Biomedical Engineering Reference
In-Depth Information
4.2
Amphetamine-Like Compounds
Amphetamines are a class of chiral molecules, synthesized from the precursor phe-
nylethylamine (Fig.
3
). Several formulations are usually found on the black market
such as tablets, lozenges, drops, injections, powder, whose colors vary from white
to pink to brown, depending on the impurities and adulterants.
They are usually taken orally and are the major class of CNS stimulants.
Amphetamine and methamphetamine possess an essentially pure psychostimu-
lant effect; however, substituted derivatives in position 3 and 4 on benzene
ring are defined as entactogene [
14
]. This class of substances includes methyl-
enedioxymethamphetamine (MDMA), methylenedioxyamphetamine (MDA),
methylenedioxyethyl-amphetamine (MDEA), and others such as the
N
-methyl-1-
(3-4-methylenedioxyphenyl)-2-butanamine (MBDB), methoxymethylenedioxyam-
phetamine (MMDA) (Fig.
4
). All of these substances are more active in the
d
form.
There are also amphetamine-like substances which combine sympathomimetic
(euphoric) and hallucinogen effects: they are primary amines, trisubstituted on the
benzene ring, that produce effects similar to mescaline. Among these the 2,5-dime-
thoxy-4-methylamphetamine (DOM) is the most important.
Fig. 3
Structures
of phenethylamine,
amphetamine, and
methamphetamine
NH
2
phenetylamine
NH
R
CH
3
R
-H Amphetamine
-CH
3
Methamphetamine
Fig. 4
Structures of
methoxyamphetamines
NH
O
R
1
R
2
O
R
1
R
2
-H
-CH
3
MDA
-CH
3
-CH
3
MDMA
-C
2
H
5
-CH
3
MDE
-CH
3
-C
2
H
5
MBDB
