Structure via PubChem · Public domain (PubChem)
endrin
Sign in to saveAlso known as 1,2,3,4,10,10-Hexachloro-6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro-1,4-endo,endo-5,8-dimethanonaphthalene, Hexadrin
Endrin is an organochlorine compound with the chemical formula C12H8Cl6O that was first produced in 1950 by Shell and Velsicol Chemical Corporation. It was primarily used as an insecticide, as well as a rodenticide and piscicide. It is a colourless, odorless solid, although commercial samples are often off-white. Endrin was manufactured as an emulsifiable solution known commercially as Endrex. The compound became infamous as a persistent organic pollutant, and for this reason it is banned in many countries.
Chemical data
- Formula
- C12H8Cl6O
- Molecular weight
- 380.9 g/mol
- IUPAC name
- (1R,2R,3R,6S,7S,8S,9S,11R)-3,4,5,6,13,13-hexachloro-10-oxapentacyclo[6.3.1.13,6.02,7.09,11]tridec-4-ene
- SMILES
- C1[C@@H]2[C@@H]3[C@H]([C@H]1[C@H]4[C@@H]2O4)[C@@]5(C(=C([C@]3(C5(Cl)Cl)Cl)Cl)Cl)Cl
- InChIKey
- DFBKLUNHFCTMDC-GKRDHZSOSA-N
- XLogP
- 3.7
- Polar surface area
- 12.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Research
1,192 papers- Endrin.Reviews of environmental contamination and toxicology · 1988
- Carcinogenicity of endrin.The Science of the total environment · 1979
- Bioremediation of the organochlorine pesticides, dieldrin and endrin, and their occurrence in the environment.Applied microbiology and biotechnology · 2009
- Endrin potentiates early-stage adipogenesis in 3T3-L1 cells by activating the mammalian target of rapamycin.Life sciences · 2022
- [Endrin poisoning].Boletin medico del Hospital Infantil de Mexico · 1990
via PubMed
Wikidata facts
- Mass
- 377.87063095599996
Show 9 more facts
- canonical SMILES
- C1C2C3C(C1C4C2O4)C5(C(=C(C3(C5(Cl)Cl)Cl)Cl)Cl)Cl
- chemical formula
- C₁₂H₈Cl₆O
- NIOSH Pocket Guide ID
- 0252
- density
- 1.70
- immediately dangerous to life or health
- 2
- decomposition point
- 392
- time-weighted average exposure limit
- 0.1
- isomeric SMILES
- C1[C@@H]2[C@@H]3[C@H]([C@H]1[C@H]4[C@@H]2O4)[C@@]5(C(=C([C@]3(C5(Cl)Cl)Cl)Cl)Cl)Cl
- Commons category
- Endrin
via Wikidata · CC0
~15 min read
Article
19 sectionsContents
- History
- Production
- Use
- Health effects
- Exposure and metabolism
- Neurological effects
- Developmental effects
- Other effects
- Monitoring Methods Used by OSHA
- 1984 poisoning outbreak in Pakistan
- Environmental behavior
- Removal from the environment
- Regulation
- United States
- International organizations
- Taiwan
- See also
- References
- External links
Endrin is an organochlorine compound with the chemical formula C12H8Cl6O that was first produced in 1950 by Shell and Velsicol Chemical Corporation. It was primarily used as an insecticide, as well as a rodenticide and piscicide. It is a colourless, odorless solid, although commercial samples are often off-white. Endrin was manufactured as an emulsifiable solution known commercially as Endrex. The compound became infamous as a persistent organic pollutant, and for this reason it is banned in many countries.
In the environment endrin exists as either endrin aldehyde or endrin ketone and can be found mainly in bottom sediments of bodies of water. Exposure to endrin can occur by inhalation, ingestion of substances containing the compound, or skin contact. Upon entering the body, it can be stored in body fats and can act as a neurotoxin on the central nervous system, which can cause convulsions, seizures, or even death.