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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
Author(s) -
Inagaki Shinsuke,
Hirashima Haruo,
Taniguchi Sayuri,
Higashi Tatsuya,
Min Jun Zhe,
KikuraHanajiri Ruri,
Goda Yukihiro,
Toyo'oka Toshimasa
Publication year - 2012
Publication title -
drug testing and analysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.065
H-Index - 54
eISSN - 1942-7611
pISSN - 1942-7603
DOI - 10.1002/dta.1327
Subject(s) - chemistry , chromatography , enantiomer , derivatization , amine gas treating , phenethylamines , phenethylamine , reagent , detection limit , methanol , high performance liquid chromatography , elution , organic chemistry , stereochemistry
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.