Endrin

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.

Endrin
Names
Preferred IUPAC name
(1aR,2R,2aR,3R,6S,6aS,7S,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
Other names
Mendrin, Compound 269, 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
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.705
EC Number
  • 200-775-7
KEGG
RTECS number
  • IO1575000
UNII
UN number 2761
  • InChI=1S/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+ Y
    Key: DFBKLUNHFCTMDC-RVVFZPGKSA-N Y
  • 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+
    Key: DFBKLUNHFCTMDC-RVVFZPGKBH
  • C1C2C3C(C1C4C2O4)C5(C(=C(C3(C5(Cl)Cl)Cl)Cl)Cl)Cl
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
GHS labelling:
Danger
H301, H310, H351, H372, H410
P201, P202, P260, P262, P264, P270, P273, P280, P281, P301+P310, P302+P350, P308+P313, P310, P314, P321, P322, P330, P361, P363, P391, P405, P501
NFPA 704 (fire diamond)
3
0
0
Flash point noncombustible
Lethal dose or concentration (LD, LC):
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)
5 mg/kg (cat, oral)
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 0.1 mg/m3 [skin]
REL (Recommended)
TWA 0.1 mg/m3 [skin]
IDLH (Immediate danger)
2 mg/m3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

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.

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