ß-Methylphenylethylamines: Common fragmentation pathways with amphetamines in electrospray ionization collision-induced dissociation
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 signif...
| Main Authors: | , , , |
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| Format: | Journal Article |
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John Wiley and Sons Ltd
2015
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| Online Access: | http://hdl.handle.net/20.500.11937/4382 |
| _version_ | 1848744500924514304 |
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| author | Brown, David Hansson, R. Oosthuizen, F. Sumner, N. |
| author_facet | Brown, David Hansson, R. Oosthuizen, F. Sumner, N. |
| author_sort | Brown, David |
| building | Curtin Institutional Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T06:02:28Z |
| format | Journal Article |
| id | curtin-20.500.11937-4382 |
| institution | Curtin University Malaysia |
| institution_category | Local University |
| last_indexed | 2025-11-14T06:02:28Z |
| publishDate | 2015 |
| publisher | John Wiley and Sons Ltd |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | curtin-20.500.11937-43822019-02-19T05:34:53Z ß-Methylphenylethylamines: Common fragmentation pathways with amphetamines in electrospray ionization collision-induced dissociation Brown, David Hansson, R. Oosthuizen, F. Sumner, N. 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. 2015 Journal Article http://hdl.handle.net/20.500.11937/4382 10.1002/dta.1816 John Wiley and Sons Ltd fulltext |
| spellingShingle | Brown, David Hansson, R. Oosthuizen, F. Sumner, N. ß-Methylphenylethylamines: Common fragmentation pathways with amphetamines in electrospray ionization collision-induced dissociation |
| title | ß-Methylphenylethylamines: Common fragmentation pathways with amphetamines in electrospray ionization collision-induced dissociation |
| title_full | ß-Methylphenylethylamines: Common fragmentation pathways with amphetamines in electrospray ionization collision-induced dissociation |
| title_fullStr | ß-Methylphenylethylamines: Common fragmentation pathways with amphetamines in electrospray ionization collision-induced dissociation |
| title_full_unstemmed | ß-Methylphenylethylamines: Common fragmentation pathways with amphetamines in electrospray ionization collision-induced dissociation |
| title_short | ß-Methylphenylethylamines: Common fragmentation pathways with amphetamines in electrospray ionization collision-induced dissociation |
| title_sort | ß-methylphenylethylamines: common fragmentation pathways with amphetamines in electrospray ionization collision-induced dissociation |
| url | http://hdl.handle.net/20.500.11937/4382 |