Toxicological chemistry and biochemistry

Chapter 1 Chemistry and Organic Chemistry 1.1 Introduction 1.2 Elements 1.2.1 Subatomic Particles and Atoms 1.2.2 Subatomic Particles 1.2.3 Atom Nucleus and Electron Cloud 1.2.4 Isotopes 1.2.5 Important Elements 1.2.6 The Periodic Table 1.2.6.1 Features of the Periodic Table 1.2.7 Electrons in Atoms 1.2.7.1 Lewis Symbols of Atoms 1.2.8 Metals, Nonmetals, and Metalloids 1.3 Chemical Bonding 1.3.1 Chemical Compounds 1.3.2 Molecular Structure 1.3.3 Ionic Bonds 1.3.4 Summary of Chemical Compounds and the Ionic Bond 1.3.5 Molecular Mass 1.3.6 Oxidation State 1.4 Chemical Reactions and Equations 1.4.1 Reaction Rates 1.5 Solutions 1.5.1 Solution Concentration 1.5.2 Water as a Solvent 1.5.3 Solutions of Acids and Bases 1.5.3.1 Acids, Bases, and Neutralization Reactions 1.5.3.2 Concentration of H + Ion and pH 1.5.3.3 Metal Ions Dissolved in Water 1.5.3.4 Complex Ions Dissolved in Water 1.5.4 Colloidal Suspensions 1.6 Organic Chemistry 1.6.1 Molecular Geometry in Organic Chemistry . 1.7 Hydrocarbons 1.7.1 Alkanes 1.7.1.1 Formulas of Alkanes 1.7.1.2 Alkanes and Alkyl Groups 1.7.1.3 Names of Alkanes and Organic Nomenclature 1.7.1.4 Summary of Organic Nomenclature as Applied to Alkanes 1.7.1.5 Reactions of Alkanes 1.7.2 Alkenes and Alkynes 1.7.2.1 Addition Reactions 1.7.3 Alkenes and Cis–trans Isomerism 1.7.4 Condensed Structural Formulas 1.7.5 Aromatic Hydrocarbons 1.7.5.1 Benzene and Naphthalene 1.7.5.2 Polycyclic Aromatic Hydrocarbons Copyright © 2003 by CRC Press LLC 1.8 Organic Functional Groups and Classes of Organic Compounds 1.8.1 Organooxygen Compounds 1.8.2 Organonitrogen Compounds 1.8.3 Organohalide Compounds 1.8.3.1 Alkyl Halides 1.8.3.2 Alkenyl Halides 1.8.3.3 Aryl Halides 1.8.3.4 Halogenated Naphthalene and Biphenyl 1.8.3.5 Chlorofluorocarbons, Halons, and Hydrogen-Containing Chlorofluorocarbons 1.8.3.6 Chlorinated Phenols 1.8.4 Organosulfur Compounds 1.8.4.1 Thiols and Thioethers 1.8.4.2 Nitrogen-Containing Organosulfur Compounds 1.8.4.3 Sulfoxides and Sulfones 1.8.4.4 Sulfonic Acids, Salts, and Esters 1.8.4.5 Organic Esters of Sulfuric Acid 1.8.5 Organophosphorus Compounds 1.8.5.1 Alkyl and Aromatic Phosphines 1.8.5.2 Organophosphate Esters 1.8.5.3 Phosphorothionate Esters 1.9 Optical Isomerism 1.10 Synthetic Polymers Supplementary References Questions and Problems Chapter 2 Environmental Chemistry 2.1 Environmental Science and Environmental Chemistry 2.1.1 The Environment 2.1.2 Environmental Chemistry 2.2 Water 2.3 Aquatic Chemistry 2.3.1 Oxidation–Reduction 2.3.2 Complexation and Chelation 2.3.3 Water Interactions with Other Phases 2.3.4 Water Pollutants 2.3.5 Water Treatment 2.4 The Geosphere 2.4.1 Solids in the Geosphere 2.5 Soil 2.6 Geochemistry and Soil Chemistry 2.6.1 Physical and Chemical Aspects of Weathering 2.6.2 Soil