25B-NBOMe

25B-NBOMe (NBOMe-2C-B, Cimbi-36, Nova, BOM 2-

CB) is a derivative of the phenethylamine psychedelic 2C-B, 25B-NBOMe
discovered in 2004 by Ralf Heim at the Free University of
Berlin. It acts as a potent full agonist for the 5HT2A
receptor.[2][3][4][5][6] Anecdotal reports from users suggest
25B-NBOMe to be an active hallucinogen at a dose of as little
as 250–500  µg, making it a similar potency to other
phenethylamine derived hallucinogens such as Bromo-
DragonFLY. Duration of effects lasts about 12–16 hours, Legal status
although the parent compound is rapidly cleared from the Legal status BR: Class F2
blood when used in the radiolabeled form in tracer doses.[6]
(Prohibited
Recently, Custodio et al (2019) evaluated the potential
involvement of dysregulated dopaminergic system, psychotropics)[1]
neuroadaptation, and brain wave changes which may DE: Anlage I
contribute to the rewarding and reinforcing properties of 25B- (Authorized
NBOMe in rodents.[7] scientific use only)
UK: Class A
The carbon-11 labeled version of this compound ([11C]Cimbi-
36) was synthesized and validated as a radioactive tracer for US: Schedule I
positron emission tomography (PET) in
[8][9][10][11][12] Identifiers
Copenhagen. As a 5-HT2A receptor agonist PET
11 IUPAC name [show]
radioligand, [ C]Cimbi-36 was hypothesized to provide a
more functional marker of these receptors. Also, [11C]Cimbi- 2-(4-bromo-2,5-dimethoxyphenyl)
36 is investigated as a potential marker of serotonin release -N-[(2-methoxyphenyl)methyl]
and thus could serve as an indicator of serotonin levels in vivo. ethanamine
[11C]Cimbi-36 is now undergoing clinical trials as a PET- CAS 1026511-90-9 (htt
ligand in humans.[13][14][15] Number
ps://commonchem
istry.cas.org/detail?
Toxicity and harm potential cas_rn=1026511-9
0-9) 
NBOMe compounds are often associated with life-threatening
PubChem 9977044 (https://p
toxicity and death.[16][17] Studies on NBOMe family of CID
compounds demonstrated that the substance exhibit ubchem.ncbi.nlm.n
neurotoxic and cardiotoxic activity.[18] Reports of autonomic ih.gov/compound/
dysfunction remains prevalent with NBOMe compounds, with 9977044)
most individuals experiencing sympathomimetic toxicity such ChemSpider 8152636 (https://w
as vasoconstriction, hypertension and tachycardia in addition
ww.chemspider.co
to hallucinations.[19][20][21][22][23] Other symptoms of
toxidrome of include agitation or aggression, seizure, m/Chemical-Struct
hyperthermia, diaphoresis, hypertonia, rhabdomyolysis, and ure.8152636.html) 
death.[19][23][17] Researchers report that NBOMe intoxication
frequently display signs of serotonin syndrome.[24] The UNII S6NAA81PHK (http
likelihood of seizure is higher in NBOMes compared to other
s://precision.fda.go
psychedelics.[18]
v/uniisearch/srs/un
ii/S6NAA81PHK)
NBOMe and NBOHs are regularly sold as LSD in blotter CompTox DTXSID50907974
papers,[17][25] which have a bitter taste and different safety Dashboard
(EPA) (https://comptox.e
profiles.[19][16] Despite high potency, recreational doses of pa.gov/dashboard/
LSD have only produced low incidents of acute toxicity.[16] chemical/details/D
Fatalities involved in NBOMe intoxication suggest that a
TXSID50907974)
significant number of individuals ingested the substance
which they believed was LSD,[21] and researchers report that Chemical and physical data
"users familiar with LSD may have a false sense of security Formula C18H22BrNO3
when ingesting NBOMe inadvertently".[19] While most Molar mass 380.282 g·mol−1
fatalities are due to the physical effects of the drug, there have
also been reports of death due to self-harm and suicide under 3D model Interactive image
(JSmol)
the influence of the substance.[26][27][19] (https://chemapps.
stolaf.edu/jmol/jm
Given limited documentation of NBOMe consumption, the
ol.php?model=CO
long-term effects of the substance remain unknown.[19]
C1%3DCC%3DCC%
NBOMe compounds are not active orally,[a] and are usually
3DC1CNCCC2%3D
taken sublingually.[29]: 3  When NBOMes are administered
CC%28%3DC%28
sublingually, numbness of the tongue and mouth followed by a
metallic chemical taste was observed, and researchers describe C%3DC2OC%29B
this physical side effect as one of the main discriminants r%29OC)
between NBOMe compounds and LSD.[30][31][32] SMILES [show]
COC1=CC=CC=C1CNCCC2=CC(=C
(C=C2OC)Br)OC
Neurotoxic and cardiotoxic actions
InChI [show]
Many of the NBOMe compounds have high potency agonist InChI=1S/C18H22BrNO3/c1-21-16
activity at additional 5-HT receptors and prolonged activation -7-5-4-6-14(16)12-20-9-8-13-1
0-18(23-3)15(19)11-17(13)22-
of 5-HT2B can cause cardiac valvulopathy in high doses and 2/h4-7,10-11,20H,8-9,12H2,1-3
chronic use.[17][22] 5-HT2B receptors have been strongly H3 
implicated in causing drug-induced valvular heart Key:SUXGNJVVBGJEFB-UHFFFAOY
disease.[33][34][35] The high affinity of NBOMe compounds for SA-N 
adrenergic α1 receptor has been reported to contribute to the
   (what is this?)  (verify)
stimulant-type cardiovascular effects.[22]

