Published:Journal of Chromatographic Science,
ISSN 0021-9665 Volume
45, Number 8, September 2007, pp. 477-485
GC–MS Analysis of Acylated Derivatives
of the Side-Chain Regioisomers of 4-Methoxy-3-Methyl-Phenethylamines
Related to Methylenedioxymethamphetamine
Tamer Awad, C. Randall Clark, and Jack DeRuiter
Department of Pharmacal Sciences, School of Pharmacy, Auburn
University, Auburn, AL 36849
The five side-chain regioisomers of 4-methoxy-3-methylphenethylamine
constitute a unique set of compounds having an isobaric relationship
with the controlled drug substance 3,4-methylenedioxymethamphetamine
(3,4-MDMA or Ecstasy). These isomeric forms of the 4-methoxy-3-methylphenethylamines
have mass spectra essentially equivalent to 3,4-MDMA, and all
have a molecular weight of 193 and major fragment ions in their
electron ionization mass spectra at m/z 58 and 135/136. Mass
spectral differentiation of 2,3- and 3,4-MDMA from primary and
secondary amine regioisomeric side chains of 4-methoxy-3-methylphenethylamines
was possible after formation of the perfluoroacyl derivatives,
pentafluoropropionamides and heptafluorobutyrylamides. The mass
spectra for these derivatives are significantly individualized,
and the resulting unique fragment ions allow for specific side-chain
identification. The individualization is the result of fragmentation
of the alkyl carbon-nitrogen bond, which yielded unique hydrocarbon
fragments. The heptafluorobutyrylamide derivatives offer more
fragment ions for molecular individualization among these regioisomeric
substances. Gas chromatographic separation on relatively non-polar
stationary phases successfully resolves these derivatives.
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