Endrin
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| Names | |
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IUPAC name
(1R,2S,3R,6S,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
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| Other names
Mendrin, Compound 269, (1aR,2S,2aS,3S,6R,6aR,7R,7aS)-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, 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
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| Identifiers | |
72-20-8 
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| 3D model (Jmol) | Interactive image |
| ChemSpider |
21782117
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| ECHA InfoCard | 100.000.705 |
| KEGG |
C18124
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| UNII |
OB9NVE7YCL
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| Properties | |
| C12H8Cl6O | |
| Molar mass | 380.907 g/mol |
| Appearance | Colorless to tan crystalline solid |
| Density | 1.77 g/cm3 |
| Melting point | 200 °C (392 °F; 473 K) (decomposes) |
| 0.23 mg/L | |
| Vapor pressure | 2.6 x 10-5 Pa |
| Hazards | |
| NFPA 704 | |
| Flash point | noncombustible |
| Lethal dose or concentration (LD, LC): | |
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LD50 (median dose)
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3 mg/kg (oral, monkey) 16 mg/kg (oral, guinea pig) 10 mg/kg (oral, hamster) 3 mg/kg (oral, rat) 7 mg/kg (oral, rabbit) 1.4 mg/kg (oral, mouse) |
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LDLo (lowest published)
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5 mg/kg (cat, oral) |
| US health exposure limits (NIOSH): | |
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PEL (Permissible)
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TWA 0.1 mg/m3 [skin] |
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REL (Recommended)
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TWA 0.1 mg/m3 [skin] |
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IDLH (Immediate danger)
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2 mg/m3 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is  ?) |
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| Infobox references | |
Endrin is an organochloride 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.
Although endrin is not currently classified as a mutagen, nor as a human carcinogen, it is still a toxic chemical in other ways with detrimental effects. Due to these toxic effects, the manufacturers cancelled all use of endrin in the United States by 1991. Food import concerns have been raised because some countries may have still been using endrin as a pesticide.
J. Hyman & Company first developed endrin in 1950. Shell International was licensed in the United States and in the Netherlands to produce it. Velsicol was the other producer in the Netherlands. Endrin was used globally until the early 1970s. Due to its toxicity, it was banned or severely restricted in many countries. In 1982, Shell discontinued its manufacturing.
In 1962, an estimated 2.3-4.5 million kilograms of endrin were sold by Shell in the USA. In 1970, Japan imported 72,000 kilograms of endrin. From 1963 until 1972, Bali used 171 to 10,700 kilograms of endrin annually for the production of rice paddies until endrin use was discontinued in 1972. Taiwan reported to show higher levels of organochlorine pesticides including endrin in soil samples of paddy fields, compared to other Asian countries such as Thailand and Vietnam. During the 1950s-1970s over two million kilograms of organochlorine pesticides were estimated of having been be released into the environment per year. Endrin was banned in the United States on October 10, 1984. Taiwan banned endrin's use as a pesticide in 1971 and regulated it as a toxic chemical in 1989.
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