Details
Stereochemistry | ACHIRAL |
Molecular Formula | C14H9Cl5 |
Molecular Weight | 354.486 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
ClC1=CC=C(C=C1)C(C2=CC=C(Cl)C=C2)C(Cl)(Cl)Cl
InChI
InChIKey=YVGGHNCTFXOJCH-UHFFFAOYSA-N
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
Molecular Formula | C14H9Cl5 |
Molecular Weight | 354.486 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DDT (dichlorodiphenyltrichloroethane) is a colorless, crystalline, tasteless and almost odorless organochloride known for its insecticidal properties and environmental impacts. First synthesized in 1874, DDT's insecticidal action was discovered by the Swiss chemist Paul Hermann Müller in 1939. It was used in the second half of World War II to control malaria and typhus among civilians and troops. After the war, DDT was also used as an agricultural insecticide and its production and use duly increased. The United States banned the use of DDT in 1972, but some countries still use the chemical. In December 2000, in a convention organized by the United Nations Environment Program, 122 nations agreed to a treaty banning twelve very toxic chemicals. Included among the twelve was DDT. However, the treaty allowed the use of DDT to combat malaria until other alternatives become available. Before it can take effect the treaty must be ratified by 50 of the nations that agreed to it in principle. DDT has also been used in the past for the treatment of lice. It is still in use outside the United States for the control of mosquitoes that spread malaria. DDT and related chemicals persist for a long time in the environment and in animal tissues. People are most likely to be exposed to DDT from food, including meat, fish, and dairy products. DDT can be absorbed by eating, breathing, or touching products contaminated with DDT. In the body, DDT is converted into several metabolic products, including the metabolite dichlorodiphenyldichloroethene (DDE). DDT and DDE are stored in the body’s fatty tissues. In pregnant women DDT and DDE can be passed to the fetus. Both chemicals are found in breast milk, resulting in exposure to nursing infants. Human health effects from DDT at low environmental doses are unknown. However, following exposure to high doses human symptoms can include vomiting, tremors or shakiness, and seizures. Laboratory animal studies showed effects on both the liver and reproduction. DDT is considered a possible human carcinogen. DDE acts as a weak androgen receptor antagonist, but not as an estrogen. p,p'-DDT, DDT's main component, has little or no androgenic or estrogenic activity. The minor component o,p'-DDT has weak estrogenic activity.
CNS Activity
Originator
Sources: https://wikivisually.com/wiki/Othmar_Zeidler
Curator's Comment: in 1874 by Othmar Zeidler under the supervision of Adolf von Baeyer
Approval Year
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/30059857/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/31521043/ |
yes | |||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
inconclusive |
PubMed
Title | Date | PubMed |
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[Effect of nonsteroidal estrogen-like substances on aromatase activity]. | 2001 May-Jun |
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Isolation and characterisation of organochlorine pesticides residues from landfill sites. | 2001 Oct |
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Organochlorine pesticide residues in sediments and biota from the coastal area of Dar es Salaam city, Tanzania. | 2002 |
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Composition and distribution of organochlorine pesticide residues in surface sediments from the Wu-Shi River Estuary, Taiwan. | 2002 |
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Organochlorine pesticide residues in catfish, Tachysurus thalassinus (Ruppell, 1835), from the South Patches of the Bay of Bengal. | 2002 |
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Current levels of DDT, PCB and trace elements in the Baltic ringed seals (Phoca hispida baltica) and grey seals (Halichoerus grypus). | 2002 |
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Stable chlorine intramolecular kinetic isotope effects from the abiotic dehydrochlorination of DDT. | 2002 |
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Bioconcentration of trace organochlorine pesticides by the rainbow trout. | 2002 |
|
Persistent chlorinated pesticides and polychlorinated biphenyls in selected fish species from Lake Tanganyika, Burundi, Africa. | 2002 |
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Intraspecific variation in trophic feeding levels and organochlorine concentrations in glaucous gulls (Larus hyperboreus) from Bjørnøya, the Barents Sea. | 2002 Apr |
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Hepatic microsomal cytochrome p450s and chlorinated hydrocarbons in largha and ribbon seals from Hokkaido, Japan: differential response of seal species to Ah receptor agonist exposure. | 2002 Apr |
|
Seasonal variation of persistent organochlorine accumulation in birds from Lake Baikal, Russia, and the role of the south Asian region as a source of pollution for wintering migrants. | 2002 Apr 1 |
|
Toxic contaminants and their biological effects in coastal waters of Xiamen, China. I. Organic pollutants in mussel and fish tissues. | 2002 Aug |
|
Persistent chlorinated pesticides in fish and cattle fat and their implications for human serum concentrations from the Sene-Gambian region. | 2002 Aug |
|
Differential expression and induction of two Drosophila cytochrome P450 genes near the Rst(2)DDT locus. | 2002 Aug |
|
Determination of organochlorine pesticides in seawater using liquid-phase hollow fibre membrane microextraction and gas chromatography-mass spectrometry. | 2002 Aug 30 |
|
Analysis of pesticides and PCB congeners in serum by GC/MS with SPE sample cleanup. | 2002 Aug 5 |
|
Burden of organochlorine pesticides in blood and its effect on thyroid hormones in women. | 2002 Aug 5 |
|
Isomer-specific activity of dichlorodyphenyltrichloroethane with estrogen receptor in adult and suckling estrogen reporter mice. | 2002 Dec |
