18 Dieldrin 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. 60-57-1 969491 C12H8Cl6O 377.870630 White powder. 175.5°C 0.000195 mg/mL at 25 °C [BIGGAR,JW & RIGGS,RI (1974)] Oral (L87) ; inhalation (L87) ; dermal (L87) Ubiquitin (P62988) Alpha-synuclein (P37840) Gamma-aminobutyric acid receptor subunit alpha-1 (P14867) Gamma-aminobutyric acid receptor subunit alpha-2 (P47869) Gamma-aminobutyric acid receptor subunit alpha-3 (P34903) Gamma-aminobutyric acid receptor subunit alpha-4 (P48169) Gamma-aminobutyric acid receptor subunit alpha-5 (P31644) Gamma-aminobutyric acid receptor subunit alpha-6 (Q16445) Gamma-aminobutyric acid receptor subunit beta-1 (P18505) Gamma-aminobutyric acid receptor subunit beta-2 (P47870) Gamma-aminobutyric acid receptor subunit beta-3 (P28472) Gamma-aminobutyric acid receptor subunit delta (O14764) Gamma-aminobutyric acid receptor subunit gamma-1 (Q8N1C3) Gamma-aminobutyric acid receptor subunit gamma-2 (P18507) Gamma-aminobutyric acid receptor subunit gamma-3 (Q99928) Gamma-aminobutyric acid receptor subunit pi (O00591) Gamma-aminobutyric acid receptor subunit rho-1 (P24046) Gamma-aminobutyric acid receptor subunit rho-2 (P28476) Gamma-aminobutyric acid receptor subunit rho-3 (A8MPY1) Gamma-aminobutyric acid receptor subunit theta (Q9UN88) Sodium/potassium-transporting ATPase subunit alpha-1 (P05023) Sodium/potassium-transporting ATPase subunit alpha-2 (P50993) Sodium/potassium-transporting ATPase subunit alpha-3 (P13637) Sodium/potassium-transporting ATPase subunit alpha-4 (Q13733) Sodium/potassium-transporting ATPase subunit beta-1 (P05026) Sodium/potassium-transporting ATPase subunit beta-2 (P14415) Sodium/potassium-transporting ATPase subunit beta-3 (P54709) Sodium/potassium-transporting ATPase gamma chain (P54710) Calcium-transporting ATPase type 2C member 1 (P98194) Calcium-transporting ATPase type 2C member 2 (O75185) Plasma membrane calcium-transporting ATPase 1 (P20020) Plasma membrane calcium-transporting ATPase 2 (Q01814) Plasma membrane calcium-transporting ATPase 3 (Q16720) Plasma membrane calcium-transporting ATPase 4 (P23634) Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 (O14983) Sarcoplasmic/endoplasmic reticulum calcium ATPase 2 (P16615) Sarcoplasmic/endoplasmic reticulum calcium ATPase 3 (Q93084) (T10, A47, A48, L87) 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) 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) 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) 3, not classifiable as to its carcinogenicity to humans. (L135) Dieldrin is used as an insecticide. (L87) Intermediate Oral: 0.0001 mg/kg/day (L134) Chronic Oral: 0.00005 mg/kg/day (L134) 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) Exposure to dieldrin results in headaches, dizziness, irritability, nausea and vomiting, cardiac arrhythmias, muscular weakness, uncontrolled muscle movements, hyperexcitability, seizures and coma. (L87) 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) 2009-03-06T18:57:55Z 2014-12-24T20:20:53Z Epoxide hydrolase 1 (P07099) Epoxide hydrolase 2 (P34913) (L87) Dieldrin C13718 34696 D004026 Dieldrin 459 true Epoxide hydrolase 1 (P07099) Epoxide hydrolase 2 (P34913) (L87) [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 C12H8Cl6O 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- InChIKey=DFBKLUNHFCTMDC-PICURKEMNA-N 380.909 377.87063112 Exogenous Solid CHEMBL1873703 10292746