Published:Journal of Chromatographic Science,
ISSN 0021-9665 Volume 45,
Number 5, May/June 2007, pp.229-235
GC–MS Studies on the Regioisomeric 2,3- and
3,4-Methylenedioxyphenethylamines Related to MDEA, MDMMA, and
MBDB
Ashley L. Thigpen, Jack DeRuiter, and C. Randall
Clark
Department of Pharmacal Sciences, School of Pharmacy, Auburn University,
Auburn, AL 36849
Three regioisomeric 3,4-methylenedioxyphenethylamines
having the same molecular weight and major mass spectral fragments
of equal mass have been reported as drugs of abuse in forensic
studies in recent years. These compounds are 3,4-methylenedioxy-N-ethylamphetamine
(MDEA), 3,4-methylenedioxy-N-N-dimethylamphetamine (MDMMA), and
N-methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine (MBDB). The
mass spectra of the regioisomers (2,3-methylenedioxyphenethylamines)
are essentially equal to the three compounds reported as drugs
of abuse. This paper reports the synthesis, mass spectral characterization,
and chromatographic analysis of these six regioisomeric amines.
The six regioisomeric methylenedioxyphenethylamines are synthesized
from commercially available starting materials. The electron impact
mass spectra of these regioisomers show some variation in the
relative intensity of the major ions with only a couple of minor
ions that may indicate side chain specific fragments. Differentiation
by mass spectrometry is only possible after the formation of the
perfluoroacyl derivatives, pentafluoropropionylamides (PFPA) and
heptafluorobutrylamides (HFBA). Gas chromatographic separation
on non-polar stationary phases (Rtx-1 and Rtx-5) is not successful
at resolving the three 3,4-methylenedioxyphenethylamines from
the three 2,3-methylenedioxyphenethylamines as the underivatized
amines. The six underivatized amines are resolved on the more
polar trifluoropropylmethyl polysiloxane Rtx-200 stationary phase
as well as a permethylated beta-cyclodextran Rtx-bDEX stationary
phase. Gas chromatographic separation is successful at resolving
the four PFPA and the four HFBA derivatives on the Rtx-200 stationary
phase as well as the permethylated beta-cyclodextran stationary
phase. The 2,3-methylenedioxyphenethylamine derivatives (compounds
4 and 6) eluted before the 3,4-methylenedioxyphenethylamine derivatives
(compounds 1 and 3) as both the PFPA and HFBA derivatives.
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