Index

A Acute poisoning, 26, 37, 38, 54, 120, 143, 146, Abamectin, 96 147, 155, 156, 226, 248 Acaricides Acute pulmonary complications, 183 use of OPs as, 26 Acylphosphorofluoridates, 27 Acceptable operator exposure level (AOEL), Ageing, 158 216 Aging, 158, 162, 194 Accidental exposure, 145 Aging reaction, 179, 194 Accidental OP poisoning, 35, 221 Agricultural exposure, 222 Acephate, 104, 105, 130, 217, 218 Airway, 153 Acetylcholine (ACh), 15, 20, 91, 143, 179, 247 Alanine transaminase (ALT), 96 Acetylcholinesterase (AChE), 18, 48, 57, 120, Alcohol poisoning, 134 217 Alderin, 80 aging of, 19 Alkalinisation, 168 catalytic mechanism of, 16 Alkyl carbenium ion, 19 constituents of, 16 Alkyl halides, 5 receptors of, 20 Alkyl phosphates, 5 Acetylcholinesterase (AChE) inhibitor, 15, 50, Alkylphosphonothiolate, 12 53, 54, 142, 247 Aluminum phosphide poisonings, 37 direct, 17, 247 American Association of Poison Control AchE inhibition, 86 Centers (AAPCC), 36 Activated charcoal, 156, 191 Amiton, 28 Active cholinergic system, 100 Anticholinergic medicines, 156, 157 Acute cholinergic syndrome, 54, 143–145, 148, Antidote administration, 155 157, 165, 168, 248 Antidotes, 143, 145, 148, 152, 191, 198 Acute OP poisoning, 38, 133, 150, 161, 166, conventional, 4 170, 248 Arrhythmias, 57, 58, 92, 154, 161, 199 Acute organophosphorus pesticide (OP) Aspiration pneumonitis and pneumonia, 165 exposures Atropine, 29, 60, 62, 83, 91, 93, 122, 123, categories of, 145 143, 144, 148, 149, 154, 156, 157, Acute organophosphorus pesticide (OP) 160, 162–164, 167, 168, 180, 182, 188, poisoning, 142, 144 191–193, 195, 196, 198, 199, 201, 202, generic guidelines for, 144 204, 248, 249 Acute pesticide poisoning, 30, 32 antagonist of, 52 in agricultural workers, 32 Atropine sulfate, 192 studies on, 30 Atropine therapy, 155 Acute Physiology and Chronic Health Atropine treatment, 153, 166 Evaluation (APACHE), 149 Aum Shinrikyo Cult, 30

M. Balali-Mood, M. Abdollahi (eds.), Basic and Clinical Toxicology 251 of Organophosphorus Compounds, DOI 10.1007/978-1-4471-5625-3, © Springer-Verlag London 2014 252 Index

Autonomic nervous system, 81, 143, 149, 167, Chlorpyrifos, 36, 50, 54, 56, 64–67, 80, 104, 248 130, 151, 158, 217, 224, 225 Azinphosmethyl, 28 Chlorpyrifos oxon, 101 Chlorpyrifos poisoning, 160 B Chlorpyriphos, 38 β-glucuronidase (BG), 128, 249 Cholinergic nerve terminals, 51 B-esterases, 53 Cholinergic pesticides, 37 Benactyzine, 193, 196, 204, 248, 249 Cholinergic syndrome, 120, 122, 123, 126, Benchmark dose lower confidence limit 134, 147, 157, 226, 246, 248 (BMDL), 216 clinical diagnosis of, 121 Benzodiazepine poisoning, 134 mechanism of, 121 Benzodiazepines, 155, 157, 163–165 Cholinesterase, 18, 19, 102, 149, 163, 179 Beta-cyclodextrin, 201 Cholinesterase activity, 34, 150 BG-Egasyn complex, 134 Cholinesterase inhibition, 129 Bicarbonate, 168 Chromosome aberration assay, 105 Bioscavengers, 200, 204, 248, 249 Chronic OP-induced neuropsychiatric disorder Bradycardia, 55, 57, 120, 149, 154, 157, 192, (COPIND), 84–86, 120 199, 226 studies