Metabolism of derivatives of toluene. 6. Tolunitriles, benzonitrile and some related compounds

Abstract

O-Tolunitrile gives rise in rabbits to phthalide and phthalic acid and increases the excretion of ethereal sulfate. m-and p-Tolunitriles are excreted almost entirely as ether-soluble acid; p-Cyanobenzoic and p-cyanohippuric acids and a small amt. of terephthalamic acid were isolated after giving p-tolunitrile. The only metabolite of m-tolunitrile detected was m-cyanobenzoic acid. At least a fifth of a dose of benzonitrile was excreted as ethereal sulfate; o-and m-cyanophenols were detected by paper chromatography of ether extracts; and in some expts. large amts. of reducing material were also excreted. m-Cyanobenzoic acid was ex-creted unchanged; no glycine conjugation could be detected. p-Cyanobenzoic acid was excreted mainly unchanged, but was conjugated to a small extent with glycine. p-Cyanohippuric acid was excreted mainly as p-cyanobenzoic acid, with no detectable glycine conjugation. Phthalic anhydride and phthalic acid were isolated after admn. of phthalamic acid, only unchanged terephthalamic acid after giving terephthalamic acid.