4-(3-isothiocyanatopyrrolidin-1-yl)-7-(n-n-dimethylaminosulfonyl)-2-1-3-benzoxadiazole and phenethylamine

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).

Topics: Acetonitriles; Animals; Calibration; Chromatography, High Pressure Liquid; Chromatography, Reverse-Phase; Hair; Illicit Drugs; Isothiocyanates; Japan; Limit of Detection; Male; Methanol; Oxadiazoles; Phenethylamines; Psychotropic Drugs; Rats; Reference Standards; Signal-To-Noise Ratio; Silicon Dioxide; Solvents; Spectrometry, Fluorescence; Spectrometry, Mass, Electrospray Ionization; Substance Abuse Detection; Water