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Comparative chemical ionization mass spectra of tricyclic antidepressant amines and related compounds
Author(s) -
Schildcrout Steven M.,
Geidner Robert M.
Publication year - 1989
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210240408
Subject(s) - chemistry , mass spectrum , chemical ionization , electron ionization , protonation , ion , polyatomic ion , medicinal chemistry , organic chemistry , ionization
Positive‐ion methane chemical ionization (CI) mass spectra were obtained for seven underivatized tricyclic amines: amitriptyline, nortriptyline, protriptyline, imipramine, desipramine, cyclobenzaprine and cyproheptadine. Some discrepancies in previously reported spectra were noted. Spectra of protriptyline, cyclobenzaprine and cyproheptadine are reported for the first time. Comparisons are made among the CI spectra and with electron ionization spectra, and relative abundances of major CI ions among the seven compounds are rationalized in terms of substituent and geometric effects. In most cases low‐mass iminium ions from anion abstraction were more abundant than [MH] + . Hydride abstraction and adduct formation with reagent‐gas ions were important. The three heterocyclic amines gave abundant [M] + ˙ by electron transfer. Protonation at the nitrogen atom on the side chain followed by amine elimination gave tricyclic aromatic fragment ions.