Analysis of 4-bromo-2,5-dimethoxyphenethylamine abuser's urine: identification and quantitation of urinary metabolites.
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.
National Research Institute of Police Science, 6-3-1 Kashiwanoha, Kashiwa City, Chiba, 277-0882, Japan. kanamori@nrips.go.jp
Tatsuyuki
T
Kanamori
Kyoko
K
Nagasawa
Kenji
K
Kuwayama
Kenji
K
Tsujikawa
Yuko T
YT
Iwata
Hiroyuki
H
Inoue
D004118:Dimethoxyphenylethylamine / Q000031:analogs & derivatives* / Q000652:urine; D053593:Forensic Toxicology; D008401:Gas Chromatography-Mass Spectrometry; D006213:Hallucinogens / Q000652:urine*; D006801:Humans; D010648:Phenylacetates / Q000652:urine; D010626:Phenylethyl Alcohol / Q000031:analogs & derivatives / Q000652:urine; D015813:Substance Abuse Detection / Q000379:methods; D019966:Substance-Related Disorders / Q000175:diagnosis
C583078:4-bromo-2,5-dimethoxyphenylacetic acid; C583080:4-bromo-2,5-dimethoxyphenylethyl alcohol; C583079:4-bromo-2-hydroxy-5-methoxyphenylacetic acid; D004118:Dimethoxyphenylethylamine; D006213:Hallucinogens; D010648:Phenylacetates; D010626:Phenylethyl Alcohol; C079321:2-(4-bromo-2,5-dimethoxyphenyl)ethylamine