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AROMATIC AMINES: An Assessment of the Biological and Environmental Effects ~ . Committee on Amines Board on Toxicology and Environmental Heath Hazards Assembly of tie Sciences National Research Council NATIONAL ACADEMY PRESS Washington, D.C. 1981

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NOTICE: The project that is the subject of this report was approved by the Governing Board of the National Research Council, whose members are drawn from the Councils of the National Academy of Sciences, the National Academy of Engineer ing, and the Institute of Medicine. The members of the Committee responsible for the report were chosen for their competences and with regard for appropriate ba lance . This report has been reviewed by a group other than the authors according to procedures approved by a Report Review Committee consisting of members of the National Academy of. Sciences. the National Academy of Engineering, and the Institute of Medicine. The National Research Council was established by the National Academy of Sciences in 1916 to associate the broad community of sc fence and technology wi th the Academy ' s purposes of furthering knowledge and of advertising the federal government. me Council operates in accordance wi th general policies determined by the Academy under the authority of its Congressional charter of 1863, which establishes the Academy as a private, non-profit, self-governing membership corporation. me Council has become the pr incipal operating agency of both the Academy of Sciences and the National Academy of Engineering in the conduct of their services to the government, the public, and the scientific and engineering communities. It is administered jointly by both Academies and the Institute of Medicine. The Academy of Engineering and the Institute of Medicine were established in 1964 and 1970, respectively, under the charter of the Academy of Sciences. At the request of and funded by the U. S . Environmental Protection Agency, Contract No. 68-01-465 5 11

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List of Par ticipants COMMITTEE ON AMTNES DAVID B. CLAYSON, University of Nebraska Medical Center, ~ha, Nebraska, Ma irman GEORGE T. BRYAN, University of Wisconsin, Center for Health Sciences. Madison, Wisconsin DAVID H. FINE, New England Institute for Life Sciences, Waltham, Massachusetts CHARLES C. IRVING, Veterens Administration, Center for Bealth Sciences, Hemphi s, Tennessee CHA=ES H. KING, Michigan Cancer Foundation, Detroit, Michigan RICHARD MONSON, Harvard School of Public Health, Boston, Massachusetts JACK L. RADOMSKI, University of Miami, Miami, Florida DONALD H. STEDMAN, University of Michigan, Ann Arbor, Michigan STEVEN R. TANNENBAUM, Massachusetts Institute of -technology, Cambridge, Massachusetts SNORRI S. THORGEIRSSON, National Cancer Institute, Bethesda, Maryland JOHN H. WEIS8UPK;ER, Taylor Dana Institute, Valbella, New York ERROL ZEIGER, National Institute of Environmental Health Sciences, Research Triangle Park, North Carolina Consultants - EMERICH FIALA, Naylor Dana Institute, Valhalla, New York MALCOLM C. BOWMAN, National Center for Toxicological Research, Jef fer son, Arkansas National Research Council Staff ROBERT J . GOLDEN, Pro j eat Director FRENCES M. PETER, Editor EPA Project Officer ALAN CARLIN, Of f ice of Research and Development, U. S. Environmental Protect ion Agency, Washington, D.C. .

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BOARD ON TOXICOLOGY AND ENVIRONMENTAL HEALTH HAZARDS RONALD W. ESTABROOK, University of Texas Medical School (Southwestern), Dallas, Texas, Chairman , THEODORE CAIRNS, DuPont Chemical Co. (retired), Greenville, Delaware VICTOR COHN, George Washington University Medical Center, Washington, D.C. JOHN W. DRAKE, National Institute of Environmental Health Sciences, Research Triangle Park, North Carolina ALBERT M. FREEMAN, Bowdoin College, Brunswick, Maine RICHARD HALL, McCormick & Company, Hunt Valley, Maryland RONALD W. HART, National Center for Toxicological Research, Jef fer son, Ar kansas PHILIP LANDRIGAN, National Institute for Occupational Safety and Health, Cincinnati, Ohio MICHAEL LIEBERMAN, Washington University School of Medicine, St. Louis, Missour i BRIAN MacMAHON, Harvard School of Public Health, Boston, Ma ssachusetts RICHARD MERRILL, University of Virginia, Charlottesville, Virginia ROBERT A. NEAL, Chemical Industry Institute of Toxicology, Research Triangle Park, North Carolina IAN NISBET, Massachusetts Audubon Society, Lincoln, Massachusetts CHARLES R. SCHUSTER, JR. , University of Chicago, Chicago, Illinois GERALD WOGAN, Massachusetts Institute of Technology, Cambridge, Massachusetts ROBERT G. TARDIFF, National Research Coincil, Washington, D.C., Execut ive Director iv

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CONTENTS Execut ive ~ '~= -~, PAGE: CHAPTER 1 - Control, Occurrence, and Identif ication 23 CHAPTER 2 - Metabolism of Aromat ic Amines 40 CHAPTER 3 - Structure-Activity Relationships Among The Carcinogen ic Aromatic Amines. . ~ . . . e ~ ~ ~ ~ ~ ~ e ~ ~ ~ ~ ~ ~ 60 CHAPTER 4 - Carcinogenic Potency and Risk Estimation 86 CHAPTER 5 - Epidemiolog ic Aspects of Exposure to Aromatic AIT ines. e e e e ~ e e ~ e e ~ e e ~ ~ ~ ~ ~ ~ ~ ~ e a.~e CHAPTER 6 Anilineeeeee.. CHPATER 7 ~ 4 ~ 4 t-Methylene-Bis (2-Chloroaniline) CHAPTER 8 - 2, 4-Diaminotoluene ~ e CHAPTER 9 - Trifluralin and CHAPTER 10 - ~ ~ ~ A; _~ CHAPTER 11 FurazOlidOnee e e e e ~ ~ ~ ~ ~ e e ~ e ~ e ~ ~ ~ ~ e ~ e ~ e e ~ ~ e ~ e e e ~ ~ ~ ~ v 102 123 168 198 228 274 288

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