGFZMQXEKIZPDR-UHFFFAOYSA-N − − Y
77

96 Escaline 3,5-methoxy-4- 2-(4-Ethoxy-3,5- RHOGRSKNWDNCDN-UHFFFAOYSA-N Y Y Y

ethoxyphenethylamine
97 ETHYL-K N-Ethyl-α-propyl-3,4-
methylenedioxyphenethylamine
98 F-2 6-(2-Aminopropyl)-5-methoxy-2-
methyl-2,3-dihydrobenzofuran
99 F2-MDA 3,4-Difluoromethyl
enedioxyamphetamine
100 G-5 3,6-Dimethoxy-4-(2-
aminopropyl)benzonorbornane
101 Ganesha 2,5-dimethoxy-3,4-
dimethylamphetamine
102 homo-Mescaline N/A
103 HOT-17 2,5-Dimethoxy-4-sec-butylthio-
N-hydroxyphenethylamine
104 HOT-2 2,5-dimethoxy-4-(β-ethylthio)-
N-hydroxyphenethylamine
dimethoxyphenyl)ethan-1-amine
1-(2H-1,3-Benzodioxol-5-yl)-N- YIJZJPAWMJJXQD-UHFFFAOYSA-N − − Y
ethylpentan-2-amine
1-(5-Methoxy-2-methyl-2,3-dihydro- XBHKBTCXRYPZMX-UHFFFAOYSA-N − − Y
1-benzofuran-6-yl)propan-2-amine
1-(2,2-Difluoro-2H-1,3-benzodioxol- BHDXKBALNFHXDV-UHFFFAOYSA-N − − Y
5-yl)propan-2-amine
1-(5,8-Dimethoxy-1,2,3,4-tetrahydro- MZFVFTFFHRCTIO-UHFFFAOYSA-N − − Y
1,4-methanonaphthalen-6-yl)propan-
2-amine
1-(2,5-Dimethoxy-3,4- RBZXVDSILZXPDM-UHFFFAOYSA-N − − Y
dimethylphenyl)propan-2-amine
3-(3,4,5-Trimethoxyphenyl)propan-1- LKINXVPAOSIISW-UHFFFAOYSA-N − − Y
amine
2-{4-[(Butan-2-yl)sulfanyl]-2,5- BUKIXGXYEUJJHQ-UHFFFAOYSA-N − − Y
dimethoxyphenyl}-N-hydroxyethan-1-
amine
2-[4-(Ethylsulfanyl)-2,5- XGFJCRNRWOXGQM-UHFFFAOYSA-N − − Y
dimethoxyphenyl]-N-hydroxyethan-1-
amine
(continued on next page)
 Table 1 (continued)
N NPSfinder® name Other names
105 IDNNA 4-Iodo-2,5-dimethoxy-a-
methylphenethyl(dimethyl)
amine
106 IRIS 5-Ethoxy-2-methoxy-4-
methylamphetamine
107 LOPHOPHINE MMDPEA
108 M-ALPHA Alpha-ethyl-N-methyl-3;4-
methylenedioxybenzylamine
109 MDA 3,4-Methylenedioxyamphetamine 1-(2H-1,3-Benzodioxol-5-yl)
110 MDAL N-Allyl-3,4-
methylenedioxyamphetamine
111 MDBU 3,4-Methylenedioxy-N-
butylamphetamine
112 MDBZ N-Benzyl-3,4-
methylenedioxyamphetamine
113 MDCPM 3,4-Methylenedioxy-N-
cyclopropylmethylamphetamine (cyclopropylmethyl)propan-2-amine
78
114 MDHOET Hydroxyethyl-3,4-
methylenedioxyamphetamine
115 MDMEOET N-Methoxyethyl-MDA
116 m-DOB 5-Bromo-2,4-
dimethoxyamphetamine
117 m-DOT 2,4-Dimethoxy-5-
methylthioamphetamine
118 MDPH 3,4-Methylenedioxyphentermine 1-(1,3-Benzodioxol-5-yl)-2-
119 MDPL N-Propargyl-3,4-
methylenedioxyamphetamine
120 MDPR N-PROPYL-3,4-
METHYLENEDIOXYAMPHETAMINE methylethyl]-1-propanamine
121 MEM 2,5-dimethoxy-4-
ethoxyamphetamine;
122 Methallylescaline 4-methallyloxy-3,5-
dimethoxyphenethylamine
123 Methamnetamine methylnaphetamine
124 METHYL-MESCALINE M-M; N-Methyl-3,4,5-
trimethoxyphenethylamine-
IUPAC InChIKey EDND UNODC NPSfinder®
(Feb (July
2020) 2019)
1-(4-Iodo-2,5-dimethoxyphenyl)-N,N- XBCUSBRGRALQID-UHFFFAOYSA-N − − Y
dimethylpropan-2-amine
1-(5-Ethoxy-2-methoxy-4- IPJRCKIREPMKNE-UHFFFAOYSA-N − − Y
methylphenyl)propan-2-amine
2-(7-Methoxy-2H-1,3-benzodioxol-5- ORXQUAPZHKCCAX-UHFFFAOYSA-N − − Y
yl)ethan-1-amine
1-(2H-1,3-Benzodioxol-5-yl)-N- NLINVDHEDVEOMJ-UHFFFAOYSA-N Y Y Y
methylpropan-1-amine
NGBBVGZWCFBOGO-UHFFFAOYSA-N − − Y
propan-2-amine
N-[1-(2H-1,3-Benzodioxol-5-yl) BMKCDDFQEGYEJC-UHFFFAOYSA-N − − Y
V. Catalani, J.M. Corkery, A. Guirguis et al.
propan-2-yl]prop-2-en-1-amine
N-[1-(2H-1,3-Benzodioxol-5-yl) RDXVRDCQDITVDV-UHFFFAOYSA-N − − Y
propan-2-yl]butan-1-amine
1-(2H-1,3-Benzodioxol-5-yl)-N- DWLUHTUYTBWOLO-UHFFFAOYSA-N − − Y
benzylpropan-2-amine
1-(2H-1,3-Benzodioxol-5-yl)-N- AEIQNPMGFQNZNV-UHFFFAOYSA-N − − Y
2-{[1-(2H-1,3-Benzodioxol-5-yl) SCUUYKMQDUDNBP-UHFFFAOYSA-N Y Y Y
propan-2-yl]amino}ethan-1-ol
1-(2H-1,3-Benzodioxol-5-yl)-N-(2- LOZJEWOZOKSOKA-UHFFFAOYSA-N − − Y
methoxyethyl)propan-2-amine
1-(5-Bromo-2,4- YFSLPSITQIUFQK-UHFFFAOYSA-N − − Y
dimethoxyphenyl)propan-2-amine
1-[2,4-Dimethoxy-5- BEMIKIUJWHLJTP-UHFFFAOYSA-N − − Y
(methylsulfanyl)phenyl]propan-
2-amine
OIZBHKBNZXRXSM-UHFFFAOYSA-N − Y Y
methylpropan-2-amine
N-[1-(2H-1,3-Benzodioxol-5-yl) LRYUTPIBTLEDJJ-UHFFFAOYSA-N − − Y
propan-2-yl]prop-2-yn-1-amine
N-[2-(1,3-Benzodioxol-5-yl)-1- LBXMQBTXOLBCCA-UHFFFAOYSA-N Y Y Y
1-(4-ethoxy-2,5- ITZLAXJQDMGDEO-UHFFFAOYSA-N − Y Y
dimethoxyphenyl)propan-2-amine
2-{3,5-dimethoxy-4-[(2-methylprop- FOXJFBFFGULACD-UHFFFAOYSA-N Y Y Y
2-en-1-yl)oxy]phenyl}ethanamine
N-Methyl-1-(naphthalen-2-yl)propan- BWWWOLYZMKACSB-UHFFFAOYSA-N Y Y Y
2-amine
N-Methyl-2-(3,4,5- OTXANOLOOUNVSR-UHFFFAOYSA-N − − Y
trimethoxyphenyl)ethan-1-amine
(continued on next page)
 Table 1 (continued)
N NPSfinder® name Other names
125 N-(2,5-Dimethoxy-4- HOT-7
propylthiophenthyl)
hydroxylamine
126 N-ethyl-1-phenyl-butane-2- N,α-DEPEA
amine
127 N-HYDROXY MDA N-Hydroxy-3,4-
methylenedioxyamphetamine
128 N-Me-3-DESMETHYL 3-Hydroxy-4,5-dimethoxy-N-
methylphenethylamine;
129 N-Me-DOB 4-Bromo-2,5-dimethoxy-N-
methylamphetamine
130 N-METHYL-2C-B 4-Bromo-N-methyl-2,5-
dimethoxyphenethylamine
131 N-Methyl-N-(alpha-methyl-3, FLEA
4-methylenedioxyphenethyl)
79
132 o-DOT 2-Methylthio-4,5-
dimethoxyamphetamine
133 PiPT N-propyl-N-isopropyl-tryptamine [2-(1H-indol-3-yl)ethyl]-N-propyl-N-
134 PMA 4-Methoxyamphetamine
135 PMMA 4-methoxy-N-methylamphetamine 1-(4-Methoxyphenyl)-N-methyl-2-
136 PROPYNYL 4-Propynyloxy-3,5-
dimethoxyphenethylamine
137 Proscaline 4-propyloxy-3,5-
dimethoxyphenethylamine
138 ψ-ALEPH 2,6-Dimethoxy-4-
methylthioamphetamine
139 TCB-2 (4-Bromo-3,6-dimethoxy-1,2-
dihydrocyclobutabenzene-1-
yl)methanamine
140 TMA-2 2,4,5-Trimethoxyamphetamine
141 TMA-6 2,4,6-trimethoxyamphetamine
IUPAC InChIKey EDND UNODC NPSfinder®
(Feb (July
2020) 2019)
N-[2-(2,5-dimethoxy-4- ASTNLROMDNGJLS-UHFFFAOYSA-N − − Y
propylsulfanylphenyl)ethyl]
hydroxylamine
N-Ethyl-1-phenylbutan-2-amine KHWYSUBVXWWBRB-UHFFFAOYSA-N Y Y Y
N-Hydroxy-1-(3,4- FNDCTJYFKOQGTL-UHFFFAOYSA-N Y Y Y
methylenedioxyphenyl)-
2-aminopropane
European Neuropsychopharmacology 49 (2021) 69–92
2,3-Dimethoxy-5-[2- ZIXMCYWHHXSJOK-UHFFFAOYSA-N − − Y
(methylamino)ethyl]phenol
1-(4-Bromo-2,5-dimethoxyphenyl)-N- GURVSGCCXMIFMQ-UHFFFAOYSA-N − − Y
methylpropan-2-amine
2-(4-bromo-2,5-dimethoxyphenyl)-N- ZRTYZUYYGULHEW-UHFFFAOYSA-N Y Y Y
methylethan-1-amine
N-Methyl-N-(alpha-methyl-3,4- ORADFQZOLNHWRQ-UHFFFAOYSA-N − − Y
methylenedioxyphenethyl)
hydroxylamine
1-[4,5-Dimethoxy-2- GQUWSNDODZTHKC-UHFFFAOYSA-N − − Y
(methylsulfanyl)phenyl]propan-
2-amine
OFXPLOPRCQJJFP-UHFFFAOYSA-N − − Y
isopropylamine
1-(4-Methoxyphenyl)propan-2-amine NEGYEDYHPHMHGK-UHFFFAOYSA-N Y Y Y
UGFMBZYKVQSQFX-UHFFFAOYSA-N Y Y Y
propanamine
2-{3,5-Dimethoxy-4-[(prop-2-yn-1- KNIWBMMJSJHUJB-UHFFFAOYSA-N − − Y
yl)oxy]phenyl}ethan-1-amine
2-(3,5-Dimethoxy-4- HYWLMSUAZVDUFW-UHFFFAOYSA-N Y Y Y
propoxyphenyl)ethanamine
1-[2,6-Dimethoxy-4- OAFDDZCNQLOKNK-UHFFFAOYSA-N − − Y
(methylsulfanyl)phenyl]propan-
2-amine
1-(3-Bromo-2,5- MPBCKKVERDTCEL-UHFFFAOYSA-N − − Y
dimethoxybicyclo[4.2.0]octa-1,3,5-
trien-7-yl)methanamine
1-(2,4,5-trimethoxyphenyl)propan-2- TVSIMAWGATVNGK-UHFFFAOYSA-N Y Y Y
amine
1-(2,4,6-trimethoxyphenyl)propan-2- DDGNOUVDFKXADP-UHFFFAOYSA-N Y Y Y
amine
 Table 2 NPSfinder® NBOMes and comparisons with EMCDDA and UNODC databases.
N NPSfinder® name Other names IUPAC EDND UNODC EWA NPSfinder®
(Feb NPS (July
2020) 2019)
1 25B-NBF 2C-B-NBF 2-(4-bromo-2;5-dimethoxyphenyl)-N-(2- Y Y Y
fluorobenzyl)ethanamine
2 25B-NBOH 2C-B-NBOH 2-({[2-(4-Bromo-2,5- Y Y
dimethoxyphenyl)ethyl]amino}methyl)phenol
25B-N(BOMe)2 25B-NNBOMe 2-(4-Bromo-2,5-dimethoxyphenyl)-N,N-bis[(2- Y Y −
methoxyphenyl)methyl]ethan-1-amine
3 25B-NBOME 4-Bromo-2,5-dimethoxy-N-(2- 2-(4-Bromo-2,5-dimethoxyphenyl)-N-[(2- − − Y
methoxybenzyl)phenethylamine methoxyphenyl)methyl]ethan-1-amine
4 25C-NBF 2C-C-NBF 2-(4-Chloro-2,5-dimethoxyphenyl)-N-[(2- Y Y Y

V. Catalani, J.M. Corkery, A. Guirguis et al.

fluorophenyl)methyl]ethan-1-amine
5 25C-NBOH 2C-C-NBOH 2-({[2-(4-Chloro-2,5- Y Y Y
dimethoxyphenyl)ethyl]amino}methyl)phenol
6 25C-NBOME 2C-C-NBOMe 2-(4-Chloro-2,5-dimethoxyphenyl)-N-[(2- Y − Y
methoxyphenyl)methyl]ethanamine
7 25D-NBOME 2c-D-Nbome 1–2-(2,5-Dimethoxy-4-methylphenyl)-N-(2- Y Y Y
methoxybenzyl)ethanamine
80

