Appendix D:

Reaction Mechanisms

Amphetamine Reactions

A1 O

H O NH4
ammonium formate
HCl
O O HN NH2
O
phenyl-2-propanone H amphetamine
H NH2
2-formamido-1-phenylpropane
formamide

A2
O
NO2
H LiAlH4
NO2
nitroethane NH2
benzaldehyde amphetamine
1-phenyl-2-nitropropene

A3

N OH
HONH2
O hydroxylamine NH2
phenyl-2-propanone phenyl-2-propanone oxime amphetamine

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 A4

NH3
O ammonia NH2
phenyl-2-propanone amphetamine

A5

Cl FeCl3 NH3
Cl NH2
allyl chloride
benzene ferric chloride 1-phenyl-2-chloropropane amphetamine

A6

CH3CN HCl
HN NH2
acetonitrile
allylbenzene O amphetamine
N-acetylamphetamine

A7
OH

HI
NH2 NH2
hydriodic acid
phenylpropanolamine amphetamine

Methamphetamine Reactions

M1

H
N
CH3NH2
O
methylamine
phenyl-2-propanone methamphetamine

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 M2
OH
H H
N N
H2

ephedrine hydrogen methamphetamine

M3
OH
H H
N N
HI
hydriodic acid
ephedrine methamphetamine

M4

Cl MgCl
Mg

benzyl chloride magnesium benzyl magnesium chloride

metal
O
CH3NH2 N
H
acetaldehyde methylamine methylimino ethane

H
N
MgCl N

methylimino ethane
benzyl magnesium chloride methamphetamine

M5 O

CH3NH2 H OH
formic acid
H
N H N
or HCl
O O
O
phenyl-2-propanone methamphetamine
H N N-formylmethamphetamine
H
N-methylformamide

© 2004 by CRC Press LLC

 M6

H
N
Cl FeCl3 CH3NH2
Cl
allyl chloride methylamine
benzene ferric chloride
1-phenyl-2-chloropropane methamphetamine

M7
OH
H
Na or Li N

HN ammonia
tetrahydrofuran
ephedrine methamphetamine

Phenylacetone Reactions

P1

OH O O

O O O
acetic anhydride
phenylacetic acid phenyl-2-propanone

P2
CN
O
CN ONa
O H
sodium ethoxide O O
benzyl cyanide ethyl acetate α-phenylacetoacetonitrile phenyl-2-propanone

P3

OH
Pb(OCOCH3)2
O O
lead acetate
phenylacetic acid phenyl-2-propanone

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 P4

OH O

O OH O
acetic acid
phenylacetic acid phenyl-2-propanone

P5
O
NO2
H
NO2 HCl
O
nitroethane
benzaldehyde 1-phenyl-2-nitropropene phenyl-2-propanone

P6

K2CrO4
OH O
potassium dichromate
phenyl-2-propanol phenyl-2-propanone

P7

Cl O
chloroacetone
benzene phenyl-2-propanone

MDA/MDMA Reactions

MD1
O 2-formamido-1-(3,4-methylenedioxypheny
propane
O O H NH2 O
or
O O O O HN H
H O NH4
isosafrole 1-(3,4-methylenedioxyphenyl)-2-propane O
O
HCl

O NH2
MDA

© 2004 by CRC Press LLC

 MD2
O
O H O NO2 LiAlH4 O
NO2
O O O NH2
nitroethane
piperonal 3,4-methylenedioxy-β-methyl-β-nitrostyrene MDA

MD3
O
O O
CH3NH2
O O HN
methylamine
3,4-methylenedioxy P-2-P MDMA

MD4
O

CH3NH2 H OH
O O HCl
or MDMA
O O H N H
H N O
O
O N-formyl-MDMA

MD5

O HBr O CH3NH2 MDMA

Br NH3 MDA
O O
safrole

Phencyclidine Analogs

PC1
O H
N KCN CN MgBr
or N
NaCN N
piperidine
cyclohexanone phenyl magnesium
bromide
1-piperidinocyclohexane
carbonitrile (PCC) phenylcyclidine (PCP)

© 2004 by CRC Press LLC

 PC2
O H
N MgBr
N
N
piperidine 1-(-1-cyclohexenyl)piperidine
cyclohexanone phenyl magnesium
bromide
phenylcyclidine (PCP)

MgBr
N
H CN
N phenyl magnesium PCP
bromide
N
2-thienyl-1-magnesium S
piperidine PCC bromide
S
N
BrMg
TCP

MgBr
O N
H CN
N phenyl magnesium PCPy
O bromide

PyCC 2-thienyl-1-magnesium S
cyclohexanone pyrrolidine
bromide
S
N
BrMg TCPy

MgBr

H N
N CN phenyl magnesium
bromide PCM O
N
O 2-thienyl-1-magnesium S
O bromide
morpholine MCC
S
N
BrMg
TCM O

© 2004 by CRC Press LLC