title: Stereoisomeric identification of norephedrine derived from methamphetamine or amphetamine: urinalysis results of 33 methamphetamine abusers and 1 amphetamine abuser in Japan.
abstract: Stereoisomeric identification of norephedrine (NE) derived from methamphetamine (MA) or amphetamine (AM) was investigated by SIM-GC/MS assay using the urine of 33 MA abusers and 1 AM abuser. The assay simultaneously identified TFA-derivatized MA and AM metabolites, including AM, p-hydroxyl-MA (p-HMA), and p-hydroxyl-AM (p-HAM). The analysis lasted approximately 43 min, with a signal-to-noise ratio of >or=3 and a detection limit of 50 ng/mL. Among 12 urine samples from different subjects, only the S (+) form of MA and its metabolites (AM, p-HMA, p-HAM) was detected, however, a (1R,2S)-(-)-NE stereoisomer was also identified. Among the urine samples of two subjects, only the R (-) form of MA and its metabolites (AM, p-HMA, p-HAM) was detected, while NE was not detected. Following urinalysis of urine obtained from 19 MA abusers and 1 AM abuser, only the (1R,2S)-(-)-NE stereoisomer was identified, while unmetabolized MA, AM, and their metabolites (p-HMA, p-HAM), showed stereoselective metabolism. Although (1R,2S)-(-)-ephedrine (EP) alone was found in the urine of 1 (S)-(+)-MA user and 1 (S)-(+)- and (R)-(-)-MA user among 33 MA users, it was not present in the urine of the remaining 31 subjects. Therefore, (1R,2S)-(-)-NE was likely not of (1R,2S)-(-)-EP origin and was most likely from (S)-(+)-AM of the MA metabolite. The production ratio of (1R,2S)-(-)-NE to (S)-(+)-AM ranged from 0.01 to 0.25 in MA abusers and was 0.12 in AM abusers.
authors: Department of Legal Medicine, Dokkyo University School of Medicine, Mibu, Tochigi 321-0293, Japan. tnagai@dokkyomed.ac.jp
authors: Toshiaki
authors: T
authors: Nagai
authors: Masahito
authors: M
authors: Kido
authors: Junko
authors: J
authors: Maeda
authors: Kazumi
authors: K
authors: Matsushima
authors: Toshio
authors: T
authors: Okazaki
authors: Akira
authors: A
authors: Kurosu
authors: Masahito
authors: M
authors: Hitosugi
authors: Shougo
authors: S
authors: Tokudome
mesh_terms: D000293:Adolescent; D000328:Adult; D000661:Amphetamine / Q000737:chemistry* / Q000652:urine*; D005260:Female; D006801:Humans; D007564:Japan; D008297:Male; D008694:Methamphetamine / Q000737:chemistry* / Q000652:urine*; D008875:Middle Aged; D015394:Molecular Structure; D010665:Phenylpropanolamine / Q000737:chemistry* / Q000652:urine*; D013237:Stereoisomerism; D015813:Substance Abuse Detection / Q000379:methods*
chemical_list: D010665:Phenylpropanolamine; D008694:Methamphetamine; D000661:Amphetamine