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GC-MS, GC-TOF-MS and GC-IRD Methods for the Differentiation of Regioisomeric and Isobaric Designer Drugs of the Piperazine Class
EP21731
Poster Title: GC-MS, GC-TOF-MS and GC-IRD Methods for the Differentiation of Regioisomeric and Isobaric Designer Drugs of the Piperazine Class
Submitted on 06 Mar 2014
Author(s): Karim M.Abdel-Hay1,2, Jack DeRuiter1 and C. Randall Clark1
Affiliations: (1) Dept. of Drug Discovery and Development, Harrison School of Pharmacy, Auburn University, Auburn, AL 36849, USA.(2) Dept. of Pharmaceutical Analytical Chemistry, Faculty of Pharmacy, Alexandria University, Alexandria, 21521, Egypt.
This poster was presented at Pittcon 2014
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Poster Information
Abstract: GC-MS, GC-TOF-MS and GC-IRD techniques provide complimentary data in the differentiation of regioisomeric and isobaric piperazine drugs of abuse and controlled substances. The mass spectra for regioisomeric and isobaric piperazines are almost identical with no marked differences that would allow for differentiation between these compounds. 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. Gas chromatography coupled with time-of-flight mass spectrometric detection (GC-TOF) provided a means of discrimination among the isobaric piperazines by confirming the elemental composition of the major fragment ions in the mass spectra of these compounds. On the other hand, GC-TOF-MS was not successful in differentiating between regioisomeric piperazines. The vapor phase infrared spectrum obtained by GC-IRD was successful in differentiating among the regioisomeric and isobaric piperazines by the characteristic bands in the region 700 – 1700 cm-1. These techniques have been applied to the analysis of the ring substituted methoxy-, methylenedioxy-, dimethoxy- and bromodimethoxy-, in both the benzyl and benzoylpiperazine series. In addition to that, isotope labeling experiments such as deuterium (D) and carbon 13 (13C) labeling were used to confirm mass spectrometric fragmentation mechanisms that result in the formation of some key fragment ions or to confirm the elemental composition of these fragment ions. The gas chromatographic resolution will be described for these piperazines on a variety of stationary phases. Summary: The mass spectra for regioisomeric and isobaric piperazines are almost identical. Perfluoroacylation 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.References: [1] R.A. Glennon, R.M. Slusher, R.A. Lyon, M. Titeler, J.D. McKenney, 5-HT1 and 5-HT2 binding characteristics of some quipazine analogues. J. Med. Chem. 29 (1986) 2375–2380
[2] R.A. Glennon, Central serotonin receptors as targets for drug research. J. Med. Chem. 30 (1987) 1–12.
[3] R. F. Staack, L. D. Paul, D. Schmid, G. Roider, B. Rolf, Proof of a 1-(3-chlorophenyl)piperazine (mCPP) intake—Use as adulterant of cocaine resulting in drug–drug interactions?, J. of Chromatogr. B, 855 (200
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