EPOXIDE INTERMEDIATES IN THE METABOLISM OF NAPHTHALENE BY THE RAT

  • 1 January 1980
    • journal article
    • research article
    • Vol. 8  (6) , 404-414
Abstract
Oxygenated metabolites (21) of naphthalene [insecticide] were isolated from rat urine, and were characterized by gas chromatography and gas chromatography-mass spectrometry [GC-MS]. Studied with naphthalene-1,4-dideuteronaphthalene confirmed that the compounds characterized by GC/MS were derived from naphthalene. Structures of a number of metabolites were confirmed by synthesis. All but one were formed by processes involving epoxidation, and structures of metabolites supported the hypothesis that multiple epoxides and a cyclic peroxide were involved in in vivo metabolism of naphthalene by rat. Anti-diepoxide of naphthalene was a mammalian metabolite. Ten methylthio metabolites were isolated in earlier studies. Excluding mercapturic acids, conjugates and related compounds, total number of isolated compounds was 31 and several additional compounds must have been present as intermediates. Structures of epoxide intermediates were indicated by precursor-product relationships.