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Name Description
id 60
T3DB ID T3D0067
Name beta Endosulfan
Class SmallMolecule
Description Endosulfan, beta is one of two stereoisomers of endosulfan. Endosulfan is an organochlorine insecticide and acaricide. It is used to control insects on food and non-food crops and as a wood preservative. Due to its toxicity and tendency to bioaccumulate, the use of endosulfan is banned in many areas. (L113)
Categories "Pesticide", "Pollutant", "Food Toxin", "Synthetic Toxin"
Types "Organic Compound", "Organochloride", "Pesticide", "Ester", "Pollutant", "Food Toxin", "Synthetic Compound"
Synonyms "Alpha-thionex", "b Endosulfan", "b-endosulfan", "B-endosulfan-beta", "b-thiodan", "Beta-benzoepin", "Beta-endosulfan", "Beta-thiodan", "Endosulfan 2", "Endosulfan b", "Endosulfan, beta", "Endosulfan-b", "? Endosulfan"
CAS Number 33213-65-9
Chemical Formula C9H6Cl6O3S
Average Molecular Mass 406.93
Monoisotopic Mass 403.82
IUPAC Name (1R,9S)-1,9,10,11,12,12-hexachloro-4,6-dioxa-5??-thiatricyclo[7.2.1.0²,?]dodec-10-en-5-one
Traditional Name (1R,9S)-1,9,10,11,12,12-hexachloro-4,6-dioxa-5??-thiatricyclo[7.2.1.0²,?]dodec-10-en-5-one
SMILES ClC1=C(Cl)[C@]2(Cl)C3COS(=O)OCC3[C@@]1(Cl)C2(Cl)Cl
InChI Identifier InChI=1/C9H6Cl6O3S/c10-5-6(11)8(13)4-2-18-19(16)17-1-3(4)7(5,12)9(8,14)15/h3-4H,1-2H2/t3?,4?,7-,8+,19?
InChI Key InChIKey=RDYMFSUJUZBWLH-QTSFFCDANA-N
Kingdom Organic Compounds
Super Class Organooxygen Compounds
Class Organic Oxoanionic Compounds
Sub Class Organosulfites
Direct Parent Cycloalkenes
Alternate Parents "Vinyl Chlorides", "Chloroalkenes", "Heterocyclic Compounds", "Organochlorides", "Alkyl Chlorides"
Geometric Description Aliphatic Heteropolycyclic Compounds
Substituents "organochloride", "alkyl chloride", "Heterocycle", "Organohalogen Compound", "Alkyl Halide", "Aliphatic Heteropolycyclic Compound", "Chloroalkene", "Vinyl Chloride", "Vinyl Halide", "Haloalkene", "Organosulfite"
Descriptors
Status Detected and Not Quantified
Origin Exogenous
Cellular Locations "Actin Cytoskeleton", "Cell junction", "Cytoskeleton", "Cytosol", "Endoplasmic reticulum", "Extracellular", "Lysosome", "Membrane", "Membrane Fraction", "Microsome", "Mitochondrial Matrix", "Nucleolus", "Peroxisome", "Plasma Membrane", "Ribosome", "Sarcoplasmic Reticulum", "Secretory vesicle"
Biofluids
Tissues
Pathways "Apoptosis", "Proteasome", "Oxidative phosphorylation", "Ovarian Steroidogenesis", "Cell cycle", "Antiviral Agents"
State Solid
Appearance Cream- to brown-colored solid.
Melting Point 106°C
Boiling Point
Solubility 0.00045 mg/mL at 20 °C [BOWMAN,BT & SANS,WW (1983)]; 0.000325 mg/mL at 22 °C [TOMLIN,C (1994)]
LogP
Route of Exposure Oral (L114) ; inhalation (L114) ; dermal (L114)
Mechanism of Toxicity Endosulfan 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. Endosulfan 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 CNS. This results in hyperexcitation and generalized seizures. Endosulfan is also an endocrine disruptor and acts as an agonist at the progesterone receptor and estrogen receptors. (T10, L113, L114, A61, A114)
Metabolism Endosulfan is absorbed by inhalation, oral, and dermal routes of exposure. It accumulates mainly in the liver, kidney, and brain, and is metabolized to polar and nonpolar metabolites by cytochrome P-450 enzymes. Endosulfan and its metabolites, which include sulfate, diol, ?-hydroxyether, lactone, and ether derivatives of endosulfan, are excreted in the urine and faeces. (L114)
Toxicity LD50: 18 mg/kg (Oral, Rat) (T14) LD50: 34 mg/kg (Dermal, Rat) (T14) LD50: 8 mg/kg (Intraperitoneal, Rat) (T14) LD50: 360 mg/kg (Subcutaneous, Rabbit) (T14) LC50: 80 mg/m3 over 4 hours (Inhalation, Rat) (T14)
Lethal Dose 50 to 500 mg/kg for an adult human. (T27)
Carcinogenicity No indication of carcinogenicity to humans (not listed by IARC).
Uses/Sources Endosulfan is used as an insecticide, acaricide, and in wood preservatives. (L114)
Minimum Risk Level Intermediate Oral: 0.005 mg/kg/day (L134) Chronic Oral: 0.002 mg/kg/day (L134)
Health Effects Endosulfan is a neurotoxin and damages the central nervous system, causing effects such as intermittent muscle twitching and myoclonic jerking. Endosulfan can also damage the kidneys, testes, and liver, and may possibly affect the body's ability to fight infection. It is also an endocrine disruptor and causes reproductive and developmental damage. (T10, L113, L114)
Symptoms Symptoms of endosulfan poisoning include hyperactivity, hyperreflexia, tremors, dizziness, headache, convulsions, lack of coordination, staggering, difficulty breathing, nausea and vomiting, diarrhea, and in severe cases, unconsciousness. (T10, L113, L114)
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. (L161)
DrugBank ID
HMDB ID
PubChem Compound ID 6434141
ChEMBL ID
ChemSpider ID 16736499
KEGG Compound ID
UniProt ID 0
OMIM ID 0
ChEBI ID 0
BioCyc ID
CTD ID
Stitch ID Endosulfan, beta
PDB ID
ACToR ID 8145
Wikipedia Link
Creation Date 2009-03-06 18:58:01
Update Date 2014-12-24 20:21:01