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Nitrogen and Phosphorus Solvents PDF

483 Pages·1990·11.571 MB·English
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SERIES EDITOR: R. SNYDER Ethel Browning's Toxicity and Metabolism of Industrial Solvents SECOND EDITION VOLUME II: Nitrogen and Phosphorus Solvents EDITORS: D.R. BUHLER Chairman, Toxicology Program, Oregon State University, Corvallis, OR 97331 DJ. REED Professor of Biochemistry, Director Environmental Health Sciences Center, Oregon State University, Corvallis, OR 97331 1990 ELSEVIER Amsterdam - New York - Oxford © 1990, Elsevier Science Publishers B.V. (Biomedical Division) All rights reserved. No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, recording or otherwise, without the prior written permission of the Publisher, Elsevier Science Publishers B.V. (Biomedical Division), P.O. Box 1527, 1000 BM Amsterdam, The Netherlands. No responsibility is assumed by the Publisher for any injury and/or damage to persons or property as a matter of products liability, negligence or otherwise, or from any use or operation of any methods, products, instructions or ideas contained in the material herein. Because of the rapid advances in the medical sciences, the Publisher recommends that independent verification of diagnoses and drug dosages should be made. Special regulations for readers in the U.S.A. This publication has been registered with the Copyright Clearance Center, Inc. (CCC), Salem, Massachusetts. Information can be obtained from the CCC about conditions under which the photocopying of parts of this publication may be made in the USA. All other copyright questions including photocopying outside the USA, should be referred to the Publisher. ISBN 0-444-81316-0 (volume) ISBN 0-444-90434-4 (series) Published by: Sole distributors for the USA and Canada: Elsevier Science Publishers B.V. Elsevier Science Publishing Company, Inc. (Biomedical Division) 655 Avenue of the Americas P.O. Box 211 New York, NY 10010 1000 AE Amsterdam USA The Netherlands Printed in The Netherlands Editorial board R. SNYDER, Ph.D., Chief Editor, Rutgers-The State University of New Jersey, Piscataway, NJ M.A. GALLO, Ph.D., UMDNJ/Robert Wood Johnson Medical School, Piscataway, NJ B.D. GOLDSTEIN, M.D., UMDNJ/Robert Wood Johnson Medical School, Piscataway, NJ D.B. MENZEL, Ph.D., Duke University, Durham, NC DJ. REED, Ph.D., Oregon State University, Corvallis, OR D.R. BUHLER, Ph.D., Oregon State University, Corvallis, OR I.G. SIPES, Ph.D., University of Arizona, Tucson, AZ R.G. THURMAN, University of North Carolina, Chapel Hill, NC V Preface to the Series The decision to undertake a second edition of Ethel Browning's Toxicity and Metabolism of Industrial Solvents was long in coming but certainly appropriate. Ethel Browning, M.D., was truly a pioneer in modern toxicology. In her preface she indicated that she drew upon the eminent publications by Patty (Industrial Hygiene and Toxicology) and Williams (Detoxication Mechanisms), but goes on to write: "An entirely new feature is, whenever it has been possible, an account of the metabolism in the body of the of the individual solvents, a process which in the opinion of many authorities forms the real basis of their toxic effects." Thus her contribution was to describe the toxicology of solvents in association with their metabolism, thereby opening the way for understanding the mechanisms of toxicity. Whereas a single volume was sufficient to encompass the known toxicology and metabolism of these compounds in 1965, the dramatic expansion of knowl- edge in toxicology requires that the effort be divided into several volumes, each devoted to a different group of compounds. The decision was made to prepare this edition in four volumes: solvents which are hydrocarbons; solvents which contain carbon, hydrogen, and oxygen; solvents which contain hydrogen and halogens; and solvents which in addition to carbon and hydrogen also contain either sulfur, phosphorus, or other elements. The editorial board that will oversee this work includes Professor Robert Snyder, Bernard D. Goldstein, and Michael A. Gallo of the Joint Graduate Program in Toxicology, Rutgers-The State University of New Jersey and the University of Medicine and Dentistry of New Jersey/Robert Wood Johnson Medical School, Professors Donald J. Reed and Donald R. Buhler of the Environ- mental Health Center of Oregon State University, Professor Daniel B. Menzel of the Southern Occupational Health Center, University of California, Professor I. Glenn Sipes, Department of Pharmacology and Toxicology, University of Arizona, and Professor Ronald G. Thurman, Department of Pharmacology, Uni- versity of North Carolina. Each volume will be edited by members of the editorial board. They, in turn, have selected authors knowledgeable in the toxicology of many chemicals to be described to write the Chapters that comprise each volume. A number of editorial decisions were made for which the editorial board takes full responsibility. For example, the selection of compounds to be discussed is not necessarily industrial solvents. Furthermore, all of the compounds discussed are not necessarily industrial solvents. However, it was decided that a thorough understanding of these compounds might help us to better appreciate the toxicol- Vll Preface to the Series ogy of those which are used for industrial purposes. The editors hope that this work will supply much useful information to researchers and students in modern mechanistic toxicology and provide the sound science that is required for the development of accurate health risk assessment. R.S. B.D.G. M.A.G. D.J.R. D.R.B. D.B.M. I.G.S. R.G.T. vm Preface to Volume 2 Ethel Browning's original book on Toxicity and Metabolism of Industrial Sol- vents included chapters on only 11 nitrogen-containing and no phosphorus type solvents. In the past thirty-four years, however, dozens of additional solvents of this type have found important industrial usage and annual production for many now exceeds hundreds of thousand tons. Human exposure to these solvents is potentially high due to their widespread use in industry. In addition, during their production or use, these solvents are often released