Table Of ContentT oxicity
and
Metabolism
of
Explosives
Author
Jehuda Yinon
Department of Isotope Research
Weizmann Institute of Science
Rehovot, Israel
Boca Raton London New York
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Library of Congress Cataloging-in-Publication Data
Yinon, Jehuda.
Toxicity and metabolism of explosives/author, Jehuda Yinon.
p. cm.
Includes bibliographical references.
ISBN 0-8493-5128-6
1. Explosives--Toxicology. 2.Explosives--Metabolism.
3. Explosives, Military--Safety measures. I. Title.
RA1270.E93Y56 1990
615.9'2--dc20 90-1344
CIP
Library of Congress Card Number 90-1344
PREFACE
It has been known for quite a long time that most explosives are toxic.
During the first 7V2 months of World War I, 17,000 TNT poisoning cases,
including 475 deaths, occurred in munition factories in the U.S. During the
1960s, several cases of sudden death in dynamite workers were reported in
the U.S. and in Europe. Intoxication with composition C-4, a widely used
plastic explosive based on RDX, occurred during and after the Vietnam War.
Because of their toxicity, explosives present a health hazard for munition
workers and military personnel who handle them and are exposed to them.
In order to decrease the rate of explosives poisoning cases, elaborate hygiene
and safety methods have to be enforced, and regular medical check-ups of
people exposed to explosives have to be carried out. A better understanding
of the toxicity, channels of absorption and metabolism of explosives by the
body, and symptoms and clinical manifestations of poisoning by these com
pounds is therefore necessary.
In the environmental field, disposal of explosives and their degradation
products from munition manufacturing plants and from disposal sites presents
a serious and potentially hazardous contamination problem. A single TNT
manufacturing plant can generate as much as 500,000 gallons of waste water
per day. In shell-loading plants, large volumes of water are used to wash out
residual explosives. All these waste waters are disposed of by discharging
them into rivers or streams.
The purpose of this monograph is to bring together the available infor
mation on human toxicity of explosives including symptoms and clinical
manifestations and toxic effects. Studies carried out on toxicity in animals,
and on metabolism and degradation of explosives have been described. En
vironmental aspects have been covered and a special paragraph has been
devoted in each chapter to the analysis of the explosive and its metabolites
in body fluids and in water and soil. General analytical methods of explosives
have not been described. Also, I have included only a short paragraph on the
physical and chemical properties of the explosive in each chapter. These
topics have been widely covered in other books.
The extent of each of the chapters, covering seven different explosives,
is relative to the amount of published information available. A great deal of
studies have been done on TNT and nitroglycerin, while very little work has
been done on HMX. It should be emphasized that only published work —
journal articles and unclassified reports — has been quoted.
Finally, I would like to thank the authors and publishers for permission
to reproduce copyrighted figures. Many thanks are due to Mrs. S. Newman
for the excellent typing of the manuscript. I am especially indebted to my
family for their patience and forbearance while I was working on the man
uscript.
THE AUTHOR
Jehuda Yinon, Ph.D., is a Senior Research Fellow at the Weizmann
Institute of Science, Rehovot, Israel. He received his B.Sc. and M.Sc. from
the Technion, Israel Institute of Technology, Haifa, Israel and his Ph.D. from
the Weizmann Institute of Science. He was a Research Associate (1971 to
1973) and a Senior Research Associate (1976 to 1977) at the Jet Propulsion
Laboratory, Pasadena, California. He spent a year (1980 to 1981) as a Visiting
Scientist at the National Institute of Environmental Health Sciences in North
Carolina and 6 months (1988—1989) as a Visiting Scientist at the EPA
Environmental Monitoring Systems Laboratory in Las Vegas, Nevada.
His main research interests are application of novel mass spectrometry
techniques in environmental, biomedical, and forensic sciences, the chemistry
of energetic materials, and the study of metabolism of explosives.
Dr. Yinon is a member of the American Society for Mass Spectrometry,
the Israel Chemical Society, and the Israel Society for Mass Spectrometry of
which he has served as President. He is a Regional Editor of Forensic Science
Review and is on the Editorial Board of the Journal of Energetic Materials.
