Methylthio metabolites of naphthalen excreted by the rat.
Eight methylthio metabolites have been found as urinary products of the metabolism of naphthalene in the rat. One was 1-methylthionaphthalene. A second was a methylthio analog and the dihydrodiol, and a third was naphthalene substituted with one hydroxyl and one methylthio group. Two compounds with common structural elements were found; one of these was prepared by synthesis from anti-1,2:3,4-naphthalene dioxide and one from 1 beta, 2 alpha-dithyroxy-3 alpha, 4 alpha-epoxy-1,2,3,4-tetrahydronaphthalene by reaction with 2-keto-4-methylthiobutyric acid or with methionine. Each of these compounds contained one methythio group and three hydroxyl groups substituted on a tetrahydronaphthalene structure. Two metabolites with two methylthio groups and two hydroxyl substituents on a tetrahydronaphthalene ring were also detected; one of these was prepared by synthesis from the dioxide. The most likely metabolic origin of these methylthio metabolites is through the reaction of epoxides (including the diepoxide) with a nucleophile which may be methyl mercaptan, 2-keto-4-methylthiobutyric acid, or methionine.
D000818:Animals; D002087:Butyrates; D055598:Chemical Phenomena; D002621:Chemistry; D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D004852:Epoxy Compounds / Q000138:chemical synthesis; D008297:Male; D013058:Mass Spectrometry; D008715:Methionine; D009281:Naphthalenes / Q000652:urine*; D051381:Rats
D002087:Butyrates; D004852:Epoxy Compounds; D009281:Naphthalenes; D008715:Methionine