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

Douwe de Boer, Lesseps .J.A.L. dos Reys, Mieke Gijzels*, Nynke Pilon*, Ingrid J.Bosman* and Robert A.A. Maes*

Laboratório de Análises de Dopagem e Bioquímica, Lisboa, Portugal
* Department of Human Toxicology, Utrecht Institute of Pharmaceutical Sciences, Utrecht, The Netherlands

The psychodelic drug 2C-B (4-bromo-2,5-dimethoxyphenethylamine) is a hallucinogenic phenalkylamine of which the abuse in Europe is increasing significantly during the recent years. Although 2C-B is active at much lower dosages, its physicochemical and pharmacodynamic profile can be compared to that of mescaline (3,4,5-trimethoxyphenethylamine). In order to be able to detect the abuse of 2C-B by analysing biological specimens, the metabolic pathways of 2C-B were evaluated in this study.

To obtain preliminary information in vitro studies were performed by incubating 2C-B in rat liver homogenates. GC/MS analysis indicated that under these conditions several metabolites were formed. The identity of some these metabolites could be revealed. These results were compared with those obtained from a so-called in vivo study, i.e. drug-of-abuse testing of a urine specimen of a subject abusing 2C-B.

This way the presence of the parent compound and of 4-bromo-2,5-dimethoxyphenylacetic acid in the urine specimen of the abuser was shown and confirmed using reference standards. Furthermore the formation of 4-bromo-2,5-dimethoxybenzoic acid and of 4-bromo-5-hydroxy-2-methoxyphenethylamine was indicated by GC/MS.

Considering the known biotransformations of mescaline in humans, it can be concluded that the metabolism of 2C-B in humans follows similar pathways compared to that of mescaline, i.e. oxidative deamination leading to phenylacetic and benzoic acid-like metabolites and O-demethylation of the aromatic methoxy groups.

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