title: Rapid enantiomeric separation and simultaneous determination of phenethylamines by ultra high performance liquid chromatography with fluorescence and mass spectrometric detection: application to the analysis of illicit drugs distributed in the Japanese market and biological samples.
abstract: A rapid enantiomeric separation and simultaneous determination method based on ultra high performance liquid chromatography (UHPLC) was developed for phenethylamine-type abused drugs using (R)-(-)-4-(N,N-dimethylaminosulfonyl)-7-(3-isothiocyanatopyrrolidin-1-yl)-2,1,3-benzoxadiazole ((R)-(-)-DBD-Py-NCS) as the chiral fluorescent derivatization reagent. The derivatives were rapidly enantiomerically separated by reversed-phase UHPLC using a column of 2.3-µm octadecylsilica (ODS) particles by isocratic elution with water-methanol or water-acetonitrile systems as the mobile phase. The proposed method was applied to the analysis of products containing illicit drugs distributed in the Japanese market. Among the products, 1-(3,4-methylenedioxyphenyl)butan-2-amine (BDB) and 1-(2-methoxy4,5-methylenedioxyphenyl)propan-2-amine (MMDA-2) were detected in racemic form. Furthermore, the method was successfully applied to the analysis of hair specimens from rats that were continuously dosed with diphenyl(pyrrolidin-2-yl)methanol (D2PM). Using UHPLC-fluorescence (FL) detection, (R)- and (S)-D2PM from hair specimens were enantiomerically separated and detected with high sensitivity. The detection limits of (R)- and (S)-D2PM were 0.12 and 0.21 ng/mg hair, respectively (signal-to-noise ratio (S/N) = 3).
authors.affiliation: Laboratory of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka, Japan.
authors.forename: Shinsuke
authors.initials: S
authors.lastname: Inagaki
authors.forename: Haruo
authors.initials: H
authors.lastname: Hirashima
authors.forename: Sayuri
authors.initials: S
authors.lastname: Taniguchi
authors.forename: Tatsuya
authors.initials: T
authors.lastname: Higashi
authors.forename: Jun Zhe
authors.initials: JZ
authors.lastname: Min
authors.forename: Ruri
authors.initials: R
authors.lastname: Kikura-Hanajiri
authors.forename: Yukihiro
authors.initials: Y
authors.lastname: Goda
authors.forename: Toshimasa
authors.initials: T
authors.lastname: Toyo'oka
mesh_terms: D000097:Acetonitriles / Q000737:chemistry; D000818:Animals; D002138:Calibration; D002851:Chromatography, High Pressure Liquid / Q000592:standards; D056148:Chromatography, Reverse-Phase; D006197:Hair / Q000737:chemistry*; D013287:Illicit Drugs / Q000032:analysis*; D017879:Isothiocyanates / Q000737:chemistry; D007564:Japan; D057230:Limit of Detection; D008297:Male; D000432:Methanol / Q000737:chemistry; D010069:Oxadiazoles / Q000737:chemistry; D010627:Phenethylamines / Q000032:analysis*; D011619:Psychotropic Drugs / Q000032:analysis*; D051381:Rats; D012015:Reference Standards; D059629:Signal-To-Noise Ratio; D012822:Silicon Dioxide / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013050:Spectrometry, Fluorescence / Q000592:standards; D021241:Spectrometry, Mass, Electrospray Ionization / Q000592:standards; D015813:Substance Abuse Detection / Q000379:methods* / Q000592:standards; D014867:Water / Q000737:chemistry
chemical_list: C107817:4-(3-isothiocyanatopyrrolidin-1-yl)-7-(N,N-dimethylaminosulfonyl)-2,1,3-benzoxadiazole; D000097:Acetonitriles; D013287:Illicit Drugs; D017879:Isothiocyanates; D010069:Oxadiazoles; D010627:Phenethylamines; D011619:Psychotropic Drugs; D012997:Solvents; C026679:octadecylsilica; D014867:Water; C029261:phenethylamine; D012822:Silicon Dioxide; D000432:Methanol; C032159:acetonitrile