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Analysis of 4-bromo-2,5-dimethoxyphenethylamine Abuser's Urine: Identification and Quantitation of Urinary Metabolites

Analysis of 4-bromo-2,5-dimethoxyphenethylamine Abuser's Urine: Identification and Quantitation of Urinary Metabolites

Tatsuyuki Kanamori, Kyoko Nagasawa, Kenji Kuwayama, Kenji Tsujikawa, Yuko T Iwata, Hiroyuki Inoue

J Forensic Sci. 2013 Jan;58(1):279-87.

PMID: 23066942

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% of the total amount of detected metabolites, followed by 4-bromo-2-hydroxy-5-methoxyphenylacetic acid (13%) and 4-bromo-2,5-dimethoxyphenylethyl alcohol (4.5%). 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. Our results suggest that MAO plays a crucial role in the metabolism of 2C-B in humans.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP352535810	4-Bromo-2,6-difluorophenylboronic acid		352535-81-0	Price

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