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

• Published in: Drug testing and analysis 2012-12, Vol.4 (12), p.1001-1008
• Main Authors: Inagaki, Shinsuke, Hirashima, Haruo, Taniguchi, Sayuri, Higashi, Tatsuya, Min, Jun Zhe, Kikura-Hanajiri, Ruri, Goda, Yukihiro, Toyo'oka, Toshimasa
• Format: Article
• Language: English
• Subjects: (R)-(−)-DBD-Py-NCS; Acetonitriles - chemistry; Animals; Calibration; chiral derivatization method; Chromatography, High Pressure Liquid - standards; Chromatography, Reverse-Phase; diphenyl(pyrrolidin-2-yl)methanol (D2PM); Hair - chemistry; Isothiocyanates - chemistry; Japan; Limit of Detection; Male; Methanol - chemistry; Oxadiazoles - chemistry; phenethylamines; Phenethylamines - analysis; Psychotropic Drugs - analysis; Rats; Reference Standards; Signal-To-Noise Ratio; Silicon Dioxide - chemistry; Solvents - chemistry; Spectrometry, Fluorescence - standards; Spectrometry, Mass, Electrospray Ionization - standards; Street Drugs - analysis; Substance Abuse Detection - methods; Substance Abuse Detection - standards; ultra high performance liquid chromatography (UHPLC); Water - chemistry
• ISSN: 1942-7603; 1942-7611
• DOI: 10.1002/dta.1327

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). Copyright © 2012 John Wiley & Sons, Ltd. 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)‐(‐)‐DBD‐Py‐NCS as the chiral derivatization reagent. The developed method was successfully applied to the analysis of hair specimens from rats that were dosed with diphenyl(pyrrolidin‐2‐yl)methanol (D2PM). (R)‐ and (S)‐D2PM from rat hair specimens were enantiomerically separated and detected high sensitivity using UHPLC‐fluorescence detection.