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Electron ionization mass spectra of ephedrines in a doping confirmatory procedure: a curious migration of the trimethylsilyl group in the N ‐acetyl‐ O ‐trimethylsilyl derivatives
Author(s) -
de Oca Porto Rodny Montes,
Pérez Arístides Rosado,
Correa Vidal Margarita Teresa
Publication year - 2007
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.3028
Subject(s) - chemistry , trimethylsilyl , pseudoephedrine , ephedrine , mass spectrum , electron ionization , chromatography , acetic anhydride , gas chromatography , mass spectrometry , ether , chemical ionization , organic chemistry , ionization , medicinal chemistry , ion , analytical chemistry (journal) , biology , neuroscience , catalysis
Abstract Ephedrines have central nervous system stimulating properties and, for this reason, some of them are forbidden in sport by the World Antidoping Agency (WADA). They are screened and quantitated in urine by several published techniques and confirmed by gas chromatography/mass spectrometry (GC/MS). In this paper, a simple confirmation procedure for norpseudoephedrine, norephedrine, ephedrine and pseudoephedrine in human urine by GC/electron ionization (EI)‐MS is described. After the addition of levallorphane as internal standard, a liquid‐liquid extraction procedure under alkaline conditions with tert ‐butyl methyl ether was applied to the samples. The analytes were derivatized with acetic acid anhydride and N ‐methyl‐ N ‐trimethylsilyltrifluoroacetamide to form N ‐acetyl‐ O ‐trimethylsilyl derivatives. The EI mass spectra of all the studied substances have many diagnostic ions with relative abundance in accordance with WADA requirements and show great structural information content. A curious migration of the trimethylsilyl group is proposed. Copyright © 2007 John Wiley & Sons, Ltd.