MDA is a
substituted methylenedioxylated phenethylamine and
amphetamine derivative.
Synonyms In addition to
3,4-methylenedioxyamphetamine, MDA is also known by other chemical synonyms such as the following: • α-Methyl-3,4-methylenedioxy-β-phenylethylamine • 1-(3,4-Methylenedioxyphenyl)-2-propanamine • 1-(1,3-Benzodioxol-5-yl)-2-propanamine
Synthesis MDA is typically
synthesized from
essential oils such as
safrole or
piperonal. Common approaches from these
precursors include: •
Bromination of safrole's
alkene functional group followed by
amine alkylation. •
Wacker oxidation of safrole to yield
3,4-methylenedioxyphenylpropan-2-one (MDP2P) followed by
reductive amination • Synthesis and
reduction of the
oxime of
MDP2P. •
Henry reaction of piperonal with
nitroethane followed by
hydrogenation. This gives
MDP2P, which can then be subjected to
reductive amination. • The "two dogs" or "dopeboy"
clandestine method, starting with
helional as a precursor. First, helional oxime is created using a reaction that involves
hydroxylamine hydrochloride. Then, a
Beckmann rearrangement is performed on the oxime with nickel acetate to form an amide. Then a
Hofmann rearrangement is done on the amide to form the freebase amine of MDA.
Detection in body fluids MDA may be quantitated in blood, plasma or urine to monitor for use, confirm a diagnosis of poisoning or assist in the forensic investigation of a traffic or other criminal violation or a sudden death. Some drug abuse screening programs rely on hair, saliva, or sweat as specimens. Most commercial amphetamine immunoassay screening tests cross-react significantly with MDA and major metabolites of MDMA, but chromatographic techniques can easily distinguish and separately measure each of these substances. The concentrations of MDA in the blood or urine of a person who has taken only MDMA are, in general, less than 10% those of the parent drug.
Analogues and derivatives Analogues of MDA include its
positional isomer 2,3-methylenedioxyamphetamine (2,3-MDA) and others.
MDMA is the
N-
methyl derivative of MDA. Some other analogues of MDA include
5-APB,
6-APB,
5-APDB,
6-APDB,
5-APBT,
6-APBT, and
SDA (3T-MDA), among others. MDA constitutes part of the core structure of the
β-adrenergic receptor agonist protokylol. ==History==