Mercapturic acid formation from sodium alkyl sulphates in the rat.
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Biomedical subjects
Publications and source records attributed to L Young.
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1. Benzylmercapturic acid and hippuric acid were isolated from the urine of rats that had been injected subcutaneously with benzyl acetate. 2. 1-Menaphthylmercapturic acid and 1-naphthoic acid were isolated from the urine of rats after the subcutaneous injection of each of the following compounds: 1-menaphthyl alcohol and its acetate, propionate, butyrate and benzoate esters. 3. A quantitative method for determining 1-menaphthylmercapturic acid in urine was developed and used to measure the excretion of this compound in the urine of rats in the 4-day period after the subcutaneous injection of 1-menaphthyl alcohol and its acetate, propionate, butyrate and benzoate esters. 4. Chromatographic evidence was obtained for the presence of S-(1-menaphthyl)glutathione and S-(1-menaphthyl)-l-cysteine in bile collected from rats with cannulated bile ducts after the animals had been injected subcutaneously with each of the following compounds: S-(1-menaphthyl)glutathione, 1-menaphthyl acetate, propionate and butyrate. 5. Benzylmercapturic acid and 1-menaphthylmercapturic acid were isolated from the urine of rats that had been injected with sodium benzyl sulphate and sodium 1-menaphthyl sulphate respectively.
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1. Various derivatives of 1- and 2-methylnaphthalene, of the type C(10)H(7).CH(2)X, were administered to rats and the urines of the dosed animals were examined for the presence of 1- and 2-menaphthylmercapturic acid by chromatographic and isolation procedures. A similar, but more limited, series of experiments was carried out with rabbits. 2. All the compounds were administered by subcutaneous injection with the exception of S-(1- and 2-menaphthyl)-l-cysteine, which were added to the food. 3. 1-Menaphthylmercapturic acid was isolated from the urine of rats after the administration of 1-menaphthyl chloride, bromide, alcohol, acetate and benzoate, S-(1-menaphthyl)-l-cysteine and S-(1-menaphthyl)glutathione. 4. 2-Menaphthylmercapturic acid was isolated from rat urine after administration of 2-menaphthyl chloride, S-(2-menaphthyl)-l-cysteine and S-(2-menaphthyl)-glutathione, and was detected chromatographically after injecting 2-menaphthyl bromide. 5. The corresponding mercapturic acids were isolated after administering 1- and 2-menaphthyl chloride and 1-menaphthyl acetate to rabbits, but not after giving 1- and 2-menaphthyl bromide and 1-menaphthyl alcohol, although chromatographic evidence of mercapturic acid excretion was obtained after injecting these compounds.
1. A premercapturic acid, i.e. a compound that yields a mercapturic acid when decomposed by acid, was isolated as a dicyclohexylammonium salt from the urine of rats and rabbits that had been dosed with bromobenzene. 2. Another premercapturic acid was isolated as its dicyclohexylammonium salt from the urine of rats that had been dosed with chlorobenzene. 3. When decomposed by acid, the premercapturic acid from the urine of animals dosed with bromobenzene gave p-bromophenylmercapturic acid, m-and p-bromophenol and NN'-diacetylcystine. 4. The premercapturic acid derived from chlorobenzene gave the corresponding chloro compounds together with NN'-diacetylcystine when decomposed by acid. 5. On the basis of these and other observations it is suggested that the premercapturic acid formed in the metabolism of bromobenzene is N-acetyl-S-(4-bromo-1,2-dihydro-2-hydroxyphenyl)-l-cysteine. 6. It is also suggested that the premercapturic acid derived from chlorobenzene has an analogous structure.
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1. The metabolism of cis- and trans-acenaphthene-1,2-diol has been studied after the administration of these compounds to rats by subcutaneous injection and by stomach tube. 2. 1,8-Naphthalic acid has been isolated as its anhydride from the urine of the dosed animals. 3. A spectrophotometric method for the determination of free and conjugated 1,8-naphthalic acid in urine has been developed and has been used in the study of the metabolism of the acenaphthene-1,2-diols. 4. The urine of rats dosed with cis-acenaphthene-1,2-diol by subcutaneous injection was shown by paper chromatography to contain both cis- and trans-acenaphthene-1,2-diol. Similar findings were obtained after the subcutaneous injection of trans-acenaphthene-1,2-diol.