Appendix D:

Reaction Mechanisms

Amphetamine Reactions
A1

O
H

NH4

ammonium formate

O
phenyl-2-propanone

O
H

NH2

formamide

HN
H

HCl
O

2-formamido-1-phenylpropane

NH2
amphetamine

A2
O

NO2
H

LiAlH4

NO2

NH2

nitroethane
benzaldehyde

1-phenyl-2-nitropropene

amphetamine

A3
N OH
O

HONH2

NH2

hydroxylamine

phenyl-2-propanone

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phenyl-2-propanone oxime

amphetamine

A4

NH3

NH2

ammonia

phenyl-2-propanone

amphetamine

A5

Cl

FeCl3

Cl

allyl chloride
benzene

ferric chloride

NH3

NH2
amphetamine

1-phenyl-2-chloropropane

A6

CH3CN

HCl

HN

acetonitrile
allylbenzene

NH2
amphetamine

O
N-acetylamphetamine

A7
OH

NH2

HI
hydriodic acid

phenylpropanolamine

NH2
amphetamine

Methamphetamine Reactions

M1
H
N
O
phenyl-2-propanone

2004 by CRC Press LLC

CH3NH2
methylamine
methamphetamine

M2
OH

H
N

H
N
H2

ephedrine

hydrogen

methamphetamine

M3
OH

H
N

H
N
HI
hydriodic acid

ephedrine

methamphetamine

M4

Cl

MgCl

Mg

benzyl chloride

magnesium
metal

benzyl magnesium chloride

CH3NH2
H

acetaldehyde

methylamine

MgCl

methylimino ethane

H
N

N
methylimino ethane

benzyl magnesium chloride

M5

methamphetamine

O
CH3NH2

OH

formic acid
or

O
phenyl-2-propanone

N
H

N-methylformamide

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H
N

N-formylmethamphetamine

HCl
methamphetamine

M6
H
N
Cl

FeCl3

benzene

ferric chloride

CH3NH2

Cl

allyl chloride

methylamine
methamphetamine

1-phenyl-2-chloropropane

M7
OH

H
N

Na or Li
ammonia
tetrahydrofuran

HN
ephedrine

methamphetamine

Phenylacetone Reactions

P1
O

OH

O
O

acetic anhydride

phenylacetic acid

phenyl-2-propanone

P2
CN

O
CN

ONa

benzyl cyanide

sodium ethoxide

ethyl acetate

-phenylacetoacetonitrile

phenyl-2-propanone

P3
OH
O
phenylacetic acid

2004 by CRC Press LLC

Pb(OCOCH3)2
lead acetate

O
phenyl-2-propanone

P4
OH

OH
acetic acid

phenylacetic acid

phenyl-2-propanone

P5
O

NO2
H

HCl

NO2

nitroethane
benzaldehyde

1-phenyl-2-nitropropene

phenyl-2-propanone

P6

OH

K2CrO4

potassium dichromate

phenyl-2-propanol

phenyl-2-propanone

P7
O
O

Cl
benzene

chloroacetone

phenyl-2-propanone

MDA/MDMA Reactions
MD1
2-formamido-1-(3,4-methylenedioxypheny
propane

O
O

NH2

O NH4

or

O
isosafrole

1-(3,4-methylenedioxyphenyl)-2-propane

HN

H
O

HCl
O
NH2

O
MDA

2004 by CRC Press LLC

MD2
O
O

NO2 LiAlH4

NO2

piperonal

NH2

nitroethane

3,4-methylenedioxy--methyl--nitrostyrene

MDA

MD3
O
O

O
CH3NH2
O

HN

methylamine

3,4-methylenedioxy P-2-P

MDMA

MD4
O
H

CH3NH2

OH
O

or

H
N

HCl
N

MDMA

H
O

N-formyl-MDMA

MD5
O

HBr

Br

CH3NH2

MDMA

NH3

MDA

safrole

Phencyclidine Analogs

PC1
O

H
N

KCN
or

CN
N

MgBr

NaCN
piperidine
cyclohexanone

2004 by CRC Press LLC

phenyl magnesium
bromide
1-piperidinocyclohexane
carbonitrile (PCC)

phenylcyclidine (PCP)

PC2
O

H
N

MgBr
N

piperidine
cyclohexanone

1-(-1-cyclohexenyl)piperidine
phenyl magnesium
bromide
phenylcyclidine (PCP)

MgBr
N

CN

H
N

phenyl magnesium
bromide

N
piperidine

PCP

2-thienyl-1-magnesium
bromide

PCC

BrMg

TCP

MgBr
O
H
N

CN

phenyl magnesium
bromide

O
cyclohexanone

pyrrolidine

PCPy

2-thienyl-1-magnesium
bromide

PyCC

S
N
BrMg

TCPy

MgBr
H
N

phenyl magnesium
bromide

O
morpholine

CN

O
MCC

PCM

2-thienyl-1-magnesium
bromide

O
S

S
N
BrMg
TCM

2004 by CRC Press LLC