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Fragmentation patterns of novel dispirocyclopiperazinium dibromides with strong analgesic activity under electrospray ionization tandem mass spectrometry conditions
Author(s) -
Wang Xin,
Sha Yaowu,
Li Runtao
Publication year - 2004
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.1407
Subject(s) - chemistry , fragmentation (computing) , tandem mass spectrometry , electrospray ionization , mass spectrometry , ion , hydrogen bromide , tandem , bromide , polyatomic ion , electrospray , medicinal chemistry , analytical chemistry (journal) , computational chemistry , stereochemistry , chromatography , organic chemistry , bromine , materials science , computer science , composite material , operating system
The fragmentation patterns of a series of dispirocyclopiperazinium dibromides with strong analgesic activity are analyzed by positive ion electrospray ionization mass spectrometry in conjunction with tandem mass spectrometry (ESI‐MS n ). Instead of the parent molecular ions, the fragment ions [MBr] + are detected as characteristic double peaks and usually the base peaks. Meanwhile, the fragment ions [M2Br] 2+ are unique for this series of diquaternary ammonium dibromides and show high intensity. Besides the common fragmentation patterns around the carbonyl group, elimination of hydrogen bromide from [MBr] + ions is another important pathway. Following the elimination, an interesting rearrangement takes place in the unsaturated spirocyclopiperazine and transforms it into a dihydropyrrole structure, whose fragmentations are similar to its precursor ion in the succeeding steps. Copyright © 2004 John Wiley & Sons, Ltd.