Methods for the Analysis of 1-(3,4-Methylenedioxyphenyl)-2-Butanamine and N-Methy 1-(3,4-Methylenedioxyphenyl)- 2-Propanamine (MDMA)

Abstract

The infrared and mass spectra of N-methyl-1-(3,4-methylenedioxyphenyl)-2-propanamine (MDMA) and 1-(3,4-methylenedioxyphenyl)-2-butanamine are quite similar. These two compounds differ only in the position of substitution of a single methyl group. MDMA is a controlled street drug known as Ecstasy, while the isomeric butanamine is a member of a new class of potential psychotherapeutic agents called entactogens. These two compounds produce similar mass spectral fragmentation patterns including a common base peak at m/z 58. Reversed-phase liquid chromatographic (RPLC) methods consisting of a C18 stationary phase and an aqueous scidic mobile phase were used to separate these two compounds. Thus, LC methods can be used to differentiate MDMA from the isomeric butanamine for forensic analysis.

Identification of N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine (MBDB), an homologue derivative of "ecstasy"

“…UV detection wavelength was set at 280 nm for all these amines, because the 3,4-methylenedioxyphenyl group is the major common chromophoric unit with high absorptivity. Finally, our method gave good results, the separation of amines was well resolved with good symetrical peak shape and the retention times were quite similar to those obtained by other authors with an acidic mobile phase and deactivated C 18 column [16,17,21,26,34].…”

“…Figures 3A, 3B and 3C show the corresponding electron impact mass spectra of MDEA, MBDB and EBDB. The electron impact mass spectra obtained for MDMA and MDEA fit those described in a previous report on the one hand [32], and in the literature on the other hand [19a, 21,25,31]. Table II gives a summary analysis of the mass spectral fragmentation of these derivatives.…”

“…And the toxicologist is called upon, therefore, to put to work the most powerful analytical techniques to separate by high performance liquid chromatography [8,[16][17][18][19][20][21][22][23][24][25][26][27]29,30], or gas chromatography [8,11,19,21,[23][24][25][26][27][29][30][31][32][33][34] and identify by mass spectrometry [8,11,19,21,[23][24][25][26][27][28][29][30][31][32][33][34], or nuclear magnetic resonance [17,19,32,35] these various "designer amphetamines". In this article, we shall pres...…”

Forensic science

“…Liquid chromatographic methods have been described for the analysis of forensic samples containing amphetamine and methamphetamine (229). Methods for the differentiation of methamphetamine from regioisomeric phenethylamines have been reported (230) as well as methods for the analysis for l-(3,4-methylenedioxyphenyl)-2-butanamine and iV-methyl-l-(3,4-methylenedioxyphenyl)-2-propanamine (MDMA) (231). Liquid chromatographic and mass spectral analysis has been reported for the l-phenyl-3butanamines (232) and l-phenyl-2-butanamines (homologs of amphetamines) (233), l-(3,4-dimethoxyphenyl)-2-propanamines (analogs of MDMA) (234), and l-(3,4-methylenedioxyphenyl)-3-propanamines (regioisomersofMDMA) (235) and for the differentiation of 3,4-methylenedioxymethamphetamine (MDMA) from regioisomeric phenethylamines (236).…”