RESUMEN
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. ß-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. ß-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.
Asunto(s)
Dimetoxifeniletilamina/análogos & derivados , Ácido Glucurónico/síntesis química , Psicotrópicos/síntesis química , Psicotrópicos/orina , Adulto , Cromatografía Liquida , Dimetoxifeniletilamina/síntesis química , Dimetoxifeniletilamina/orina , Glucurónidos/síntesis química , Humanos , Masculino , Espectrometría de Masas , Detección de Abuso de SustanciasRESUMEN
The cactus alkaloid 3,4-dimethoxyphenethylamine and its naturally occurring N-methylated homologs inhibited the deamination of tyramine and tryptamine by rat brain monoamine oxidase. In contrast, the beta-hydroxylated derivatives of this series failed to inhibit the action of monoamine oxidase on both tyramine and tryptamine.