8 25E-NBOME 2C-E-NBOMe 2-(4-Ethyl-2,5-dimethoxyphenyl)-N-[(2- Y Y Y

methoxyphenyl)methyl]ethan-1-amine
9 25G-NBOME 2,5-Dimethoxy-N-(2-methoxybenzyl)- 2-(2,5-Dimethoxy-3,4-dimethylphenyl)-N-[(2- Y Y Y
3,4-dimethylphenethylamine methoxyphenyl)methyl]ethan-1-amine
10 25H-NBOME 2C-H-NBOMe 2-(2,5-Dimethoxyphenyl)-N-[(2- − Y Y
methoxyphenyl)methyl]ethan-1-amine
11 25H-NBOME-(3,4,5- N/A. 2-(2,3-dimethoxyphenyl)-N-(3,4,5- − Y −
TRIMETHOXYBENZYL trimethoxybenzyl)ethanamine
ANALOGUE)
12 25I-NB4OME N/A 2-(4-Iodo-2,5-dimethoxyphenyl)-N-[(4- Y Y Y
methoxyphenyl)methyl]ethan-1-amine
13 25I-NBF 2C-I-NBF 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2- Y Y Y
fluorophenyl)methyl]ethanamine
14 25I-NBOH Cimbi-27 2-(4-Iodo-2,5-dimethoxyphenyl)-N-[(2- Y Y Y
hydroxyphenyl)methyl]ethanamine
15 25IP-NBOME 2C-iP-NBOMe 2-[2,5-Dimethoxy-4-(propan-2-yl)phenyl]-N- Y Y Y
[(2-methoxyphenyl)methyl]ethan-1-amine
16 25N-NBOME N-Bomb 2-(2,5-dimethoxy-4-nitrophenyl)-N-(2- Y Y Y
methoxybenzyl)ethanamine
17 25P-NBOME 2C-P-NBOMe 2-(2,5-Dimethoxy-4-propylphenyl)-N-[(2- − Y Y
methoxyphenyl)methyl]ethan-1-amine
(continued on next page)
 Table 2 (continued)
N NPSfinder® name Other names IUPAC EDND UNODC EWA NPSfinder®
(Feb NPS (July
2020) 2019)
18 25T-2-NBOME 2C-T-2-NBOMe 2-[4-(Ethylsulfanyl)-2,5-dimethoxyphenyl]-N- − − Y
[(2-methoxyphenyl)methyl]ethan-1-amine
19 25T-4-NBOME 2C-T-4-NBOMe 2-{2,5-Dimethoxy-4-[(propan-2- − − Y
yl)sulfanyl]phenyl}-N-[(2-
methoxyphenyl)methyl]ethan-1-amine
20 2CBCB-NBOME NBOMe-TCB-2 N-(2-methoxybenzyl)-1-[(7R)-3-bromo-2,5- − − Y
dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-
yl]methanamine
21 2CBFLY-NBOME NBOMe-2C-B-FLY N-(2-Methoxybenzyl)-1-(8-bromo-2,3,6,7- − − Y
tetrahydrobenzo[1,2-b:4,5-b’]difuran-4-yl)−2-

European Neuropsychopharmacology 49 (2021) 69–92

aminoethane
22 2C-TFM-NBOME NBOMe-2C-TFM; 25TFM-NBOMe; 2-(4-trifluoromethyl-2,5-dimethoxyphenyl)-N- − − Y
Cimbi-138 [(2-methoxyphenyl)methyl]ethanamine
23 3,4-DMA NBOME N-(Ortho-methoxybenzyl)−3,4- 1-(3,4-Dimethoxyphenyl)-N-[(2- Y − Y
dimethoxyamphetamine methoxyphenyl)methyl]propan-2-amine
24 30C-NBOME 25C-NB345OMe 2-(4-Chloro-2,5-dimethoxyphenyl)-N-[(3,4,5- Y Y Y
trimethoxyphenyl)methyl]ethan-1-amine
25 4-EA NBOME 4-Ethyl-N-(o- 1-(4-Ethylphenyl)-N-[(2- Y − Y
methoxybenzyl)amphetamine methoxyphenyl)methyl]propan-2-amine
81

26 4-MMA-NBOME N/A N-[(2-Methoxyphenyl)methyl]-N-methyl-1-(4- Y − Y

methylphenyl)propan-2-amine
27 CIMBI-5 25I-NBOMe 2-(4-Iodo-2,5-dimethoxyphenyl)-N-[(2- Y Y Y
methoxyphenyl)methyl]ethan-1-amine
28 MESCALINE-NBOME N/A N-(2-Methoxybenzyl)-2-(3,4,5- − − Y
trimethoxyphenyl)ethan-1-amine
29 N-MOB-5-APB 5-APB-NBOMe 1-(benzofuran-5-yl)-N-(2- − − Y
methoxybenzyl)propan-2-amine
30 N-PROPYL-DOB N-Pr-DOB N-[1-(4-Bromo-2,5-dimethoxyphenyl)propan-2- − − Y
yl]propan-1-amine
31 RH-34 N/A. 3-(2-{[(2- − − Y
Methoxyphenyl)methyl]amino}ethyl)quinazoline-
2,4(1H,3H)-dione
32 25E-NBOH 2C-E-NBOH 2-({[2-(4-Ethyl-2,5- Y Y −
dimethoxyphenyl)ethyl]amino}methyl)phenol
33 25F-NBOME 2C-F-NBOMe 2-(4-Fluoro-2,5-dimethoxyphenyl)-N-[(2- − Y −
methoxyphenyl)methyl]ethan-1-amine
34 25H-NBOH 2C-H-NBOH 2-({[2-(2,5- − Y −
Dimethoxyphenyl)ethyl]amino}methyl)phenol
35 25I-NB34MD 4-Iodo-2,5-dimethoxy-N-(3,4- N-[(2H-1,3-Benzodioxol-5-yl)methyl]-2-(4-iodo- Y Y Y
methylenedioxybenzyl)phenethylamine 2,5-dimethoxyphenyl)ethan-1-amine
36 25I-NBMD N/A 2-(2-{[(2H-1,3-Benzodioxol-4- Y Y Y
yl)methyl]amino}ethyl)−5-iodo-4-
methoxyphenol
 Table 3 NPSfinder® FLYs and comparisons with EMCDDA and UNODC databases.
N NPSfinder® name Other names IUPAC EDND UNODC EWA NPSfinder®
(Feb NPS (July
2020) 2019)
1 DOB-5-HEMIFLY 4-Benzofuranethanamine, 1-(7-Bromo-5-methoxy-2,3-dihydro-1-benzofuran-4-yl)propan-2- − − Y
7-bromo-2,3-dihy amine
2 M-HEMIFLY Hemi-flyscaline 2-(6,7-Dimethoxy-2,3-dihydro-1-benzofuran-4-yl)ethan-1-amine − − Y
3 MESCALINE-FLY M-FLY 2-(8-Methoxy-2,3,5,6-tetrahydrobenzo[1,2-b:5,4-b ]difuran-4- − − Y
yl)ethan-1-amine

V. Catalani, J.M. Corkery, A. Guirguis et al.

4 I-SF DOI-5-hemiFLY 1-(7-Iodo-5-methoxy-2,3-dihydro-1-benzofuran-4-yl)propan-2- − − Y
amine
5 ME-3,5-IFLY ψ-DOM-FLY 1-(4-Methyl-2,3,5,6-tetrahydrobenzo[1,2-b:5,4-b ]difuran-8- − − Y
yl)propan-2-amine
6 2C-I-FLY N/A. 2-(8-Iodo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b ]difuran-4- − − Y
yl)ethan-1-amine
7 TFM-FLY N/A 1-[8-(Trifluoromethyl)−2,3,6,7-tetrahydrobenzo[1,2-b:4,5- − − Y
b ]difuran-4-yl]propan-2-amine
82

8 DOM-FLY N/A 1-(8-Methyl-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b ]difuran-4- − − Y

yl)propan-2-amine
9 2C-B-DFLY 2C-B-dragonFLY 2-(8-Bromobenzo[1,2-b:4,5-b ]difuran-4-yl)ethan-1-amine − − Y
10 2C-I-DFLY N/A. 2-(8-Iodobenzo[1,2-b:4,5-b ]difuran-4-yl)ethan-1-amine − − Y
11 DOM-DFLY N/A. 1-(8-Methylbenzo[1,2-b:4,5-b ]difuran-4-yl)propan-2-amine − − Y
12 TFM-DFLY DOTFM-dragonFLY 1-[8-(Trifluoromethyl)furo[2,3-f][1]benzofuran-4-yl]propan-2- − − Y
amine
13 2C-B-PLY 2C-B-butterFLY 2-(10-Bromo-2,3,4,7,8,9-hexahydrobenzo[1,2-b:4,5-b ]dipyran-5- − − Y
yl)ethan-1-amine
14 2C-B-FLY N/A 2-(4-bromo-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-8- Y Y Y
yl)ethanamine
15 3C-B-FLY 8-bromo-2,3,6,7-tetrahydro-a- 1-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b’]difuran-4- − Y −
methyl-benzo[1,2-b:4,5-b’]difuran-4- yl)propan-2-amine
ethanamine
16 BROMO-DRAGONFLY Bromo-DragonFLY (1-(8-bromobenzo[1,2-b;4,5-b’]difuran-4-yl)−2-aminopropane Y Y Y
17 TFMFLY N/A (2R)-1-(8-trifluoromethyl-2,3,6,7-tetrahydrobenzo[1,2-b:4,5- − − Y
b’]difuran-4-yl)−2-aminoethane
 Table 4 NPSfinder® tryptamines and comparisons with EMCDDA and UNODC databases.
N NPSfinder® name Other names IUPAC EDND UNODC EWA NPSfinder®
(Feb NPS (July
2020) 2019)
1 4-ACETOXY-N,N- 4-AcO-DiPT 3-[2-[di(propan-2-yl)amino]ethyl]-1H-indol-4-yl] − − Y
DIISOPROPYLTRYPTAMINE acetate
2 4-ACO-AET N/A 1-(4-Methyl-1H-indol-3-yl)butan-2-amine − − Y
3 4-ACO-EIPT Ethipracetin 3-(2-(ethyl(isopropyl)amino)ethyl)-1H-indol-4-yl − − Y
acetate
4 4-H2PO4-DMT N,N-Dimethyl-4- 3-[2-(Dimethylamino)ethyl]-1H-indol-4-yl dihydrogen − − Y
phosphoryloxytryptamine phosphate
5 4-HO-DALT Dalocin 3-{2-[Di(prop-2-en-1-yl)amino]ethyl}−1H-indol-4-ol − − Y

European Neuropsychopharmacology 49 (2021) 69–92

6 4-HO-MPMI 4-Hydroxy-N-methyl-(α,N- 3-[(1-Methylpyrrolidin-2-yl)methyl]-1H-indol-4-ol − − Y
trimethylene)tryptamine
7 4-PRO-DIPT N,N-Diisopropyl-4- 1-(3-{2-[Di(propan-2-yl)amino]ethyl}-1H-indol-4- − − Y
propionyltryptamine yl)propan-1-one
8 5-BROMO-DMT 5-Bromo-N,N-dimethyltryptamine [2-(5-Bromo-1H-indol-3-yl)ethyl]dimethylamine − − Y
9 5-METHOXY-N-METHYL- 5-MeO-MPMI 5-Methoxy-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}- − − Y
(α,N- 1H-indole
TRIMETHYLENE)TRYPTAMINE
10 MEXAMINE 5-MT 2-(5-Methoxy-1H-indol-3-yl)ethanamine − − Y
83

11 ALPHA- αET 3-(2-aminobutyl)indole − − Y

ETHYLTRYPTAMINE
12 2,3-DIHYDRO-N,N- CHEMBL159503 2-(2,3-dihydro-1H-indol-3-yl)-N,N- − − Y
DIMETHYL-1H-INDOLE-3- dimethylethanamine
ETHANAMINE
13 N,N- DET N,N-Diethyl-2-(1H-indol-3-yl)ethan-1-amine − − Y
DIETHYLTRYPTAMINEDiethyltryptamine
14 DIMEMEBFE 5-MeO-BFE N,N-Dimethyl-2-(5-methoxybenzofuran-3- − − Y
yl)ethanamine
15 MPT Methylpropyltryptamine N-[2-(1H-Indol-3-yl)ethyl]-N-methylpropan-1-amine − − Y
16 N-OMEGA- N/A 3-(2-Methylaminoethyl)indole − − Y
METHYLTRYPTAMINE
17 RU-28306 3,4,5-tetrahydro-N,N- N,N-dimethyl-2-azatricyclo[6.3.1.04;12]dodeca- − − Y
dimethylbenz[cd]indol-4-amine 1(12);3;8;10-tetraen-6-amine;
18 4-ACETOXY-N,N- 4-AcO-DiPT [3-[2-[di(propan-2-yl)amino]ethyl]-1H-indol-4-yl] Y Y Y
DIISOPROPYLTRYPTAMINE acetate
19 2-ME-DMT 2,N,N-Trimethyltryptamine N,N-dimethyl-2-(2-methyl-1H-indol-3-yl)ethanamine Y Y Y
20 4-ACO-DALT 4-Acetyloxy-N,N-diallyltryptamine [3-[2-[bis(prop-2-enyl)amino]ethyl]-1H-indol-4-yl] Y Y Y
acetate
21 4-ACETOXY-N,N- 4-ACO-DET [3-[2-(diethylamino)ethyl]-1H-indol-4-yl] acetate Y Y Y
DIETHYLTRYPTAMINE
(continued on next page)
 Table 4 (continued)
N NPSfinder® name Other names IUPAC EDND UNODC EWA NPSfinder®
(Feb NPS (July
2020) 2019)
22 4-ACO-DMT 4-acetoxy-N,N-dimethyltryptamine [3-[2-(dimethylamino)ethyl]-1H-indol-4-yl] acetate Y Y Y
23 4-ACO-DPT 4-acetoxy-N,N-propilltryptamine [3-[2-(dipropylamino)ethyl]-1H-indol-4-yl] acetate Y Y Y
24 4-ACETOXY-N-ETHYL-N- 4-ACO-MET [3-[2-[ethyl(methyl)amino]ethyl]-1H-indol-4-yl] Y Y Y
METHYLTRYPTAMINE acetate
25 4-ACETOXY-N-METHYL-N- 4-ACO-MiPT [3-[2-[methyl(propan-2-yl)amino]ethyl]-1H-indol-4- Y Y Y
ISOPROPYLTRYPTAMINE yl]
acetate
26 4-HYDROXY-N,N- 4-HO-DET 3-[2-(diethylamino)ethyl]-1H-indol-4-ol Y Y Y
DIETHYLTRYPTAMINE
27 4-HYDROXY-N,N- 4-HO-DiPT 3-[2-[di(propan-2-yl)amino]ethyl]-1H-indol-4-ol Y Y Y

V. Catalani, J.M. Corkery, A. Guirguis et al.

DIISOPROPYLTRYPTAMINE
28 4-HYDROXY- 4-HO-DPT 3-[2-(dipropylamino)ethyl]-1H-indol-4-ol Y Y Y
DIPROPYLTRYPTAMINE
29 4-HYDROXY-N-ETHYL-N- 4-HO-EPT 3-[2-[ethyl(propyl)amino]ethyl]-1H-indol-4-ol Y Y Y
PROPYLTRYPTAMINE
30 4-HO-MCPT 4-Hydroxy-N-methyl-N- 3-[2-[Cyclopentyl(methyl)amino]ethyl]-1H-indol-4-ol Y Y Y
cyclopropyltryptamine
84

31 4-HYDROXY-N-METHYL-N- 4-HO-MET 3-[2-[ethyl(methyl)amino]ethyl]-1H-indol-4-ol Y Y Y