In vitro studies, 25C-NBOMe has been shown to exhibit cytotoxicity on neuronal cell lines SH-
SY5Y, PC12, and SN471, and the compound was more potent than methamphetamine at reducing
the visibility of the respective cells; the neurotoxicity of the compound involves activation of
MAPK/ERK cascade and inhibition of Akt/PKB signaling pathway.[18] 25C-NBOMe, including the
other derivative 25D-NBOMe, reduced the visibility of cardiomyocytes H9c2 cells, and both
substances downregulated expression level of p21 (CDC24/RAC)-activated kinase 1 (PAK1), an
enzyme with documented cardiac protective effects.[18]

Preliminary studies on 25C-NBOMe have shown that the substance is toxic to development, heart
health, and brain health in zebrafish, rats, and Artemia salina, a common organism for studying
potential drug effects on humans, but more research is needed on the topic, the dosages, and if the
toxicology results apply to humans. Researchers of the study also recommended further
investigation of the drug's potential in damaging pregnant women and their fetus due to the
substance's damaging effects to development.[36][37]

Emergency treatment
At present, there are no specific antidotes for NBOMes, and all acute intoxication is managed by
symptomatic treatments, such as administration of benzodiazepines, antipsychotic drugs, and
antiarrhythmic agents, such as beta blockers; some emergency interventions are intended to
specifically treat rhabdomyolysis, which may lead to critical complications such as metabolic
acidosis and acute kidney injury.[18]

Analogues and derivatives

Substituted benzofurans:
Analogues and derivatives of 2C-B:
2C-B-FLY
25-N: 2C-B-BUTTERFLY
2C-B-DRAGONFLY
25B-N1POMe
25B-NAcPip 2CBFly-NBOMe (NBOMe-2CB-Fly)
DOB-FLY
25-NB:
N-(2C)-fentanyl:
25B-NB
25B-NB23DM N-(2C-B) fentanyl[38]
25B-NB25DM N-(2C-B-FLY) fentanyl[39]
25B-NB3OMe
Other:
25B-NB4OMe
25B-NBF BOB
25B-NBMD BOH-2C-B, β-Hydroxy-2C-B, βOH-
25B-NBOH 2CB[40][41]
25B-NBOMe (NBOMe-2CB) BMB
DMBMPP 2C-B-5-hemifly
2C-B-aminorex (2C-B-AR)
25-NM:
2C-B-AN
25B-NMe7BF 2C-B-BZP
25B-NMe7BT 2C-B-FLY-NB2EtO5Cl
25B-NMe7Bim 2C-B-PP
25B-NMe7Box 2CB-Ind
25B-NMe7DHBF βk-2C-B (beta-keto 2C-B)
25B-NMe7Ind N-Ethyl-2C-B
25B-NMe7Indz TCB-2 (2C-BCB)
25B-NMePyr

Legal status

Canada

As of October 31, 2016; 25B-NBOMe is a controlled substance (Schedule III) in Canada.[42]

Russia

[ ]
Banned as a narcotic drug since May 5, 2015.[43]

Sweden
In Sweden, the Riksdag added 25B-NBOMe to schedule I ("substances, plant materials and fungi
which normally do not have medical use") as narcotics in Sweden as of August 1, 2013, published
by the Medical Products Agency in their regulation LVFS 2013:15 listed as 25B-NBOMe 2-(4-
bromo-2,5-dimetoxifenyl)-N-(2-metoxibensyl)etanamin.[44]

United Kingdom

This substance is a Class A drug in the United Kingdom as a result of the N-benzylphenethylamine
catch-all clause in the Misuse of Drugs Act 1971.[45]

United States
In November 2013, the U.S. Drug Enforcement Administration placed 25B-NBOMe (along with
25I-NBOMe and 25C-NBOMe) in Schedule I of the Controlled Substances Act, making it illegal to
manufacture, buy, possess, process, or distribute.[46]

China

As of October 2015 25B-NBOMe is a controlled substance in China.[47]

Czech Republic

25B-NBOMe is banned in the Czech Republic.[48]

Notes
a. The potency of N-benzylphenethylamines via buccal, sublingual, or nasal absorption is
50-100 greater (by weight) than oral route compared to the parent 2C-x
compounds.[28] Researchers hypothesize the low oral metabolic stability of N-
benzylphenethylamines is likely causing the low bioavailability on the oral route,
although the metabolic profile of this compounds remains unpredictable; therefore
researchers state that the fatalities linked to these substances may partly be explained
by differences in the metabolism between individuals.[28]

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