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Name Description
id 11
T3DB ID T3D0012
Name Clofenotane
Class SmallMolecule
Description Insecticide. Clofenotane is a major component of commercial DDT (other names *Gespan*, *Gesarol*, *Geverol*, *Chlorophenotane*). Use banned or discouraged in many countries Clofenotane belongs to the family of Diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups[1]. (Reference: [1] Diphenylmethane: http://en.wikipedia.org/wiki/Diphenylmethane).
Categories "Cigarette Toxin", "Pesticide", "Pollutant", "Food Toxin", "Synthetic Toxin"
Types "Organic Compound", "Organochloride", "Pesticide", "Pollutant", "Food Toxin", "Metabolite", "Cigarette Toxin", "Synthetic Compound"
Synonyms "1,1'-(2,2,2-Trichloroethane-1,1-diyl)bis(4-chlorobenzene)", "1,1'-(2,2,2-Trichloroethylidene)bis(4-chloro)-Benzene", "1,1'-(2,2,2-Trichloroethylidene)bis(4-chlorobenzene)I", "1,1,1-Trichloro-2,2-bis(4,4'-dichlorodiphenyl)ethane", "1,1,1-Trichloro-2,2-bis(4-chlorophenyl)-Ethane", "1,1,1-Trichloro-2,2-bis(p-chlorophenyl)-Ethane", "1,1,1-Trichloro-2,2-bis(p-chlorophenyl)ethane", "1,1,1-Trichloro-2,2-bis-(4'-chlorophenyl)ethane", "1,1,1-Trichloro-2,2-di(4-chlorophenyl)-ethane", "1,1,1-Trichloro-2-2-bis(4-chlorophenyl)ethane", "1,1,1-Trichlorobis(chlorophenyl)ethane", "1,1-Bis(4-chlorophenyl)-2,2,2-trichloroethane", "1,1-Bis(p-Chlorophenyl)-2,2,2-trichIoroethane", "1,1-Bis-(p-chlorophenyl)-2,2,2-trichloroethane", "1-Chloro-4-[2,2,2-trichloro-1-(4-chlorophenyl)ethyl]benzene", "2,2,2-Trichloro-1,1-bis(4-chlorophenyl)ethane", "2,2,2-Trichloro-1,1-bis(p-chlorophenyl)-Ethane", "2,2,2-Trichlorobis(4-chlorophenyl)ethane", "2,2-Bis(p-chlorophenyl)-1,1,1-trichloroethane", "Bis(p-chlorophenyl)-2,2,2-trichloroethane", "Chlofenotan", "Chlorophenothane", "Chlorphenotane", "DDT", "Dicophane, BAN", "Diphenyltrichloroethane", "p,p'-DDT, BSI", "Zeidane", "Zerdane", "Zithiol"
CAS Number 50-29-3
Chemical Formula C14H9Cl5
Average Molecular Mass 354.49
Monoisotopic Mass 351.91
IUPAC Name 1-chloro-4-[2,2,2-trichloro-1-(4-chlorophenyl)ethyl]benzene
Traditional Name detox
SMILES ClC1=CC=C(C=C1)C(C1=CC=C(Cl)C=C1)C(Cl)(Cl)Cl
InChI Identifier InChI=1S/C14H9Cl5/c15-11-5-1-9(2-6-11)13(14(17,18)19)10-3-7-12(16)8-4-10/h1-8,13H
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)", "benzenoid aromatic compound (ChEBI)", "chlorophenylethane (ChEBI)", "Organochlorine pesticides (KEGG)", "Organochlorine insecticides (KEGG)", "an insecticide (MetaCyc)"
Status Detected and Not Quantified
Origin Exogenous
Cellular Locations "Membrane"
State Solid
Appearance White powder.
Melting Point 108.5 - 109°C
Boiling Point
Solubility 5.5e-06 mg/mL at 25°C
LogP 6.91
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 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. 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 Acute Oral: 0.0005 mg/kg/day (L134) Intermediate Oral: 0.0005 mg/kg/day (L134)
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
PubChem Compound ID 3036
ChemSpider ID 2928
KEGG Compound ID C04623
UniProt ID 0
ChEBI ID 16130
BioCyc ID CPD-1125
CTD ID D003634
Stitch ID DDT, P,P'-
ACToR ID 381
Wikipedia Link
Creation Date 2009-03-06 18:57:55
Update Date 2014-12-24 20:20:52