title: Synthesis and Analysis of Glucuronic Acid-Conjugated Metabolites of 4-Bromo-2,5-Dimethoxyphenethylamine.
abstract: In the study reported here, two glucuronic acid-conjugated metabolites of 4-bromo-2,5-dimethoxyphenethylamine (2C-B)-a ring-substituted psychoactive phenethylamine-were chemically synthesized for the first time and a method for analyzing them in urine was developed. β-D-Glucuronide of 4-bromo-2,5-dimethoxyphenylethylalcohol was successfully synthesized using methyl 2,3,4-tri-Ο-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucuronate as a glucuronyl donor and boron trifluoride diethylether complex as a Lewis acid catalyst. β-D-Glucuronide of 4-bromo-2,5-dimethoxyphenylacetic acid was synthesized by condensing 4-bromo-2,5-dimethoxyphenylacetic acid and benzyl D-glucuronate followed by benzyl group deprotection based on catalytic hydrogenation. Two glucuronic acid-conjugated metabolites of 2C-B in urine were qualitatively and semiquantitatively evaluated via direct liquid chromatography/mass spectrometry (LC/MS) analysis of a diluted urine sample. The simple method proposed is expected to be useful for studying the metabolic fate of 2C-B.
authors.affiliation: National Research Institute of Police Science, 6-3-1, Kashiwanoha, Kashiwa, 277-0882, Japan.
authors.forename: Tatsuyuki
authors.initials: T
authors.lastname: Kanamori
authors.affiliation: National Research Institute of Police Science, 6-3-1, Kashiwanoha, Kashiwa, 277-0882, Japan.
authors.forename: Tadashi
authors.initials: T
authors.lastname: Yamamuro
authors.affiliation: National Research Institute of Police Science, 6-3-1, Kashiwanoha, Kashiwa, 277-0882, Japan.
authors.forename: Kenji
authors.initials: K
authors.lastname: Kuwayama
authors.affiliation: National Research Institute of Police Science, 6-3-1, Kashiwanoha, Kashiwa, 277-0882, Japan.
authors.forename: Kenji
authors.initials: K
authors.lastname: Tsujikawa
authors.affiliation: National Research Institute of Police Science, 6-3-1, Kashiwanoha, Kashiwa, 277-0882, Japan.
authors.forename: Yuko T
authors.initials: YT
authors.lastname: Iwata
authors.affiliation: National Research Institute of Police Science, 6-3-1, Kashiwanoha, Kashiwa, 277-0882, Japan.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Inoue
mesh_terms: D000328:Adult; D002853:Chromatography, Liquid; D004118:Dimethoxyphenylethylamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000652:urine; D020723:Glucuronic Acid / Q000138:chemical synthesis*; D020719:Glucuronides / Q000138:chemical synthesis; D006801:Humans; D008297:Male; D013058:Mass Spectrometry; D011619:Psychotropic Drugs / Q000138:chemical synthesis* / Q000652:urine*; D015813:Substance Abuse Detection
chemical_list: D004118:Dimethoxyphenylethylamine; D020719:Glucuronides; D011619:Psychotropic Drugs; D020723:Glucuronic Acid; C079321:2-(4-bromo-2,5-dimethoxyphenyl)ethylamine
keywords: 2C-B; chemical synthesis; forensic science; glucuronic acid-conjugated metabolite; metabolism; urine