Fragmentation pathways of heroin-related alkaloids revealed by ion trap and quadrupole time-of-flight tandem mass spectrometry

Rapid Communications in Mass Spectrometry : RCM
Zhengxiang ZhangHuwei Liu

Abstract

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).

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Citations

Sep 15, 2011·Journal of Mass Spectrometry : JMS·Lubertus BijlsmaWilfried M A Niessen
Dec 15, 2010·Rapid Communications in Mass Spectrometry : RCM·Bernadett BiriSándor Kéki
Feb 28, 2014·Rapid Communications in Mass Spectrometry : RCM·Lajos NagySándor Kéki
May 3, 2011·Analytical Chemistry·T A BrettellJ R Almirall
Jul 6, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jinjun ShanWenjun Tong

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