Metabolism of polycyclic compounds. 16. The metabolism of 1:2-dihydronaphthalene and 1:2-epoxy-1:2:3:4-tetrahydronaphthalene

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Abstract
The action of L-cysteine on l,2-epoxy-l,2,3,4-tetrahydronaphthalene in neutral solution or on 2-bromo-l-hydroxy-l,2,3,4-tetrahydronaphthalene in alkaline solution yielded in each case the 2 isomeric forms of S-(2-hydroxy-1,2,3,4-tetrahydro-l-naphthyl)-L-cysteine. The epoxide and N-acetylcysteine similarly gave 2 isomeric forms of N-acetyl-s-(2-hydroxy-1,2,3,4-tetrahydro-l-naphthyl)-L-cysteine, which were also obtained by the acetylation of the cysteine derivatives. Rabbits treated with either 1,2-dihydronaphthalene or l,2-epoxy-l,2,3,4-tetrahydronaphthalene excrete both the optical isomers of trans-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene and one of the 2 isomers of N-acetyl-S-(2-hydroxy-l,2,3,4-tetrahydro-l-naphthyl)-L-cysteine, together with small amounts of S-(2-hydroxy-l,2,3,4-tetrahydro-l-naphthyl)-L-cysteine and a substance believed to be a S-(2-hydroxy-l,2,3,4-tetra-hydro-l-naphthyl)-cysteinylglycine derivative. A glucosiduronic acid of trans-1,2-dihydro-1,2,3,4-tetrahydronaphthalene was also present. Small amounts of all the known naphthalene metabolites were also present in the urine of rabbits after administration of 1,2-dihydronaphthalene.