Structures and Mutagenic Properties of Products Obtained by C‐Nitrosation of Opipramol

Abstract

Reaction of the tricyclic psychotropic drug opipramoi (1) with an excess of HNO, affords a product mixture mutagenic for Salmonella typhimurium. The main product is a tetracyclic furoxan 2 (yield ca. 80%), resulting from nitrosation at C(10) and C(11) of 1. Compound 2 is not mutagenic. The essential mutagen is a nitroarene 3 formed via contraction of the central ring of 1, and nitrosation at C(2). Its yield is extremely low ( < 0.1 %). Nitroarenes have previously not been encountered as mutagenic products o f the interaction of drugs with nitrite.

Mechanism of the oxidative degradation of dibenzoazepine derivatives via manganese(III) complexes in acidic phosphate media

“…The radical and intermediate products were detected using EPR, 1 H NMR and 13 C NMR and these results were discussed in detail in our earlier study [25,26] (product 2, Scheme 1), which was different from the C-nitrosation reaction of opipramol [27]. Acridine belongs to a group of nitrogen-containing heterocyclic PAH molecules, which have recently been suggested as possible causes for the spectra observed for interstellar medium, including the unidentified IR emission bands and diffuse interstellar bands [28,29].…”