The metabolic interconversion of arecoline and arecoline 1-oxide in the rat.
1. Tritiation of arecoline hydrochloride by catalytic exchange in aqueous media (done by The Radiochemical Centre) gave arecaidine hydrochloride of high specific radioactivity; this on treatment with diazomethane gave [(3)H]arecoline, which was oxidized with peroxyacetic acid to [(3)H]arecoline 1-oxide. 2. Arecoline 1-oxide gave arecaidine 1-oxide on acid hydrolysis and 1,2-dihydro-1-methylnicotinic acid methyl ester on thermal decomposition. 3. [(3)H]Arecoline hydrochloride was metabolized in the rat into the (3)H-labelled derivatives of arecoline 1-oxide, arecaidine 1-oxide, arecaidine, N-acetyl-S-(3-carboxy-1-methylpiperid-4-yl)-l-cysteine and an unidentified metabolite; some unchanged arecoline was also excreted. [(3)H]Arecoline 1-oxide gave the same metabolities, but in different amounts. 4. The possible relevance of these findings to betel-nut carcinogenesis is discussed.
D000818:Animals; D002845:Chromatography; D002849:Chromatography, Gas; D004247:DNA / Q000032:analysis; D003978:Diazomethane; D004952:Esters / Q000378:metabolism; D005260:Female; D006868:Hydrolysis; D008099:Liver / Q000032:analysis / Q000378:metabolism; D009539:Nicotinic Acids / Q000378:metabolism* / Q000494:pharmacology; D010084:Oxidation-Reduction; D011506:Proteins / Q000032:analysis; D012313:RNA / Q000032:analysis; D051381:Rats; D013696:Temperature; D014316:Tritium
D004952:Esters; D009539:Nicotinic Acids; D011506:Proteins; D014316:Tritium; D003978:Diazomethane; D012313:RNA; D004247:DNA