ETHYLTRYPTAMINE4-HO-
MET
32 4-HO-MPT 4-hydroxy-N-methyl-N- 3-[2-[methyl(propyl)amino]ethyl]-1H-indol-4-ol Y Y Y
propyltryptamine
33 4-HYDROXY-MIPT 4-hydroxy-N,N-methyl- 3-[2-[methyl(propan-2-yl)amino]ethyl]-1H-indol-4-ol Y Y Y
isopropyltryptamine
34 5-MEO-AMT 5-methoxy-alpha-methyltryptamine 1-(5-methoxy-1H-indol-3-yl)propan-2-amine Y Y Y
35 5-MEO-DALT 5-METHOXY DIALLYLTRYPTAMINE N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-prop-2- Y Y Y
enylprop-2-en-1-amine
36 5-MEO-DET 5-methoxy-N,N-diethyltryptamine N,N-diethyl-2-(5-methoxy-1H-indol-3-yl)ethanamine Y Y Y
37 5-METHOXY-N,N- 5-MeO-DiPT N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-propan-2- Y Y Y
DIISOPROPYLTRYPTAMINE ylpropan-2-amine
38 5-METHOXY-N,N- 5-MeO-DMT 2-(5-methoxy-1H-indol-3-yl)-N,N- Y Y Y
DIMETHYLTRYPTAMINE dimethylethanamine
39 5-MEO-DPT 5-METHOXY-N,N- N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N- Y Y Y
DIPROPYLTRYPTAMINE propylpropan-1-amine
40 5-MEO-EIPT 5-Methoxy-N-ethyl-N- N-Ethyl-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]propan- Y Y Y
isopropyltryptamine 2-amine
41 5-MEO-MALT N-etyl-N-isopropyl-5- N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N-methylprop- Y Y Y
metoxitryptamine 2-en-1-amine
(continued on next page)
 Table 4 (continued)
N NPSfinder® name Other names IUPAC EDND UNODC EWA NPSfinder®
(Feb NPS (July
2020) 2019)
42 5-MEO-MET 5-metoxy-N-ethyl-N-methyl- N-Ethyl-2-(5-methoxy-1H-indol-3-yl)-N-methylethan- Y Y Y
tryptamine 1-amine
43 5-MeO-MiPT 5-methoxy-N-methyl-N- N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N- Y Y Y
isopropyltryptamine methylpropan-2-amine
44 5-MEO-NBPBRT 5-Methoxy-N-(4- N-[(4-bromophenyl)methyl]-2-(5-methoxy-1H-indol- Y − Y
bromobenzyl)tryptamine 3-yl)ethanamine
45 5-MEO-NIPT N-Isopropyl-5-methoxytryptamine N-[2-(5-methoxy-1H-indol-3-yl)ethyl]propan-2-amine Y Y Y
46 5-METHOXY-N,N- 5-MeO-pyr-T 5-methoxy-3-(2-pyrrolidin-1-ylethyl)−1H-indole Y Y Y
TETRAMETHYLENETRYPTAMINE

European Neuropsychopharmacology 49 (2021) 69–92

47 4-MEO-MIPT N-Isopropyl-4-methoxy-N- N-[2-(4-Methoxy-1H-indol-3-yl)ethyl]-N- Y − Y
methyltryptamine methylpropan-2-amine
48 INDAPEX 5-MeO-2-TMT 2-(5-Methoxy-2-methyl-1H-indol-3-yl)-N,N- Y − Y
dimethylethan-1-amine
49 α,N,N- alpha-TMT 1-(1H-indol-3-yl)-N,N-dimethylpropan-2-amine Y Y Y
TRIMETHYLTRYPTAMINE
50 α-METHYLTRYPTAMINE AMT 1-(1H-indol-3-yl)propan-2-amine Y Y Y
51 DALT N,N-diallyltryptamine N-[2-(1H-indol-3-yl)ethyl]-N-prop-2-enylprop-2-en-1- Y Y Y
amine
52 N,N- DIPT N-[2-(1H-indol-3-yl)ethyl]-N-propan-2-ylpropan-2- Y Y Y
85

DIISOPROPYLTRYPTAMINE amine
53 N,N- DMT 2-(1H-indol-3-yl)-N,N-dimethylethanamine Y Y Y
DIMETHYLTRYPTAMINE
54 N,N- DPT N-[2-(1H-indol-3-yl)ethyl]-N-propylpropan-1-amine Y Y Y
DIPROPYLTRYPTAMINE
55 EPT N-Ethyl-N-propyltryptamine 3-[2-(Ethyl(propyl)amino)ethyl]-1H-indole Y Y Y
56 MCPT N-methyl-N-cyclopropyltryptamine 3-{2-[cyclopropyl(methyl)amino]ethyl}-1H-indole Y Y Y
57 N-ETHYL-N- MET Ethyl-(2-(1H-indol-3-yl)-ethyl)-methylamine Y Y Y
METHYLTRYPTAMINE
58 MIPT n-methyl-n-isopropyltryptamine N-[2-(1H-indol-3-yl)ethyl]-N-methylpropan-2-amine Y Y Y
59 4-AcO-MALT 4-Acetyloxy-N-methyl-N- 3-(2-(allyl(methyl)amino)ethyl)-1H-indol-4-yl acetate − Y −
allyltryptamine
60 4-MeO-DMT 4-Methoxy-N,N-dimethyltryptamine 2-(4-methoxy-1H-indol-3-yl)-N,N-dimethylethan-1- − Y −
amine
61 4-METHYL-ALPHA- 4-Me-αET 1-(4-Methyl-1H-indol-3-yl)butan-2-amine − Y −
ETHYLTRYPTAMINEMethyl-
alpha-ethyltryptamine
62 NMT N-Methyltryptamine 2-(1H-indol-3-yl)-N-methylethan-1-amine − Y −
64 6-MeO-DIPT 6-Methoxy-N,N-diisopropyltryptamine N-isopropyl-N-(2-(6-methoxy-1H-indol-3- − Y −
yl)ethyl)propan-2-amine
65 4-OH-T 4-Hydroxytryptamine 3-(2-aminoethyl)−1H-indol-4-ol − Y −
66 5-HTP 5-Hydroxytryptophan (S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic − Y −
acid
 Table 5 NPSfinder® lysergamides and comparisons with EMCDDA and UNODC databases.
N NPSfinder® name Other names IUPAC EDND UNODC NPSfinder®
(Feb EWA NPS
2020) (July 2019)
1 MiPLA Methylisopropyllysergamide N,7-dimethyl-N-propan-2-yl-6,6a,8,9-tetrahydro-4H-indolo[4,3- − − Y
fg]quinoline-9-carboxamide
2 D-LYSERGIC ACID D-iso-Lysergic Acid (6aR,9R)-N,7-dimethyl-N-propyl-6,6a,8α,9-tetrahydro-4H- − − Y
N-(METHYLOPROPYL) AMIDE N-Methyl-N-propylamide indolo[4,3-fg]quinoline-9-carboxamide
3 LYSERGIC ACID LAMPA (6aR,9R)-N,7-dimethyl-N-propyl-6,6a,8,9-tetrahydro-4H- − − Y
N-METHYL-N-PROPYLAMIDE indolo[4,3-fg]quinoline-9-carboxamide
4 N METHYL LYSERGIC ACID MLD-41 (6aR,9R)-N,N-diethyl-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3- − − Y
DIETHYLAMIDE fg]quinoline-9-carboxamide
5 N-Propylnorlysergic acid PRO-LAD (6aR,9R)-N,N-diethyl-7-propyl-4,6,6a,7,8,9-hexahydroindolo-[4,3- − − Y

V. Catalani, J.M. Corkery, A. Guirguis et al.

N,N-diethylamide fg]quinoline-9-carboxamide
6 6-PROPYNYL-6-NOR- LYSERGIC PARGY-LAD (6aR,9R)-N,N–diethyl-7-prop-2-ynyl-6,6a,8,9-tetrahydro-4H- − − Y
ACID DIETHYLAMIDE indolo[4,3-fg]quinoline-9-carboxamide
7 LSM-775 N-Morpholinyllysergamide [(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3- − − Y
fg]quinolin-9-yl]-morpholin-4-ylmethanone
8 LYSERGIC ACID AMIDE LSA (6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3- − Y Y
fg]quinoline-9-carboxamide
9 6-ETHYL-6-NOR-LYSERGIC ACID ETH-LAD 6aR,9R)-N,N,7-Triethyl-4,6,6a,7,8,9-hexahydroindolo-[4,3- Y Y Y
86

