1227_AppD.pdf

Appendix D: Reaction Mechanisms

 Amphetamine Reactions A1

O H

O

NH4

ammonium formate

O phenyl-2-propanone

O H

HN NH2

formamide

H  

HCl

NH2

O

amphetamine

2-formamido-1-phenylpropane

A2 O

NO2 H

LiAlH4

NO2

NH2

nitroethane benzaldehyde

amphetamine

1-phenyl-2-nitropropene

A3 N OH O

HONH2

NH2

hydroxylamine

phenyl-2-propanone

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phenyl-2-propanone oxime

 

amphetamine

A4

O

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

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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

 

Mg

benzyl chloride

magnesium metal

O

MgCl

benzyl magnesium chloride

N

CH3NH2 H

acetaldehyde

methylamine

MgCl

methylimino ethane

H N

N methylimino ethane

benzyl magnesium chloride

M5

methamphetamine

O CH3NH2

H

OH

formic acid

N

or

O

O

O phenyl-2-propanone

H

N H

N-methylformamide

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H N

H

N-formylmethamphetamine

HCl methamphetamine

M6 H N Cl benzene

allyl chloride

FeCl3 ferric chloride

CH3NH2

Cl

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

O

O

acetic anhydride

phenylacetic acid

phenyl-2-propanone

P2 CN

O CN

ONa

O

benzyl cyanide

sodium ethoxide

ethyl acetate

O

H

O

α-phenylacetoacetonitrile

phenyl-2-propanon

P3 OH O phenylacetic acid

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Pb(OCOCH 3)2 lead acetate

O phenyl-2-propanon

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

OH

K2CrO4

O

potassium dichromate

phenyl-2-propanol

phenyl-2-propanon

P7 O Cl benzene

O

chloroacetone

phenyl-2-propanon

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

O O

H

O

NH2

O

O NH4

O

or

O

O isosafrole

O

H

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

HN

H O

O

HCl O NH2

O MDA

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MD2 O O

O

H

O

NO2

NO2

O

LiAlH4

NH2

O

O

nitroethane

3,4-methylenedioxy-β-methyl- β-nitrostyrene

piperonal

MDA

MD3 O O

O CH3NH2 O

HN

O

methylamine

3,4-methylenedioxy P-2-P

MDMA

MD4 O H

CH3NH2

O

O

or

O

O

OH

H N

H

HCl N

O

MDMA

H O

O

N-formyl-MDMA

MD5 O

O

HBr

O

Br

O

CH3NH2

MDMA

NH3

MDA

safrole

 Phencyclidine Analogs PC1 O

H N

KCN or

NaCN piperidine cyclohexanone

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CN

 

MgBr

N phenyl magnesium  bromide 1-piperidinocyclohexane carbonitrile (PCC)

N

phenylcyclidine (PCP)

PC2 O

H N

 

MgBr

N piperidine cyclohexanone

N

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

MgBr N

CN

H N

phenyl magnesium bromide

N piperidine

PCP

S

2-thienyl-1-magnesium bromide

PCC

S

N

BrMg

TCP

MgBr O H N

N

CN

phenyl magnesium bromide

O cyclohexanone

pyrrolidine

PCPy

2-thienyl-1-magnesium bromide

PyCC

S

S N BrMg

TCPy

MgBr H N

phenyl magnesium bromide

N

O morpholine

N

CN

O MCC

PCM

2-thienyl-1-magnesium bromide

O S

S N BrMg TCM

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O