title: Determination of the metabolites of the new designer drugs bk-MBDB and bk-MDEA in human urine.
abstract: This is the first report on identifying the specific metabolites of the new designer drugs 2-methylamino-1-(3,4-methylenedioxyphenyl)butan-1-one (bk-MBDB) and 2-ethylamino-1-(3,4-methylenedioxyphenyl)propan-1-one (bk-MDEA) in human urine using synthesized standards. Based on GC/MS and LC/MS, we identified N-dealkylation, demethylenation followed by O-methylation, and beta-ketone reduction as their major metabolic pathways. The quantitative analyses by LC/MS revealed that both demethylenation followed by O-methylation and beta-ketone reduction were superior to N-dealkylation and that both bk-MBDB and bk-MDEA were mainly metabolized into their corresponding 4-hydroxy-3-methoxy metabolites (4-OH-3MeO metabolites). After hydrolysis, the concentrations of 4-OH-3MeO metabolites and 3-hydroxy-4-methoxy metabolites of both bk-MBDB and bk-MDEA dramatically increased, suggesting that the metabolites mainly exist as their conjugates.
authors.affiliation: Forensic Science Laboratory, Osaka Prefectural Police Headquarters, 1-3-18, Hommachi, Chuo-ku, Osaka 541-0053, Japan. k_zaitsu_fsl_opp@ybb.ne.jp
authors.forename: Kei
authors.initials: K
authors.lastname: Zaitsu
authors.forename: Munehiro
authors.initials: M
authors.lastname: Katagi
authors.forename: Hiroe T
authors.initials: HT
authors.lastname: Kamata
authors.forename: Tooru
authors.initials: T
authors.lastname: Kamata
authors.forename: Noriaki
authors.initials: N
authors.lastname: Shima
authors.forename: Akihiro
authors.initials: A
authors.lastname: Miki
authors.forename: Hitoshi
authors.initials: H
authors.lastname: Tsuchihashi
authors.forename: Yasushige
authors.initials: Y
authors.lastname: Mori
mesh_terms: D015104:3,4-Methylenedioxyamphetamine / Q000031:analogs & derivatives* / Q000652:urine; D015198:Designer Drugs / Q000032:analysis; D053593:Forensic Toxicology; D008401:Gas Chromatography-Mass Spectrometry; D006213:Hallucinogens / Q000652:urine*; D006801:Humans; D006868:Hydrolysis; D008745:Methylation
chemical_list: D015198:Designer Drugs; D006213:Hallucinogens; C051570:N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine; D015104:3,4-Methylenedioxyamphetamine; C544129:2-ethylamino-1-(3,4-methylenedioxyphenyl)propan-1-one; C051800:3,4-methylenedioxyethamphetamine; C544130:2-methylamino-1-(3,4-methylenedioxyphenyl)butan-1-one