on, 84 Breathing, 154 Chronic OP-induced neuropsychiatric disorders Bronchorrhoea, 56, 149, 154, 157, 226 (COPIND), 126, 134 Bronchospasm, 149, 154, 157, 198 diagnostic criteria for, 126, 127 BuChE activity, 163 mechanism of, 127 BuChE mixing study, 163 Chronic toxicity, 80, 101, 216, 227, 248, 249 Butyrylcholinesterase (BChE), 53, 67, 150, 169 Class I poisoning, 35 Clinical outcomes, 147 Clinical scoring tools, 149 C Clinical toxicity, 34 California department of pesticide regulation, Clonidine, 144, 167, 201 103 Cochrane review, 161 Carbamate insecticides, 38 Coformulants, 151 Carbamate pesticides, 46 Cognitive deficit, 64, 66, 91, 126, 166 Carbamate poisoning, 36 Combination therapy, 94 Carbamates, 36–38, 48, 56, 122, 144, 156, 218 Compound preparation, 58 Carboxylesterase activity, 86, 100, 128, 130, Contaminated foods, 81 180, 249 Cortical blindness, 56 Carboxylesterase isozymes, 128 Criminal exposures, 146 Carcinogenic, mutagenic and reproductive Cross-sectional studies, 32 toxic compounds (CMR), 219 Cumulative risk assessment, 217 Carcinogenicity, 80 Cyanide, 26 Cardiac arrhythmias, 90, 184 Cyclohexanone, 58, 147 Case fatality-acute poisoning, 169, 227, 233, Cyclosarin, 29, 33 247 CYP450 enzymes, 53, 147 Case studies, 32 Catecholamine release, 167, 168 D Catecholamine system, 101 Daphnia Central nervous system (CNS), 50, 51, 149, effects of, 233 248 DDT, 28, 80 Chemical risk assessment, 217 Decontamination, 123, 152, 155, 180, 189, Chemical terrorism, 30, 34, 247 190, 201, 203, 246 Chemical warfare agents (CWA), 12, 26, 214 dermal, 155, 156 Chemical Warfare Nerve Agents (CWNAs), 3, gastrointestinal, 156 4, 20, 26, 27, 29, 53, 235, 246, 247 Defoliant, 3 Chemical Weapons Convention (CWC), 219 use of OPs as, 26 Chlorfenvinphos, 17, 97 Delayed polyneuropathy, 34, 80, 249 Index 253

Demethon, 229 Exposure, 30, 33, 37, 39, 46, 48, 54–61, 64–68, Demeton, 28 80–82, 85, 96, 100, 103, 104, 106, 121, Di-isopropyl phosphorofluoridate (DFP), 80 125, 126, 145, 148, 152, 153, 179, Di-isopropylfluorophosphate (DFP), 27 181–187, 192, 203, 204, 214, 216–218, Dialkyl phosphate (DAP), 227 224–226, 229, 230, 249, 250 Dialkyl phosphonates intentional, 35 formation, 7 non-intentional, 35 Diarrhoea, 56, 164 route of, 32 Diazepam, 164, 188, 193, 195, 196, 202 Extracorporeal blood purification, 169 Diazinon, 17, 38, 50, 54, 56, 62, 65, 66, 80, 101, 122, 158, 160, 169, 218, 233 F Dichlorvos, 17, 28, 62, 66, 92, 96, 97, 105, Famphur, 233 122, 127, 215 Fao Peninsula, 29 Dieldrin, 28 Fasciculations, 55, 120, 122, 149, 155, 163, Dietary exposure, 104 165, 183 Diethyl nitrosamine-initiated paraneoplastic Fatal poisoning, 37 lesions, 106 Fatal toxicity, 46 Diethyl phosphorofluoridate, 27 Fenitrothion, 17, 55, 94, 96 Diethyldithiophosphate (DEDTP), 228 Fenthion, 54, 62, 93, 94, 104, 105, 122, 144, Diethylphosphate (DEP), 228 147, 150, 158, 162, 165, 233 Diethylthiophosphate (DETP), 228 Fenthion exposure, 166 Dimethoate, 92, 102, 122, 145, 147, 150, 151, Fluorophosphoric acid 155, 158, 161, 162 alkyl esters of, 5 Dimethoate