DIETHYLAMIDE fg]quinoline-9-carboxamide
10 1CP-LSD 1-Cyclopropionyl-D-lysergic acid (6aR,9R)-4-cyclopropionyl-N,N-diethyl-7-methyl-4,6,6a,7,8,9- − − Y
diethylamide hexahydroindolo[4,3-fg]quinoline-9-carboxamide
11 1-PROPIONYL-D-LYSERGIC ACID 1P-LSD (6aR,9R)-4-(3-deuteriopropanoyl)-N,N-diethyl-7-methyl-6,6a,8,9- Y Y Y
DIETHYLAMIDE tetrahydroindolo[4,3-fg]quinoline-9-carboxamide
12 1P-ETH-LAD 1-propionyl-6-ethyl-6-nor-lysergic (6aR,9R)-4-propionyl-N,N-diethyl-7-ethyl-4,6,6a,7,8,9- Y Y Y
acid diethyamide hexahydroindolo[4,3-fg]quinoline-9-carboxamide
13 AL-LAD 6-allyl-6-nor-lysergic acid (6aR,9R)-N,N-Diethyl-7-(prop-2-en-1-yl)-4,6,6a,7,8,9- Y Y Y
diethylamide hexahydroindolo-[4,3-fg]quinoline-9-carboxamide
14 1B-LSD 1-butanoyl-lysergic acid diethylamide (6aR,9R)-4-butyryl-N,N-diethyl-7-methyl-4,6,6a,7,8,9- Y Y Y
hexahydroindolo[4,3-fg]quinoline-9-carboxamide
15 ALD-52 1-acetyl-LSD (6aR,9R)-4-Acetyl-N,N-diethyl-7-methyl-4,6,6a,7,8,9- Y Y Y
hexahydroindolo[4,3-fg]quinoline-9-carboxamide
16 LYSERGIC ACID LSZ [(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3- − Y Y
2,4-DIMETHYLAZETIDIDE fg]quinoline-9-yl]-[(2S,4S)-2,4-dimethylazetidin-1-yl]methanone
17 LYSERGIC ACID METHYL ESTER Methyl 9,10-didehydro-6- methyl (6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3- Y Y −
methylergoline-8beta-carboxylate fg]quinoline-9-carboxylate
18 1M-LSD 1-methyl-LSD (6aR,9R)-N,N-diethyl-4,7-dimethyl-4,6,6a,7,8,9- − Y −
hexahydroindolo[4,3-fg]quinoline-9-carboxamide
19 2-Bromo-LSD 2-Bromo-N,N-diethyllysergamide (6aR,9R)-5-bromo-N,N-diethyl-7-methyl-4,6,6a,7,8,9- − Y −
hexahydroindolo[4,3-fg]quinoline-9-carboxamide
 European Neuropsychopharmacology 49 (2021) 69–92
Fig. 1 Psychedelic NPS identified by the NPSfinder®. The subclassification of the phenethylamines class is presented as well.
Fig. 2 NPSfinder® comparison with UNODC and EMCDAA databases.
Across the three databases, 976 molecules were here con-
sidered as ‘putative psychedelics’ due to lack of data on
their psychoactive activity; out of these, 946 resulted to be
previously unknown molecules to both the EMCDDA and the
UNODC databases.
NPSfinder® results for the tryptamine and lysergamide
classes were more in line with the EMCDDA and UNODC fig-
ures. However, NPSfinder® still showed a higher number of
entries, i.e. 65 tryptamines compared to 50 reported by the
UNODC and 44 by the EMCDDA. Lysergamides accounted for
16 entries in the NPSfinder®, 11 in the UNODC and 7 in the
EMCDDA databases (Fig. 2).
Across the three classes of substances the total number
of either novel or putative psychedelics, previously unmen-
tioned by both the UNODC and EMCDDA, amounted to 994.
4. Discussion
To the best of our knowledge, the present paper provides a
unique insight into the previously under-recognised number
of psychedelic molecules. Indeed, some 994 novel/putative
novel psychedelics molecules were here first identified with
the help of systematic, multilingual, (open) web crawling
activities. This project is part of a larger study carried out
by our research group that analyses the differences be-
87
tween the extent of the NPS phenomenon online versus
the real-world situation. The discrepancy between the num-
bers of various NPS classes found after the analysis of the
NPSfinder® web activity and the number reported by of-
ficial sources has already been reported by this group in
previous publications (Arillotta et al., 2020; Orsolini et al.,
2020; Schifano et al., 2020; Zangani et al., 2020). How-
ever, the current psychedelic NPS data, and especially so for
phenethylamines which were here 10-fold higher in number
than those previously identified by specialized databases,
are unprecedented. Hence, it is here suggested that exam-
ining the online scenarios is of great potential to assess the
NPS phenomenon. Even if it is not possible to guarantee with
100% certainty that the discussed NPS in fact exist and are
being used, scanning and analysing the web can still be of
help in predicting and assessing the real world psychedelic
NPS scenario (Corazza et al., 2013; Schifano et al., 2015).
The striking differences between the NPSfinder® and the
remaining databases can, however, be explained in con-
sidering that the online drug scenario is different from
the reactive, event-based, reporting to official databases
(Schifano et al., 2003). Indeed, limitations and challenges
encountered in the NPS identification (UNODC, 2013), e.g.
not limited to appropriate analytical techniques, reference
standards availability, lack of analytical libraries for novel
substances, etc. slow down the NPS identification process
 V. Catalani, J.M. Corkery, A. Guirguis et al.
and reduce considerably the amount of molecules actually
detected and reported. These challenges are not encoun-
tered online, where information is very easily accessed and
shared, in a fast and very often anonymous way. Aware of
the limitations that surround the analytical NPS identifi-
cation, one should not assume that the “real” drug mar-
ket is described only by the substances that are officially
reported and consider other sources to be used as sup-
portive/integrative tools. The best resource could be the
web, e.g. the virtual space/world where everything hap-
pens in the modern era, including drug-related activities
(Corazza et al., 2013).
The results presented here support the idea that psycho-
nauts favour drugs with entheogenic/psychedelic properties
(Móró et al., 2011; Orsolini et al., 2015a, 2015b) and their
drug intake shows high similarities with ancient shamanic
ritual plant consumption (Orsolini et al., 2016). In the NPS
era, these mind navigators are exposed to a large variety of
easily available new psychedelic compounds. One could ar-
gue that psychonauts experiment with this large number of
unknown molecules to achieve new inner explorations and
deeper trips into the mind to access areas and realms never
‘dreamt of’ before. The attitude of psychonauts towards
psychedelics can help explain why phenethylamine entries
reported by NPSfinder® are much higher than the ones re-
ported by the UNODC or EMCDDA, while for the overall NPS
the number is ‘only’ five-fold higher.
Another consideration is that the consumption of
psychedelic NPS is still seen as advantageous by psycho-
nauts, and therefore by online drug users as well, who are
attracted to the idea of the evolutionary role and posi-
tive effects (e.g. increased empathy levels, better estab-
lishment/strengthening of attachment bonds in an environ-
ment, improvement of own social status) that psychedelics
have had for millennia (Orsolini et al., 2016).
Unfortunately, some modern psychedelics exhibit high
toxicity levels (Luethi and Liechti, 2020) and their inges-
tion should be considered unsafe (Schifano et al., 2017,
2016). The recreational use of NBOMes has caused, on
many occasions, severe toxic effects, leading to fatalities,
even after emergency medical intervention (Bersani et al.,
2014; Kamińska et al., 2020; Luethi and Liechti, 2020;
Morini et al., 2017; Poulie et al., 2019).Fatalities and
near misses have been reported as well after the use
of the psychedelic Bromo-dragonFLY (Andreasen et al.,
2009; Iwersen-Bergmann et al., 2019) and 2,5-dimethoxy-
4-bromoamphetamine (DOB) (Balíková, 2005). Fatalities
and intoxications have been reported also following the
use of synthetic tryptamines (alpha-methyltryptamine,
5-methoxy-N,N-diisopropyltryptamine (‘Foxy’), etc.)
(Tittarelli et al., 2014). Alpha-methyltryptamine was
reported in 22 cases of drug related poisoning deaths in
England and Wales (Office for National Statistics, 2019).
The extreme toxicity (e.g. severe agitation, tachycar-
dia, hyperthermia, seizures, rhabdomyolysis, metabolic
acidosis, renal failure, multi-organ failure, and coma);
(Poulie et al., 2019) of some psychedelic NPS such as
the NBOMes is associated with distinct selectivity for
the 5-HT2A receptor (Braden et al., 2006; Luethi and
Liechti, 2020; Rickli et al., 2015b), resulting in high clinical
potency (EMCDDA-Europol, 2014; Nichols et al., 2008).
Moreover, psychedelic NPS can induce, consistently with
88
their pharmacodynamics, paranoid and full-blown system-
atic delusions, mood alteration towards hypomanic states,
suicidal thoughts, and depression states (Martinotti et al.,
2015). When the use of these drugs is sporadic then the
psychotic features are reversible, but when it is more
frequent and at high doses then psychotic disorders are
long-lasting and can culminate in a ‘lysergic psychoma’
(Martinotti et al., 2015).
Whilst for some of psychedelic NPS the related phar-
macology and toxicity from in vivo/in vitro studies are
available (e.g. phenethylamines (Eshleman et al., 2018;
Jensen et al., 2017; Luethi et al., 2018; Luethi and
Liechti, 2020); tryptamines (Halberstadt et al., 2019;
Rickli et al., 2016); lysergamides (Brandt et al., 2019, 2018),
for most NPS here mentioned there is a lack of reliable
data. Hence, the substances here listed and categorised as
tryptamines, phenethylamines, and lysergamides possess a
likely misusing element, and may be considered as potent
and potentially dangerous recreational drugs. On this basis,
the findings highlighted by NPSfinder® can be considered
a reason of concern, with the scientific world and health
care institutions facing thousands of substances for which
very little knowledge, if anything, is known. Furthermore,
serious concern arises from the very limited data available
on the human absorption, distribution, metabolism, and ex-
cretion properties of these substances, with no knowledge
about possible drug-drug interactions or toxic metabolites.
Complex behavioural and medical toxicity (Schifano et al.,
2019a, 2019b) issues could be the issues that healthcare
professionals will need to face, without any ad hoc inter-
vention and harm reduction strategies in place.
A final consideration to be made is that, while the num-
ber of substances listed between the two official databases
provides a full overview of NPS historical data regarding
the different NPS appearance over the last 15 years or so,
NPSfinder® reports a more dynamic, and possibly current,
picture of their existence and diffusion. NPSfinder® ability
to continuously scan the web and detect new psychedelics
in ‘real time’ makes it more focused on the present time
and can provided some levels of understanding about future
trends (Corkery et al., 2017).
4.1. Limitations
Current NPSfinder® results cannot confirm in any possible
way the prevalence levels of use of psychedelics or their
circulating number in the real-world market. However, cur-
rent findings still suggest the interest shown by psycho-
nauts, and the possible interest of the much wider com-
munity of ‘recreational’ drug users, towards these cate-
gories of substances. Although it is not possible to guaran-
tee with 100% certainty that the discussed NPS in fact exist
and are being used, it is here suggested that scanning and
analysing the web can represent a valuable option to assess-
ing/predicting current/future real-world drug scenarios. In-
deed, the present data analysis strategy carried out for each
molecule identified by the web crawler consisted as well in
a detailed search against several databases and web pages,
including vendor websites. These ancillary activities have
possibly helped in “tracing” the new NPS, confirming their
presence on the online markets and hence increasing the
 European Neuropsychopharmacology 49 (2021) 69–92
levels of likelihood that the molecules here discussed exist
and are potentially being used.
One could argue that some of the psychonauts here dis-
cussing the range of NPS online did not possess a deep un-
derstanding of both chemistry and appropriate analytical
techniques; hence, it is possible that some chemical names
and structures stated in web discussion fora were poten-
tially incorrect. However, most websites scanned by the web
crawler were here psychonauts’ websites. As illustrated by
previous studies (Orsolini et al., 2015a, 2015b), psycho-
nauts may well be perceived as “educated and informed”
users, with highly advanced levels of academic background,
usually providing reliable and detailed information on psy-
choactive compounds/combinations. However, there is still
the chance that some substances may have here been mis-
labelled or referred to with slang denominations or com-
mon names. To overcome these possible biases in data ac-
quisition activities, a thorough analysis and data evalua-
tion was carried out, and the authors were able to assign a
proper/unique chemical name and structure to all the sub-
stances here commented.
It must be emphasised here that the NPSfinder® crawling
activity has been conducted so far only on the surface web.
Further studies from our group will focus on both the deep
web and the darknet, since there may be more informa-
tion in the hidden web (Orsolini et al., 2017). Since previous
studies have highlighted the importance of other languages
like Chinese, Japanese and Arabic in NPS-related studies,
these will need to be added to the NPSfinder® capabilities.
Furthermore, a range of multidisciplinary (e.g. docking, vir-
tual screening, computational model; Kontoyianni, 2017)
investigations are being carried out by our group in or-
der to properly classify all the ‘unknown’ molecules (Ap-
pendix 2) found by the NPSfinder. Docking studies focussing
on the 5-HT2A receptor will be essential to understand these
molecules’ possible clinical activity, recreational profile and
impact on healthcare systems.
4.2. Conclusions
NPSfinder® has the potential to identify a large num-
ber of new and previously unmentioned NPS, including
psychedelics, with the chance of providing information on
current and future drug trends. It may help explaining how
a drug moves through the journey from manufacturing to
distribution in both the virtual and real markets.
NPSfinder® could be used as a support for the Euro-
pean and United Nation Early Warning Systems. Its ability
to identify a molecule shortly after being mentioned on the
web for the first time can make it a very important tool
for a range of activities, including: informing, influencing
and impacting law-making, monitoring/surveillance, phar-
macovigilance, law-enforcement, understanding sales and
use, and for drafting both treatment/management guide-
lines and educational packages. Predictive data regarding
these molecules’ acute and long-term effects, adverse ef-
fects and abuse potential could be generated, through in
silico, in vitro, and in vivo studies in order to minimise the
impact that NPS currently have on healthcare systems. In-
deed, some of the novel psychedelic molecules here iden-
89
tified could exhibit very severe toxicity levels. Future work
will hopefully include the creation of ad hoc reports/fact
sheets for those newly identified NPS that are considered
more threatening to public health. These reports will be
shared with official sources, stakeholders and public health
organisations to help researchers identify which substance
to study first.
Moreover, NPSfinder® can be used as an effective moni-
toring tool. As reported in the 2009 Integrated and Balanced
Strategy to Counter the World Drug Problem, systematic
global monitoring is recognised as a powerful tool against
drug problems (LSS/RAB/DPA/UNODC, 2016). This unique
web-crawler has the potential to scan the web systemat-
ically, consistently, and globally, since no country borders
are available on the web.
The monitoring ability of NPSfinder® could be useful in
the current situation the world is facing due to the COVID-
19 pandemic. As reported by the EMCDDA, restrictions on
movement enforced all across Europe and worldwide (i.e.,
China, India, etc.) may evolve into serious disruption of the
drug markets (UNODC, 2020) with a possible rise in online
drugs purchases. The use of NPS, and of psychedelics in par-
ticular, may increase during the COVID-19 as individuals seek
to self-medicate to deal with the trauma of isolation and
anxiety about the virus (Chiappini et al., 2020). Through the
analysis of the NPSfinder® activity we may be able to notice
possible changes in the online drug markets that can reflect
the real-world situation (Catalani et al., 2021).
Role of the funding source
The author(s) received no specific funding for this work.
Contributors
FS and AV conceived the idea of the manuscript and have co-
ordinated the whole project. VC, FN, CZ, DA, and LG have
carried out the process of both data collection and systema-
tisation. VC performed the literature searching, the analysis
of data and drafted the manuscript. JMC provided data from
the EMCDDA and UNODC databases for the purposes of this
research. FS, AG and JMC have contributed to the literature
overview and have contributed as well to the drafting of the
paper itself.
Conflict of interest
All other authors declare that they have no conflicts of in-
terest.
Acknowledgements
Special thanks to Damicom srl (I) for having provided here
full access to the NPSfinder database.
 V. Catalani, J.M. Corkery, A. Guirguis et al.
Supplementary materials
Supplementary material associated with this article can be
found, in the online version, at doi:10.1016/j.euroneuro.
2021.03.006.
References
Abdulrahim, D., Bowden-Jones, O., 2015. Guidance on the Clin-
ical Management of Acute and Chronic Harms of Club Drugs
and Novel Psychoactive Substances [WWW Document]. URL http:
//neptune- clinical- guidance.co.uk/clinical- guidance- 2/
Andreasen, M.F., Telving, R., Birkler, R.I.D., Schumacher, B., Jo-
hannsen, M., 2009. A fatal poisoning involving Bromo-Dragonfly.
Forensic Sci. Int. 183, 91–96. doi:10.1016/j.forsciint.2008.11.
001.
Arillotta, D., Schifano, F., Napoletano, F., Zangani, C., Gilgar, L.,
Guirguis, A., Corkery, J.M., Aguglia, E., Vento, A., 2020. Novel
opioids: systematic web crawling within the e-psychonauts’ sce-
nario. Front. Neurosci. 14, 149. doi:10.3389/fnins.2020.00149.
Balíková, M., 2005. Nonfatal and fatal DOB (2,5-dimethoxy-4-
bromamphetamine) overdose. Forensic Sci. Int. 153, 85–91.
doi:10.1016/j.forsciint.2005.04.022.
Bersani, F.S., Corazza, O., Albano, G., Valeriani, G., Santacroce, R.,
Bolzan Mariotti Posocco, F., Cinosi, E., Simonato, P., Mar-
tinotti, G., Bersani, G., Schifano, F., 2014. 25C-NBOMe: prelim-
inary data on pharmacology, psychoactive effects, and toxicity
of a new potent and dangerous hallucinogenic drug. Biomed Res.
Int. 2014, 73474. doi:10.1155/2014/734749.
Bey, T., Patel, A., 2007. Phencyclidine intoxication and adverse ef-
fects: a clinical and pharmacological review of an illicit drug.
Calif. J. Emerg. Med. 8, 9–14.
Booth, M., 2000. A Magick Life: A Biography of Aleister Crowley.
Coronet Books.
Braden, M.R., Parrish, J.C., Naylor, J.C., Nichols, D.E., 2006.
Molecular interaction of serotonin 5-HT2A receptor residues
Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl
phenethylamine agonists. Mol. Pharmacol. 70, 1956–1964.
doi:10.1124/mol.106.028720.
Brandt, S.D., Kavanagh, P.V., Twamley, B., Westphal, F., El-
liott, S.P., Wallach, J., Stratford, A., Klein, L.M., McCorvy, J.D.,
Nichols, D.E., Halberstadt, A.L., 2018. Return of the ly-
sergamides. Part IV: analytical and pharmacological character-
ization of lysergic acid morpholide (LSM-775). Drug Test. Anal.
10, 310–322. doi:10.1002/dta.2222.
Brandt, S.D., Kavanagh, P.V., Westphal, F., Stratford, A., El-
liott, S.P., Dowling, G., Wallach, J., Halberstadt, A.L., 2019.
Return of the lysergamides. Part V: analytical and behavioural
characterization of 1-butanoyl- d -lysergic acid diethylamide
(1B-LSD). Drug Test. Anal. 11, 1122–1133. doi:10.1002/dta.2613.
Carroll, F.I., Lewin, A.H., Mascarella, S.W., Seltzman, H.H.,
Reddy, P.A., 2012. Designer drugs: a medicinal chemistry per-
spective. Ann. N.Y. Acad. Sci. doi:10.1111/j.1749-6632.2011.
06199.x.
Carroll, P.J., Peter, J., 1987. Liber Null & Psychonaut. S. Weiser.
Catalani, V., Arillotta, D., Corkery, J.M., Guirguis, A., Vento, A.,
Schifano, F., 2021. Identifying new/emerging psychoactive sub-
stances at the time of COVID-19; a web-based approach. Front.
Psychiatry 11, 1638. doi:10.3389/FPSYT.2020.632405.
Chiappini, S., Guirguis, A., John, A., Corkery, J.M., Schifano, F.,
2020. COVID-19: the hidden impact on mental health and drug
addiction. Front. Psychiatry 11, 767. doi:10.3389/fpsyt.2020.
00767.
Corazza, O., Assi, S., Simonato, P., Corkery, J., Bersani, F.S.,
Demetrovics, Z., Stair, J., Fergus, S., Pezzolesi, C.,
Pasinetti, M., Deluca, P., Drummond, C., Davey, Z., Blaszko, U.,
90
Moskalewicz, J., Mervo, B., Di Furia, L., Farre, M., Flesland, L.,
Pisarska, A., Shapiro, H., Siemann, H., Skutle, A., Sferrazza, E.,
Torrens, M., Sambola, F., van der Kreeft, P., Scherbaum, N.,
Schifano, F., 2013. Promoting innovation and excellence to face
the rapid diffusion of novel psychoactive substances in the EU:
the outcomes of the ReDNet project. Hum. Psychopharmacol.
28, 317–323. doi:10.1002/hup.2299.
Corkery, J.M., Durkin, E., Elliott, S., Schifano, F., Gh-
odse, A.H., 2012. The recreational tryptamine 5-MeO-
DALT (N,N-diallyl-5-methoxytryptamine): a brief review.
Prog. Neuro-Psychopharmacol. Biol. Psychiatry 39, 259–262.
doi:10.1016/j.pnpbp.2012.05.022.
Corkery, J.M., Orsolini, L., Papanti, D., Schifano, F., 2017. From
concept(ion) to life after death/the grave: the ‘natural’ history
and life cycle(s) of novel psychoactive substances (NPS). Hum.
Psychopharmacol. 32. doi:10.1002/hup.2566.
Dean, B.V., Stellpflug, S.J., Burnett, A.M., Engebretsen, K.M., 2013.
2C or not 2C: phenethylamine designer drug review. J. Med. Tox-
icol. 9, 172–178. doi:10.1007/s13181- 013- 0295- x.
Deluca, P., Davey, Z., Corazza, O., Di Furia, L., Farre, M.,
Flesland, L.H., Mannonen, M., Majava, A., Peltoniemi, T.,
Pasinetti, M., Pezzolesi, C., Scherbaum, N., Siemann, H.,
Skutle, A., Torrens, M., van der Kreeft, P., Iversen, E., Schi-
fano, F., 2012. Identifying emerging trends in recreational drug
use; outcomes from the Psychonaut Web Mapping Project. Prog.
Neuropsychopharmacol. Biol. Psychiatry 39, 221–226. doi:10.
1016/j.pnpbp.2012.07.011.
Dinis-Oliveira, R.J., Pereira, C.L., da Silva, D.D., 2018. Pharmacoki-
netic and pharmacodynamic aspects of peyote and mescaline:
clinical and forensic repercussions. Curr. Mol. Pharmacol. 12,
184–194. doi:10.2174/1874467211666181010154139.
Duxbury, S.W., 2018. Information creation on online drug forums:
how drug use becomes moral on the margins of science. Curr.
Sociol. 66, 431–448. doi:10.1177/0011392115596055.
EDND, 2019. EDND - Login page [WWW Document]. URL https://
ednd2.emcdda.europa.eu/ednd/login (accessed 11.18.19).
EMCDDA-Europol, 2014. EMCDDA–Europol Joint Report on
a new psychoactive substance 4-iodo-2,5-dimethoxy-
N-(2-methoxybenzyl)phenethylamine (25I-NBOMe) |
www.emcdda.europa.eu. Lisbon.
EMCDDA, 2019a. European Drug Report 2019. Trends and Develop-
ments, Lisbon.
EMCDDA, 2019b. The EU Early Warning System on new psy-
choactive substances (NPS) [WWW Document]. URL https:
//www.emcdda.europa.eu/publications/topic-overviews/
eu- early- warning- system_en (accessed 10.23.19).
Eshleman, A.J., Wolfrum, K.M., Reed, J.F., Kim, S.O., John-
son, R.A., Janowsky, A., 2018. Neurochemical pharmacology
of psychoactive substituted N-benzylphenethylamines: high po-
tency agonists at 5-HT2A receptors. Biochem. Pharmacol. 158,
27–34. doi:10.1016/j.bcp.2018.09.024.
Fiorella, D., Rabin, R.A., Winter, J.C., 1995. Role of 5-HT2A and 5-
HT2C receptors in the stimulus effects of hallucinogenic drugs II:
reassessment of LSD false positives. Psychopharmacology 121,
357–363. doi:10.1007/BF02246075.
Freedman, D.X., 1968. On the use and abuse of LSD. Arch.
Gen. Psychiatry 18, 330–347. doi:10.1001/archpsyc.1968.
01740030074008.
Google [WWW Document], 2019. URL https://www.google.co.uk/
(accessed 10.24.19).
Green, A.R., 2008. Gaddum and LSD: the birth and growth of ex-
perimental and clinical neuropharmacology research on 5-HT in
the UK. Br. J. Pharmacol. doi:10.1038/bjp.2008.207.
Griffiths, R.R., Grob, C.S., 2010. Hallucinogens as medicine. Sci.
Am. 303, 77–79. doi:10.1038/scientificamerican1210-76.
Halberstadt, A.L., Chatha, M., Stratford, A., Grill, M., Brandt, S.D.,
2019. Comparison of the behavioral responses induced by
phenylalkylamine hallucinogens and their tetrahydrobenzodi-
 European Neuropsychopharmacology 49 (2021) 69–92
furan (“FLY”) and benzodifuran (“DragonFLY”) analogs. Neu-
ropharmacology 144, 368–376. doi:10.1016/j.neuropharm.2018.
10.037.
Halberstadt, A.L., Geyer, M.A., 2011. Multiple receptors contribute
to the behavioral effects of indoleamine hallucinogens. Neu-
ropharmacology doi:10.1016/j.neuropharm.2011.01.017.
Hall, F.S., Miczek, K.A., 2019. Emerging threats in addiction: will
novel psychoactive substances contribute to exacerbating the
ongoing drug overdose epidemic? Psychopharmacology doi:10.
1007/s00213- 019- 05271- 7.
Heller, S., McNaught, A., Stein, S., Tchekhovskoi, D., Pletnev, I.,
2013. InChI – the worldwide chemical structure identifier stan-
dard. J. Cheminform. doi:10.1186/1758- 2946- 5- 7.
Hofmann, A., 1959. Psychotomimetic drugs; chemical and phar-
macological aspects. Acta Physiol. Pharmacol. Neerl. 8, 240–
258.
Iwersen-Bergmann, S., Lehmann, S., Heinemann, A., Schröder, C.,
Müller, A., Jungen, H., Andresen-Streichert, H., Pueschel, K.,
Vidal, C., Mercer-Chalmers-Bender, K., 2019. Mass poisoning
with NPS: 2C-E and Bromo-DragonFly. Int. J. Legal Med. 133,
123–129. doi:10.1007/s00414- 018- 1882- 9.
Jensen, A.A., McCorvy, J.D., Leth-Petersen, S., Bundgaard, C.,
Liebscher, G., Kenakin, T.P., Bräuner-Osborne, H., Kehler, J.,
Kristensen, J.L., 2017. Detailed characterization of the in
vitro pharmacological and pharmacokinetic properties of
N-(2-Hydroxybenzyl)-2, 5-Dimethoxy-4-Cyanophenylethylamine
(25CN-NBOH), a highly selective and brain-penetrant 5-HT2A re-
ceptor agonist. J. Pharmacol. Exp. Ther. 361, 441–453. doi:10.
1124/jpet.117.239905.
Kamińska, K., Świt, P., Malek, K., 2020. 2-(4-Iodo-2,5-
dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
(25I-NBOME): a harmful hallucinogen review. J. Anal. Toxicol.
doi:10.1093/JAT/BKAA022.
Kataja, K., Törrönen, J., Hakkarainen, P., Tigerstedt, C., 2018. A
virtual academy of polydrug use: masters, novices and the art
of combinations. NAD Nord. Stud. Alcohol Drugs 35, 413–427.
doi:10.1177/1455072518770351.
Kometer, M., Schmidt, A., Jäncke, L., Vollenweider, F.X., 2013.
Activation of serotonin 2A receptors underlies the psilocybin-
induced effects on α oscillations, N170 visual-evoked poten-
tials, and visual hallucinations. J. Neurosci. 33, 10544–10551.
doi:10.1523/JNEUROSCI.3007-12.2013.
Kontoyianni, M., 2017. Docking and virtual screening in drug dis-
covery. In: Methods in Molecular Biology. Humana Press Inc.,
pp. 255–266. doi:10.1007/978- 1- 4939- 7201- 2_18.
Labate, B.C., Jungaberle, H., 2011. The Internationalization of
Ayahuasca, Anthropology of Consciousness. Lit Verlag.
López-Giménez, J.F., González-Maeso, J., 2018. Hallucinogens and
serotonin 5-HT2A receptor-mediated signaling pathways. In:
Current Topics in Behavioral Neurosciences. Springer Verlag,
pp. 45–73. doi:10.1007/7854_2017_478.
LSS/RAB/DPA/UNODC, 2016. New psychoactive substances:
overview of trends, challenges and legal approaches [WWW Doc-
ument]. URL https://www.unodc.org/documents/commissions/
CND/CND_Sessions/CND_59/ECN72016_CRP2_V1601405.pdf
(accessed 4.16.20).
Luethi, D., Liechti, M.E., 2020. Designer drugs: mechanism of ac-
tion and adverse effects. Arch. Toxicol. 94, 1085–1133. doi:10.
1007/s00204- 020- 02693- 7.
Luethi, D., Trachsel, D., Hoener, M.C., Liechti, M.E., 2018.
Monoamine receptor interaction profiles of 4-thio-substituted
phenethylamines (2C-T drugs). Neuropharmacology 134, 141–
148. doi:10.1016/j.neuropharm.2017.07.012.
Martinotti, G., Di Nicola, M., Quattrone, D., Santacroce, R.,
Schifano, F., Murray, R., Di Giannantonio, M., Giovanni Mar-
tinotti, C., 2015. Novel psychoactive substances and induced
phenomena in psychopathology: the lysergic psychoma. Psy-
chopathol. Addict. J. Psychopathol. 21, 400–405.
91
Maurer, H.H., 2010. Chemistry, pharmacology, and metabolism of
emerging drugs of abuse. Ther. Drug Monit. doi:10.1097/FTD.
0b013e3181eea318.
Morini, L., Bernini, M., Vezzoli, S., Restori, M., Moretti, M.,
Crenna, S., Papa, P., Locatelli, C., Osculati, A.M.M., Vignali, C.,
Groppi, A., 2017. Death after 25C-NBOMe and 25H-NBOMe con-
sumption. Forensic Sci. Int. 279, e1–e6. doi:10.1016/j.forsciint.
2017.08.028.
Móró, L., Simon, K., Bárd, I., Rácz, J., 2011. Voice of the psycho-
nauts: coping, life purpose, and spirituality in psychedelic drug
users. J. Psychoact. Drugs 43, 188–198. doi:10.1080/02791072.
2011.605661.
Nichols, D.E., 2018. Chemistry and structure-activity relationships
of psychedelics. In: Current Topics in Behavioral Neurosciences,
pp. 1–43. doi:10.1007/7854_2017_475.
Nichols, D.E., 2016. Psychedelics. Pharmacol. Rev. 68 (2), 264–355.
doi:10.1124/pr.115.011478.
Nichols, D.E., Frescas, S.P., Chemel, B.R., Rehder, K.S., Zhong, D.,
Lewin, A.H., 2008. High specific activity tritium-labeled
N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine
(INBMeO): a high-affinity 5-HT2A receptor-selective ago-
nist radioligand. Bioorganic Med. Chem. 16, 6116–6123.
doi:10.1016/j.bmc.2008.04.050.
Nichols, D.E., Sassano, M.F., Halberstadt, A.L., Klein, L.M.,
Brandt, S.D., Elliott, S.P., Fiedler, W.J., 2015. N-Benzyl-5-
methoxytryptamines as potent serotonin 5-HT2 receptor fam-
ily agonists and comparison with a series of phenethylamine
analogues. ACS Chem. Neurosci. 6, 1165–1175. doi:10.1021/
cn500292d.
Ninnemann, A., Stuart, G.L., 2013. The NBOMe series: a novel, dan-
gerous group of hallucinogenic drugs. J. Stud. Alcohol Drugs 74,
977–978. doi:10.15288/jsad.2013.74.977.
Office for National Statistics, 2019. Deaths related to drug
poisoning by selected substances [WWW Document]. URL
https://www.ons.gov.uk/peoplepopulationandcommunity/
birthsdeathsandmarriages/deaths/datasets/
deathsrelatedtodrugpoisoningbyselectedsubstances (accessed
5.5.20).
Orsolini, L., Corkery, J.M., Chiappini, S., Guirguis, A., Vento, A.,
De Berardis, D., Papanti, D., Schifano, F., 2020. New/designer
benzodiazepines”: an analysis of the literature and psycho-
nauts’ trip reports. Curr. Neuropharmacol. 18 (9), 809–837.
doi:10.2174/1570159X18666200110121333.
Orsolini, L., Papanti, D., Corkery, J., Schifano, F., 2017. An insight
into the deep web; why it matters for addiction psychiatry?
Hum. Psychopharmacol. Clin. Exp. 32, e2573. doi:10.1002/hup.
2573.
Orsolini, L., Papanti, G.D., Francesconi, G., Schifano, F., 2015a.
Mind navigators of chemicals’ experimenters? A web-based de-
scription of E-psychonauts. Cyberpsychol. Behav. Soc. Netw. 18,
296–300. doi:10.1089/cyber.2014.0486.
Orsolini, L., Papanti, G.D., Francesconi, G., Schifano, F., 2015b.
Navigating in the virtual mind of the web’: the E-psychonauts’
profiling. Eur. Psychiatry 30, 1045. doi:10.1016/s0924-9338(15)
30822-1.
Orsolini, L., St John-Smith, P., McQueen, D., Papanti, D.,
Corkery, J., Schifano, F., 2016. Evolutionary considera-
tions on the emerging subculture of the E-psychonauts and
the novel psychoactive substances: a comeback to the
shamanism? Curr. Neuropharmacol. 15. doi:10.2174/
1570159x15666161111114838.
Osmond, H., 1957. A review of the clinical effects of psy-
chotomimetic agents. Ann. N.Y. Acad. Sci. 66, 418–434. doi:10.
1111/j.1749-6632.1957.tb40738.x.
Papaseit, E., Farré, M., Pérez-Mañá, C., Torrens, M., Ventura, M.,
Pujadas, M., de la Torre, R., González, D., 2018. Acute phar-
macological effects of 2C-B in humans: an observational study.
Front. Pharmacol. 9. doi:10.3389/fphar.2018.00206.
 V. Catalani, J.M. Corkery, A. Guirguis et al.
Passie, T., Halpern, J.H., Stichtenoth, D.O., Emrich, H.M.,
Hintzen, A., 2008. The pharmacology of LSD: a review. CNS Neu-
rosci. Ther. 14, 295–314. doi:10.1111/j.1755-5949.2008.00059.
x.
Poulie, C.B.M., Jensen, A.A., Halberstadt, A., Kristensen, J.L.,
2019. Dark classics in chemical neuroscience: NBOMes. ACS
Chem. Neurosci. doi:10.1021/acschemneuro.9b00528.
PubChem [WWW Document], 2019. URL https://pubchem.ncbi.
nlm.nih.gov/ (accessed 10.24.19).
PubMed-NCBI [WWW Document], 2019. URL https://www.ncbi.nlm.
nih.gov/pubmed/ (accessed 10.24.19).
Rickli, A., Kopf, S., Hoener, M.C., Liechti, M.E., 2015a. Pharmaco-
logical profile of novel psychoactive benzofurans. Br. J. Pharma-
col. 172, 3412–3425. doi:10.1111/bph.13128.
Rickli, A., Luethi, D., Reinisch, J., Buchy, D., Hoener, M.C.,
Liechti, M.E., 2015b. Receptor interaction profiles of novel
N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-
substituted phenethylamines (2C drugs). Neuropharmacology
99, 546–553. doi:10.1016/j.neuropharm.2015.08.034.
Rickli, A., Moning, O.D., Hoener, M.C., Liechti, M.E., 2016. Recep-
tor interaction profiles of novel psychoactive tryptamines com-
pared with classic hallucinogens. Eur. Neuropsychopharmacol.
26, 1327–1337. doi:10.1016/j.euroneuro.2016.05.001.
Sakashita, Y., Abe, K., Katagiri, N., Kambe, T., Saitoh, T., Ut-
sunomiya, I., Horiguchi, Y., Taguchi, K., 2015. Effect of psilocin
on extracellular dopamine and serotonin levels in the mesoac-
cumbens and mesocortical pathway in awake rats. Biol. Pharm.
Bull. 38, 134–138. doi:10.1248/bpb.b14-00315.
Schifano, F., Deluca, P., Baldacchino, A., Peltoniemi, T.,
Scherbaum, N., Torrens, M., Farrě, M., Flores, I., Rossi, M.,
Eastwood, D., Guionnet, C., Rawaf, S., Agosti, L., Di Furia, L.,
Brigada, R., Majava, A., Siemann, H., Leoni, M., Tomasin, A.,
Rovetto, F., Ghodse, A.H., 2006. Drugs on the web; the Psy-
chonaut 2002 EU project. Prog. Neuro-Psychopharmacol. Biol.
Psychiatry 30, 640–646. doi:10.1016/j.pnpbp.2005.11.035.
Schifano, F., Leoni, M., Martinotti, G., Rawaf, S., Rovetto, F., 2003.
Importance of cyberspace for the assessment of the drug abuse
market: preliminary results from the Psychonaut 2002 project.
In: Cyberpsychology and Behavior, pp. 405–410. doi:10.1089/
109493103322278790.
Schifano, F., Napoletano, F., Arillotta, D., Zangani, C., Gilgar, L.,
Guirguis, A., Corkery, J.M., Vento, A., 2020. The clinical chal-
lenges of synthetic cathinones. Br. J. Clin. Pharmacol. doi:10.
1111/bcp.14132.
Schifano, F., Napoletano, F., Chiappini, S., Guirguis, A., Cork-
ery, J.M., Bonaccorso, S., Ricciardi, A., Scherbaum, N.,
Vento, A., 2019a. New/emerging psychoactive substances and
associated psychopathological consequences. Psychol. Med. 1–
13. doi:10.1017/S0033291719001727.
Schifano, Fabrizio, Napoletano, F., Chiappini, S., Orsolini, L.,
Guirguis, A., Corkery, J.M., Bonaccorso, S., Ricciardi, A.,
Scherbaum, N., Vento, A., 2019b. New psychoactive substances
(NPS), psychedelic experiences and dissociation: clinical and
clinical pharmacological issues. Curr. Addict. Rep. 6, 140–152.
doi:10.1007/s40429- 019- 00249- z.
92
Schifano, F., Orsolini, L., Duccio Papanti, G., Corkery, J.M., 2015.
Novel psychoactive substances of interest for psychiatry. World
Psychiatry 14, 15–26. doi:10.1002/wps.20174.
Schifano, F., Orsolini, L., Papanti, D., Corkery, J., 2017. NPS: med-
ical consequences associated with their intake. In: Current Top-
ics in Behavioral Neurosciences. Springer Verlag, pp. 351–380.
doi:10.1007/7854_2016_15.
Schifano, F., Papanti, G.D., Orsolini, L., Corkery, J.M., 2016.
Novel psychoactive substances: the pharmacology of stimu-
lants and hallucinogens. Exp. Rev. Clin. Pharmacol. doi:10.1586/
17512433.2016.1167597.
Seidler, R., 2001. Lysergic acid diethylamide LSD. Curr. Ther. 42,
77–78. doi:10.1016/0002- 9378(70)90029- 3.
Tang, M.H.Y., Ching, C.K., Tsui, M.S.H., Chu, F.K.C., Mak, T.W.L.,
2014. Two cases of severe intoxication associated with analyt-
ically confirmed use of the novel psychoactive substances 25B-
NBOMe and 25C-NBOMe. Clin. Toxicol. 52, 561–565. doi:10.3109/
15563650.2014.909932.
Teitler, M., Leonhardt, S., Appel, N.M., De Souza, E.B., Glen-
non, R.A., 1990. Receptor pharmacology of MDMA and related
hallucinogens. Ann. N.Y. Acad. Sci. 600, 626–638. doi:10.1111/
j.1749-6632.1990.tb16915.x.
Tittarelli, R., Mannocchi, G., Pantano, F., Romolo, F.,
2014. Recreational use, analysis and toxicity of
tryptamines. Curr. Neuropharmacol. 13, 26–46. doi:10.2174/
1570159x13666141210222409.
Trachsel, D., Lehmann, D., Enzensperger, C., 2013. Phenethy-
lamine: Von der Struktur zur Funktion. Nachtschatten.
UNODC, 2020. COVID-19 is changing the route of illicit drug flows,
says UNODC report. Vienna.
UNODC, 2019. UNODC Early Warning Advisory on New Psychoac-
tive Substances [WWW Document]. URL https://www.unodc.
org/LSS/Page/NPS (accessed 4.2.20).
UNODC, 2016. Terminology and Information on Drugs, Third ed. New
York.
UNODC, 2013. The Challenge of New Psychoactive Substances.
Global SMART Programe, Vienna.
UNODC EWA, 2020. March 2020- Recently scheduled benzo-
diazepines Flualprazolam and Etizolam associated with
multiple post-mortem and DUID cases in UNODC EWA.
URL https://www.unodc.org/LSS/Announcement/Details/
ad0c279b- b4d4- 49f3- b638- cd87755d2d42 (accessed 4.10.20).
Winter, J.C., 2009. Hallucinogens as discriminative stimuli in ani-
mals: LSD, phenethylamines, and tryptamines. Psychopharma-
cology doi:10.1007/s00213- 008- 1356- 8.
Zangani, C., Schifano, F., Napoletano, F., Arillotta, D., Gilgar, L.,
Guirguis, A., Corkery, J.M., Gambini, O., Vento, A., 2020.
The e-psychonauts’ ‘spiced’ world; assessment of the synthetic
cannabinoids’ information available online. Curr. Neuropharma-
col. 18. doi:10.2174/1570159x18666200302125146.
Another random document with
no related content on Scribd:
sprinkling of persons of a higher grade, who formed the small
Opposition. Though the opinions of these were of the most moderate
shade of what would now be called “liberalism,” the slightest
expression of them was attended with positive risk. Spies were
employed to watch such of them as had any social position; in several
cases there were trials for sedition, with sentences of transportation;
and only the impossibility of finding grounds for indictment
prevented more. The negative punishment of exclusion from office,
and from every favour of Government and its supporters, was the
least; and it was universally applied. Burns nearly lost his
excisemanship for too free speaking; and a letter is extant, addressed
by him to one of the commissioners of the Scottish Board of Excise,
in which, without denying his Liberalism, he protests that it is within
the bounds of devout attachment to the Constitution, and implores
the commissioner, as “a husband and a father” himself, not to be
instrumental in turning him, with his wife and his little ones, “into
the world, degraded and disgraced.” Part of the poet’s crime seems to
have been his having subscribed to an Edinburgh Liberal paper
which had been started by one Captain Johnstone. This Johnstone
was imprisoned after the publication of a few numbers; and the very
printer of the paper, though himself a Tory, was nearly ruined by his
connection with it. No subsequent attempt was made during the
Dundas reign to establish an Opposition newspaper. From 1795 to as
late as 1820, according to Lord Cockburn, not a single public meeting
on the Opposition side of politics was, or could be, held in
Edinburgh. Elections of members of Parliament, whether for burghs
or for counties, in Scotland, were a farce: they were transacted
quietly, by those whose business it was, in town-halls or in the
private rooms of hotels; and the people knew of the matter only by
the ringing of a bell, or by some other casual method of
announcement. Abject Toryism, or submission to Dundas and the
existing order of things, pervaded every department and every corner
of established or official life in Scotland,—the Church, the Bench, the
Bar, the Colleges and Schools; and so powerfully were any elements
of possible opposition that did exist kept down by the pressure of
organised self-interest, and by the fear of pains and penalties, that
the appearance at last from the Solway to Caithness was that of
imperturbable political stagnation.
 Once, indeed, a crisis occurred which put the Scottish people
nearly out in their calculations. This was in March 1801, when Pitt
resigned office, and Dundas along with him, and a new ministry was
formed under Pitt’s temporary substitute, Mr. Addington, afterwards
Lord Sidmouth. Dundas out of power was a conception totally new to
the Scottish mind,—an association, or rather a dissociation, of ideas
utterly paralysing. “For a while,” says Lord Brougham, “all was
uncertainty and consternation; all were seen fluttering about like
birds in an eclipse or a thunderstorm; no man could tell whom he
might trust; nay, worse still, no man could tell of whom he might ask
anything.” Dundasism, which had hitherto meant participation in
place and patronage, now seemed in danger of losing that meaning;
and the bulk of the Scottish population feared that they might have
to choose between the name and the thing. They were faithful to
Dundas, however; and they were rewarded. The Addington ministry,
which had come into power principally to conclude peace with
France by the Treaty of Amiens, came to an end after that Treaty had
been rendered nugatory by the recommencement of the war; and in
May 1804 Pitt returned to the helm. Dundas, who had in the interim
been raised to the peerage by the title of Viscount Melville, then
resumed his place in his friend’s cabinet, to yield his Parliamentary
service thenceforward in the Upper House, and official service
mainly in the First Lordship of the Admiralty. Scotland then rolled
herself up comfortably once more for her accustomed slumber,—the
only difference being that her bedside guardian had to be thought of
no longer as her Harry Dundas, but less familiarly now as her Lord
Melville. So for another year; but then what a reawakening! It was in
April 1805 that, in consequence of the report of a Committee of the
House of Commons that had been appointed for the investigation of
alleged abuses in the naval service, the Whigs, through Mr.
Whitbread as their spokesman, opened an attack on Lord Melville on
charges of malversation of office, and misappropriation of public
moneys, during his former Treasurership of the Navy, either directly,
or by collusion with his principal financial subordinate. The attack
grew fiercer and fiercer, as well as more extensive in its scope; and,
although it was evidently inspired mainly by the political
vindictiveness of a party made furious by long exclusion from office,
it became more formidable from the fact that some of Pitt’s own
friends either abetted it fully or thought that the irregularities in
account-keeping which had been disclosed ought not to pass without
Parliamentary censure. Pitt reeled under such a blow at once to his
private feelings and his administration; and, after doing his best to
resist, he had to consent that Lord Melville should quit office, and
that Lord Melville’s name should be struck off from the list of His
Majesty’s Privy Council till the charges against him were formally
and publicly tried. The trial was to be in the shape of an
impeachment before the House of Lords. Before it could come on Pitt
was dead. He died on the 23d of January 1806; and the longexcluded
Whigs had then their turn of power for somewhat more than a year
in what is remembered as the Fox and Grenville ministry,—a name
accurate only till the 13th of September 1806, when Fox followed his
great rival to the grave, and Lord Grenville became Premier singly. It
was in April and May 1806, when this Fox and Grenville ministry
was new in office, that the great trial of Lord Melville in Westminster
Hall was begun and concluded. The charges against him had been
formulated into ten articles; and he was acquitted upon all the ten,—
unanimously on the only one which vitally impeached his personal
integrity, by overwhelming majorities on five of the others, and by
smaller but still decisive majorities on the remaining four. On the
whole, it was a triumphant acquittal; and it was received as such
throughout Scotland,—where, at one of the dinners held in honour of
the event by the jubilant Scottish Tories, there was sung a famous
song beginning with this stanza:—
“Since here we are set in array round the table,
Five hundred good fellows well met in a hall,
Come listen, brave boys, and I’ll sing as I’m able
How innocence triumphed and pride got a fall.
But push round the claret,—
Come, stewards, don’t spare it;
With rapture you’ll drink to the toast that I give:
Here, boys,
Off with it merrily:
‘Melville for ever, and long may he live!’”

