title: GC-MS analysis of methamphetamine impurities: reactivity of (+)- or (-)-chloroephedrine and cis- or trans-1,2-dimethyl-3-phenylaziridine.
abstract: S-(+)-Methamphetamine is frequently found as the only isomer in urine specimens from methamphetamine abuseres. Enantiomerically pure S-(+)-methamphetamine can be synthesized from ephedrine or pseudoephedrine via chloroephedrine intermediates. These intermediates are unstable and capable of cyclizing to form cis- and trans-1,2-dimethyl-3-phenyl aziridine. Studies were done to determine if these intermediates could be detected when using a common gas chromatographic-mass spectrometric analytical method (derivatization with heptafluorobutyric anhydride, HFBA) for toxicological screening of methamphetamine. Analysis of (+)- or (-)-chloroephedrine after extraction into hexane and derivatization with HFBA indicated that both pseudoephedrine and ephedrine were the major compounds detected. Direct derivatization of a hexane solution of cis-1,2-dimethyl-3-phenyl aziridine yielded only the derivatives of ephedrine and pseudoephedrine, indicating that the aziridine intermediate is responsible for the formation of the ephedrine or pseudoephedrine. These studies indicate that the aziridine intermediates would not be detected in methamphetamine samples following HFBA derivatization.
authors.affiliation: Department of Pathology, School of Medicine, Medical College of Virginia, Virginia Commonwealth University, Richmond 23298, USA.
authors.forename: V
authors.initials: V
authors.lastname: Lekskulchai
authors.forename: K
authors.initials: K
authors.lastname: Carter
authors.forename: A
authors.initials: A
authors.lastname: Poklis
authors.forename: W
authors.initials: W
authors.lastname: Soine
mesh_terms: D001388:Aziridines / Q000032:analysis / Q000737:chemistry*; D004340:Drug Contamination; D004809:Ephedrine / Q000031:analogs & derivatives / Q000032:analysis / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods*; D008694:Methamphetamine / Q000031:analogs & derivatives* / Q000737:chemistry*; D015813:Substance Abuse Detection / Q000379:methods*
chemical_list: C420126:1,2-dimethyl-3-phenylaziridine; D001388:Aziridines; C420125:chloroephedrine; D008694:Methamphetamine; D004809:Ephedrine