Determination of the metabolites of the new designer drugs bk-MBDB and bk-MDEA in human urine.
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.
Zaitsu
Kei
K
Forensic Science Laboratory, Osaka Prefectural Police Headquarters, 1-3-18, Hommachi, Chuo-ku, Osaka 541-0053, Japan. k_zaitsu_fsl_opp@ybb.ne.jp
Katagi
Munehiro
M
Kamata
Hiroe T
HT
Kamata
Tooru
T
Shima
Noriaki
N
Miki
Akihiro
A
Tsuchihashi
Hitoshi
H
Mori
Yasushige
Y
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
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