Melville did live for some time longer, restored to his place in the
Privy Council, and rehabilitated in honour, but never again in office,
hardly caring to concern himself further with politics, and spending
his last years mainly in Scotland. He died on the 27th of May 1811, in
the seventieth year of his age.
 That system of the government of Scotland by proconsulship of
which he had been so conspicuously the representative did not by
any means die with him. It was continued, with variations and
modifications, through those successive ministries of the later part of
the reign of George III. and the whole of the reign of George IV.
which fill up the interval between the death of Pitt and the eve of the
Reform Bill; nay, not only so continued, but continued with the
accompanying phenomenon that it was still a Dundas that exercised,
occasionally at least, what did remain of the proconsulship. Robert
Dundas, 2d Viscount Melville, who died as late as 1851, was a
member of most of the successive administrations mentioned, from
Perceval’s of 1809–12, through Liverpool’s of 1812–27, to Canning’s
and the Duke of Wellington’s of 1827–30, holding one or other of his
father’s old posts in these administrations, and so or otherwise
maintaining the hereditary Dundas influence in Scottish affairs while
Toryism kept the field. But, while this prolongation of the Dundas
influence in the second Lord Melville is not to be forgotten, it is the
father, Henry Dundas, 1st Lord Melville, that has left the name of
Dundas most strikingly impressed upon the history of Scotland, and
it is the stretch of two-and-twenty years between 1783 and 1806,
during which this greatest of the Dundases exercised the
proconsulship, that has to be remembered especially and
distinctively in Scottish annals as the time of the Dundas Despotism.

