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Urinary Metabolites of 2-Acetylaminofluorene and Related Compounds in the Rhesus Monkey^*

Makoto Enomoto, Prabhakar Lotlikar, James A. Miller and Elizabeth C. Miller

( McArdle Memorial Laboratory for Cancer Research and Department of Pathology, Medical School, University of Wisconsin, Madison, Wisconsin)

The urinary metabolites of 2-acetylaminofluorene (AAF) and related compounds were determined by paper chromatography after oral administration to young, adult, female monkeys (Macacus rhesus). AAF, N-hydroxy-AAF, and 2-aminofluorene each gave rise to AAF and conjugates of N-hydroxy-AAF and 7-hydroxy-AAF in the urine. Thus the rhesus monkey has the ability to hydroxylate AAF on the nitrogen and 7-carbon atoms, to reduce N-hydroxy-AAF to AAF, and to N-acetylate 2-aminofluorene. No 1-, 3-, or 5-hydroxy derivatives of AAF were detected in these urines. Only small amounts of 1- and 3-hydroxy-AAF were excreted in the urine when large amounts of these respective compounds were fed. N-Hydroxy-AAF was isolated in crystalline form from the urine after administration of AAF by a procedure which involved the intermediate isolation of the poorly soluble cupric chelate of N-hydroxy-AAF.

4-Aminobiphenyl appeared to be metabolized by the rhesus monkey to yield small amounts of N-hydroxy-4-acetylaminobiphenyl in the urine. Ingestion of either 2-aminonaphthalene or its N-acetyl derivative appeared to give a trace of a urinary metabolite with the properties of the corresponding N-hydroxy-N-acetyl derivative.

^* This investigation was supported by Grants C355 and HE-06287 of the National Institutes of Health, United States Public Health Service; a grant from the Jane Coffin Childs Memorial Fund for Medical Research; and by the Alexander and Margaret Stewart Trust Fund. We are grateful to Mrs. JoEllen McDowell of the Wisconsin Primate Center for valuable technical assistance.

On leave from the Department of Pathology, University of Tokyo. International Postdoctoral Research Fellow, U.S. Public Health Service, 1961–62.

Received 7/16/62.