Gas Chromatographic–Mass Spectrometric and Liquid Chromatographic Analysis ...

Published: Journal of Chromatographic Science, Volume 33, Number 6, June 1995, pp. 328-337.

Gas Chromatographic–Mass Spectrometric and Liquid Chromatographic Analysis of Designer Butanamines Related to MDMA
C. Randall Clark, Jack DeRuiter, and Allen Valaer, F. Taylor Noggle

A series of N-substituted, 1-(3,4-methylenedioxyphenyl)-2-butanamines (MDP-2-B) is prepared from piperonal via the 2-butanone intermediate. The analytical properties of these compounds are compared with the structurally similar 3,4-methylenedioxyamphetamine (MDA) derivatives, a popular series of drugs of abuse. The ultraviolet absorption properties of these compounds are determined by the methylenedioxyphenyl ring, which shows major absorption bands in the 285- and 235-nm range. The primary amine (MDP-2-B) and the N-substituted derivatives of MDP-2-B are separated by reversed-phase liquid chromatography under acidic mobile-phase conditions. The compounds are not completely resolved by gas chromatography on an HP-1 phase, and the separation is complicated by extensive thermal degradation of the N-hydroxy derivative (MDP-2-OHB). The mass spectra for these compounds provide specific structural information for the identification of these compounds. The amines undergo a-cleavage reactions to produce ions at [M-135]+ from the loss of the 3,4-methylenedioxybenzyl radical and [M-29]+ from loss of the other a-group, the ethyl radical.

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