“The Dundas Despotism!” O phrase of fear, unpleasing to a

modern ear! What a Scotland that must have been which this phrase
describes! A country without political life, without public meetings,
without newspapers, without a hustings: could any endurable
existence be led in such a set of conditions,—could any good come
out of it?
Incredible as it may seem, there is evidence that the Scottish
people did contrive, in some way or other, to lead not only an
endurable but a very substantial and jolly existence through the
Dundas Despotism, and that not only a great deal of good, but much
of what Scotland must now regard as her best and most
characteristic produce, had its genesis in that time, though the
exodus has been later. The various liberties of the human subject
may be classified and arranged according to their degrees of
importance; and a great many of them may exist where the liberty of
voting for members of parliament and of openly talking politics is
absent. So it was in Scotland through the reign of Henry Dundas and
his Toryism. The million and a half of human beings who then
composed Scotland, and were scattered over its surface, in their
various parishes, agricultural or pastoral, and in their towns and
villages, went through their daily life with a great deal of energy and
enjoyment, notwithstanding that Dundas, and the lairds and the
provosts and bailies as his agents, elected the members of parliament
and transacted all the political business of the country; nay, out of
the lairds and the bailies themselves, and all the business of
electioneering, they extracted a good deal of fun. What mattered it to
them that now and then some long-tongued fellow who had started a
newspaper was stowed away in jail, or that an Edinburgh lawyer like
Muir was transported for being incontinent in his politics? Could not
people let well alone, obey the authorities, earn their oatmeal, and
drink their whisky in peace? Few of Scott’s novels come down so far
as to this period of Scottish life, and it has not been much described
in our other literature of fiction; but till lately there were many alive
who remembered it, and delighted in recalling its savageries and its
humours. O the old Scottish times of the lairds, the “moderate”
ministers, the provosts and the bailies!—the lairds speaking broad
Scotch, farming their own lands, carousing together, seeing their
daughters married, and writing to London for appointments for their
sons; the “moderate” ministers making interest for their sons,
preaching “Blair and cauld morality” on Sundays, and jogging to
christenings or to Presbytery dinners through the week; the provosts
and bailies in their shops in the forenoon, or meeting in the morning
at their “deid-chack” after a man was hanged! Every considerable
town then had its hangman, who was frequently a well-to-do person
that sold fish or some such commodity. And then, all through society,
the flirtations, the friendships, and the long winter evenings at the
fireside, with the cracks between the “gudeman” and his neighbours,
and the alternative of a hand at cards or a well-thumbed book for the
young folks! What stalwart old fellows, both of the douce and of the
humorous type, oracular and respected in their day, and whose
physiognomies and maxims are still preserved in local memory, lived
and died in those days and made them serve their turn! Nay, of the
Scotsmen who have been eminent in the intellectual world, what a
number belong by their birth to the reign of Dundas, and were
nurtured amid its torpid influences! Burns closed his life in the midst
of it; Dugald Stewart and James Watt lived through it; Scott, Jeffrey,
Chalmers, Wilson, Hamilton, and Carlyle are all, more or less,
specimens of what it could send forth. Vixere fortes ante
Agamemnona: there was pith in Scotland before there was
Parliamentary Reform.
Naturally it was in Edinburgh that the various elements of
Scottish life at this time were seen in their closest contact and their
most intimate union or antagonism. It was here that Dundas lived
when he was in Scotland; and here were the central threads of that
official network by which, through Dundas, Scotland was connected
with the English Government. Edinburgh was then still the chief city
of Scotland, even in population; for, though now Glasgow has far
outstripped it in that particular, then the two cities were happy in
numbering little more than 80,000 each. At least, in the census of
1801 Edinburgh stands for 82,000, or almost exactly neck to neck
with Glasgow, which stands for 83,000. Dundee, which came next,
reckoned but 29,000; Aberdeen, 27,000; and Leith and Paisley each
about 20,000. Few other Scottish towns had a population of more
than 10,000.
Was there ever another such city to live in as Edinburgh?
“And I forgot the clouded Forth,
The gloom that saddens heaven and earth,
The bitter east, the misty summer,
And gray metropolis of the North.”