into the environment where they may impact wildlife. In this edition of Browning's Toxicity and Metabolism of Industrial Solvents, therefore, it was appropriate to increase consideration of the number of industrial solvents that contain nitrogen to 66 and to add chapters on 5 of the major organophosphate type solvents. The introduction of new nitrogen- and phosphorus-containing solvents into industrial use has, in general, been paralleled by a literal explosion of knowledge about their properties, toxicity and metabolism. Since most researchers are now well aware of the role of biotransformation in determining toxicity so well identified by Dr. Browning in the first edition of this series, this relationship has been the focus or the driving force behind much of the recent metabolism data incorporated in the various solvent chapters. Even relatively simple compounds such as N-methylformamide undergo complex metabolic transformation in mam- mals. Such information and the mechanistic consideration contained in this volume should aid greatly in risk assessment and the safe use of nitrogen-contain- ing solvents. D.R. Buhler DJ. Reed / would like to acknowledge the outstanding contributions made to this volume by my secretary Ms. Bonnie Hommel who typed and retyped and retyped all of the chapters, and my Research Assistant Ms. Marilyn C. Henderson who proofread all of the chapters, did much of the library work and also wrote two of the chapters. D.R. Buhler IX Preface to Volume 2 Ethel Browning's original book on Toxicity and Metabolism of Industrial Sol- vents included chapters on only 11 nitrogen-containing and no phosphorus type solvents. In the past thirty-four years, however, dozens of additional solvents of this type have found important industrial usage and annual production for many now exceeds hundreds of thousand tons. Human exposure to these solvents is potentially high due to their widespread use in industry. In addition, during their production or use, these solvents are often released into the environment where they may impact wildlife. In this edition of Browning's Toxicity and Metabolism of Industrial Solvents, therefore, it was appropriate to increase consideration of the number of industrial solvents that contain nitrogen to 66 and to add chapters on 5 of the major organophosphate type solvents. The introduction of new nitrogen- and phosphorus-containing solvents into industrial use has, in general, been paralleled by a literal explosion of knowledge about their properties, toxicity and metabolism. Since most researchers are now well aware of the role of biotransformation in determining toxicity so well identified by Dr. Browning in the first edition of this series, this relationship has been the focus or the driving force behind much of the recent metabolism data incorporated in the various solvent chapters. Even relatively simple compounds such as N-methylformamide undergo complex metabolic transformation in mam- mals. Such information and the mechanistic consideration contained in this volume should aid greatly in risk assessment and the safe use of nitrogen-contain- ing solvents. D.R. Buhler DJ. Reed / would like to acknowledge the outstanding contributions made to this volume by my secretary Ms. Bonnie Hommel who typed and retyped and retyped all of the chapters, and my Research Assistant Ms. Marilyn C. Henderson who proofread all of the chapters, did much of the library work and also wrote two of the chapters. D.R. Buhler IX Contributors K.M. Abdo P.A. Cossum National Toxicology Program Chemical Industry Institute of Research Triangle Park Toxicology NC Research Triangle Park USA NC 27709 USA A.E. Ahmed University of Texas Medical Branch A. El-Hraiki Galveston, TX 77550 Toxicology Program USA Oregon State University Corvallis, OR 97331 R.O. Beauchamp Jr. USA Chemical Industry Institute of Toxicology J.R. Fowles Research Triangle Park Toxicology Program NC 27709 Oregon State University USA Corvallis, OR 97331 USA RJ. Bull Pharmacology/Toxicology Program A. Gescher Washington State University Pharmaceutical Sciences Institute Pullman, WA 99163 Aston University, Aston Triangle USA Birmingham, B4 7ET UK C.C. Conaway Naylor Dana Institute for Disease DJ. Gilroy Prevention Toxicology Program Dana Road Oregon State University Valhalla, NY 10595 Corvallis, OR 97331 USA USA XI Contributors M.C. Henderson R.E. Menzer Dept. of Agricultural Chemistry Department of Entomology Oregon State University The University of Maryland Corvallis, OR 97331 College Park, Maryland 20742 USA USA R.C. Hiles M.A. Nelson Hazelton Laboratories America Inc. Pharmacology/Toxicology Program Madison, WI Washington State University USA Pullman, WA 99163 USA R.C. Howe Toxicology Program D.E. Rickert Oregon State University Dept. of Drug Metabolism Corvallis, OR 97331 Glaxo Inc. USA Research Triangle Park NC G.I. Hussein USA University of Texas Medical Branch Galveston, TX 77550 D.K. Schlenk USA Toxicology Program Oregon State University J. Kelly Corvallis, OR 97331 Toxicology Program USA Oregon State University Corvallis, OR 97331 T.T. Sherer USA Pharmacology/Toxicology Program Washington State University J.L. Larson Pullman, WA 99163 Pharmacology/Toxicology Program USA Washington State University Pullman, WA 99163 K.D. Stout USA Pharmacology/Toxicology Program Washington State University R.L. Melnick Pullman, WA 99163 National Institute of Environmental USA Health Sciences Research Triangle Park, NC 27709 USA xii Contributors C.E. Thomas M.L. Walsh Environmental Health Sciences and Dept. of Agricultural Chemistry Dept. of Biochemistry and Biophysics Oregon State University Oregon State University Corvallis, OR 97331 Corvallis, OR 97331 USA USA J.-L. Wang M.D. Threadgill Dept. of Agricultural Chemistry Pharmaceutical Sciences Institute Oregon State University Aston University Corvallis, OR 97331 Aston Triangle USA Birmingham, B4 7ET UK S.S. Wong Toxicology Program IJ. Tinsley Oregon State University Dept. of Agricultural Chemistry Corvallis, OR 97331 Oregon State University USA Corvallis, OR 97331 USA K.E. Tomaszewski National Institute of Environmental Health Sciences Research Triangle Park, NC 27709 USA Xlll

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