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Fragmentation pathways of heroin‐related alkaloids revealed by ion trap and quadrupole time‐of‐flight tandem mass spectrometry
Author(s) -
Zhang Zhengxiang,
Yan Bo,
Liu Kelin,
Bo Tao,
Liao Yiping,
Liu Huwei
Publication year - 2008
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.3686
Subject(s) - chemistry , thebaine , tandem mass spectrometry , mass spectrometry , chromatography , ion trap , fragmentation (computing) , noscapine , electrospray ionization , electrospray , selected reaction monitoring , quadrupole ion trap , collision induced dissociation , morphine , codeine , alkaloid , stereochemistry , medicine , computer science , pharmacology , operating system
The electrospray ionization (ESI) ion trap and quadrupole time‐of‐flight (QqToF) mass spectra of heroin and seven related alkaloids, i.e., morphine, codeine, O ‐6‐monoacetylmorphine (6‐MAM), thebaine, acetylcodeine, papaverine and narcotine, have been extensively investigated in this work. The ESI mass spectrometric fragmentation pathways of protonated 6‐MAM, heroin, acetylcodeine, and thebaine were comprehensively elucidated for the first time with the aid of high‐resolution mass spectrometry. It was found that cleavage of the piperidine ring was the featured fragmentation route of six of the compounds, although not of papaverine and narcotine. In addition, a simple high‐performance liquid chromatography (HPLC)‐based separation method gave baseline resolution of all eight components. This study could play an important role in the screening for these alkaloids in different matrices by HPLC coupled to tandem mass spectrometry (MS/MS). Copyright © 2008 John Wiley & Sons, Ltd.