Identification of urinary metabolites of 2-isopropylnaphthalene in rats

Metabolism of 2-isopropylnaphthalene in rats was found to proceed through the oxidation of the isopropyl chain of the molecule. Four unconjugated metabolites were isolated from the urine and identified: 2-(2-naphthyl)propionic acid, 2-(2-naphthyl)-2-propanol, 2-(2-naphthyl)-1,2-propanediol, and 2-(2-naphthyl)-2-hydroxypropionic acid, together with a small amount of the unchanged compound. Identification was made by means of mass, infrared, and nuclear magnetic resonance spectroscopy. The presence of glucuronides of four metabolites described above was also suggested by thin-layer and gas-liquid chromatography of the extract that was obtained after enzymatic hydrolysis.