title: Urinary excretion profiles of N-hydroxy-3,4-methylenedioxymethamphetamine in rats.
abstract: N-hydroxy-3,4-methylenedioxymethamphetamine (N-OH-MDMA) is a psychedelic illicit drug that has recently been circulating in Japan. The aims of this study were (i) to optimise enzymatic hydrolysis conditions of the conjugated forms of N-OH-MDMA and its demethylated metabolite N-hydroxy-3,4-methylenedioxyamphetamine (N-OH-MDA), (ii) to investigate the urinary excretion profiles of N-OH-MDMA in rats, and (iii) to compare urinary excretion profiles of N-OH-MDMA and 3,4-methylenedioxymethamphetamine (MDMA). Conjugated forms of the N-hydroxylated compounds (N-OH-MDMA and N-OH-MDA) were almost successfully hydrolysed to their nonconjugated forms under anaerobic conditions after helium purging of the solution. The sum of N-OH-MDMA and N-OH-MDA was used to evaluate the amount of excreted N-hydroxylated metabolites because of degradation of N-OH-MDMA to N-OH-MDA during hydrolysis. Up to 24 h after oral administration of N-OH-MDMA oxalate, the main urinary metabolites were MDMA (14.3% of dose) and 3,4-MDA (7.7% of dose). Most of the N-hydroxylated forms were excreted as glucuronide conjugates. The total amount of N-hydroxylated metabolites after hydrolysis was 1.1% of dose. Urinary excretion profiles of MDMA were similar to that of N-OH-MDMA. It may be difficult to differentiate between abuse of MDMA and N-OH-MDMA by urine analysis.
authors.affiliation: Third Department of Forensic Science, National Research Institute of Police Science, Kashiwa, Chiba, Japan. tujikawa@nrips.go.jp
authors.forename: Kenji
authors.initials: K
authors.lastname: Tsujikawa
authors.forename: Toshiyasu
authors.initials: T
authors.lastname: Mikuma
authors.forename: Kenji
authors.initials: K
authors.lastname: Kuwayama
authors.forename: Hajime
authors.initials: H
authors.lastname: Miyaguchi
authors.forename: Tatsuyuki
authors.initials: T
authors.lastname: Kanamori
authors.forename: Yuko T
authors.initials: YT
authors.lastname: Iwata
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Inoue
mesh_terms: D015104:3,4-Methylenedioxyamphetamine / Q000031:analogs & derivatives / Q000652:urine; D000284:Administration, Oral; D000818:Animals; D006868:Hydrolysis; D006900:Hydroxylation; D008297:Male; D018817:N-Methyl-3,4-methylenedioxyamphetamine / Q000008:administration & dosage / Q000737:chemistry / Q000652:urine*; D051381:Rats; D017207:Rats, Sprague-Dawley
chemical_list: D015104:3,4-Methylenedioxyamphetamine; C062690:N-hydroxy-1-(3,4-methylenedioxyphenyl)-2-aminopropane; D018817:N-Methyl-3,4-methylenedioxyamphetamine