title: In vivo metabolism of 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in the rat: identification of urinary metabolites.
abstract: The in vivo metabolism of 4-bromo-2,5-dimethoxyphenethylamine (2C-B), a ring-substituted psychoactive phenethylamine, in the rat was studied. Male Wistar rats were administered 10 mg/kg of 2C-B hydrochloride orally, and 24 h urine fractions were collected. After enzymatic hydrolysis of the urine samples, the metabolites were extracted by liquid-liquid extraction and analyzed by gas chromatography-mass spectrometry. 2-(4-Bromo-2,5-dimethoxyphenyl)-ethanol, 4-bromo-2,5-dimethoxyphenylacetic acid, 2-(2-hydroxy-4-bromo-5-methoxyphenyl)-ethylamine, 2-(2-methoxy-4-bromo-5-hydroxyphenyl)-ethylamine, 1-acetoamino-2-(2-hydroxy-4-bromo-5-methoxyphenyl)-ethane, and 1-acetoamino-2-(2-methoxy-4-bromo-5-hydroxyphenyl)-ethane were identified as 2C-B metabolites. These findings suggest that at least two metabolic pathways for 2C-B are operative in rats. The first pathway leads to the corresponding aldehyde metabolite by deamination, which is subsequently reduced or oxidized, to give the corresponding alcohol and carboxylic acid metabolites. The second pathway leads to the corresponding 2-O-desmethyl or 5-O-desmethyl metabolites in which the amino group is subsequently acetylated.
authors.affiliation: National Research Institute of Police Science, Chiba, Japan.
authors.forename: Tatsuyuki
authors.initials: T
authors.lastname: Kanamori
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Inoue
authors.forename: Yuko
authors.initials: Y
authors.lastname: Iwata
authors.forename: Yoshihito
authors.initials: Y
authors.lastname: Ohmae
authors.forename: Tohru
authors.initials: T
authors.lastname: Kishi
mesh_terms: D004290:DOM 2,5-Dimethoxy-4-Methylamphetamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000493:pharmacokinetics* / Q000652:urine; D000818:Animals; D008401:Gas Chromatography-Mass Spectrometry; D006213:Hallucinogens / Q000138:chemical synthesis / Q000493:pharmacokinetics* / Q000652:urine; D008297:Male; D051381:Rats; D017208:Rats, Wistar
chemical_list: D006213:Hallucinogens; D004290:DOM 2,5-Dimethoxy-4-Methylamphetamine; C003943:2,5-dimethoxy-4-bromoamphetamine