Published:Journal of Chromatographic Science,
ISSN 0021-9665 Volume
45, Number 8, September 2007, pp. 468-476
Chromatographic and Mass Spectral Studies on
Methoxy Methyl Methamphetamines Related to 3,4-Methylenedioxymethamphetamine
Tamer Awad, Jack DeRuiter, and C. Randall Clark
Department of Pharmacal Sciences, School of Pharmacy, Auburn
University, Auburn, AL 36849
The methoxy methyl methamphetamines are a unique
set of compounds having an isobaric relationship with the controlled
drug substance 3,4-methylenedioxymethamphetamine (3,4-MDMA or
Ecstasy). The various isomeric forms of the methoxy methyl methamphetamines
have mass spectra essentially equivalent to 3,4-MDMA, all have
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 3,4-MDMA from some of the methoxy methyl methamphetamines
was possible after formation of the perfluoroacyl derivatives,
pentafluoropropionamides (PFPA) and heptafluorobutyramides (HFBA).
Perfluoroacyl derivatization provided unique and characteristic
mass spectral fragment ions when the methoxy group is substituted
at the 2- or 4-position of the aromatic ring relative to the
alkylamine side chain group. Perfluoroacyl derivatization did
not offer any characteristic ions for discrimination of 3,4-MDMA
from the 3-methoxy ring substituted methyl methamphetamines.
Gas chromatographic separation on non-polar stationary phases
successfully resolved subsets of the methoxy methyl methamphetamines,
based on ring position of the methoxy group, from 2,3- and 3,4-MDMA
as the PFPA and HFBA derivatives.
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