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
Journal of forensic sciences January 1, 2013 DOI: 10.1111/j.1556-4029.2012.02289.x via PubMed
Summary
AI-generated from the abstractThe main breakdown product of the hallucinogenic drug 2C-B in human urine is 4-bromo-2,5-dimethoxyphenylacetic acid, accounting for 73% of detected metabolites. Two other metabolites, 4-bromo-2-hydroxy-5-methoxyphenylacetic acid and 4-bromo-2,5-dimethoxyphenylethyl alcohol, made up 13% and 4.5% respectively. In contrast, the primary metabolites reported in rat urine were different compounds and appeared only in small amounts in humans, indicating species-specific differences in how 2C-B is processed. The most abundant human metabolite likely forms through deamination by monoamine oxidase (MAO) followed by oxidation, suggesting MAO plays a crucial role in human 2C-B metabolism.
Study at a glance
| Characteristics | Case study Case report Peer reviewed |
|---|---|
| Sample size | 1 |
| Population | Human user of 2C-B |
| Keywords | Drug metabolism Drug processing Substance breakdown Metabolic pathways 2c-b |
| Citations | 20 |
| Key finding | 4-Bromo-2,5-dimethoxyphenylacetic acid is the most abundant metabolite of 2C-B in human urine, comprising 73% of detected metabolites, and its formation suggests a crucial role for monoamine oxidase in human 2C-B metabolism. |
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.