Mass spectral studies on aryl‐substituted N‐carbamoyl/N‐thiocarbamoyl narcotine and related compounds

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Abstract
Positive ion mass spectral fragmentation of new N‐carbamoyl/N‐thiocarbamoyl derivatives of narcotine and compounds closely related to it are reported and discussed. The techniques used include electron impact (EI), fast‐atom bombardment (FAB), matrix‐assisted laser desorption/ionization time‐of‐flight (MALDI‐TOF) and electrospray ionization tandem mass spectrometry (ESI‐MS/MS). Prominent peaks in the mass spectra of these compounds appear to involve C‐C bond cleavage β to the amine nitrogen with loss of the 4,5‐dimethoxy(1H)isobenzofuranone moiety from their molecular ions, along with another prominent peak at m/z 382. No molecular ion peaks of these compounds were recorded in EI, whereas intense [M + H]+ ion peaks were observed in FAB and ESI spectra. MALDI also yielded [M + H]+ ion peaks in good agreement with FAB and ESI studies. Copyright © 2002 John Wiley & Sons, Ltd.