Metabolism of polycyclic compounds. 7. The metabolism of naphthalene, 1-naphthol and 1:2-dihydroxy-1:2-dihydronaphthalene by animals

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Abstract
1-Naphthol injd. into animals is mostly excreted either as free naphthol, naphthylsulfuric acid or naphthylglucuronide. The naphthol excreted is readily extracted from the neutral urine with ether. l,2-Dihydroxy-l,2-dihydronaphthalene (napthalenediol) injd. into animals is largely broken down, partly excreted unchanged, partly coverted to free 1-naphthol, naphthylsulfuric acid and a glucuronide liberating 1-naphthol on hydrolysis. About 20% of injd. naphthalene is excreted either as free 1-naphthol, naph-thalenediol, naphthylsulfuric acid or glucuronides. With repeated dosing of naphthalene to male rats the proportion of diol excreted increases, while the amt. of the glucuronide fraction (estimated as such or by the naphthol liberated on prolonged hydrolysis) decreases. The converse effect of decrease in diol excretion with increase in the glucuronide fraction was seen on repeated dosage of female rats. Only a small proportion of the 1-naphthol present in urine of animals dosed with naphthalene-diol or with naphthalene was not extracted from neutral urine by ether. These findings are discussed in relation to naphthalene metabolism.