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Structural determination of the novel fragmentation routes of zwitteronic morphine opiate antagonists naloxonazine and naloxone hydrochlorides using electrospray ionization tandem mass spectrometry.
Rapid Commun Mass Spectrom. 2007; 21(6):1062-74.RC

Abstract

Electrospray ionization quadrupole time-of-flight (ESI-QqToF) mass spectra of the zwitteronic salts naloxonazine dihydrochloride 1 and naloxone hydrochloride 2, a common series of morphine opiate receptor antagonists, were recorded using different declustering potentials. The singly charged ion [M+H-2HCl](+) at m/z 651.3170 and the doubly charged ion [M+2H-2HCl](2+) at m/z 326.1700 were noted for naloxonazine dihydrochloride 1; and the singly charged ion [M+H-HCl](+) at m/z 328.1541 was observed for naloxone hydrochloride 2. Low-energy collision-induced dissociation tandem mass spectrometry (CID-MS/MS) experiments established the fragmentation routes of these compounds. In addition to the characteristic diagnostic product ions obtained, we noticed the formation of a series of radical product ions for the zwitteronic compounds 1 and 2, and also the formation of a distonic ion product formed from the singly charged ion [M+H-HCl](+) of naloxone hydrochloride 2. Confirmation of the various established fragmentation routes was effected by conducting a series of ESI-CID-QqTof-MS/MS product ion scans, which were initiated by CID in the atmospheric pressure/vacuum interface using a higher declustering potential. Deuterium labeling was also performed on the zwitteronic salts 1 and 2, in which the hydrogen atoms of the OH and NH groups were exchanged with deuterium atoms. Low-energy CID-QqTof-MS/MS product ion scans of the singly charged and doubly charged deuteriated molecules confirmed the initial fragmentation patterns proposed for the protonated molecules. Precursor ion scan analyses were also performed with a conventional quadrupole-hexapole-quadrupole tandem mass spectrometer and allowed the confirmation of the genesis of some diagnostic ions.

Authors+Show Affiliations

Laboratoire de Physico-Chimie des Interfaces et Applications FRE CNRS 2485, Fédération Chevreul FR CNRS 2638, Site de Béthune, IUT de Béthune BP819, 62408 Béthune, France.No affiliation info availableNo 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

17310471

Citation

Joly, Nicolas, et al. "Structural Determination of the Novel Fragmentation Routes of Zwitteronic Morphine Opiate Antagonists Naloxonazine and Naloxone Hydrochlorides Using Electrospray Ionization Tandem Mass Spectrometry." Rapid Communications in Mass Spectrometry : RCM, vol. 21, no. 6, 2007, pp. 1062-74.
Joly N, Vaillant C, Cohen AM, et al. Structural determination of the novel fragmentation routes of zwitteronic morphine opiate antagonists naloxonazine and naloxone hydrochlorides using electrospray ionization tandem mass spectrometry. Rapid Commun Mass Spectrom. 2007;21(6):1062-74.
Joly, N., Vaillant, C., Cohen, A. M., Martin, P., El Essassi, M., Massoui, M., & Banoub, J. (2007). Structural determination of the novel fragmentation routes of zwitteronic morphine opiate antagonists naloxonazine and naloxone hydrochlorides using electrospray ionization tandem mass spectrometry. Rapid Communications in Mass Spectrometry : RCM, 21(6), 1062-74.
Joly N, et al. Structural Determination of the Novel Fragmentation Routes of Zwitteronic Morphine Opiate Antagonists Naloxonazine and Naloxone Hydrochlorides Using Electrospray Ionization Tandem Mass Spectrometry. Rapid Commun Mass Spectrom. 2007;21(6):1062-74. PubMed PMID: 17310471.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Structural determination of the novel fragmentation routes of zwitteronic morphine opiate antagonists naloxonazine and naloxone hydrochlorides using electrospray ionization tandem mass spectrometry. AU - Joly,Nicolas, AU - Vaillant,Celine, AU - Cohen,Alejandro M, AU - Martin,Patrick, AU - El Essassi,Mokhtar, AU - Massoui,Mohamed, AU - Banoub,Joseph, PY - 2007/2/21/pubmed PY - 2007/5/10/medline PY - 2007/2/21/entrez SP - 1062 EP - 74 JF - Rapid communications in mass spectrometry : RCM JO - Rapid Commun Mass Spectrom VL - 21 IS - 6 N2 - Electrospray ionization quadrupole time-of-flight (ESI-QqToF) mass spectra of the zwitteronic salts naloxonazine dihydrochloride 1 and naloxone hydrochloride 2, a common series of morphine opiate receptor antagonists, were recorded using different declustering potentials. The singly charged ion [M+H-2HCl](+) at m/z 651.3170 and the doubly charged ion [M+2H-2HCl](2+) at m/z 326.1700 were noted for naloxonazine dihydrochloride 1; and the singly charged ion [M+H-HCl](+) at m/z 328.1541 was observed for naloxone hydrochloride 2. Low-energy collision-induced dissociation tandem mass spectrometry (CID-MS/MS) experiments established the fragmentation routes of these compounds. In addition to the characteristic diagnostic product ions obtained, we noticed the formation of a series of radical product ions for the zwitteronic compounds 1 and 2, and also the formation of a distonic ion product formed from the singly charged ion [M+H-HCl](+) of naloxone hydrochloride 2. Confirmation of the various established fragmentation routes was effected by conducting a series of ESI-CID-QqTof-MS/MS product ion scans, which were initiated by CID in the atmospheric pressure/vacuum interface using a higher declustering potential. Deuterium labeling was also performed on the zwitteronic salts 1 and 2, in which the hydrogen atoms of the OH and NH groups were exchanged with deuterium atoms. Low-energy CID-QqTof-MS/MS product ion scans of the singly charged and doubly charged deuteriated molecules confirmed the initial fragmentation patterns proposed for the protonated molecules. Precursor ion scan analyses were also performed with a conventional quadrupole-hexapole-quadrupole tandem mass spectrometer and allowed the confirmation of the genesis of some diagnostic ions. SN - 0951-4198 UR - https://www.unboundmedicine.com/medline/citation/17310471/Structural_determination_of_the_novel_fragmentation_routes_of_zwitteronic_morphine_opiate_antagonists_naloxonazine_and_naloxone_hydrochlorides_using_electrospray_ionization_tandem_mass_spectrometry_ L2 - https://doi.org/10.1002/rcm.2935 DB - PRIME DP - Unbound Medicine ER -