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Characterisation of nicotine and related compounds using electrospray ionisation with ion trap mass spectrometry and with quadrupole time-of-flight mass spectrometry and their detection by liquid chromatography/electrospray ionisation mass spectrometry.
Rapid Commun Mass Spectrom. 2007; 21(4):557-66.RC

Abstract

Electrospray ionisation ion trap mass spectrometry (ESI-MS(n)) has been used to study the fragmentation patterns of nicotine and nine of its related compounds. From this study certain characteristic fragmentations are apparent with generally the pyrrolidine or piperidine ring being subject to chemical modifications. The structures of the product ions proposed for the ESI-MS(n) study have been supported by results from electrospray ionisation quadrupole time-of-flight mass spectrometry (ESI-QTOF-MS). Compounds with pyrrolidine and piperidine rings that possess an unsubstituted N atom have been shown to lose NH(3) at the MS(2) stage. Those compounds with N-methyl groups lose CH(3)NH(2) at the MS(2) stage. The loss of NH(3) or CH(3)NH(2) leaves the corresponding rings opened and this is followed by ring closure at the pyridine-2 carbon atom. Mono-N-oxides fragment in a similar way but the di-N-oxide can also fragment by cleavage of the bond between the pyridine and pyrrolidine rings. Cotinine also can undergo cleavage of this bond between the rings. This data therefore provides useful information on how substituents and the nature of the non-pyridine ring can affect the fragmentation patterns of nicotine and its related compounds. This information can be used in the characterisation of these compounds by liquid chromatography/electrospray ionization mass spectrometry (LC/ESI-MS) which results in the separation of nicotine and its related compounds with limits of detection (LODs) ranging from 15 to 105 ng/mL. The use of LC/ESI-MS to study nicotine-containing samples resulted in the simultaneous and unambiguous identification of seven of the compounds discussed in this paper: cotinine identified at retention time 12.5 min (with its [M+H](+) ion at m/z 177), nornicotine 16.0 min (m/z 149), anatabine 18.0 min (m/z 161), myosmine 18.5 min (m/z 147), anabasine 20.4 min (m/z 163), nicotine 22.2 min (m/z 163), and nicotyrine 31.4 min (m/z 159). For quality control of nicotine replacement therapy products, these nicotine impurities can be readily identified and determined at levels up to 0.3% for single impurities and up to 1.0% for total impurities.

Authors+Show Affiliations

School of Biomedical Sciences, University of Ulster, Coleraine, BT52 1SA, UK.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

17245795

Citation

Smyth, Thomas J., et al. "Characterisation of Nicotine and Related Compounds Using Electrospray Ionisation With Ion Trap Mass Spectrometry and With Quadrupole Time-of-flight Mass Spectrometry and Their Detection By Liquid Chromatography/electrospray Ionisation Mass Spectrometry." Rapid Communications in Mass Spectrometry : RCM, vol. 21, no. 4, 2007, pp. 557-66.
Smyth TJ, Ramachandran VN, McGuigan A, et al. Characterisation of nicotine and related compounds using electrospray ionisation with ion trap mass spectrometry and with quadrupole time-of-flight mass spectrometry and their detection by liquid chromatography/electrospray ionisation mass spectrometry. Rapid Commun Mass Spectrom. 2007;21(4):557-66.
Smyth, T. J., Ramachandran, V. N., McGuigan, A., Hopps, J., & Smyth, W. F. (2007). Characterisation of nicotine and related compounds using electrospray ionisation with ion trap mass spectrometry and with quadrupole time-of-flight mass spectrometry and their detection by liquid chromatography/electrospray ionisation mass spectrometry. Rapid Communications in Mass Spectrometry : RCM, 21(4), 557-66.
Smyth TJ, et al. Characterisation of Nicotine and Related Compounds Using Electrospray Ionisation With Ion Trap Mass Spectrometry and With Quadrupole Time-of-flight Mass Spectrometry and Their Detection By Liquid Chromatography/electrospray Ionisation Mass Spectrometry. Rapid Commun Mass Spectrom. 2007;21(4):557-66. PubMed PMID: 17245795.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Characterisation of nicotine and related compounds using electrospray ionisation with ion trap mass spectrometry and with quadrupole time-of-flight mass spectrometry and their detection by liquid chromatography/electrospray ionisation mass spectrometry. AU - Smyth,Thomas J, AU - Ramachandran,V N, AU - McGuigan,Alex, AU - Hopps,Jason, AU - Smyth,W Franklin, PY - 2007/1/25/pubmed PY - 2007/5/2/medline PY - 2007/1/25/entrez SP - 557 EP - 66 JF - Rapid communications in mass spectrometry : RCM JO - Rapid Commun Mass Spectrom VL - 21 IS - 4 N2 - Electrospray ionisation ion trap mass spectrometry (ESI-MS(n)) has been used to study the fragmentation patterns of nicotine and nine of its related compounds. From this study certain characteristic fragmentations are apparent with generally the pyrrolidine or piperidine ring being subject to chemical modifications. The structures of the product ions proposed for the ESI-MS(n) study have been supported by results from electrospray ionisation quadrupole time-of-flight mass spectrometry (ESI-QTOF-MS). Compounds with pyrrolidine and piperidine rings that possess an unsubstituted N atom have been shown to lose NH(3) at the MS(2) stage. Those compounds with N-methyl groups lose CH(3)NH(2) at the MS(2) stage. The loss of NH(3) or CH(3)NH(2) leaves the corresponding rings opened and this is followed by ring closure at the pyridine-2 carbon atom. Mono-N-oxides fragment in a similar way but the di-N-oxide can also fragment by cleavage of the bond between the pyridine and pyrrolidine rings. Cotinine also can undergo cleavage of this bond between the rings. This data therefore provides useful information on how substituents and the nature of the non-pyridine ring can affect the fragmentation patterns of nicotine and its related compounds. This information can be used in the characterisation of these compounds by liquid chromatography/electrospray ionization mass spectrometry (LC/ESI-MS) which results in the separation of nicotine and its related compounds with limits of detection (LODs) ranging from 15 to 105 ng/mL. The use of LC/ESI-MS to study nicotine-containing samples resulted in the simultaneous and unambiguous identification of seven of the compounds discussed in this paper: cotinine identified at retention time 12.5 min (with its [M+H](+) ion at m/z 177), nornicotine 16.0 min (m/z 149), anatabine 18.0 min (m/z 161), myosmine 18.5 min (m/z 147), anabasine 20.4 min (m/z 163), nicotine 22.2 min (m/z 163), and nicotyrine 31.4 min (m/z 159). For quality control of nicotine replacement therapy products, these nicotine impurities can be readily identified and determined at levels up to 0.3% for single impurities and up to 1.0% for total impurities. SN - 0951-4198 UR - https://www.unboundmedicine.com/medline/citation/17245795/Characterisation_of_nicotine_and_related_compounds_using_electrospray_ionisation_with_ion_trap_mass_spectrometry_and_with_quadrupole_time_of_flight_mass_spectrometry_and_their_detection_by_liquid_chromatography/electrospray_ionisation_mass_spectrometry_ L2 - https://doi.org/10.1002/rcm.2871 DB - PRIME DP - Unbound Medicine ER -