NCJ Number
243769
Journal
Journal of Forensic Sciences Volume: 58 Issue: 1 Dated: January 2013 Pages: 279-287
Date Published
January 2013
Length
9 pages
Annotation
The metabolites of 4-bromo-2,5-dimethoxyphenethylamine (2C-B), a psychoactive drug with hallucinogenic activity, were investigated in a urine sample from a user of 2C-B.
Abstract
The metabolites of 4-bromo-2,5-dimethoxyphenethylamine (2C-B), a psychoactive drug with hallucinogenic activity, were investigated in a urine sample from a user of 2C-B. The urine sample was deconjugated enzymatically and the metabolites were recovered by liquid-liquid extraction. The extract was analyzed by gas chromatography/mass spectrometry after derivatization, and the results were used to identify and quantitate the metabolites. 4-Bromo-2,5-dimethoxyphenylacetic acid was the most abundant metabolite of 2C-B in human urine and accounted for 73 percent of the total amount of detected metabolites, followed by 4-bromo-2-hydroxy-5-methoxyphenylacetic acid (13 percent) and 4-bromo-2,5-dimethoxyphenylethyl alcohol (4.5 percent). According to the literature, the main metabolites of 2C-B in rat urine are N-(4-bromo-2-methoxy-5-hydroxyphenylethyl)acetamide and N-(4-bromo-2-hydroxy-5-methoxyphenylethyl)acetamide. However, these metabolites accounted for only a small proportion of the total amount of detected metabolites in human urine, which indicates that there are significant species-specific differences in the metabolism of 2C-B. 4-Bromo-2,5-dimethoxyphenylacetic acid, which was the most abundant metabolite in human urine, is thought to be generated by deamination of 2C-B by monoamine oxidase (MAO) followed by oxidation by aldehyde dehydrogenase. The results suggest that MAO plays a crucial role in the metabolism of 2C-B in humans. Abstract published by arrangement with John Wiley & Sons.