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Name Description
id 51
T3DB ID T3D0056
Name Diazinon
Class SmallMolecule
Description Nonsystemic insecticide for rice and fruit trees. Cholinesterase inhibitor. Diazinon is used against animal ectoparasites Diazinon has been shown to exhibit apoptotic and antibiotic functions (A7691, A7692).
Categories "Pesticide", "Household Toxin", "Food Toxin", "Synthetic Toxin"
Types "Organic Compound", "Pesticide", "Organophosphate", "Insecticide", "Food Toxin", "Metabolite", "Household Toxin", "Synthetic Compound"
Synonyms "Agridin 60", "Alfa-tox", "Antigal", "Antlak", "Bassadinon", "Basudin", "Bazuden", "Bazudin", "Bazudine", "Ciazinon", "Compass", "Dacutox", "Dassitox", "Dazzel", "Delzinon", "Diagran", "Dianon", "Diazide", "Diazinone", "Diazitol", "Diazol", "Dicid", "Diethyl 2-isopropyl-4-methyl-6-pyrimidyl thionophosphate", "Diethyl dimpylatum", "Dimpylate", "Dipofene", "Disonex", "Dizictol", "Diziktol", "Dizinil", "Dizinon", "Drawizon", "Dyzol", "Ektoband", "Exodin", "Fezudin", "Flytrol", "Galesan", "Gardentox", "Isopropylmethylpyrimidyl diethyl thiophosphate", "Kayazinon", "Kayazol", "Knox-out", "Meodinon", "Nedcidol", "Neocidol", "Neodinon", "Neotsidol", "Nipsan", "Nucidol", "O,O-Diethyl 2-isopropyl-4-methylpyrimidyl-6-thiophosphate", "Oleodiazinon", "Optimizer", "Root guard", "Sarolex", "Spectracide", "Spertacide", "Srolex", "Terminator"
CAS Number 333-41-5
Chemical Formula C12H21N2O3PS
Average Molecular Mass 304.35
Monoisotopic Mass 304.10
IUPAC Name O,O-diethyl O-6-methyl-2-(propan-2-yl)pyrimidin-4-yl phosphorothioate
Traditional Name O,O-diethyl O-2-isopropyl-6-methylpyrimidin-4-yl phosphorothioate
SMILES CCOP(=S)(OCC)OC1=NC(=NC(C)=C1)C(C)C
InChI Identifier InChI=1S/C12H21N2O3PS/c1-6-15-18(19,16-7-2)17-11-8-10(5)13-12(14-11)9(3)4/h8-9H,6-7H2,1-5H3
InChI Key InChIKey=FHIVAFMUCKRCQO-UHFFFAOYSA-N
Kingdom Organic Compounds
Super Class Organophosphorus Compounds
Class Organothiophosphorus Compounds
Sub Class Organic Thiophosphoric Acids and Derivatives
Direct Parent Pyrimidines and Pyrimidine Derivatives
Alternate Parents "Pyrimidines and Pyrimidine Derivatives", "Organooxygen Compounds", "Organonitrogen Compounds"
Geometric Description Aromatic Heteromonocyclic Compounds
Substituents "organonitrogen compound", "pyrimidine", "Heterocycle", "Organooxygen Compound", "Aromatic Heteromonocyclic Compound", "Thiophosphate Triester"
Descriptors "a small molecule (MetaCyc)", "organic thiophosphate (ChEBI)", "organothiophosphate insecticide (ChEBI)", "Organophosphorus insecticides (KEGG)", "pyrimidines (ChEBI)"
Status Detected and Not Quantified
Origin Exogenous
Cellular Locations "Membrane"
Biofluids
Tissues
Pathways
State Liquid
Appearance Colorless oil (pure) or pale to dark brown liquid (technical).
Melting Point < 25°C
Boiling Point
Solubility 0.04 mg/mL at 25°C
LogP 3.81
Route of Exposure Oral (L162) ; inhalation (L162) ; dermal (L162)
Mechanism of Toxicity Diazinon is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.
Metabolism Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.
Toxicity LD50: 66 mg/kg (Oral, Rat) (T14) LD50: 180 mg/kg (Dermal, Rat) (T14) LD50: 65 mg/kg (Intraperitoneal, Rat) (T14) LD50: 58 mg/kg (Subcutaneous, Mouse) (T14) LD50: 180 mg/kg (Intravenous, Mouse) (T14)
Lethal Dose 25 g for an adult human. (T4)
Carcinogenicity Spraying and application of nonarsenical insecticides entail exposures that are probably carcinogenic to humans (Group 2A). (L135)
Uses/Sources Diazinon is used as an insecticide in agriculture, mainly on fruit and vegetable field crops. (L162)
Minimum Risk Level Intermediate Inhalation: 0.01 mg/m3 (L134) Acute Oral: 0.006 mg/kg/day (L134) Intermediate Oral: 0.002 mg/kg/day (L134) Chronic Oral: 0.0007 mg/kg/day (L134)
Health Effects Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.
Symptoms The symptoms associated with diazinon poisoning in humans include weakness, headaches, tightness in the chest, blurred vision, nonreactive pinpoint pupils, excessive salivation, difficulty breathing, sweating, nausea, vomiting, diarrhea, abdominal cramps, and slurred speech. (L163)
Treatment If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.
DrugBank ID
HMDB ID HMDB32943
PubChem Compound ID 3017
ChEMBL ID CHEMBL388560
ChemSpider ID 2909
KEGG Compound ID C14324
UniProt ID 0
OMIM ID 0
ChEBI ID 34682
BioCyc ID
CTD ID D003976
Stitch ID Diazinon
PDB ID
ACToR ID 411
Wikipedia Link
Creation Date 2009-03-06 18:58:00
Update Date 2014-12-24 20:20:59