PMID: 11916016Mar 28, 2002Paper

In vivo metabolism of 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in the rat: identification of urinary metabolites

Journal of Analytical Toxicology
T KanamoriT Kishi

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.

Citations

Dec 4, 2003·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Li-Chan LinCheng-Huang Lin
Nov 4, 2004·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Helena CarmoMaria de Lourdes Bastos
Jul 7, 2007·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·T KanamoriT Kishi
Jul 17, 2007·Forensic Science International : Synergy·Katerina BeránkováMarie Balíková
May 21, 2011·Journal of Forensic Sciences·Tatsuyuki KanamoriHiroyuki Inoue
Dec 10, 2013·Journal of Forensic Sciences·Sarah KerriganKelsie Bryand
Jun 28, 2005·Forensic Science International : Synergy·Marie Balíková
Nov 23, 2016·Journal of Forensic Sciences·Tatsuyuki KanamoriHiroyuki Inoue
Sep 19, 2006·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Denis S TheobaldHans H Maurer
Apr 8, 2006·Biomedical Papers of the Medical Faculty of the University Palacký, Olomouc, Czechoslovakia·Katerina Beránková, Marie Balíková
Aug 5, 2010·Therapeutic Drug Monitoring·Hans H Maurer
Sep 4, 2010·Therapeutic Drug Monitoring·Frank T Peters, Jorge A Martinez-Ramirez
May 13, 2020·Annals of the New York Academy of Sciences·F Ivy CarrollP Anantha Reddy
Nov 21, 2015·Therapeutic Drug Monitoring·Elli TyrkköRobert Kronstrand
Mar 30, 2018·Frontiers in Pharmacology·Esther PapaseitDébora González
Jan 29, 2017·Journal of Analytical Toxicology·Adrian StollerEvangelia Liakoni

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