Chemistry 2.7 The Atmosphere 2.8 Atmospheric Chemistry 2.8.1 Gaseous Oxides in the Atmosphere 2.8.2 Hydrocarbons and Photochemical Smog 2.8.3 Particulate Matter 2.9 The Biosphere Copyright © 2003 by CRC Press LLC 2.10 The Anthrosphere and Green Chemistry 2.10.1 Green Chemistry References Supplementary References Questions and Problems Chapter 3 Biochemistry 3.1 Biochemistry 3.1.1 Biomolecules 3.2 Biochemistry and the Cell 3.2.1 Major Cell Features 3.3 Proteins 3.3.1 Protein Structure 3.3.2 Denaturation of Proteins 3.4 Carbohydrates 3.5 Lipids 3.6 Enzymes 3.7 Nucleic Acids 3.7.1 Nucleic Acids in Protein Synthesis 3.7.2 Modified DNA 3.8 Recombinant DNA and Genetic Engineering 3.9 Metabolic Processes 3.9.1 Energy-Yielding Processes Supplementary References Questions and Problems Chapter 4 Metabolic Processes 4.1 Metabolism in Environmental Biochemistry 4.1.1 Metabolism Occurs in Cells 4.1.2 Pathways of Substances and Their Metabolites in the Body 4.2 Digestion 4.2.1 Carbohydrate Digestion 4.2.2 Digestion of Fats 4.2.3 Digestion of Proteins 4.3 Metabolism of Carbohydrates, Fats, and Proteins 4.3.1 An Overview of Catabolism 4.3.2 Carbohydrate Metabolism 4.3.3 Metabolism of Fats 4.3.4 Metabolism of Proteins 4.4 Energy Utilization by Metabolic Processes 4.4.1 High-Energy Chemical Species 4.4.2 Glycolysis 4.4.3 Citric Acid Cycle 4.4.4 Electron Transfer in the Electron Transfer Chain 4.4.5 Electron Carriers 4.4.6 Overall Reaction for Aerobic Respiration 4.4.7 Fermentation 4.5 Using Energy to Put Molecules Together: Anabolic Reactions Copyright © 2003 by CRC Press LLC 4.6 Metabolism and Toxicity 4.6.1 Stereochemistry and Xenobiotics Metabolism Supplementary References Questions and Problems Chapter 5 Environmental Biological Processes and Ecotoxicology 5.1 Introduction 5.2 Toxicants 5.3 Pathways of Toxicants into Ecosystems 5.3.1 Transfers of Toxicants between Environmental Spheres 5.3.2 Transfers of Toxicants to Organisms 5.4 Bioconcentration 5.4.1 Variables in Bioconcentration 5.4.2 Biotransfer from Sediments 5.5 Bioconcentration and Biotransfer Factors 5.5.1 Bioconcentration Factor 5.5.2 Biotransfer Factor 5.5.3 Bioconcentration by Vegetation 5.6 Biodegradation 5.6.1 Biochemical Aspects of Biodegradation 5.6.2 Cometabolism 5.6.3 General Factors in Biodegradation 5.6.4 Biodegradability 5.7 Biomarkers 5.8 Endocrine Disrupters and Developmental Toxicants 5.9 Effects of Toxicants on Populations 5.10 Effects of Toxicants on Ecosystems Supplementary References Questions and Problems Chapter 6 Toxicology 6.1 Introduction 6.1.1 Poisons and Toxicology 6.1.2 History of Toxicology 6.1.3 Future of Toxicology 6.1.4 Specialized Areas of Toxicology. 