One regrets that this is all that our noble Laureate’s experience of
Edinburgh enabled him to say. The east winds do bite there fearfully
now and then, and blow a dust of unparalleled pungency in your eyes
as you cross the North Bridge; but, with that exception, what a city!
Gray! why, it is gray, or gray and gold, or gray and gold and blue, or
gray and gold and blue and green, or gray and gold and blue and
green and purple, according as the heaven pleases, and you choose
your ground! But, take it when it is most sombrely gray, where is
another such gray city? The irregular ridge of the Old Town, with its
main street of lofty antique houses rising gradually from Holyrood
up to the craggy Castle; the chasm between the Old Town and the
New, showing grassy slopes by day, and glittering supernaturally
with lamps at night; the New Town itself, like a second city spilt out
of the Old, fairly built of stone, and stretching downwards over new
heights and hollows, with gardens intermixed, till it reaches the flats
of the Forth! Then Calton Hill in the midst, confronted by the
precipitous curve of the Salisbury Crags; Arthur Seat looking over all
like a lion grimly keeping guard; the wooded Corstorphines lying soft
away to the west, and the larger Pentlands looming quiet in the
southern distance! Let the sky be as gray and heavy as the absence of
the sun can make it, and where have natural situation and the hand
of man combined to exhibit such a mass of the city picturesque? And
only let the sun strike out, and lo! a burst of new glories in and
around. The sky is then blue as sapphire overhead; the waters of the
Forth are clear to the broad sea; the hills and the fields of Fife are
distinctly visible from every northern street and window; still more
distant peaks are discernible on either horizon; and, as day goes
down, the gables and pinnacles of the old houses blaze and glance
with the radiance of the sunset. It is such a city that no one, however
familiar with it, can walk out in its streets for but five minutes at any
hour of the day or of the night, or in any state of the weather, without
a new pleasure through the eye alone. Add to this the historical
associations. Remember that this is the city of ancient Scottish
royalty; that there is not a close or alley in the Old Town, and hardly
a street in the New, that has not memories of the great or the quaint
attached to it; that the many generations of old Scottish life that have
passed through it have left every stone of it, as it were, rich with
legend. To an English poet all this might be indifferent; but hear the
Scottish poets:—
“Edina! Scotia’s darling seat!
All hail thy palaces and towers!”

was the salutation of Burns, when first brought from his native
Ayrshire to behold the Scottish capital. “Mine own romantic town,”
was the outburst of Scott, in that famous passage where, after
describing Edinburgh as seen from the Braids, he makes even an
English stranger beside himself with rapture at the sight:—
“Fitz-Eustace’ heart felt closely pent;
As if to give his rapture vent,
 The spur he to his charger lent,
And raised his bridle hand,
And, making demi-volte in air,
Cried, ‘Where’s the coward that would not dare
To fight for such a land?’”

Here, though it is an Englishman that is supposed to speak, it is a

Scotsman that supplies the words; but there can be no such objection
in the case of the following lines from a sonnet, entitled “Written in
Edinburgh,” by Tennyson’s friend, Arthur Hallam:—
“Even thus, methinks, a city reared should be,
Yea, an imperial city, that might hold
Five times a hundred noble towns in fee ...
Thus should her towers be raised; with vicinage
Of clear bold hills, that curve her very streets,
As if to indicate, ’mid choicest seats
Of Art, abiding Nature’s majesty,—
And the broad sea beyond, in calm or rage
Chainless alike, and teaching liberty.”