poisoning, 147 Foliant program, 14 Dimethyl phosphorofluoridate, 27 Food poisoning Dimethyldithiophosphate (DMDTP), 228 in Singapore, 34 Dimethylphosphate (DMP), 228 Fourth generation chemical weapons, 14 Dimethylthiophosphate (DMTP), 228 Fresh frozen plasma (FFP), 169, 200 Dimicron, 38 Fungicides, 3, 10, 28, 247 Diphenyl methyl phosphonate, 5 use of OPs as, 26 DUMBELS, 148, 156 G Dyspnea, 183 G agents, 4, 12, 13, 20, 27, 178–181, 189, 190 DZN immunotoxicity, 95 Gacyclidine, 196, 204, 248, 249 Gastric lavage, 156 E GB, 27 ECG, 120, 149 GD, 27 Electromyography (EMG), 184 Glasgow Coma Score (GCS), 67, 150, 155 Electrophysiology Glove-and-stocking type, 83 peripheral, 168 Glutathione (GSH), 92 Electrostatic steering, 16 Glycopyrrolate, 157 Emesis, 191 Guidance, 215, 216, 234, 246 forced, 156 Gulf war syndrome, 85, 93 Endosulfan, 96 Endotracheal intubation, 198 H Enhanced elimination, 168, 169 Haemodialysis, 169 Environmental exposure, 34, 92, 225, 226, 246 Halabjah, 4, 29, 201–203, 225, 247 Enzyme aging, 53 Health monitoring, 235 Epidemic paralysis, 34 Health-care professionals, 32 Epidemiology, 32, 247 Healthcare workers, 145, 153, 155 EPN, 130 protection of, 152 Ethanol, 247 Hemoperfusion (HP), 199 Ethion poisoning, 34 Hepatotoxicity, 96, 97, 195 Ethylthiometon, 94 Heptachlor, 28 254 Index

Herbicides, 10, 220 Matsumoto, 26, 30, 86, 178, 181, 188, 221, 247 use of OPs as, 26 terrorist attacks in, 4 HI-6, 168, 194, 204 terrorists attacks in, 30 Human exposure, 215 Mental disorders, 39 Human poisoning, 32 Mercaptophos, 28 Hydrogen iodide, 5 Methamidophos, 62, 105, 122, 217, 218 hyoscine, 157 Methyl parathion, 105 Hypertension, 149, 161 Methyl phosphor chloride, 26 pregnancy-induced, 92 Methylparathion (MP), 102 Hypotension, 57, 58, 92, 147, 149, 153–155, Methylphosphonofluoridate, 12 157, 163, 164, 167, 170, 226 Michaelis-Arbuzov rearrangement, 6 Michaelis-Becker reaction, 7 I Michaelis-Menten model, 16 Industrial exposure, 224 Miosis, 55, 56, 60, 120, 155, 182, 188, 192, Insecticides, 3, 9, 11, 27, 28, 36, 38, 46, 54, 80, 202, 203, 222 81, 127, 129, 143, 147, 198, 214, 220, Monocrotophos, 17, 62, 66, 104, 105, 122, 215, 234, 248 233 development of, 5 Morbidity, 30, 37, 38, 166 use of OPs as, 26 Mortality, 30, 34, 36–40, 48, 68, 104, 146, 157, Integrated Pest Management (IPM), 33 160, 161, 166, 167, 169, 170, 178, 183, Intentional self-poisoning, 3, 143, 145, 147, 196, 201, 203, 225, 247 152, 170, 247 rate of, 29, 95 Intermediate syndrome (IMS), 48, 54, 58, 59, Muda Agricultural Development Authority 62, 63, 67, 80, 91, 120, 122, 134, 154, (MADA), 132 165, 185, 203, 226, 248 Muscarinic, 52, 53, 58, 60, 122, 156, 192, 193, clinical presentation of, 122 226, 248 mechanisms of, 123 Muscarinic receptors, 57, 60, 121, 143 International Program on Chemical Safety Muscarinic transmission, 55, 56 (IPCS), 149 Mydriasis, 149, 192 International Program on Chemical Safety Myopathy, 59, 62, 123, 226 Poison Severity Score, 67 Intraperitoneal administrations, 95 N Iran-Iraq war, 26, 29, 178, 199, 201, 219, 225 N-dealkyated