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    ß-Methylphenylethylamines: Common fragmentation pathways with amphetamines in electrospray ionization collision-induced dissociation

    236281_236281.pdf (899.2Kb)
    Access Status
    Open access
    Authors
    Brown, David
    Hansson, R.
    Oosthuizen, F.
    Sumner, N.
    Date
    2015
    Type
    Journal Article
    
    Metadata
    Show full item record
    Citation
    Brown, D. and Hansson, R. and Oosthuizen, F. and Sumner, N. 2015. ß-Methylphenylethylamines: Common fragmentation pathways with amphetamines in electrospray ionization collision-induced dissociation. Drug Testing and Analysis. 8 (3-4): pp. 344-350.
    Source Title
    Drug Testing and Analysis
    DOI
    10.1002/dta.1816
    ISSN
    1942-7603
    School
    Department of Chemistry
    Remarks

    This is the peer reviewed version of the following article: Brown, D. and Hansson, R. and Oosthuizen, F. and Sumner, N. 2015. ß-Methylphenylethylamines: Common fragmentation pathways with amphetamines in electrospray ionization collision-induced dissociation. Drug Testing and Analysis. 8 (3-4): pp. 344-350., which has been published in final form at http://doi.org/10.1002/dta.1816. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving at http://olabout.wiley.com/WileyCDA/Section/id-820227.html#terms

    URI
    http://hdl.handle.net/20.500.11937/4382
    Collection
    • Curtin Research Publications
    Abstract

    β-Methylphenylethylamines are positional isomers of amphetamines and have been discovered in sporting supplements. Although the fragmentation of the β-methylphenylethylamine and N-methyl-β-methylphenylethylamine in gas chromatography-electron ionization-mass spectrometry (GC-EI-MS) systems is significantly different to their amphetamine and methylamphetamine isomers, under electrospray ionization commonly used in liquid chromatography-mass spectrometry (LC-MS) systems, the fragmentation of each of the isomeric pairs is almost identical. The similarities in fragmentation make it possible for the misidentification of the β-methylphenylethylamines as the illicit amphetamines. It is proposed that the similarities are due to a fragmentation pathway involving a common phenonium ion intermediate. By careful control of fragmentation energies in liquid chromatography-tandem mass spectrometry (LC-MS/MS) systems and/or close examination of the relative abundances of product ions formed by collision-induced dissociation (qualifier ratios), it is possible to distinguish the β-methylphenylethylamines from the amphetamines, even if significant retention time separation is not achieved. In liquid chromatography-electrospray ionization-quadrupole time of flight (LC-ESI-QTOF) systems the mass spectra of the β-methylphenylethylamines are identical to their amphetamine isomers. In such systems, retention time separation of the isomers is critical to avoid misidentification. During this study β-methylphenylethylamine and N-methyl-β-methylphenylethylamine have been identified in commercially available sporting supplements and oral fluid samples taken during the course of road-side drugs-in-drivers and workplace testing programmes.

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