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Fragmentation pathways of heroin-related alkaloids revealed by ion trap and quadrupole time-of-flight tandem mass spectrometry.
Rapid Commun Mass Spectrom. 2008 Sep; 22(18):2851-62.RC

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).

Authors+Show Affiliations

Beijing National Laboratory for Molecular Sciences, Ministry of Education, Institute of Analytical Chemistry, College of Chemistry and Molecular Engineering, Peking University, Beijing, P.R. China.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

18712703

Citation

Zhang, Zhengxiang, et al. "Fragmentation Pathways of Heroin-related Alkaloids Revealed By Ion Trap and Quadrupole Time-of-flight Tandem Mass Spectrometry." Rapid Communications in Mass Spectrometry : RCM, vol. 22, no. 18, 2008, pp. 2851-62.
Zhang Z, Yan B, Liu K, et al. Fragmentation pathways of heroin-related alkaloids revealed by ion trap and quadrupole time-of-flight tandem mass spectrometry. Rapid Commun Mass Spectrom. 2008;22(18):2851-62.
Zhang, Z., Yan, B., Liu, K., Bo, T., Liao, Y., & Liu, H. (2008). Fragmentation pathways of heroin-related alkaloids revealed by ion trap and quadrupole time-of-flight tandem mass spectrometry. Rapid Communications in Mass Spectrometry : RCM, 22(18), 2851-62. https://doi.org/10.1002/rcm.3686
Zhang Z, et al. Fragmentation Pathways of Heroin-related Alkaloids Revealed By Ion Trap and Quadrupole Time-of-flight Tandem Mass Spectrometry. Rapid Commun Mass Spectrom. 2008;22(18):2851-62. PubMed PMID: 18712703.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Fragmentation pathways of heroin-related alkaloids revealed by ion trap and quadrupole time-of-flight tandem mass spectrometry. AU - Zhang,Zhengxiang, AU - Yan,Bo, AU - Liu,Kelin, AU - Bo,Tao, AU - Liao,Yiping, AU - Liu,Huwei, PY - 2008/8/21/pubmed PY - 2008/10/31/medline PY - 2008/8/21/entrez SP - 2851 EP - 62 JF - Rapid communications in mass spectrometry : RCM JO - Rapid Commun Mass Spectrom VL - 22 IS - 18 N2 - 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). SN - 0951-4198 UR - https://www.unboundmedicine.com/medline/citation/18712703/Fragmentation_pathways_of_heroin_related_alkaloids_revealed_by_ion_trap_and_quadrupole_time_of_flight_tandem_mass_spectrometry_ L2 - https://doi.org/10.1002/rcm.3686 DB - PRIME DP - Unbound Medicine ER -