6.1.5 Toxicological Chemistry 6.2 Kinds of Toxic Substances 6.3 Toxicity-Influencing Factors 6.3.1 Classification of Factors 6.3.2 Form of the Toxic Substance and Its Matrix 6.3.3 Circumstances of Exposure 6.3.4 The Subject 6.4 Exposure to Toxic Substances 6.4.1 Percutaneous Exposure 6.4.1.1 Skin Permeability 6.4.2 Barriers to Skin Absorption 6.4.2.1 Measurement of Dermal Toxicant Uptake 6.4.2.2 Pulmonary Exposure Copyright © 2003 by CRC Press LLC 6.4.3 Gastrointestinal Tract 6.4.4 Mouth, Esophagus, and Stomach 6.4.5 Intestines 6.4.6 The Intestinal Tract and the Liver 6.5 Dose–Response Relationships 6.5.1 Thresholds 6.6 Relative Toxicities 6.6.1 Nonlethal Effects 6.7 Reversibility and Sensitivity 6.7.1 Hypersensitivity and Hyposensitivity 6.8 Xenobiotic and Endogenous Substances 6.8.1 Examples of Endogenous Substances 6.9 Kinetic and Nonkinetic Toxicology 6.9.1 Kinetic Toxicology 6.10 Receptors and Toxic Substances 6.10.1 Receptors 6.11 Phases of Toxicity 6.12 Toxification and Detoxification 6.12.1 Synergism, Potentiation, and Antagonism 6.13 Behavioral and Physiological Responses 6.13.1 Vital Signs 6.13.2 Skin Symptoms 6.13.3 Odors 6.13.4 Eyes 6.13.5 Mouth 6.13.6 Gastrointestinal Tract 6.13.7 Central Nervous System 6.14 Reproductive and Developmental Effects References Supplementary References Questions and Problems Chapter 7 Toxicological Chemistry 7.1 Introduction 7.1.1 Chemical Nature of Toxicants 7.1.2 Biochemical Transformations 7.2 Metabolic Reactions of Xenobiotic Compounds 7.2.1 Phase I and Phase II Reactions 7.3 Phase I Reactions 7.3.1 Oxidation Reactions 7.3.2 Hydroxylation 7.3.3 Epoxide Hydration 7.3.4 Oxidation of Noncarbon Elements 7.3.5 Alcohol Dehydrogenation 7.3.6 Metabolic Reductions 7.3.7 Metabolic Hydrolysis Reactions 7.3.8 Metabolic Dealkylation 7.3.9 Removal of Halogen 7.4 Phase II Reactions of Toxicants 7.4.1 Conjugation by Glucuronides 7.4.2 Conjugation by Glutathione Copyright © 2003 by CRC Press LLC 7.4.3 Conjugation by Sulfate 7.4.4 Acetylation 7.4.5 Conjugation by Amino Acids 7.4.6 Methylation 7.5 Biochemical Mechanisms of Toxicity 7.6 Interference with Enzyme Action 7.6.1 Inhibition of Metalloenzymes 7.6.2 Inhibition by Organic Compounds 7.7 Biochemistry of Mutagenesis 7.8 Biochemistry of Carcinogenesis 7.8.1 Alkylating Agents in Carcinogenesis 7.8.2 Testing for Carcinogens 7.9 Ionizing Radiation References Questions and Problems Chapter 8 Genetic Aspects of Toxicology 8.1 Introduction 8.1.1 Chromosomes 8.1.2 Genes and Protein Synthesis 8.1.3 Toxicological Importance of Nucleic Acids 8.2 Destructive Genetic Alterations 8.2.1 Gene Mutations 8.2.2 Chromosome Structural Alterations, Aneuploidy, and Polyploidy 8.2.3 Genetic Alteration of Germ Cells and Somatic Cells 8.3 Toxicant Damage to DNA 8.4 Predicting and Testing for Genotoxic Substances 8.4.1 Tests for Mutagenic Effects 8.4.2 The Bruce Ames Test and Related Tests 8.4.3 Cytogenetic Assays 8.4.4 Transgenic Test Organisms 8.5 Genetic Susceptibilities and Resistance to Toxicants 8.6 Toxicogenomics 8.6.1 Genetic Susceptibility to Toxic Effects of Pharmaceuticals References Supplementary Reference Questions and Problems Chapter 9 Toxic Responses 9.1 Introduction 9.2 Respiratory System 9.3 Skin 9.3.1 Toxic Responses of Skin 9.3.2 Phototoxic Responses of Skin 9.3.3 Damage to Skin Structure and Pigmentation 9.3.4 Skin Cancer 9.4 The Liver . 