SOFT/TIAFT 98 - Mass Spectrometric Identification of Some Sulphur-Containing ...

SOFT - TIAFT 1998

Poster Session 3

Thursday October 8, 1998

MASS SPECTROMETRIC IDENTIFICATION OF SOME SULPHUR-CONTAINING PHENALKYLAMINE DESIGNER DRUGS

Ingrid J. Bosman¹, Edwin B. Siderius¹, Douwe de Boer²,Lesseps J.A.L. dos Reys² and Robert A.A. Maes¹

1. Department of Human Toxicology, Utrecht Institute of Pharmaceutical Sciences, Utrecht, The Netherlands;
2. Laboratório de Análises de Dopagem e Bioquímica, Lisboa, Portugal

The continuous search for new phenalkylamine designer drugs has provided the drugs-of-abuse market with drugs such as substituted 3,4-methylenedioxyphenalkyl and 2,5-dimethoxy-phenalkylamine analogues. The most recent development in Europe is the marketing of sulphur containing phenalkylamine designer drugs. In this study the mass spectrometric characteristics of two alkylthio-phenalkylamine compounds are described which have been found on the European drugs-of-abuse market. The identity of these alkylthiophenalkylamines have been confirmed by comparing them either with reference compounds or if not available as reference compounds by ¹H and ¹³C nuclear magnetic resonance spectroscopy.

The first compound is para -methylthioisopropylamine, also known as para -methylthio-amphetamine (MTA). If not derivatized, its electron ionisation (EI) mass spectrum proved to be almost identical to that of 4-hydroxy-3-methoxyamphetamine (HMA). However, because both compounds have different functional groups, most derivatisation methods result in end-products, which can be distinguished by GC/MS analysis. This is demonstrated by the EI mass spectra of non-derivatized MTA and HMA, as well as their N -TFA and N -TFA-O -TMS derivatives.

The second compound is 4-ethylthio-2,5-dimethoxyphenethylamine (2C-T-2). In general 2,5-dimethoxyphenethylamine analogues substituted at the 4-position have EI mass spectra with closely related fragmentation patterns. This is demonstrated by the EI mass spectra of the N -TFA derivatives of 2,5-dimethoxyphenethylamine, 4-bromo-2,5-dimethoxyphenethyalkylamine (2C-B) and 2C-T-2.

Because the EI mass spectra of the N-TFA derivatives of para-methylthioamphetamine and of 2C-T-2 are characteristic, it can be concluded that these sulphur containing phenalkyl-amine designer drugs can easily be identified using mass spectrometry.

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