title: Enantiomer analysis of a new street drug, 3,4-methylenedioxy-N-methyl-butanamine, in rat urine.
abstract: A new street drug, 3,4-methylenedioxy-N-methyl-butanamine (MBDB), has been found in Japan recently. The stereoisomer monitoring and the urinary excretion kinetics are not determined in biological fluids even though abused MBDB is a racemic form [enantiomer ratio (-/+) = 1.00]. The present studies were done by high-performance liquid chromatography (HPLC) equipped with a chiral activity column at 40 degrees C using urine specimens from five Wistar rats. Urine samples were collected over six time intervals after a single oral administration of racemic MBDB (30 mg/kg). Unchanged MBDB and 3,4-methylenedioxybutanamine (BDB), an N-demethylated metabolite, were found in the rats' urine. Each enantiomer of MBDB and BDB was monitored (peak resolution > 1.00) by HPLC analysis within 30 min. For both MBDB and BDB, the (+)-isomers were excreted a little more than the (-)-isomers. The stereoselective disposition of BDB was more remarkable than that of MBDB and was observed in the urine throughout the study (p < 0.05). The urinary excretion of MBDB showed significant difference between the two enantiomers from 4 to 20 h (p < 0.05). The amount of MBDB excreted up to 24 h was 34.7+/-2.8% of the administered dose: 17.6+/-1.4% for (+)-isomer and 17.1+/-1.5% for (-)-isomer. The amount of BDB was 4.9+/-1.0%; 2.9+/-0.6% for (+)-isomer and 2.0+/-0.4% for (-)-isomer. The enantiomer ratio (-/+) of MBDB and BDB was 1.00 or a little smaller. The ratio (-/+) of MBDB changed from 1.00+/-0.02 to 0.88+/-0.09 by 24 h, and that of BDB from 0.68+/-0.03 to 0.78+/-0.02. The ratio (-/+) for MBDB and BDB accumulated up to 24 h was 0.97+/-0.01 and 0.70+/-0.06, respectively, and the total ratio (-/+) of the two substances was 0.93+/-0.02 (p < 0.05). These findings suggested that the stereoselective disposition of racemic MBDB was different from that of 3,4-dimethylenedioxyamphetamine and 3,4-dimethylenedioxymethamphetamine and was similar to that of methamphetamine.
authors.affiliation: Department of Legal Medicine, Dokkyo University School of Medicine, Mibu, Tochigi, Japan.
authors.forename: Toshiaki
authors.initials: T
authors.lastname: Nagai
authors.forename: Kazumi
authors.initials: K
authors.lastname: Matsushima
authors.forename: Atsuko
authors.initials: A
authors.lastname: Suzuki
authors.forename: Atsuko
authors.initials: A
authors.lastname: Saotome
authors.forename: Akira
authors.initials: A
authors.lastname: Kurosu
authors.forename: Hirohisa
authors.initials: H
authors.lastname: Nihei
authors.forename: Kazumi
authors.initials: K
authors.lastname: Kuroyanagi
authors.forename: Shogo
authors.initials: S
authors.lastname: Tokudome
mesh_terms: D015104:3,4-Methylenedioxyamphetamine / Q000031:analogs & derivatives* / Q000493:pharmacokinetics / Q000652:urine*; D000818:Animals; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation / Q000379:methods; D013287:Illicit Drugs / Q000493:pharmacokinetics / Q000652:urine*; D008297:Male; D051381:Rats; D017208:Rats, Wistar; D013237:Stereoisomerism; D015813:Substance Abuse Detection / Q000379:methods*
chemical_list: D013287:Illicit Drugs; C051570:N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine; C069611:1-(3,4-methylenedioxyphenyl)-2-butanamine; D015104:3,4-Methylenedioxyamphetamine