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A Mass Spectrometric Investigation of Some Tricyclic Antidepressants and Their Synthons

✍ Scribed by Albion Rubello; Giulio Volpe; Donato Favretto; Pietro Traldi

Publisher: John Wiley and Sons
Year: 1996
Tongue: English
Weight: 456 KB
Volume: 10
Category: Article
ISSN: 0951-4198
DOI: 10.1002/(sici)1097-0231(19960715)10:9<1097::aid-rcm580>3.0.co;2-0

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✦ Synopsis

The electron impact and fast-atom bombardment mass spectrometric behaviour of five tricyclic antidepressants (desipramine, imipramine, clomipramine, trimipramine and lofepramine) and of their synthons (iminodibenzyl and 3-chloroiminodibenzyl) have been studied in detail with the aid of metastable-ion studies, deuterium labelling experiments and accurate mass measurements. Electron ionization leads to spectra mainly comprising fragments related to the alkyl-amino chain, when present. The two synthons exhibit molecular species in an isomeric form. The comparison of fast-atom bombardment mass spectra of the free bases with those of their corresponding hydrochlorides reveals unusual differences indicating that the protonation mechanism occurring in the gas phase is somehow different from the one taking place in solution.

Scheme 1

The tricyclic psychotherapeutic drugs are particularly effective for the treatment of psychiatric disorders, e.g. mania and schizophrenia.' The first synthesized and suct

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