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Differentiation of methoxybenzoylpiperazines (OMeBzPs) and methylenedioxybenzylpiperazines (MDBPs) By GC‐IRD and GC‐MS
Author(s) -
AbdelHay Karim M.,
DeRuiter Jack,
Randall Clark C.
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.348
Subject(s) - gas chromatography–mass spectrometry , chemistry , chromatography , mass spectrometry
The designer drug 3,4‐methylenedioxybenzylpiperazine (3,4‐MDBP), its positional isomer 2,3‐methylenedioxybenzylpiperazine (2,3‐MDBP) and three regioisomeric ring‐substituted methoxybenzoylpiperazines (OMeBzPs) have identical elemental composition and no marked differences in their mass spectra with only the three methoxybenzoylpiperazine regioisomers showing one unique major fragment ion at m/z 152. Perfluoroacylation of the secondary amine nitrogen of these isomeric piperazines gave mass spectra with differences in the relative abundance of some fragment ions but did not alter the fragmentation pathway to provide unique ions for discrimination among these isomers. Exact mass determination using gas chromatography coupled to time‐of‐flight mass spectrometry (GC‐TOF‐MS) did not provide any discrimination among these compounds since the main fragment ions are of identical elemental composition. Gas chromatography coupled to infrared detection (GC‐IRD) provides direct confirmatory data for the identification of the carbonyl containing compounds and the differentiation of the psychoactive designer drug 3,4‐MDBP from its direct (2,3‐MDBP) and indirect (OMeBzPs) regioisomers. The mass spectra in combination with the vapour phase infrared spectra provide for specific confirmation of each of the isomeric piperazines. The underivatized and perfluoroacyl derivative forms of the five piperazines involved in this study were resolved on a stationary phase of 100% trifluoropropyl methyl polysiloxane (Rtx‐200). Copyright © 2011 John Wiley & Sons, Ltd.