compounds, 18 N-methyl-D-aspartate (NMDA) receptors, 90, L 180 Lacrimation, 55, 56, 120 NA tabun exposure, 203 Lactate dehydrogenase (LDH), 96 Nematocides LD50 doses, 56 use of OPs as, 26 LD50 values, 104 Nerve agents (NAs), 9, 14, 27–30, 33, 50, 54, LD50value, 46 55, 57, 58, 61, 80, 81, 103, 104, 120, LD50, 214 169, 178, 219, 220, 222, 225, 227, 247 LD50 doses, 147, 181 Nerve conduction velocities (NCV), 82, 184 LD50 values, 233 Nerve gas, 12 Low-density lipoprotein (LDL), 93 Neuromuscular junction, 17, 52, 121, 122, 143, 149, 165, 179, 248 M Neuromuscular transmission, 58 Magnesium, 167 Neuropathy, 54, 59, 62, 82, 83, 125, 126, 168, Magnesium sulfate, 199, 204, 248, 249 185 Majnoon island, 4, 29, 203, 225, 247 Neuropathy target eaterase (NTE), 185 Malathion, 28, 38, 48, 66, 103, 105, 148, 218, Neuropathy target esterase (NTE), 80, 125, 170 225, 229 Neuropsychiatric disorders, 80 studies on, 103 Nicotine, 144 Malondialydehyde (MDA), 92 Nicotinic, 53, 60, 63, 90, 149, 165, 167, 192, Maternal toxicity, 101 226 Index 255

Nicotinic antagonists, 167 community based retrospective studies of, Nicotinic cholinergic receptors, 52 36 Nicotinic polymorphisms, 123 electrophysiological studies, 122 Nicotinic receptors, 52, 60, 121 OP synthesis, 5 Nicotinic transmission, 55 OP toxicity, 123 Non-intentional pesticide poisoning, 31 OP toxicology Non-occupational exposure, 34 aspects of, 26 Non-persistent agents, 179 OP-based insecticides, 11 Non-steroidal anti-inflammatory drug OP-enzyme Michaelis complex, 19 (NSAIDs), 90 OP-induced delayed polyneuropathy (OPIDN), Non-toxic OPs 54, 81, 82, 84, 120, 170, 226 biotransformation of, 18 OP-induced delayed polyneuropathy (OPIDP), Novichok agents, 4, 14, 20, 178, 247 123, 124, 134 NTE, 125 Optico-autonomic-peripheral neuropathy, Nucleophilic substitution reaction, 7, 16 93 Organization for prohibition of chemical weapons (OPCW), 4 O Organophosphate, 247 Obidoxime, 158, 160–162, 194, 195, Organophosphate (OP) compounds, 128 248 Organophosphate exposure, 127 Occupational exposure, 33, 80, 81, 95, 131, Organophosphate induced delayed 145, 155, 214, 219, 221–225 polyneuropathy (OPIDPN), 56 Occupational exposure limits (OEL), 219 Organophosphate intoxification, 59 Occupational pesticide poisoning, 31, 32 Organophosphates, 9, 20, 48, 50, 53, 55 Occupational poisoning, 80 synthesis of, 7 Octamethylpyrophosphortetramide (OMPA), Organophosphorus (OP), 26 27 Organophosphorus compounds (OPs), 2, 80, Ocular toxicity, 93, 94 120, 230, 234, 246, 249, 250 Omethoate, 102 accumulation of, 230 OP acute intoxication, 82 applications of, 3 OP exposure, 37, 60, 67, 82, 84–86, 104–106, as AChE inhibitors, 15, 17 129, 163, 200, 224 as health hazards, 39, 58, 63, 67 biological monitoring of, 227 as nerve agents, 12 classification of, 33 biotransformation of, 20 experimental studies on, 64 chronic effects of, 233 OP hepatotoxicity, 96, 97 classification of, 46 OP immunotoxicity, 95 ecotoxicology studies on, 230 OP insecticides, 54, 120, 222, 228, 235 fate and behaviour of, 229 OP intoxication, 36, 82, 