期刊
EUROPEAN JOURNAL OF MASS SPECTROMETRY
卷 18, 期 3, 页码 287-299出版社
SAGE PUBLICATIONS LTD
DOI: 10.1255/ejms.1185
关键词
methamphetamine; derivatisation; perfluoroacylation; phenethylamine regioisomers; mass spectrometry
资金
- US Department of Justice, Office of Justice Programs, National Institute of Justice [2006-DN-BX-K016]
The mass spectra of the perfluoroacyl derivatives of methamphetamine show a unique and characteristic fragment ion identified as the N-methylperfluoroatkylnitrile cation (CnF2n+1CNCH3)(+). This ion appears at various m/z values depending on the nature of the perfluoroacyl species and is generated via rearrangement of the perfluoroacyl immonium fragment formed by loss of the benzyl-radical from the molecular ion. Analogous ions have been described in the mass spectra of other methamphetamine-like side chain substances regardless of the aromatic ring substitution pattern. The scope and limitation of this rearrangement pathway were evaluated in this study by preparing a set of substituted phenethylamines and related compounds of varying structure. The perfluoroacyl moiety leads to the formation of the highest abundance of the N-methyl nitrite cation fragment while hydrocarbon acyl groups do not show the N-methylnitrile cation as a significant peak. The N-methyl group is required for the formation of the N-methyl nitrite cation and higher N-alkyl homologues eliminate the corresponding alkene species from the acyl immonium fragment. The loss of benzaldehyde and acetone from the perfluoroacylimmonium species produces the highest relative abundance of the unique N-methylperfluoroalkylnitrile cation.
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