Metabolism of polycyclic compounds. 25. The metabolism of anthracene and some related compounds in rats

Abstract

Anthracene is converted by rats into trans-1, 2-dihydro-1, 2-dihydroxy- and 1, 2-dihydroxyanthracene which are excreted mainly as sulfuric acid and glucuronic acid conjugates. 1-and 2-Hydroxyanthracene, either free or conjugated, are not present as urinary metabolites. N-Acetyl-S-(1, 2-dihydro-2-hydroxy-l-an-thryl)cysteine is excreted and decomposed by mineral acid to give 1-anthrylmercapturic acid, 1-and 2-hydroxyanthracene, and anthracene. Anthracene is converted into trans-9, 10-dihydro-9, 10-dihydrox-yanthracene by rats. The cis-dihydrodihydroxy compound was also identified, but it could have been formed as an artifact during the enzymic hydrolysis of the glucuronic acid conjugate of the trans-isomer. 2-Hydroxy-9, 10-anthraquinone, anthrone and conjugates of 9-hydroxy-, 9, 10-dihydroxy- and 2, 9, 10-trihydroxyanthracene, which were metabolic products of the trans-isomer in rats, were also detected in the urine of rats treated with anthracene. 9, 10-Anthra-quinone and anthrone were metabolized by rats to 2-hydroxy-9, 10-anthraquinone and conjugates of 9-hydroxy-, 9, 10-dihydroxy- and 2, 9, 10-trihydroxy-anthracene; 9, 10-anthraquinone also yielded anthrone and the sulfuric ester of 2-hydroxy-9, 10-anthraquinone.