83, 86, 90, 93 historical development of, 26, 30 causes of, 91 in agrochemical industry, 11 OP occupational poisoning, 33 organic derivatives of, 26 OP pesticide mass poisoning, 34 studies on, 127, 134, 155, 200, 217, 230, OP pesticides, 3, 4, 26, 28, 36, 38, 39, 68, 80, 247 81, 83, 92, 93, 100, 120, 122, 123, 127, synthesis of, 3, 5, 7, 246 178, 185, 192, 193, 199, 201, 214, 217, systematic studies on, 247 230, 235, 246, 247, 249, 250 transdermal absorption of, 155 exposures of, 53 uses of, 103 immunotoxity of, 95 Organophosphorus compounds (OPs) exposure, toxicity of, 81 214, 234, 249 OP pesticides poisoning, 39 Organophosphorus compounds (OPs) toxicity, OP poisoning, 26, 34–36, 39, 48, 50, 57, 235 61–63, 91, 100, 123, 144, 148, 163, 222, Organophosphorus-induced delayed 224, 227 polyneuropathy (OPIDN) 256 Index

phases of, 82, 83 Phosphonate, 5, 7, 18, 179, 247 studies on, 83 Phosphonic acid, 9 Outcomes, 35, 103, 145–147, 149, 151, 154, Phosphonic acids, 26 160, 161, 169, 199 Phosphonites, 9 Oxidation states, 2 Phosphonofluoridate, 12 Oxime therapy, 160, 162, 164, 185, 193–195 Phosphoramidate, 122 Oximes, 29, 83, 121–123, 152, 158, 160–163, synthesis of, 7 168, 179, 193, 194, 198, 199, 201, 202, Phosphoric acids, 26 204, 227, 249 Phosphorus trichloride (PCl3), 7 Oximes therapy, 157 Phosphoryl bond (P = O), 2, 9, 11, 247 Oxon, 18, 50, 53, 56, 62, 101, 147 Phosphoryl-enzyme complex, 19 metabolites of, 100 reactivation of, 19, 20 Phosphoryl-oxime compound (POX), 158 P Phosphorylation, 18, 83, 91, 97, 121, 125, 179, Pancuronium, 168 217 Paralysis, 55, 56, 83, 84, 120, 125, 149, 168, Phosphotriesterase (PTE), 16 183, 192, 226, 248 Pilocarpine, 60, 144 Paraoxonase (PON1), 53, 101, 169 Plasma β-glucuronidase (BG), 131, 132 Parasympathetic ganglia, 167 Plasma β-glucuronidase (BG) activity, 130, Parasympathetic nerves, 57 133, 135 Parasympathetic nervous system, 51, 148 Plasma β-glucuronidase (BG) assay, 129 Parasympathetic neurones, 51, 52 Plasma cholinesterase (ChE), 121, 150 Parasympathetic overactivity, 39 Plasma pseudo-choline esterase (ChE), 93 Parasympathetic pathway, 91 Poisoning, 34–37, 39, 53, 56, 58, 68 Parathion, 3, 5, 17, 27, 28, 34, 65–67, 90, 103, phases of, 60 105, 147, 247 Poisoning epidemiology, 120 Parathion poisoning, 134 Pralidoxime, 53, 62, 93, 158, 160–162, 168, Paraxon, 27 170, 194, 248 Peak expiratory flow rates, 163 Preeclampsia, 92 Pentavalent OP compounds, 9 Profenofos, 36, 151, 160 Pentavalent phosphorus, 9 Prophylactic benzodiazepine, 163 Periodic table, 2 Pseudocholinesterase, 179 Peripheral nervous systems (PNS), 50 Pseudomonas diminuta, 190 Peripheral neuropathy, 82, 85 Public hygiene, 224 Perkow product, 7 Pyrethroids, 3, 135 Persian Gulf war syndrome, 126, 186, 225 Persistent agents, 12, 179 R Pesticide mortality, 35 Randomised controlled trials (RCTs), 160, 162, Pesticide poisoning, 36, 38, 95 168 Pesticide self-poisoning, 31 RBC cholinesterase, 101, 151, 181 Pesticide toxicity, 132, 219 Regulations, 3, 39, 144, 147, 215, 218, 221, Pesticides, 3, 10, 20, 27, 30–33, 35, 36, 39 