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Name Description
id 37
T3DB ID T3D0041
Name Endrin
Class SmallMolecule
Description Endrin has been found as a contaminant throughout the environment, including foodstuffs, fish, human milk, etc. Endrin belongs to the family of Benzoxepines. These are organic compounds containing a benzene ring fused to an oxepine ring (unsaturated seven-member heterocycle with one oxygen atom replacing a carbon atom.).
Categories "Pesticide", "Pollutant", "Food Toxin", "Synthetic Toxin"
Types "Organic Compound", "Organochloride", "Pesticide", "Ether", "Pollutant", "Food Toxin", "Metabolite", "Synthetic Compound"
Synonyms "3,4,5,6,9,9-Hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaph[2,3-b]oxirene", "Endrex", "Endricol", "Endrine", "Hexachloroepoxyoctahydro-endo, endo-dimethanonaphthalene", "Hexachloroepoxyoctahydro-endo,endo-dimethanonaphthalene", "Hexachloroepoxyoctahydro-endo,endo-dimethanonapthalene", "Hexadrin", "Latka 269", "Mendrin", "Nendrin", "Oktanex", "Stardrin", "Stardrin 20"
CAS Number 72-20-8
Chemical Formula C12H8Cl6O
Average Molecular Mass 380.91
Monoisotopic Mass 377.87
IUPAC Name 3,4,5,6,13,13-hexachloro-10-oxapentacyclo[6.3.1.1³,?.0²,?.0?,¹¹]tridec-4-ene
Traditional Name endrin
SMILES ClC1=C(Cl)C2(Cl)C3C4CC(C5OC45)C3C1(Cl)C2(Cl)Cl
InChI Identifier 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
InChI Key InChIKey=DFBKLUNHFCTMDC-UHFFFAOYNA-N
Kingdom Organic Compounds
Super Class Heterocyclic Compounds
Class Oxepanes
Sub Class
Direct Parent Oxepanes
Alternate Parents "Oxanes", "Vinyl Chlorides", "Chloroalkenes", "Dialkyl Ethers", "Epoxides", "Organochlorides", "Alkyl Chlorides"
Geometric Description Aliphatic Heteropolycyclic Compounds
Substituents "organochloride", "alkyl chloride", "oxane", "dialkyl ether", "oxirane", "oxepane", "Ether", "Organooxygen Compound", "Organohalogen Compound", "Alkyl Halide", "Aliphatic Heteropolycyclic Compound", "Chloroalkene", "Vinyl Chloride", "Vinyl Halide", "Haloalkene"
Descriptors
Status Detected and Not Quantified
Origin Exogenous
Cellular Locations "Membrane"
Biofluids
Tissues
Pathways
State Solid
Appearance White powder.
Melting Point 226 - 230°C
Boiling Point
Solubility 0.00025 mg/mL at 25°C
LogP 5.2
Route of Exposure Oral (L111)
Mechanism of Toxicity 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)
Metabolism 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)
Toxicity LD50: 3 mg/kg (Oral, Rat) (T14) LD50: 12 mg/kg (Dermal, Rat) (T14)
Lethal Dose
Carcinogenicity 3, not classifiable as to its carcinogenicity to humans. (L135)
Uses/Sources Endrin is used as a pesticide. (L111)
Minimum Risk Level Intermediate Oral: 0.002 mg/kg/day (L134) Chronic Oral: 0.0003 mg/kg/day (L134)
Health Effects Endrin 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)
Symptoms Symptoms that may result from endrin poisoning are headaches, dizziness, nervousness, confusion, nausea, vomiting, and convulsions. (L112)
Treatment Treatment is symptomatic, aimed at controlling convulsions, coma, and respiratory depression. If ingested, gastric lavage may be performed, followed by administering activated charcoal powder. (L150)
DrugBank ID
HMDB ID HMDB31211
PubChem Compound ID 3048
ChEMBL ID
ChemSpider ID 2940
KEGG Compound ID
UniProt ID 0
OMIM ID 0
ChEBI ID 0
BioCyc ID DIHYDROKAEMPFEROL-CMPD
CTD ID D004732
Stitch ID Endrin
PDB ID
ACToR ID 572
Wikipedia Link http://en.wikipedia.org/wiki/Endrin
Creation Date 2009-03-06 18:57:58
Update Date 2014-12-24 20:20:57