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Name Description
id 16
T3DB ID T3D0017
Name Dieldrin
Class SmallMolecule
Description 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.
Categories "Pesticide", "Pollutant", "Synthetic Toxin"
Types "Organic Compound", "Organochloride", "Pesticide", "Ether", "Pollutant", "Synthetic Compound"
Synonyms "(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"
CAS Number 60-57-1
Chemical Formula C12H8Cl6O
Average Molecular Mass 380.91
Monoisotopic Mass 377.87
IUPAC Name (1R,2S,3S,6R,7R,8S,9S,11R)-3,4,5,6,13,13-hexachloro-10-oxapentacyclo[6.3.1.1³,?.0²,?.0?,¹¹]tridec-4-ene
Traditional Name dieldrin
SMILES [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 Identifier 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-
InChI Key InChIKey=DFBKLUNHFCTMDC-PICURKEMNA-N
Kingdom Organic Compounds
Super Class Heterocyclic Compounds
Class Oxepanes
Sub Class
Direct Parent Oxepanes
Alternate Parents "Oxanes", "Vinyl Chlorides", "Chloroalkenes", "Dialkyl Ethers", "Epoxides", "Organochlorides", "Alkyl Chlorides"
Geometric Description Aliphatic Heteropolycyclic Compounds
Substituents "organochloride", "alkyl chloride", "oxane", "dialkyl ether", "oxirane", "oxepane", "Ether", "Organooxygen Compound", "Organohalogen Compound", "Alkyl Halide", "Aliphatic Heteropolycyclic Compound", "Chloroalkene", "Vinyl Chloride", "Vinyl Halide", "Haloalkene"
Descriptors "organochlorine insecticide (ChEBI)", "Organochlorine pesticides (KEGG)", "Organochlorine insecticides (KEGG)", "organochlorine compound (ChEBI)", "epoxide (ChEBI)"
Status Detected and Not Quantified
Origin Exogenous
Cellular Locations "Cell junction", "Cytosol", "Endoplasmic reticulum", "Extracellular", "Lysosome", "Membrane", "Microsome", "Mitochondrion", "Nucleolus", "Peroxisome", "Plasma Membrane", "Sarcoplasmic Reticulum", "Synaptic Vesicle"
Biofluids
Tissues
Pathways "Apoptosis", "Base excision repair", "Proteasome", "Phenylalanine metabolism", "Oxidative phosphorylation", "Circadian rhythm", "Insulin secretion"
State Solid
Appearance White powder.
Melting Point 175.5°C
Boiling Point
Solubility 0.000195 mg/mL at 25 °C [BIGGAR,JW & RIGGS,RI (1974)]
LogP
Route of Exposure Oral (L87) ; inhalation (L87) ; dermal (L87)
Mechanism of Toxicity 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)
Metabolism 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)
Toxicity 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)
Lethal Dose
Carcinogenicity 3, not classifiable as to its carcinogenicity to humans. (L135)
Uses/Sources Dieldrin is used as an insecticide. (L87)
Minimum Risk Level Intermediate Oral: 0.0001 mg/kg/day (L134) Chronic Oral: 0.00005 mg/kg/day (L134)
Health Effects 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)
Symptoms Exposure to dieldrin results in headaches, dizziness, irritability, nausea and vomiting, cardiac arrhythmias, muscular weakness, uncontrolled muscle movements, hyperexcitability, seizures and coma. (L87)
Treatment 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)
DrugBank ID
HMDB ID
PubChem Compound ID 969491
ChEMBL ID CHEMBL1873703
ChemSpider ID 10292746
KEGG Compound ID C13718
UniProt ID 0
OMIM ID 0
ChEBI ID 34696
BioCyc ID
CTD ID D004026
Stitch ID Dieldrin
PDB ID
ACToR ID 459
Wikipedia Link Dieldrin
Creation Date 2009-03-06 18:57:55
Update Date 2014-12-24 20:20:53