223, 246, 250 regulation of, 215 Regulatory guidance, 46 Phenol, 5 Reproductive toxicity, 102, 103, 216, 249 Phosphates, 7, 9, 18, 247 studies of, 100 Phosphinate, 5 Residential exposure, 225 Phosphine derivatives, 5 Respiratory failure, 38, 54, 58, 60, 90, 91, Phosphine oxides, 6, 9 120, 147, 151, 153, 155, 165, 180, 183, Phosphines 203 tertiary, 7 Respiratory muscle paralysis, 62 Phosphinic acid, 9, 26 Resuscitation, 152–155, 164, 166, 170, 248 Phosphinites, 9 Risk assessment, 143, 144, 147, 153, 215, 216, Phosphites, 9 218, 246 Index 257

S Tetraethylpyrophosphate (TEPP), 27 Saccadic abnormalities, 60 Thickening agents, 179 Salivation, 55, 56, 120, 149, 233 Thion, 147 Sarin, 4, 12, 13, 26–30, 33, 50, 54, 56, 57, Thionophosphorus esters, 27 59, 61, 92, 104, 120, 121, 167, 169, Thiophenols 178–182, 184, 186, 188, 189, 199, reactions of, 7 201–203, 219, 221, 222, 225, 247 Thiophosphate, 7, 18 computational studies on, 18 Thiophosphoric acids, 26 half-life of, 13 Thiophosphoryl bond (P = S), 2, 11, 18, 20, role in Tokyo subway terrorist attack, 86 247 Sarin (GB), 178 Toxic pesticides, 32 Sarin incident, 221 Toxicity, 4, 5, 9, 12, 14, 20, 27, 35, 46, 54, Secondary contamination, 33, 145, 152, 153, 67, 80, 103, 128, 142, 147, 155, 179, 155, 187, 188, 224 180, 182, 187, 191–195, 198, 200, 214, risks of, 189 216–218, 224, 230, 233, 248–250 Seizures, 55, 56, 60, 61, 120, 153, 155, 163, Toxicogenomics, 146 184, 195, 196, 202 Toxicovigilance programs, 32 Self-poisoning, 37, 38, 147 Trialkyl phosphites, 5, 7 Sensorimotor neuropathy, 82 Trichlorfon, 28 Simplified Acute Physiology Score (SAPS), Tricresyl phosphate (TCP), 83 149 Triethylphosphate (TEP), 26 SN2 nucleophilic substitution, 6 Triorthocresyl phosphate (TOCP), 123, 180 Sodium bicarbonate, 168, 198, 204, 248, 249 Triphenyl phosphine, 7 Solvent, 54, 58, 81, 147, 153, 161 Triphenyl phosphite, 5 Soman, 4, 12, 13, 27, 50, 54, 56, 57, 61, 90, Trivalent phosphorus esters, 6 104, 120, 121, 179–181, 184, 186, 196, 199, 201, 204, 247 U Soman (GD), 178 U.S. Environmental Protection Agency’s Spirometry, 163, 165 (EPA), 215 Standard resuscitation, 143 Unintentional poisoning, 144, 248 Succinyl choline, 191 Suicidal attempts, 32, 37, 39, 85 V Suicidal OP poisoning, 34 V agents, 4, 12, 20, 28, 178, 180 Suicidal poisoning, 221 Vagal cholinergic system, 57 Survey of California department of public VE, 178 health-occupational health branch, 223 VG, 4, 28, 178 Suxamethonium, 153, 191 VM, 178 Synaptic cholinergic transmission VR, 28, 178 regulation of, 52 VX, 4, 12–14, 28, 54, 57, 61, 86, 92, 120, 121, 178–181, 189, 191, 199 T in Iran-Iraq war, 29 Tabun, 4, 12, 13, 19, 27, 29, 57, 120, 121, 178, solvents for, 13 180, 181, 199, 203, 204, 225, 247 synthesis of, 27 W Tabun (GA), 178 Wittig reaction, 7 Tachycardia, 55, 57, 149, 191, 192, 195, 199, Working Party on Pesticide Residues (WPPR), 201 81 Teratogenicity, 80 World Health Organisation (WHO), 53 Terbufos, 229 classification, 35 Tetraethylpyrophosphate World Health Organization (WHO), 3, 32, 214, synthesis of, 247 215, 250