9.5 Blood and the Cardiovascular System 9.5.1 Blood 9.5.2 Hypoxia 9.5.3 Leukocytes and Leukemia Copyright © 2003 by CRC Press LLC 9.5.4 Cardiotoxicants 9.5.5 Vascular Toxicants 9.6 Immune System 9.7 Endocrine System 9.8 Nervous System 9.9 Reproductive System 9.10 Developmental Toxicology and Teratology 9.10.1 Thalidomide 9.10.2 Accutane 9.10.3 Fetal Alcohol Syndrome 9.11 Kidney and Bladder References Supplementary References Questions and Problems Chapter 10 Toxic Elements 10.1 Introduction 10.2 Toxic Elements and the Periodic Table 10.3 Essential Elements 10.4 Metals in an Organism 10.4.1 Complex Ions and Chelates 10.4.2 Metal Toxicity 10.4.3 Lithium 10.4.4 Beryllium 10.4.5 Vanadium 10.4.6 Chromium 10.4.7 Cobalt 10.4.8 Nickel 10.4.9 Cadmium 10.4.10 Mercury 10.4.10.1 Absorption and Transport of Elemental and Inorganic Mercury 10.4.10.2 Metabolism, Biologic Effects, and Excretion 10.4.10.3 Minimata Bay 10.4.11 Lead 10.4.11.1 Exposure and Absorption of Inorganic Lead Compounds 10.4.11.2 Transport and Metabolism of Lead 10.4.11.3 Manifestations of Lead Poisoning 10.4.11.4 Reversal of Lead Poisoning and Therapy 10.4.12 Defenses Against Heavy Metal Poisoning 10.5 Metalloids: Arsenic 10.5.1 Sources and Uses 10.5.2 Exposure and Absorption of Arsenic . 10.5.3 Metabolism, Transport, and Toxic Effects of Arsenic 10.6 Nonmetals 10.6.1 Oxygen and Ozone 10.6.2 Phosphorus 10.6.3 The Halogens 10.6.3.1 Fluorine 10.6.3.2 Chlorine 10.6.3.3 Bromine 10.6.3.4 Iodine Copyright © 2003 by CRC Press LLC 10.6.4 Radionuclides 10.6.4.1 Radon 10.6.4.2 Radium 10.6.4.3 Fission Products References Supplementary Reference Questions and Problems Chapter 11 Toxic Inorganic Compounds 11.1 Introduction 11.1.1 Chapter Organization 11.2 Toxic Inorganic Carbon Compounds 11.2.1 Cyanide 11.2.1.1 Biochemical Action of Cyanide 11.2.2 Carbon Monoxide 11.2.3 Biochemical Action of Carbon Monoxide 11.2.4 Cyanogen, Cyanamide, and Cyanates 11.3 Toxic Inorganic Nitrogen Compounds 11.3.1 Ammonia 11.3.2 Hydrazine 11.3.3 Nitrogen Oxides 11.3.4 Effects of NO 2 Poisoning 11.3.5 Nitrous Oxide 11.4 Hydrogen Halides 11.4.1 Hydrogen Fluoride 11.4.2 Hydrogen Chloride 11.4.3 Hydrogen Bromide and Hydrogen Iodide 11.5 Interhalogen Compounds and Halogen Oxides 11.5.1 Interhalogen Compounds 11.5.2 Halogen Oxides 11.5.3 Hypochlorous Acid and Hypochlorites 11.5.4 Perchlorates 11.6 Nitrogen Compounds of the Halogens 11.6.1 Nitrogen Halides 11.6.2 