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Name Description
id 46
T3DB ID T3D0050
Name O,P'-DDT
Class SmallMolecule
Description DDT, O,P'- is an isomer of dichlorodiphenyltrichloroethane, an organochlorine insecticide. It is the major component of commercial mixtures of DDT. DDT was once a widely used pesticide, but today its agricultural use has been banned worldwide due to its toxicity and tendency to bioaccumulate. However, it still has limited use in disease vector control. (L84)
Categories "Pesticide", "Synthetic Toxin"
Types "Organic Compound", "Organochloride", "Pesticide", "Synthetic Compound"
Synonyms "1,1,1-Trichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane", "1-Chloro-2-(2,2,2-trichloro-1-(4-chlorophenyl)ethyl)benzene", "2,2,2,o,p'-Pentachloroethylidenebisbenzene", "2,2-Bis(o,p-chlorophenyl)-1,1,1-trichloroethane", "2-(2-Chlorophenyl)-2-(4-chlorophenyl)-1,1,1-trichloroethane", "DDT-o,p'", "o,p'-DDT", "O,P'-ddt", "o,p'-DDT (r)-isomer", "o,p-DDT", "Ortho,para'-DDT", "p,p'-DDT"
CAS Number 789-02-6
Chemical Formula C14H9Cl5
Average Molecular Mass 354.49
Monoisotopic Mass 351.91
IUPAC Name 1-chloro-4-[2,2,2-trichloro-1-(2-chlorophenyl)ethyl]benzene
Traditional Name o,p'-DDT
SMILES ClC1=CC=C(C=C1)C(C1=CC=CC=C1Cl)C(Cl)(Cl)Cl
InChI Identifier InChI=1S/C14H9Cl5/c15-10-7-5-9(6-8-10)13(14(17,18)19)11-3-1-2-4-12(11)16/h1-8,13H
InChI Key InChIKey=CVUGPAFCQJIYDT-UHFFFAOYSA-N
Kingdom Organic Compounds
Super Class Benzenoids
Class Benzene and Substituted Derivatives
Sub Class Diphenylmethanes
Direct Parent Diphenylmethanes
Alternate Parents "Chlorobenzenes", "Aryl Chlorides", "Organochlorides", "Alkyl Chlorides"
Geometric Description Aromatic Homomonocyclic Compounds
Substituents "chlorobenzene", "aryl chloride", "organochloride", "alkyl chloride", "Aromatic Homomonocyclic Compound", "Halobenzene", "Aryl Halide", "Organohalogen Compound", "Alkyl Halide", "Diphenylmethane"
Descriptors
Status Detected and Not Quantified
Origin Exogenous
Cellular Locations "Membrane"
Biofluids
Tissues
Pathways
State Solid
Appearance White powder.
Melting Point
Boiling Point
Solubility 8.5e-05 mg/mL at 25 °C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
LogP
Route of Exposure Oral (L85)
Mechanism of Toxicity DDT toxicity occurs via at least four mechanisms, possibly all functioning simultaneously. DDT reduces potassium transport across the membrane. DDT inhibits inactivation of the porous channels through which sodium ions pass. The channels activate (open) normally but are inactivated (closed) slowly, thus interfering with the active transport of sodium out of the nerve axon during repolarization, causing a state of hyperexcitability. DDT inhibits neuronal adenosine triphosphatases (ATPases), particularly Na+K+-ATPase, and Ca2+-ATPase which play vital roles in neuronal repolarization. DDT also inhibits the ability of calmodulin, a calcium mediator in nerves, to transport calcium ions that are essential for the release of neurotransmitters. All these inhibited functions reduce the rate of depolarization and increase the sensitivity of neurons to small stimuli that would not elicit a response in a fully depolarized neuron. DDT is also believed to adversely affect the reproductive system by mimicking endogenous hormones and binding to the estrogen and adrogen receptors. (T10, L85)
Metabolism DDT is absorbed in the stomach and intestine, after which it enters the lymphatic system and is carried throughout the body and incorporated into fatty tissues. Metabolism of DDT occurs mainly via cytochrome P-450 enzymes in the liver and kidney, where it undergoes reductive dechlorination to DDD (dichlorodiphenyldichloroethane) and DDE (dichlorodiphenyldichloroethylene). These compounds are further degraded into additional metabolites, mainly DDA (bis(p-chlorophenyl) acetic acid), which are excreted in the urine. (L85)
Toxicity LD50: 87 mg/kg (Oral, Rat) (L141) LD50: 1931 mg/kg (Dermal, Rat) (L141) LD50: 1500 mg/kg (Subcutaneous, Rat) (L141)
Lethal Dose
Carcinogenicity DDT is possibly carcinogenic to humans (Group 2B). (L2151)
Uses/Sources DDT is used as a pesticide and in disease vector control. (L84)
Minimum Risk Level
Health Effects Exposure to DDT causes loss of weight and anorexia. DDT poisoning affects CNS function in humans, but pathologic changes are observed in the liver and reproductive organs. Hypertrophy of hepatocytes and subcellular organelles such as mitochondria, proliferation of smooth endoplasmic reticulum, centrolobular necrosis after exposure to high concentrations, and an increase in the incidence of hepatic tumors have been noted. (T10)
Symptoms Acute signs of DDT poisoning include paresthesia after oral ingestion. Studies have shown that a mammal poisoned with DDT-type agents displays periodic persistent tremoring and/or convulsive seizures that are suggestive of repetitive discharges in neurons. These repetitive tremors and seizures can be initiated by tactile and auditory stimuli. (T10)
Treatment Treatment of DDT exposure should be primarily directed towards decontamination and supportive care, as there is no specific antidote. The use of gastric lavage and activated charcoal for large ingestions may be effective. (L140)
DrugBank ID
HMDB ID
PubChem Compound ID 13089
ChEMBL ID CHEMBL364900
ChemSpider ID 12543
KEGG Compound ID C14187
UniProt ID 0
OMIM ID 0
ChEBI ID 0
BioCyc ID
CTD ID C016340
Stitch ID DDT, O,P'-
PDB ID
ACToR ID 0
Wikipedia Link
Creation Date 2009-03-06 18:57:59
Update Date 2014-12-24 20:20:58