Dieldrin
描述
Dieldrin is a chlorinated hydrocarbon used as an insecticide, either by itself or as a component of the closely related insectide aldrin. As dieldrin is neurotoxin and tends to bioaccumulate, its use is now banned in most parts of the world. (L86) Dieldrin is a chlorinated hydrocarbon originally produced in 1948 by J. Hyman & Co, Denver, as an insecticide. Dieldrin is closely related to aldrin, which reacts further to form dieldrin. Aldrin is not toxic to insects; it is oxidized in the insect to form dieldrin which is the active compound. Both dieldrin and aldrin are named after the Diels-Alder reaction which is used to form aldrin from a mixture of norbornadiene and hexachlorocyclopentadiene.
类别
"Pesticide", "Pollutant", "Synthetic Toxin"
同义词
"(1Aalpha,2beta,2aalpha,3beta,6beta,6aalpha,7beta,7aalpha)-3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphtho[2,3-b]oxirene", "(1R,4S,4AS,5R,6R,7S,8S,8ar)-1,2,3,4,10,10-hexachloro-1,4,4a,5,6,7,8,8a-octahydro-6,7-epoxy-1,4:5,8-dimethanonaphthalene", "1,2,3,4,10,10-Hexachloro-6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro-1,4-endo-exo-5,8-dimethanonaphthalene", "Aldrin epoxide", "Alvit", "Alvit 55", "Deildrin", "Dieldren", "Dieldrex", "Dieldrine", "Dieldrite", "Dieldrix", "Dielmoth", "Dildrin", "Dorytox", "Exo-dieldrin", "HEOD", "Hexachloroepoxyoctahydro-endo,exo-dimethanonaphthalene", "Illoxol", "Insectlack", "Kombi-albertan", "Murdiel", "Octalox", "Oxralox", "Panoram D-31", "Quintox", "Shelltox", "Termitox", "Termitoxrm"
IUPAC 名称
(1R,2S,3S,6R,7R,8S,9S,11R)-3,4,5,6,13,13-hexachloro-10-oxapentacyclo[6.3.1.1³,⁶.0²,⁷.0⁹,¹¹]tridec-4-ene
简化分子线性输入规范
[H][C@]12O[C@@]1([H])[C@@]1([H])C[C@]2([H])[C@@]2([H])[C@]1([H])[C@@]1(Cl)C(Cl)=C(Cl)[C@]2(Cl)C1(Cl)Cl
InChI 标识符
InChI=1/C12H8Cl6O/c13-8-9(14)11(16)5-3-1-2(6-7(3)19-6)4(5)10(8,15)12(11,17)18/h2-7H,1H2/t2-,3+,4+,5-,6-,7+,10+,11-
键
InChIKey=DFBKLUNHFCTMDC-PICURKEMNA-N
大分类
Lipids and lipid-like molecules
另外分类
"Alkyl chlorides", "Chloroalkenes", "Dialkyl ethers", "Epoxides", "Hydrocarbon derivatives", "Organochlorides", "Oxacyclic compounds", "Oxanes", "Oxepanes", "Vinyl chlorides"
取代基
"Aliphatic heteropolycyclic compound", "Alkyl chloride", "Alkyl halide", "Chloroalkene", "Dialkyl ether", "Ether", "Haloalkene", "Hydrocarbon derivative", "Monoterpenoid", "Norbornane monoterpenoid", "Organic oxygen compound", "Organochloride", "Organohalogen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Oxane", "Oxepane", "Oxirane", "Vinyl chloride", "Vinyl halide"
分子框架
Aliphatic heteropolycyclic compounds
外部描述符
"Organochlorine insecticides", "Organochlorine pesticides", "epoxide", "organochlorine compound", "organochlorine insecticide"
地位
Detected and Not Quantified
蜂窝位置
"Cell junction", "Cytosol", "Endoplasmic reticulum", "Extracellular", "Lysosome", "Membrane", "Microsome", "Mitochondrion", "Nucleolus", "Peroxisome", "Plasma Membrane", "Sarcoplasmic Reticulum", "Synaptic Vesicle"
途径
"Apoptosis", "Base excision repair", "Proteasome", "Phenylalanine metabolism", "Oxidative phosphorylation", "Circadian rhythm", "Insulin secretion"
熔点/沸点/溶解度
175.5°C//0.000195 mg/mL at 25 °C [BIGGAR,JW & RIGGS,RI (1974)]
暴露途径
Oral (L87) ; inhalation (L87) ; dermal (L87)
毒性机制
Dieldrin antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions. Dieldrin also inhibits Na+ K+ ATPase and Ca2+ and Mg2+ ATPase which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the CNS. This results in hyperexcitation and generalized seizures. Dieldrin also binds to alpha-synuclein, leading to the formation of intracellular fibrils. (T10, L87)
代谢
Dieldrin is absorbed throught the gastrointestinal tract, lungs and skin. Following absorption, dieldrin is redistributed primarily to fat via the lymphatic system. Dieldrin is metabolized by liver microsomal monooxygenases and epoxide hydratases. Its metabolites, of which the primary one is 9-hydroxydieldrin, are excreted in the faeces. (L87)
毒性值
LD50: 38 mg/kg (Oral, Rat) (T14)
LD50: 56 mg/kg (Dermal, Rat) (T14)
LD50: 49 mg/kg (Subcutaneous, Rat) (L142)
LD50: 9 mg/kg (Intravenous, Rat) (T14)
LC50: 13 mg/m3 over 4 hours (Inhalation, Rat) (L142)
致癌性
3, not classifiable as to its carcinogenicity to humans. (L135)
用途/来源
Dieldrin is used as an insecticide. (L87)
最低风险等级
Intermediate Oral: 0.0001 mg/kg/day (L134)
Chronic Oral: 0.00005 mg/kg/day (L134)
健康影响
Dieldrin is a neurotoxin and works by overstimulating the central nervous system. Ingestion of large amounts of dieldrin causes convulsions and death. However, chronic exposure to lower amounts of dieldrin also has adverse effects because dieldrin accumulates in the body. Dieldrin is known to damage the nervous system, liver, and immune system. (L87)
症状
Exposure to dieldrin results in headaches, dizziness, irritability, nausea and vomiting, cardiac arrhythmias, muscular weakness, uncontrolled muscle movements, hyperexcitability, seizures and coma. (L87)
治疗
Treatment is symptomatic, aimed at controlling convulsions, coma, and respiratory depression. If ingested, gastric lavage may be performed, followed by administering activated charcoal powder. (L143)
创建于
2009-03-06 18:57:55 UTC
更新于
2014-12-24 20:20:53 UTC