Azides 11.6.3 Monochloramine and Dichloramine 11.7 Inorganic Compounds of Silicon 11.7.1 Silica 11.7.2 Asbestos 11.7.3 Silanes 11.7.4 Silicon Halides and Halohydrides 11.8 Inorganic Phosphorus Compounds 11.8.1 Phosphine 11.8.2 Phosphorus Pentoxide 11.8.3 Phosphorus Halides 11.8.4 Phosphorus Oxyhalides 11.9 Inorganic Compounds of Sulfur 11.9.1 Hydrogen Sulfide 11.9.2 Sulfur Dioxide and Sulfites 11.9.3 Sulfuric Acid Copyright © 2003 by CRC Press LLC 11.9.4 Carbon Disulfide 11.9.5 Miscellaneous Inorganic Sulfur Compounds References Questions and Problems Chapter 12 Organometallics and Organometalloids 12.1 The Nature of Organometallic and Organometalloid Compounds 12.2 Classification of Organometallic Compounds 12.2.1 Ionically Bonded Organic Groups 12.2.2 Organic Groups Bonded with Classical Covalent Bonds 12.2.3 Organometallic Compounds with Dative Covalent Bonds 12.2.4 Organometallic Compounds Involving ð -Electron Donors 12.3 Mixed Organometallic Compounds 12.4 Organometallic Compound Toxicity 12.5 Compounds of Group 1A Metals 12.5.1 Lithium Compounds 12.5.2 Compounds of Group 1A Metals Other Than Lithium 12.6 Compounds of Group 2A Metals 12.6.1 Magnesium 12.6.2 Calcium, Strontium, and Barium 12.7 Compounds of Group 2B Metals 12.7.1 Zinc 12.7.2 Cadmium 12.7.3 Mercury 12.8 Organotin and Organogermanium Compounds 12.8.1 Toxicology of Organotin Compounds 12.8.2 Organogermanium Compounds 12.9 Organolead Compounds 12.9.1 Toxicology of Organolead Compounds 12.10 Organoarsenic Compounds 12.10.1 Organoarsenic Compounds from Biological Processes 12.10.2 Synthetic Organoarsenic Compounds 12.10.3 Toxicities of Organoarsenic Compounds 12.11 Organoselenium and Organotellurium Compounds 12.11.1 Organoselenium Compounds 12.11.2 Organotellurium Compounds References Supplementary References Questions and Problems Chapter 13 Toxic Organic Compounds and Hydrocarbons 13.1 Introduction 13.2 Classification of Hydrocarbons 13.2.1 Alkanes 13.2.2 Unsaturated Nonaromatic Hydrocarbons 13.2.3 Aromatic Hydrocarbons 13.3 Toxicology of Alkanes 13.3.1 Methane and Ethane 13.3.2 Propane and Butane 13.3.3 Pentane through Octane Copyright © 2003 by CRC Press LLC 13.3.4 Alkanes above Octane 13.3.5 Solid and Semisolid Alkanes 13.3.6 Cyclohexane 13.4 Toxicology of Unsaturated Nonaromatic Hydrocarbons 13.4.1 Propylene 13.4.2 1,3-Butadiene 13.4.3 Butylenes 13.4.4 Alpha-Olefins 13.4.5 Cyclopentadiene and Dicyclopentadiene 13.4.6 Acetylene 13.5 Benzene and Its Derivatives 13.5.1 Benzene 13.5.1.1 Acute Toxic Effects of Benzene 13.5.1.2 Chronic Toxic Effects of Benzene 13.5.1.3 Metabolism of Benzene 13.5.2 Toluene, Xylenes, and Ethylbenzene 13.5.3 Styrene 13.6 Naphthalene 13.6.1 Metabolism of Naphthalene 13.6.2 Toxic Effects of Naphthalene 13.7 Polycyclic Aromatic Hydrocarbons 13.7.1 PAH Metabolism References Questions