The metabolism of tetralin.
1. [1-(14)C]Tetralin was synthesized and fed to rabbits. 2. Of the radioactivity, 87-90% was excreted in the urine within two days and 0.5-3.7% on the third day. The faeces contained 0.6-1.8%. No radioactivity was found in the breath and negligible amounts were retained in the tissues. About 90-99% of an administered dose was accounted for. 3. The main metabolite in the urine was the glucuronide of alpha-tetralol (52.4%). Other conjugated metabolites were beta-tetralol (25.3%), 4-hydroxy-alpha-tetralone (6.1%), cis-tetralin-1,2-diol (0.4%) and trans-tetralin-1,2-diol (0.6%). 4. beta-Tetralone, alpha-naphthol, 1,2-dihydronaphthalene and naphthalene, previously reported as metabolites, are artifacts, and tetralin, alpha-tetralone, beta-naphthol, 5-hydroxytetralin, and 6-hydroxytetralin are not metabolites. 5. The major metabolite of tetralin, alpha-tetralol and alpha-tetralone is the glucuronide of alpha-tetralol, which was isolated as methyl (1,2,3,4-tetrahydro-1-naphthyl tri-O-acetyl-beta-d-glucosid)uronate; the major metabolite of beta-tetralol and beta-tetralone is the glucuronide of beta-tetralol, which was characterized as methyl (1,2,3,4-tetrahydro-2-naphthyl tri-O-acetyl-beta-d-glucosid)uronate. 5-Hydroxytetralin is conjugated with glucuronic acid, and was characterized as methyl (5,6,7,8-tetrahydro-1-naphthyl tri-O-acetyl-beta-d-glucosid)uronate. 6-Hydroxytetralin is conjugated with glucuronic acid, and was characterized as methyl (5,6,7,8-tetrahydro-2-naphthyl tri-O-acetyl-beta-d-glucosid)uronate. 6. A metabolic sequence accounting for the observed biological transformation products is proposed.
D000818:Animals; D001345:Autoradiography; D002245:Carbon Dioxide / Q000378:metabolism; D055598:Chemical Phenomena; D002621:Chemistry; D002854:Chromatography, Paper; D002855:Chromatography, Thin Layer; D005243:Feces / Q000032:analysis; D005260:Female; D005965:Glucuronates / Q000378:metabolism* / Q000652:urine; D009281:Naphthalenes / Q000378:metabolism* / Q000652:urine; D009905:Optical Rotatory Dispersion; D011817:Rabbits; D011865:Radioisotope Dilution Technique; D013053:Spectrophotometry
D005965:Glucuronates; D009281:Naphthalenes; D002245:Carbon Dioxide