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Name Description
id 23
T3DB ID T3D0025
Name P,P'-DDD
Class SmallMolecule
Description DDD, P,P'- is an isomer of dichlorodiphenyldichloroethane, an organochlorine insecticide. It is a 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", "Pollutant", "Synthetic Toxin"
Types "Organic Compound", "Organochloride", "Pesticide", "Pollutant", "Synthetic Compound"
Synonyms "(Dichlorodiphenyl)dichloroethane", "1, 1-Bis(4-chlorophenyl)-2,2-dichloroethane", "1, 1-Bis(p-chlorophenyl)-2,2-dichloroethane", "1,1'-(2,2-dichloroethane-1,1-diyl)bis(4-chlorobenzene)", "1,1'-(2,2-dichloroethylidene)bis[4-chlorobenzene]", "1,1-Bis(4-chlorophenyl)-2,2-dichloroethane", "1,1-Bis(p-Chlorophenyl)-2,2-dichloroethane", "1,1-Dichloor-2,2-bis(4-chloor fenyl)-ethaan", "1,1-Dichlor-2,2-bis(4-chlor-phenyl)-aethan", "1,1-Dichloro-2, 2-bis(4-chlorophenyl)ethane", "1,1-Dichloro-2, 2-bis(p-chlorophenyl)ethane", "1,1-Dichloro-2, 2-di(4-chlorophenyl)ethane", "1,1-Dichloro-2,2-bis(4'-chlorophenyl)ethane", "1,1-Dichloro-2,2-bis(4'-chlorophenyl)ethane (DDD)", "1,1-Dichloro-2,2-bis(4-chlorophenyl)ethane", "1,1-Dichloro-2,2-bis(p-chlorophenyl)ethane", "1,1-Dichloro-2,2-bis(parachlorophenyl)ethane", "1,1-Dichloro-2,2-di(4-chlorophenyl)ethane", "1,1-Dicloro-2,2-bis(4-cloro-fenil)-etano", "1-Chloro-4-[2,2-dichloro-1-(4-chlorophenyl)ethyl]benzene", "2,2-Bis(4-chlorophenyl)-1,1-dichloroethane", "2,2-Bis(p-chlorophenyl)-1, 1-dichloroethane", "2,2-Bis(p-chlorophenyl)-1,1-dichloroethane", "2,2-bis-(4-chlorophenyl)-1,1-dichloroethane", "4,4'-DDD solution", "DDD", "DDD(p,p')", "Dichloro-2,2-bis(p-chlorophenyl)ethane", "Dichlorodiphenyl dichloroethane", "Dichlorodiphenyldichloroethane", "Dilene", "p, p'-(dichlorodiphenyl)dichloroethane", "p,p'-(dichlorodiphenyl)dichloroethane", "P,P'-ddd", "p,p'-DDD", "P,p'-dichlorodip henyl dichloroethane", "p,p'-dichlorodiphenyl dichloroethane", "p,p'-Dichlorodiphenyl-2,2-dichloroethylene", "p,p'-dichlorodiphenyldichloroethane", "p,p'-dichlorodiphenyldichloroethane (DDD)", "p,p'-TDE", "p,p-DDD", "Rhothane", "Rhothane d-3", "Rothane", "TDE", "Tetrachlorodiphenylethane"
CAS Number 72-54-8
Chemical Formula C14H10Cl4
Average Molecular Mass 320.04
Monoisotopic Mass 317.95
IUPAC Name 1-chloro-4-[2,2-dichloro-1-(4-chlorophenyl)ethyl]benzene
Traditional Name dichlorodiphenyldichloroethane
SMILES ClC(Cl)C(C1=CC=C(Cl)C=C1)C1=CC=C(Cl)C=C1
InChI Identifier InChI=1S/C14H10Cl4/c15-11-5-1-9(2-6-11)13(14(17)18)10-3-7-12(16)8-4-10/h1-8,13-14H
InChI Key InChIKey=AHJKRLASYNVKDZ-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 "organochlorine insecticide (ChEBI)", "chlorophenylethane (ChEBI)", "Organochlorine pesticides (KEGG)"
Status Detected and Not Quantified
Origin Exogenous
Cellular Locations "Membrane"
Biofluids
Tissues
Pathways
State Solid
Appearance White powder.
Melting Point 109.5°C
Boiling Point
Solubility 9e-05 mg/mL at 25 °C [BIGGAR,JW & RIGGS,RI (1974)]
LogP
Route of Exposure Oral (L85)
Mechanism of Toxicity DDD toxicity occurs via at least four mechanisms, possibly all functioning simultaneously. DDD reduces potassium transport across the membrane. DDD inhibits the inactivation of voltaged-gated sodium channels. 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 and resulting in a state of hyperexcitability. DDD inhibits neuronal adenosine triphosphatases (ATPases), particularly Na+K+-ATPase, and Ca2+-ATPase which play vital roles in neuronal repolarization. DDD 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. DDD is also believed to adversely affect the reproductive system by mimicking endogenous hormones and binding to the estrogen and adrogen receptors. (T10, L85)
Metabolism DDD 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 DDD occurs mainly via cytochrome P-450 enzymes in the liver and kidney. Its metabolites, mainly DDA (bis(p-chlorophenyl) acetic acid), are excreted in the urine. (L85)
Toxicity LD50: 113 mg/kg (Oral, Rat) (L138)
Lethal Dose 5 g/kg for an adult human. (L138)
Carcinogenicity Not directly listed by IARC, but carcinogenicity studies of this DDT metabolite are discussed in connection with DDT (L2151).
Uses/Sources DDD is found in DDT, which is used as a pesticide and in disease vector control. (L84)
Minimum Risk Level
Health Effects DDT has been shown to cause mild anemia. 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 DDT exposure causes ataxia and abnormal stepping. 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 6294
ChEMBL ID CHEMBL196590
ChemSpider ID 6057
KEGG Compound ID C06636
UniProt ID 0
OMIM ID 0
ChEBI ID 27841
BioCyc ID CPD-8985
CTD ID D003632
Stitch ID DDD, P,P'-
PDB ID
ACToR ID 379
Wikipedia Link
Creation Date 2009-03-06 18:57:56
Update Date 2014-12-24 20:20:55