and Problems Chapter 14 Organooxygen Compounds 14.1 Introduction 14.1.1 Oxygen-Containing Functional Groups 14.2 Alcohols 14.2.1 Methanol 14.2.2 Ethanol 14.2.3 Ethylene Glycol 14.2.4 The Higher Alcohols 14.3 Phenols 14.3.1 Properties and Uses of Phenols 14.3.2 Toxicology of Phenols 14.4 Oxides 14.5 Formaldehyde 14.5.1 Properties and Uses of Formaldehyde 14.5.2 Toxicity of Formaldehyde and Formalin 14.6 Aldehydes and Ketones 14.6.1 Toxicities of Aldehydes and Ketones 14.7 Carboxylic Acids 14.7.1 Toxicology of Carboxylic Acids 14.8 Ethers 14.8.1 Examples and Uses of Ethers 14.8.2 Toxicities of Ethers 14.9 Acid Anhydrides 14.9.1 Toxicological Considerations 14.10 Esters 14.10.1 Toxicities of Esters Copyright © 2003 by CRC Press LLC References Questions and Problems Chapter 15 Organonitrogen Compounds 15.1 Introduction 15.2 Nonaromatic Amines 15.2.1 Lower Aliphatic Amines 15.2.2 Fatty Amines 15.2.3 Alkyl Polyamines 15.2.4 Cyclic Amines 15.3 Carbocyclic Aromatic Amines 15.3.1 Aniline 15.3.2 Benzidine 15.3.3 Naphthylamines 15.4 Pyridine and Its Derivatives 15.5 Nitriles 15.6 Nitro Compounds 15.6.1 Nitro Alcohols and Nitro Phenols 15.6.2 Dinoseb 15.7 Nitrosamines 15.8 Isocyanates and Methyl Isocyanate 15.9 Pesticidal Compounds 15.9.1 Carbamates 15.9.2 Bipyridilium Compounds 15.10 Alkaloids References Questions and Problems Chapter 16 Organohalide Compounds 16.1 Introduction 16.1.1 Biogenic Organohalides 16.2 Alkyl Halides 16.2.1 Toxicities of Alkyl Halides 16.2.2 Toxic Effects of Carbon Tetrachloride on the Liver 16.2.3 Other Alkyl Halides 16.2.4 Hydrochlorofluorocarbons 16.2.5 Halothane 16.3 Alkenyl Halides 16.3.1 Uses of Alkenyl Halides 16.3.2 Toxic Effects of Alkenyl Halides 16.3.3 Hexachlorocyclopentadiene 16.4 Aryl Halides 16.4.1 Properties and Uses of Aryl Halides 16.4.2 Toxic Effects of Aryl Halides 16.5 Organohalide Insecticides 16.5.1 Toxicities of Organohalide Insecticides 16.5.2 Hexachlorocyclohexane 16.5.3 Toxaphene 16.6 Noninsecticidal Organohalide Pesticides 16.6.1 Toxic Effects of Chlorophenoxy Herbicides 16.6.2 Toxicity of TCDD Copyright © 2003 by CRC Press LLC 16.6.3 Alachlor 16.6.4 Chlorinated Phenols 16.6.5 Hexachlorophene References Questions and Problems Chapter 17 Organosulfur Compounds 17.1 Introduction 17.1.1 Classes of Organosulfur Compounds 17.1.2 Reactions of Organic Sulfur 17.2 Thiols, Sulfides, and Disulfides 17.2.1 Thiols 17.2.2 Thiols as Antidotes for Heavy Metal Poisoning 17.2.3 Sulfides and Disulfides 17.2.4 Organosulfur Compounds in Skunk Spray 17.2.5 Carbon Disulfide and Carbon Oxysulfide 17.3 Organosulfur Compounds Containing Nitrogen or Phosphorus 17.3.1 Thiourea Compounds 17.3.2 Thiocyanates 17.3.3 Disulfiram 17.3.4 Cyclic Sulfur and Nitrogen Organic Compounds 17.3.5 Dithiocarbamates 17.3.6 Phosphine Sulfides 17.3.7 Phosphorothionate and