At the time with which we are concerned this city had the
advantage of containing, as has been said, only about eighty
thousand people. For comfortable social purposes, that is about the
extreme size to which a city should go. The size of London is
overwhelming and paralysing. There can be no intimacy, no unity of
interest, in such a vast concourse. Ezekiel might be preaching in
Smithfield, Camberwell might be swallowed up by an earthquake,
and the people of St. John’s Wood would know nothing of either fact
till they saw it announced in the newspapers next morning. Hardly
since the days of the Gordon Riots has London ever been all agitated
simultaneously. In Ancient Athens, on the other hand, we have an
illustration of what a town of moderate size could be and produce.
That such a cluster of men as Pericles, Socrates, Æschylus,
Sophocles, Euripides, Aristophanes, Plato, Phidias, Alcibiades,
Xenophon, and others,—men of an order that we only expect to see
now far distributed through space and time, nantes rari in gurgite
vasto,—should have been swimming contemporaneously or nearly so
in such a small pond as Athens was, and that this affluence in
greatness should have been kept up by so small a population for
several ages, seems miraculous. The peculiar fineness of the Hellenic
nerve may have had something to do with the miracle; but the
compactness of the place,—the aggregation of so many finely and
variously endowed human beings precisely in such numbers as to
keep up among them a daily sense of mutual companionship,—must
also have had its effect. In “Modern Athens” the conditions of its
ancient namesake are not all reproduced. To say nothing of any
difference that there may be in respect of original brain-and-nerve
equipment between the modern and the ancient Athenian, “Modern
Athens” is, unfortunately, not a separate body-politic, with separate
interests and a separate power of legislation. There are no walls now
round the Edinburgh territory; nor have the Edinburgh people the
privilege of making wars and concluding treaties with even the
nearest portions of the rest of Great Britain. They cannot meet
periodically on the Castle Esplanade to pass laws for themselves in
popular assembly, and hear consummate speeches beginning “O men
of Edinburgh.” But, with many such differences, there are some
similarities. Everybody in Edinburgh knows, or may know,
everybody else, at least by sight; everybody meets everybody else in
the street at least once every day or two; the whole town is within
such convenient compass that, even to go from one extremity of it to
the other extremity, there is no need to take a cab unless it rains. It is
a city capable of being simultaneously and similarly affected in all its
parts. An idea administered to one knot of the citizens is as good as
administered to the whole community; a joke made on the Mound at
noon will ripple gradually to the suburbs, and into the surrounding
country, before the evening. If such is the case even now, when the
population is over 260,000, must it not have been still better when
the population was only 80,000, and that population was more shut
in within itself by the absence as yet of telegraphs and railroads?
Moreover, the eighty thousand people who were in Edinburgh
when Henry Dundas ruled Scotland were people of a rather peculiar,
and yet rather superior, mixture of sorts. There never has been any
very large amount of trade or of manufacture in Edinburgh, nor
much of the wealth or bustle that arises from trade and manufacture.
For the roar of mills and factories, and for a society ranging
correspondingly from the great millionaire uppermost to crowds of
operatives below, all toiling in the pursuit of wealth, one must go to
Glasgow. In Edinburgh the standard of the highest income is much
lower, and the standard of the lowest is perhaps higher, than in
Glasgow; nor is wealth of so much relative importance in the social
estimate. Roughly classified, the society of Edinburgh in the days to
which we are now looking back consisted, as the society of
Edinburgh still consists, of an upper stratum of lawyers and resident
gentry, college officials, and clergy, reposing on, but by no means
separated from, a community of shopkeepers and artisans sufficient
for the wants of the place. Let us glance at these components of the
society of Old Edinburgh in succession:—
First, The Lawyers and Resident Gentry.—These two classes
may be taken together, as to a certain extent identical. From the time
of the Union, such of the old nobility of Scotland as had till then
remained in their native country, occupying for a part of the year the
homely but picturesque residences of their ancestors in the Old Town
of Edinburgh, had gradually migrated southwards, leaving but a few
families of their order to keep up their memory in the ancient capital
of Holyrood and St. Giles. In the room of this ancient nobility, and,
indeed, absorbing such families of the old nobility as had remained,
there had sprung up,—as might have been expected from the fact
that Edinburgh, though it had parted with its Court and Legislature,
was still the seat of the supreme Scottish law-courts,—a new
aristocracy of lawyers. The lawyers,—consisting, first, of the judges
as the topmost persons, with their incomes of several thousands a
year, and then of the barristers, older and younger, in practice or out
of practice, but including also the numerous body of the “Writers to
the Signet” and other law-agents,—are now, and for the last century
or two have been, the dominant class in the Edinburgh population.
From the expense attending education for the legal profession, the
members of it, till within a time comparatively recent, were generally
scions of Scottish families of some rank and substance; and, indeed,
it was not unusual for Scottish lairds or their sons to become
nominally members of the Scottish bar, even when they did not
intend to practise. The fact of the substitution of the legal profession
for the old Scottish aristocracy in the dominant place in Edinburgh
society is typified by the circumstance that the so-called “Parliament
House,”—retaining that name because it enshrines the hall where the
Estates of the Scottish Kingdom held their meetings during the last
eighty years of the time when Scotland had no Parliaments but her
own,—is now the seat of the supreme Scottish law-courts, and the
daily resort of the interpreters of the laws in these courts. Any day
yet, while the courts are in session, the Parliament House, with its
long oaken ante-room, where scores of barristers in their wigs and
gowns, accompanied by writers in plainer costume, are incessantly
pacing up and down, and its smaller inner chambers, where the
judges on the bench, in their crimson robes, are trying cases, is the
most characteristic sight in Edinburgh. Even now the general hour of
breakfast in Edinburgh is determined by the time when the courts
open in the morning; and, dispersed through their homes, or at
dinner-parties, in the evening, it is the members of the legal
profession that lead the social talk. In the old Dundas days it was the
same, with the addition that then the lawyers were perhaps more
numerous in proportion to the rest of the community than they are
now, and were more closely inter-connected by birth and marriage
with the Scottish nobility and lairds.
Of hardly less importance socially was the Academical Element.
As Edinburgh possesses a University, as its University has long been
in high repute, and as, by reason of the comparative cheapness of
board and education in Edinburgh, many families, after a residence
in England or the Colonies, have been attracted thither for the sake
of the education of their sons, or, without going thither themselves,
have sent their sons thither, the business of education has always
been prominent, if not paramount, among the industries of the city.
The teachers of the public and of other schools have always formed a
considerable class numerically, as well as in rank; while to the
University professors, partly from the higher nature of their
teaching-duties, partly from the traditional dignity conferred on
them by the great reputation of some of their body in past times, and
partly from some superiority in their emoluments, there has alway
been accorded a degree of social consideration not attached to the
same function anywhere out of Scotland. The reputation of the
Medical School of Edinburgh, in particular, has always invested the
professors in the Medical Faculty of the University with special
distinction; and, as these professors have been generally also at the
head of the medical practice of the city, the Medical element, and
with it the Scientific element, in Edinburgh society have from times
long past been, to a considerable extent, in union with the
professorial.
 In all Scottish cities The Clergy have, from time immemorial,
exercised an amount of social influence not willingly allowed to any
other class of persons. This arises partly from the same causes which
give the clergy influence in other parts of Britain, but partly from the
peculiar affection of the Scottish people for the national theology
with which they have been saturated through so many centuries of
clerical teaching. In Edinburgh, in consequence of the perpetuation
there of relics of that old Scottish aristocracy which never was
completely brought into subjection to Presbytery, and in
consequence of the presence in society of a distinct intellectual
element in the lawyers, the clergy have not perhaps had, relatively,
the same weight as in other towns. Still they were powerful even in
the old Edinburgh of the Dundas rule. At the very least, a negative
respect was paid to them by the preservation throughout the place of
an external Presbyterian decorum and strictness; and in all houses
“the minister” was treated with distinction. Add to this that there
generally were among the Edinburgh clergy men possessing claims
to respect in addition to those belonging to their profession. Some,
even in that age of “Moderatism,” were remarkable for their
eloquence and zeal as preachers and as pastors; others had literary
pretensions; and others were professors in the University as well as
parish clergymen. More, indeed, than now, the professorial and the
clerical elements were then intermixed in Edinburgh. Perhaps,
however, that which gave the greatest dignity to the clerical or
ecclesiastical element in Edinburgh was the annual meeting in that
city, every May, of the General Assembly of the Church of Scotland.
In the history of Scottish society since the Union there is, perhaps, no
one fact of greater importance than the regular and uninterrupted
succession of those annual “General Assemblies” in Edinburgh for
the discussion of the affairs of the National Church. Let an
Englishman fancy that during the last two centuries there had been
no Parliament in England, no meetings of the House of Lords or of
the House of Commons, but that regularly during that period there
had been annual convocations of representatives of the whole body
of the English Clergy, together with such leading members of the
laity as churchwardens or the like from all the English parishes, and
that these convocations had sat ten days in every year, discussing all
public matters in any way bearing on the Church, and making laws
affecting the entire ecclesiastical organisation of England, and he will
have an idea of the extent to which the national history of Scotland
since her union with England is bound up in the records of her
“General Assemblies.” The General Assembly, in fact, from the year
1707 to the Disruption of the Scottish Church in 1843, was, to some
extent, a veritable Parliament, in which, though the secular
Parliament had been abolished, the united people of Scotland still
saw their nationality preserved and represented. All through the year
the clergy individually, in the thousand parishes or so into which
Scotland was divided, managed their own parochial affairs with the
assistance of select laymen called elders; these clergymen, again,
with some of their elders, held frequent district meetings, called
“presbyteries,” in order to regulate by deliberation and voting the
church affairs of their districts; there were still larger meetings,
periodically held, called “provincial synods”; but the grand
rendezvous of all, the supreme court of appeal and ecclesiastical
legislation, was the annual General Assembly in Edinburgh. The time
of its meeting was one of bustle and excitement. Black coats
swarmed in the streets; the Assembly was opened with military
pomp and circumstance by a Lord High Commissioner representing
the Crown; this Commissioner sat on a throne during the meetings,
and held levees and dinner-parties in Holyrood Palace all through
the ten days; the clergy, with lay representatives, some of whom were
usually noblemen or baronets, deliberated and debated during those
ten days, under a president of their own choosing called the
“Moderator”; the proceedings were in parliamentary form, and the
decisions by a majority of votes; and in many cases,—as in trials of
clergymen for moral or ecclesiastical misdemeanour,—barristers
were called in to plead professionally, as they did in the secular law-
courts. As was natural in a deliberative assembly almost all the
members of which were of the speaking class, the speaking was of a
very high order,—far higher, indeed, than has ever been heard in
these later days in the British Parliament; while at the same time
there was ample opportunity for the exercise of business talent and
of all the tact and skill of party-leadership. Much of the general
politics of Scotland took necessarily the form of church politics; and,
indeed, the connections between church politics and state politics
were pretty close. The vast majority of the clergy were adherents of
Dundas in general politics, and bent on swaying church polity in the
same direction; while the small minority of “Evangelicals” or “High-
Fliers,” as they were called, corresponded to the proscribed
“Liberals” in secular politics. The leading clergymen of both parties
were to be found in or near Edinburgh.
Respecting the Mercantile and Artisan classes it need only be
repeated that they were by no means separated by any social
demarcation from the fore-mentioned classes, but were intertwined
with these by family-relationships, and often also by the sympathies
belonging to superior natural intelligence and superior education.
Booksellers and printers were more numerous in Edinburgh
proportionally than in any other British town.
In a population of such dimensions, composed as has been
described, there was necessarily a good deal of leisure; and leisure
leads to sociability. Edinburgh in those days was one of the most
sociable towns in the world. By that time “society,” in the
conventional sense, had, with a few lingering exceptions, shifted
itself out of the Old Town into the New, or into the suburbs; and,
with this change, there had been a considerable change of manners.
Much of the formality, and at the same time much of the coarseness,
of an older stage of Scottish life had been civilised away,—the absurd
etiquette of the old dancing assemblies, for example, and the more
monstrous excesses of hard drinking. But the convivial spirit, and
many of the old convivial forms, remained. Dinner parties were
frequent; and the old custom of “toasts” and “sentiments” by the
hosts and the guests over their wine was still in fashion. Lord
Cockburn’s description of those dinner parties of his youth is one of
the best passages in his book. But it is on the supper parties that he
dwells with most evident affection. There were various kinds of
supper parties: the oyster supper at taverns, the bachelor supper in
lodgings, and the real domestic supper, to which both sexes were
invited; which last Lord Cockburn vaunts as a delightful institution
of Edinburgh, which the advancing lateness of the dinner-hour had
unhappily superseded. In short, in every form and way, from the set
dinner party, with its immense consumption of claret, in the houses
of the more wealthy, to the homely tea parties of gentlewomen of
moderate means, living in the suburbs of the Old Town, or in flats in
the New Town, and the roystering suppers of young men, where
culinary deficiencies were compensated by good humour and the
whisky punch, people were in the habit of incessantly meeting to
spend the evenings together. Lord Cockburn mentions, as illustrative
of the continuance of those sociable habits of the Edinburgh folks to
a somewhat later period than that with which we are immediately
concerned, the fact that for a great many years after his marriage,
which was in 1811, he had not spent above one evening in every
month, on the average, in solitude, i.e. without either being out as a
guest, or having friends with him at home. Even Sydney Smith,
though not native and to the manner born, and, with his English
tastes, more fastidious in his ideas of conviviality, retained to the last
a pleasant recollection of those Edinburgh hospitalities, as
experienced by him during his stay in Edinburgh from 1797 to 1802.
“When shall I see Scotland again?” he says in one of his letters:
“never shall I forget the happy days passed there, amidst odious
smells, barbarous sounds, bad suppers, excellent hearts, and the
most enlightened and cultivated understandings.”
Sydney Smith’s allusion to “the enlightened and cultivated
understandings” he encountered amid such roughish surroundings,
suggests the mention of what was, all in all, the most characteristic
feature of Edinburgh society at the close of the eighteenth century
and the beginning of the nineteenth—its intellectualism. In a
community composed in so large a measure of practitioners of the
learned professions, it was inevitable that there should be more of
interest in matters intellectual than is common, more of a habit of
reasoning and discussion, more play and variety in the choice of
topics for conversation. What mattered it that many of the most
intellectual men and women gave expression to their ideas in broad
Scotch? Ideas may be expressed in broad Scotch, and yet be the ideas
of cultivated minds; at all events, it was so then in Edinburgh, where
many excellent lawyers, University professors, and medical men kept
up the broad Scotch in their ordinary conversation, though the
majority had gone over to the English in all save accent, and some
were sedulous in trying to Anglicise themselves even in that. But,
whether the dialect was English or Scotch, there was a great deal of
very pleasant and very substantial talk. True, in Sydney Smith’s
recollection of the conversation of the Edinburgh people at the time
he moved among them, two great faults are specified. It ran too
much, he records, to that species of jocosity, perfectly torturing to an
Englishman, which the Scotch themselves called wut; and it also ran
too much, he records, into disputation and dialectics. “Their only
idea of wit,” he says, speaking of the Scotch generally, but of the
Edinburgh people in particular, “or rather of that inferior variety of
the electric talent which prevails occasionally in the North, and
which, under the name of wut, is so infinitely distressing to people of
good taste, is laughing immoderately at stated intervals.” And again
—“They are so imbued with metaphysics that they even make love
metaphysically: I overheard a young lady of my acquaintance, at a
dance in Edinburgh, exclaim, in a sudden pause of the music, ‘What
you say, my lord, is very true of love in the abstract, but——,’ here
the fiddlers began fiddling furiously, and the rest was lost.” This is
somewhat unfair. Wut, in its place, is as good as wit, and may be a
great deal heartier. As practised in the north, it corresponds more
with what is properly humour. It consists in a general openness to
the ludicrous view of things, a general disposition to call each other
Tam and Sandy, a general readiness to tell and to hear Scottish
stories the fun of which lies in the whole series of conceptions (often
too local) that they call up, rather than in any sudden flash or quip at
the close. At all events, the Scotch like their wut, and find it
satisfying. As for the dialectics, there is, perhaps, too much of that.
The excess in this direction is due, doubtless, in part to the
omnipresence of the lawyers. But wut and dialectics make a very
good mixture; and, dashed as this mixture is and always has been in
Edinburgh with finer and higher ingredients, there has been no town
in Britain for the last century and a half of greater deipnosophistic
capabilities, all things considered.
One element which Englishmen who do not know Edinburgh
always imagine as necessarily wanting in it never has been wanting.
Whether from the influence of the lawyers, and of the relics of the old
Scottish baronage and baronetage, acting conjointly as a
counterpoise to the influence of the clergy, or from other less obvious
causes, there has always been in Edinburgh a freer undercurrent of
speculative opinion, a tougher traditional scepticism, a greater
latitude of jest at things clerical and Presbyterian, than in other
Scottish towns. From the early part of the eighteenth century, when
Allan Ramsay, Dr. Archibald Pitcairn, and others, did battle with the
clergy in behalf of theatrical entertainments and other forms of the
festive, there has never been wanting a strong anti-clerical and even
free-thinking clique in Edinburgh society; and towards the end of the
century, when David Hume and Hugo Arnot were alive or
remembered, no city in Britain sheltered such a quantity of cosy
infidelity. Of hundreds of stories illustrative of this, take one of the
mildest:—Pitcairn, going about the streets one Sunday, was obliged
by a sudden pelt of rain to take refuge in a place he was not often in,
—a church. The audience was scanty; and he sat down in a pew
where there was only another sitter besides,—a quiet, grave-looking
countryman, listening to the sermon with a face of the utmost
composure. The preacher was very pathetic; so much so that at one
passage he began to shed tears copiously, and to use his pocket-
handkerchief. Interested in this as a physiological phenomenon for
which the cause was not apparent, Pitcairn turned to the
countryman, and asked in a whisper, “What the deevil gars the man
greet?” “Faith,” said the man, slowly turning round, “ye wad maybe
greet yoursel’ if ye was up there and had as little to say.” Pitcairn was
the type of the avowed Edinburgh infidel; of which class there were
not a few whose esoteric talk when they met together was of an out-
and-out kind; but the countryman was the type of a still more
numerous class, who kept up exterior conformity, but tested all
shrewdly enough by a pretty tough interior instinct. Indeed, long
after Pitcairn’s time, a kind of sturdy scepticism, quite distinct from
what would be called “infidelity,” was common among the educated
classes in Edinburgh. Old gentlemen who went duly to church, who
kept their families in great awe, and who preserved much etiquette in
their habits towards each other, were by no means strait-laced in
their beliefs; and it was not till a considerably later period, when a
more fervid religious spirit had taken possession of the Scottish
clergy themselves, and flamed forth in more zealous expositions of
peculiar Calvinistic doctrine from the pulpit than had been
customary in the days of Robertson and Blair, that evangelical
orthodoxy obtained in Edinburgh its visible and intimate alliance
with social respectability. Moreover, even those who were then
indubitably orthodox and devout by the older standard were devout
after a freer fashion, and with a far greater liberty both of conduct
and of rhetoric, than would now be allowable in consistency with the
same reputation. There is no point on which Lord Cockburn lays
more stress than on this. “There is no contrast,” he says, “between
those old days and the present that strikes me so strongly as that
suggested by the differences in religious observances, not so much by
the world in general, as by deeply religious people. I knew the habits
of the religious very well, partly through the piety of my mother and
her friends, the strict religious education of her children, and our
connection with some of the most distinguished of our devout
clergymen. I could mention many practices of our old pious which
would horrify modern zealots. The principles and feelings of the
persons commonly called evangelical were the same then that they
are now; the external acts by which these principles and feelings
were formerly expressed were materially different.”
Among the differences, Lord Cockburn notes in particular the
much laxer style, as it would now be called, in which Sunday was
observed by pious people and even by the most pious among the
clergy. There seems also to have been more freedom of speech, in the
direction of what would now be called profane allusion, among the
admittedly pious. One of the gems of Lord Cockburn’s book is his
portrait of one venerable old lady, a clergyman’s widow, sitting
neatly dressed in her high-backed leather chair, with her
grandchildren round her, the very model of silver-haired serenity, till
one of her granddaughters, in reading the newspaper to her,
stumbled on a paragraph which told how the reputation of a certain
fair one at the court of the Prince Regent had suffered from some
indiscreet talk of his about his own relations with her, but then
starting up, and exclaiming, with an indignant shake of her
shrivelled fist,—“The dawmed villain! does he kiss and tell?” There
were not a few old ladies of this stamp in Edinburgh in Lord
Cockburn’s boyhood and youth; some of whom survived far into the
present century, too old to part with their peculiarities, even to
please the clergy. “Ye speak, sir, as if the Bible had just come oot,”
said one such old lady, who lingered long in Edinburgh, to a young
clergyman who was instructing her on some point of Christian
practice on which she was disposed to differ from him. The
continuation in the society of Edinburgh of a considerable sprinkling
of such free-speaking gentlewomen of the old Scottish school,
intermingled with as many of the other sex using a still rougher
rhetoric, imparted, we are told, a flavour of originality to the
convivial conversation of the place for which there is now no exact
equivalent.
Presided over by such seniors, the young educated men of the
time did not stint themselves in the choice or the range of their
convivial topics. They discussed everything under the sun and down
to the centre. Who has not heard of the Speculative Society of
Edinburgh, founded in 1764 in connection with the University, and
kept up from that time to this by successive generations of students;
of which Lord Cockburn says that it “has trained more young men to
public spirit, talent, and liberal thought, than all the other private
institutions in Scotland”? Between 1780 and 1800 this society was in
all its glory, discussing, week after week, as its minutes inform us,
such topics as these:—“Ought any permanent support to be provided
for the poor?” “Ought there to be an established religion?” “Was the
execution of Charles I. justifiable?” “Should the slave trade be
abolished?” “Has the belief in a future state been of advantage to
mankind, or is it ever likely to be so?” “Is it for the interest of Britain
to maintain what is called the balance of Europe?” Here surely was
scepticism enough to keep thought alive; and that such questions,
discussed not only in the Speculative Society, but also in minor
associations of the same kind, and carried doubtless also, with other
more scientific topics, into private assemblages, should have been
ventilated in Edinburgh at that day, shows that, even under the
Dundas Despotism, there was no lack of intellectual freedom.
It is but a continuation of what we have been saying to add that
the old Edinburgh of those defunct decades had already an
established reputation as a literary metropolis. The rise of the
literary reputation of Edinburgh may date, for all purposes except
such as shallow present scholarship would call merely antiquarian,
from the time when Allan Ramsay set up his circulating library in the
High Street, and supplied the lieges furtively with novels, plays, and
song-books, including his own poems. This was about the year 1725,
when his countryman, Thomson, was publishing in London the first
portion of his Seasons. Thomson himself, and his contemporaries or
immediate successors, Mallet, Smollett, Armstrong, Meikle,
Macpherson, and Falconer, all rank in the list of literary Scots; but
they were Scoti extra Scotiam agentes, and had, most of them, but
an incidental connection with Edinburgh. The poets Robert Blair and
James Beattie, the philosopher Reid, and the theologian and critic
Dr. George Campbell, were not only literary Scots, but literary Scots
whose lives were spent on their own side of the Tweed; but, with the
exception of Blair, none of them were natives of Edinburgh, and even
Blair did not live there. After Ramsay, in short, the early literary
fame of Edinburgh is associated with the names of a cluster of men
who, born in different parts of Scotland, had, from various chances,
taken up their abode in Edinburgh, and who resided there, more or
less permanently, during the latter half of the eighteenth century.
The most prominent men of this cluster were these:—David Hume
(1711–1776), known as a philosophical writer since the year 1738, and
who, though he spent a good many years of his literary life in
England and in France, was for the last twenty years of it, and these
the most busy, a resident in Edinburgh; Hume’s senior and survivor,
Henry Home, Lord Kames (1696–1782), one of the judges of the
Court of Session, still remembered for the contrast between the
coarse Scottish facetiousness of his manners and the studied fineness
of his writings; the learned and eccentric Burnet, Lord Monboddo
(1714–1799), also a judge of Session, at whose Attic suppers in the
Old Town all the talent and beauty of Edinburgh were for many years
regularly assembled; the pompous but sensible Dr. Hugh Blair
(1718–1799), Professor of Belles Lettres in the University, and one of
the clergymen of the city; his more celebrated colleague, Dr.
Robertson the historian (1722–1793), Principal of the University, and
likewise one of the city clergymen; the minor historical writers and
antiquarians, Tytler of Woodhouselee (1711–1792), Dr. Henry (1718–
1790), Lord Hailes (1726–1792), Dr. Adam Ferguson (1724–1816),
and Dr. Gilbert Stuart (1742–1786); the poet John Home, author of
the tragedy of Douglas (1722–1808), once the Rev. Mr. Home, but
long bereft of that title, and known since 1779 as a retired man of
letters in Edinburgh; the illustrious Adam Smith (1723–1790),
settled in Edinburgh during the last twenty years of his life in the
post of commissioner of customs; the hardly less illustrious Dugald
Stewart (1753–1828), elected Professor of Mathematics in the
University as early as 1774, but thence transferred in 1785 to the
chair of Moral Philosophy, where he completed his fame; and, lastly,
not to overburden the list, the novelist and essayist Henry Mackenzie
(1745–1831), an acknowledged literary celebrity ever since 1771,
when he had published his Man of Feeling. In a class by himself,
unless we choose to associate him with the Creeches, Smellies, and
other “wuts” of a lower grade, whose acquaintance Burns made in his
leisure hours during his first visit to Edinburgh in 1786, we may
mention Burns’s immediate predecessor in the poetry of the Scottish