SOFT - TIAFT 1998 Poster Session 3 Thursday October 8, 1998

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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