|
[Bioindication of organochlorine pesticides by night heron in Taihu wetland ecosystem]. | 2002 Feb |
|
Association of maternal blood pressure and hemoglobin level with organochlorines in human milk. | 2002 Jan |
|
Distribution and fate of organochlorine pesticide residues in sediments from the selected rivers in Taiwan. | 2002 Jul |
|
Organochlorine chemical residues in fish from the Mississippi River basin, 1995. | 2002 Jul |
|
Induction and inhibition of aromatase (CYP19) activity by various classes of pesticides in H295R human adrenocortical carcinoma cells. | 2002 Jul 1 |
|
Factors influencing nominal effective concentrations of chemical compounds in vitro: medium protein concentration. | 2002 Jun |
|
Impact of protein binding on the availability and cytotoxic potency of organochlorine pesticides and chlorophenols in vitro. | 2002 Jun 14 |
|
DDT inhibits the functional activation of murine macrophages and decreases resistance to infection by Mycobacterium microti. | 2002 Jun 5 |
|
Membrane-contaminant interaction found by 3D force field calculations. | 2002 Mar |
|
Dissolved organic carbon--contaminant interaction descriptors found by 3D force field calculations. | 2002 Mar |
|
Distribution of organobrominated and organochlorinated contaminants in Belgian human adipose tissue. | 2002 Mar |
|
The organochlorine pesticide residues and antioxidant enzyme activities in human breast tumors: is there any association? | 2002 Mar |
|
Effects of 1,1,1-trichloro-2,2-bis(p-chlorophenyl)-ethane (p,p'-DDT) on 3T3-L1 and 3T3-F442A adipocyte differentiation. | 2002 Mar 1 |
|
Headspace solid-phase microextraction in combination with gas chromatography and tandem mass spectrometry for the determination of organochlorine and organophosphorus pesticides in whole numan blood. | 2002 Mar 25 |
|
Effect of molecular structures on the solubility enhancement of hydrophobic organic compounds by environmental amphiphiles. | 2002 May |
|
Residential pesticide use during pregnancy among a cohort of urban minority women. | 2002 May |
|
Associations between weight loss-induced changes in plasma organochlorine concentrations, serum T(3) concentration, and resting metabolic rate. | 2002 May |
|
Detailed low-dose study of 1,1-bis(p-chlorophenyl)-2,2,2- trichloroethane carcinogenesis suggests the possibility of a hormetic effect. | 2002 May 1 |
|
Comparative investigation of multiple organs of mice and rats in the comet assay. | 2002 May 27 |
|
Persistent organochlorine residues and their bioaccumulation profiles in resident and migratory birds from North Vietnam. | 2002 Oct |
|
Biosorption of organochlorine pesticides using fungal biomass. | 2002 Oct |
|
Organochlorine hydrocarbons in human breast milk collected in Hong Kong and Guangzhou. | 2002 Oct |
|
Persistent organochlorine pollutants in human serum of 50-65 years old women in the Flanders Environmental and Health Study (FLEHS). Part 1: Concentrations and regional differences. | 2002 Sep |
|
Development of a fish reporter gene system for the assessment of estrogenic compounds and sewage treatment plant effluents. | 2002 Sep |
|
Assessing the estrogenic potential of organochlorine pesticides in primary cultures of male rainbow trout (Oncorhynchus mykiss) hepatocytes using vitellogenin as a biomarker. | 2002 Sep 16 |
|
Evidence for a stabilizer element in the untranslated regions of Drosophila glutathione S-transferase D1 mRNA. | 2002 Sep 20 |
|
A single p450 allele associated with insecticide resistance in Drosophila. | 2002 Sep 27 |
|
Pesticides in surface water, sediment, and rainfall of the northeastern Pantanal basin, Brazil. | 2002 Sep-Oct |
|
Lipophil-mediated reduction of toxicants in humans: an evaluation of an ayurvedic detoxification procedure. | 2002 Sep-Oct |
|
Great tit (Parus major) nestlings as biomonitors of organochlorine pollution. | 2003 Jan |
|
Metabolism of DDT [1,1,1-Trichloro-2,2-bis(4-chlorophenyl)ethane] by Alcaligenes denitrificans ITRC-4 under aerobic and anaerobic conditions. | 2003 Jan |
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 15:52:50 UTC 2023
by
admin
on
Sat Dec 16 15:52:50 UTC 2023
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Record UNII |
CIW5S16655
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QP53AB01
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WHO-VATC |
QP53AB51
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WHO-ATC |
P03AB01
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NCI_THESAURUS |
C737
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NCI_THESAURUS |
C45386
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WHO-ATC |
P03AB51
Created by
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Code System | Code | Type | Description | ||
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CIW5S16655
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DDT
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200
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DB13424
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m4113
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SUB06700MIG
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100000084311
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3036
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C44364
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C493852
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16130
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DDT
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50-29-3
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D003634
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CHEMBL416898
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200-024-3
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2202
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4396
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8939
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DTXSID4020375
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PRIMARY |
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ACTIVE MOIETY |