Structural characterization of the urinary metabolites of iprindole in rat

Abstract

1. The in vivo metabolism of iprindole in rat is described. Each rat received a single dose of iprindole (10 mg/kg) and urine was collected for 48 h. 2. Fourteen metabolites of iprindole were isolated from rat urine after enzymic hydrolysis and their structures were determined by a computerized g.l.c.-mass spectrometric technique, before and after appropriate chemical derivatization. 3. Three concurrent metabolic pathways have been identified for iprindole in rat; aromatic ring hydroxylation is a minor pathway. 4. This is the first reported comprehensive study on the in vivo metabolism of iprindole in rat.

Non-innocuous Consequences of Metabolic Oxidation of Alkyls on Arenes

“…Another 3-alkylindole, iprindole ( 54 , Chart ), was in the 1960–70s a licensed anti­depressant that gave rise to drug–drug interactions. In vivo metabolism gives rise to extensive hydroxyl­ations in the cyclo-octane ring, which clearly have potential for forming RMs of the discussed types. Mechanistically, however, based on the above examples of 3-methyl­indole and NVP ( 4 ), direct dehydrogenation to give methylene­indoles as RMs is clearly plausible as well.…”