To my wife, Bracha,
and my children Moshe, Yoav, and Einat
TABLE OF CONTENTS
Chapter 1
2,4,6-Trinitrotoluene (TNT)......................................................................1
I. Physical and Chemical Properties.......................................................1
II. Human Toxicity...................................................................................3
A. Introduction.............................................................................3
B. Channels of Absorption..........................................................4
C. Symptoms and Clinical Manifestations..................................5
1. Dermatitis......................................................................5
2. Gastritis........................................................................6
3. Cyanosis......................................................................6
4. Toxic Jaundice.............................................................6
5. Aplastic Anemia..........................................................7
6. Other Symptoms..........................................................8
D. Toxic Effects...........................................................................8
1. Hepatic Effects............................................................8
2. Hematologic Effects...................................................9
3. Other Toxic Effects...................................................10
E. Epidemiology..........................................................................11
F. Treatment of TNT Toxicity..................................................14
G. Prevention and Industrial Hygiene........................................14
III. Toxicity in Animals...........................................................................15
A. Monkeys................................................................................15
B. Dogs......................................................................................16
C. Cats........................................................................................18
D. Rabbits and Guinea Pigs......................................................18
E. Rats........................................................................................19
F. Mice........................................................................................21
IV. Carcinogenicity and Mutagenicity.....................................................21
V. Metabolism and Degradation............................................................23
A. Disposition............................................................................23
B. Metabolism............................................................................24
C. Photochemical Degradation....................................................31
D. Microbial Degradation...........................................................33
VI. Environmental Aspects......................................................................36
A. Introduction...........................................................................36
B. Characterization of TNT Wastewaters.................................38
C. Treatment of TNT Wastewaters...........................................39
D. Toxicity of TNT Wastewaters to Fish.................................42
VII. Analysis of TNT................................................................................42
A. Analysis of TNT and its Metabolitesi n Urine.......................42
1. Color Tests...............................................................42
2. Gas Chromatography (GC)........................................44
3. Mass Spectrometry....................................................44
4. High Performance Liquid Chromatography-Mass
Spectrometry (LC-MS)..............................................45
B. Analysis of TNT and its Metabolites in Blood...................48
C. Analysis of TNT and its Degradation Products in Water and
Soil.........................................................................................51
1. Gas Chromatography (GC)........................................51
2. High Performance Liquid Chromatography
(HPLC)......................................................................53
3. Other Methods...........................................................57
References......................................................................................................60
Chapter 2
Tetryl............................................................................................................69
I. Physical and Chemical Properties.....................................................69
II. Human Toxicity.................................................................................70
A. Symptoms and Clinical Manifestations................................70
1. Tetryl Dermatitis........................................................70
2. Other Manifestations.................................................71
B. Epidemiology and Industrial Hygiene.................................72
III. Toxicity in Animals...........................................................................73
IV. Carcinogenicity and Mutagenicity.....................................................75
V. Degradation........................................................................................75
VI. Environmental Aspects......................................................................77
VII. Analysis of Tetryl in Water and Soil................................................78
References......................................................................................................79
Chapter 3
Nitroglycerin (NG)......................................................................................81
I. Physical and Chemical Properties.....................................................81
II. Human Toxicity.................................................................................82
A. Introduction...........................................................................82
B. Symptoms and Clinical Manifestations................................83
C. Toxic Effects.........................................................................84
D. Epidemiology and Industrial Hygiene.................................85
III. Toxicity in Animals...........................................................................86
A. Rats and Mice........................................................................86
B. Rabbits...................................................................................87
C. Dogs......................................................................................88
D. Various Animals ...................................................................89
E. Toxicity of Metabolites of NG............................................90
IV. Genotoxicity and Teratogenicity......................................................90
V. Metabolism and Degradation............................................................91
A. Disposition........................................................ 91
B. Metabolism...................... 93
1. Metabolism Studies in vivo.......................................93
2. Metabolism Studies in vitro......................................94
C. Microbial Degradation...........................................................99
VI. Environmental Aspects....................................................................100
VII. Analysis of NG...............................................................................101
A. Analysis of NG and its Metabolites in Blood and
Plasma.................................................................................101
1. Gas Chromatography (GC)......................................101
2. High Performance Liquid Chromatography
(HPLC)....................................................................108
3. Gas Chromatography-Mass Spectrometry
(GC-MS)...................................................................110
B. Analysis of NG and its Metabolites in Various Body
Fluids...................................................................................113
C. Analysis of NG and its Degradation Products in Medicinal
Formulations........................................................................115
D. Analysis of NG and its Degradation Products in
Wastewater...........................................................................117
References....................................................................................................117
Chapter 4
Pentaerythritol Tetranitrate (PETN)......................................................123
I. Physical and Chemical Properties...................................................123
II. Human Toxicity.................................................................................124
III. Toxicity in Animals.........................................................................125
IV. Metabolism and Degradation...........................................................126
A. Metabolism and Degradation of PETN..............................126
B. Metabolism and Degradation of PE-tri-N...........................128
V. Analysis of PETN...........................................................................128
A. Analysis of PETN in Blood and Urine..............................128
B. Analysis of PETN in Wastewater........................................130
References....................................................................................................131
Chapter 5
Ethylene Glycol Dinitrate (EGDN).........................................................133
I. Physical and Chemical Properties...................................................133
II. Human Toxicity...............................................................................134
A. Symptoms and Clinical Manifestations..............................134
B. Epidemiology and Industrial Hygiene................................134
III. Toxicity in Animals............................................... 136
IV. Metabolism and Degradation...........................................................138
A. Oxidation of Hemoglobin...................................................138
B. Metabolism of EGDN.........................................................139
V. Analysis of EGDN...........................................................................141
A. Analysis of EGDN in Blood................................................141
B. Analysis of EGDN in Water................................................142
References....................................................................................................142
Chapter 6
Cyclotrimethylenetrinitramine (RDX)....................................................145
I. Physical and Chemical Properties...................................................145
II. Human Toxicity...................... 147
A. Symptoms and Clinical Manifestations..............................147
B. Epidemiology and Industrial Hygiene................................149
III. Toxicity in Animals.........................................................................150
A. Rats......................................................................................150
B. Various Animals.................................................................152
IV. Metabolism and Degradation...........................................................154
A. Hydrolysis............................................................................154
B. Photolysis............................................................................154
C. Metabolism............................................................................154
D. Biodegradation...................................................... 155
V. Environmental Aspects....................................................................156
VI. Analysis of RDX................................................................. 156
A. Analysis of RDX in Body Fluids and Tissues...................157
B. Analysis of RDX in Water and Soil...................................159
References......................................................... 162
Chapter 7
Cyclotetramethylenetetranltramine( HMX)............................................165
I. Physical and Chemical Properties...................................................165
II. Environmental Aspects....................................................................166
III. Analysis of HMX.................................................... 167
A. Analysis of HMX in Water.................................................167
B. Analysis of HMX in Soil....................................................169
References................................................................................................169
Index............................................................................................................171
