Resumen de Synthesis and Analysis of Glucuronic Acid-Conjugated Metabolites of 4-Bromo-2, 5-Dimethoxyphenethylamine
Tatsuyuki Kanamori, Tadashi Yamamuro, Kenji Kuwayama, Kenji Tsujikawa, Yuko T. Iwata, Hiroyuki Inoue
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. b-D-Glucuronide of 4-bromo-2,5-dimethoxyphenylethylalcohol was successfully synthesized using methyl 2,3,4-tri-Ο-acetyl-1-O-(trichloroacetimidoyl)-a-D-glucuronate as a glucuronyl donor and boron trifluoride diethylether complex as a Lewis acid catalyst. b-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
