Basic information
- CAS
128-10-9- Standard SMILES
ClC1=C(Cl)C2(Cl)C3C4CC(C5OC45)C3C1(Cl)C2(Cl)Cl- InChIKey
DFBKLUNHFCTMDC-UHFFFAOYSA-N- Molecular formula
- C12H8Cl6O
- Average molar mass
- 380.9 g/mol
- Monoisotopic mass
- 377.870631
Overview
Endrin can cause developmental toxicity according to The Environmental Protection Agency (EPA).
Names & identifiers
- Preferred name
- 2,7:3,6-Dimethanonaphth[2,3-b]oxirene, 3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-
- IUPAC
- 3,4,5,6,13,13-hexachloro-10-oxapentacyclo[6.3.1.13,6.02,7.09,11]tridec-4-ene
- English name
- 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
- Molecular formula
- C12H8Cl6O
- Molecular weight
- 380.91
Names & synonyms
128-10-9NSC 231371exo-1,4-endo-5,8-Dimethanonaphthalene1,4:5,8-Dimethanonaphthalene, 1,2,3,4,10,10-hexachloro-6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro-2,7:3,6-Dimethanonaphth(2,3-b)oxirene, 3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-Dimethanonaphth[2,3-b]oxirene, 3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-RefChem:2488812,7:3,6-Dimethanonaphth(2,3-b)oxirene, 3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-(9CI)Endrin isomer3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphtho[2,3-b]oxireneEndrin 20 ECEndrin and metabolites
Show more names
Nsc2313711,4,4a,5,6,7,8,8a-Octahydro-1,2,3,4,11,11-hexachloro-6,7-epoxy-1,4:5,8-dimethanonaphthalene2,7:3,6-Dimethanonaphth[2,3-b]oxirene, 3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro- (9CI)
Deildrin2,7:3,6-Dimethanonaphth[2,3-b]oxirene, 3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-, (1a.alpha.,2.beta.,2a.alpha.,3.beta.,6.beta.,6a.alpha.,7.beta.,7a.alpha.)-Alvit, DieldrexSD 3419 IlloxolNCGC00091352-021,2,3,4,10,10-Hexachloro-6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro-endo,exo-1,4:5,8-dimethanonaphthalene2,7:3,6-Dimethanonaphth[2,3-b]oxirene, 3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-, (1a.alpha.,2.beta.,2a.beta.,3.alpha.,6.alpha.,6a.beta.,7.beta.,7a.alpha.)-3,4,5,6,13,13-hexachloro-10-oxapentacyclo[6.3.1.1<3,6>.0<2,7>.0<9,11>]tridec-4 -ene
Properties
Computed structural properties
- XLogP
- 3.7
- Topological polar surface area
- 12.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 516
Experimental & physicochemical properties
LogP
5.20
5.11
Solubility0.00025 mg/mL at 25 °C
Melting Point226 - 230 °C
Physical DescriptionSolid
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety & protection
Minimum Risk LevelIntermediate Oral: 0.002 mg/kg/day (L134)
Chronic Oral: 0.0003 mg/kg/day (L134)
Toxicology
TreatmentTreatment is symptomatic, aimed at controlling convulsions, coma, and respiratory depression. If ingested, gastric lavage may be performed, followed by administering activated charcoal powder. (L150)
Health EffectsEndrin poisoning affects primarily the nerve system. Exposure causes various harmful effects including hyperexcitability, severe central nervous system damage, and death. Endrin is also believed to cause birth defects. (T10, L112)
Exposure RoutesOral (L111)
Toxicity Summary
Endrin 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 and causing hyperexcitability of the central nervous system. Endrin 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 central nervous system. Endrin also causes increased lipid peroxidation, decreased membrane fluidity, and DNA damage in hepatocytes, but the exact mechanism is unknown. (T10, L112)
Signs and SymptomsSymptoms that may result from endrin poisoning are headaches, dizziness, nervousness, confusion, nausea, vomiting, and convulsions. (L112)
Carcinogen Classification3, not classifiable as to its carcinogenicity to humans. (L135)
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Endrin is absorbed orally and distributed primarily to the fat and skin. The major biotransformation product is anti-l 2-hydroxyendrin and the corresponding sulfate, as well as glucuronide metabolites. Anti- and syn-12-hydroxyendrin and 12-ketoendrin are the main toxic metabolites of endrin. Endrin and its metabolites are excreted in urine and feces. (L112)
Cellular LocationsMembrane
Uses & manufacturing
UsesEndrin is used as a pesticide. (L111)
Additional notes
DefinitionChEBI: LSM-36947 is a monoterpenoid.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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