Phosphorodithioate Esters 17.4 Sulfoxides and Sulfones 17.5 Sulfonic Acids, Salts, and Esters 17.6 Organic Esters of Sulfuric Acid 17.7 Miscellaneous Organosulfur Compounds 17.7.1 Sulfur Mustards 17.7.2 Sulfur in Pesticides 17.7.3 Sulfa Drugs 17.8 Organically Bound Selenium References Questions and Problems Chapter 18 Organophosphorus Compounds 18.1 Introduction 18.1.1 Phosphine 18.2 Alkyl and Aryl Phosphines 18.3 Phosphine Oxides and Sulfides 18.4 Phosphonic and Phosphorous Acid Esters 18.5 Organophosphate Esters 18.5.1 Orthophosphates and Polyphosphates 18.5.2 Orthophosphate Esters 18.5.3 Aromatic Phosphate Esters 18.5.4 Tetraethylpyrophosphate 18.6 Phosphorothionate and Phosphorodithioate Esters 18.7 Organophosphate Insecticides 18.7.1 Chemical Formulas and Properties 18.7.2 Phosphate Ester Insecticides 18.7.3 Phosphorothionate Insecticides Copyright © 2003 by CRC Press LLC 18.7.4 Phosphorodithioate Insecticides 18.7.5 Toxic Actions of Organophosphate Insecticides 18.7.5.1 Inhibition of Acetylcholinesterase 18.7.5.2 Metabolic Activation 18.7.5.3 Mammalian Toxicities 18.7.5.4 Deactivation of Organophosphates 18.8 Organophosphorus Military Poisons References Supplementary Reference Questions and Problems Chapter 19 Toxic Natural Products 19.1 Introduction 19.2 Toxic Substances from Bacteria 19.2.1 In Vivo Bacterial Toxins 19.2.1.1 Toxic Shock Syndrome 19.2.2 Bacterial Toxins Produced Outside the Body 19.3 Mycotoxins 19.3.1 Aflatoxins 19.3.2 Other Mycotoxins 19.3.3 Mushroom Toxins 19.4 Toxins from Protozoa 19.5 Toxic Substances from Plants 19.5.1 Nerve Toxins from Plants 19.5.1.1 Pyrethrins and Pyrethroids 19.5.2 Internal Organ Plant Toxins 19.5.3 Eye and Skin Irritants 19.5.4 Allergens 19.5.5 Mineral Accumulators 19.5.6 Toxic Algae 19.6 Insect Toxins 19.6.1 Bee Venom 19.6.2 Wasp and Hornet Venoms 19.6.3 Toxicities of Insect Venoms 19.7 Spider Toxins 19.7.1 Brown Recluse Spiders 19.7.2 Widow Spiders 19.7.3 Other Spiders 19.8 Reptile Toxins 19.8.1 Chemical Composition of Snake Venoms 19.8.2 Toxic Effects of Snake Venom 19.9 Nonreptile Animal Toxins References Supplementary References Questions and Problems Chapter 20 Analysis of Xenobiotics 20.1 Introduction 20.2 Indicators of Exposure to Xenobiotics 20.3 Determination of Metals Copyright © 2003 by CRC Press LLC 20.3.1 Direct Analysis of Metals 20.3.2 Metals in Wet-Ashed Blood and Urine 20.3.3 Extraction of Metals for Atomic Absorption Analysis 20.4 Determination of Nonmetals and Inorganic Compounds 20.5 Determination of Parent Organic Compounds 20.6 Measurement of Phase I and Phase II Reaction Products 20.6.1 Phase I Reaction Products 20.6.2 Phase II Reaction Products 20.6.3 Mercapturates 20.7 Determination of Adducts 20.8 The Promise of Immunological Methods References Supplementary References Questions and Problems Copyright ©