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 |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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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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Acute hepatotoxicity of DDT: effect on glucocorticoid receptors and serum transcortin. | 2000 May |
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Anaerobic bioventing of unsaturated zone contaminated with DDT and DNT. | 2001 |
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Distribution of DDT residues in fish from the Songkhla Lake, Thailand. | 2001 |
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Mixtures of four organochlorines enhance human breast cancer cell proliferation. | 2001 Apr |
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Analyses of lindane, vinclozolin, aldrin, p,p'-DDE, o,p'-DDT and p,p'-DDT in human serum using gas chromatography with electron capture detection and tandem mass spectrometry. | 2001 Aug 25 |
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Gas exchange of OCPs across the air-water interface at the creek adjoining Mumbai harbour, India. | 2001 Dec |
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Surfactant-enhanced solubilization and anaerobic biodegradation of 1,1,1-trichloro-2,2-bis(p-chlorophenyl)-ethane (DDT) in contaminated soil. | 2001 Jan-Feb |
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Modulatory effects of neonatal exposure to TCDD, or a mixture of PCBs, p,p'-DDT, and p-p'-DDE, on methylnitrosourea-induced mammary tumor development in the rat. | 2001 Jul |
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Optimization of a yeast estrogen screen and its applicability to study the release of estrogenic isoflavones from a soygerm powder. | 2001 Jul |
|
Organochlorine pesticides, polychlorinated biphenyls, and butyltin compounds in blubber and livers of stranded California sea lions, elephant seals, and harbor seals from coastal California, USA. | 2001 Jul |
|
Sex-associated expression of mouse hepatic and renal CYP2B enzymes by glucocorticoid hormones. | 2001 Jul 15 |
|
Determination of organochlorine pesticides and chlorobenzenes in strawberries by using accelerated solvent extraction combined with sorptive enrichment and gas chromatography/mass spectrometry. | 2001 Jul-Aug |
|
Differing effects of endocrine-disrupting chemicals on basal and FSH-stimulated progesterone production in rat granulosa-luteal cells. | 2001 Jun |
|
The global distribution of PCBs and organochlorine pesticides in butter. | 2001 Mar 15 |
|
Plasma levels of persistent organohalogens and hormone levels in adult male humans. | 2001 Mar-Apr |
|
Anaerobic biodegradation of DDT residues (DDT, DDD, and DDE) in estuarine sediment. | 2001 May |
|
Effects of environmental antiandrogens on reproductive development in experimental animals. | 2001 May-Jun |
|
Relationship between two consecutive lactations and fat level in persistent organochlorine compound concentrations in human breast milk. | 2001 May-Jun |
|
Association of DDT with spontaneous abortion: a case-control study. | 2001 Oct |
|
Organochlorines and 8-hydroxy-2'-deoxyguanosine (8-OHdG) in cancerous and noncancerous breast tissue: do the data support the hypothesis that oxidative DNA damage caused by organochlorines affects breast cancer? | 2001 Oct |
|
Identification of a novel class of insect glutathione S-transferases involved in resistance to DDT in the malaria vector Anopheles gambiae. | 2001 Oct 15 |
|
Determination of DDT and its metabolites in cattle dip soil available in aqueous phase after remediation. | 2001 Sep |
|
Current levels of DDT, PCB and trace elements in the Baltic ringed seals (Phoca hispida baltica) and grey seals (Halichoerus grypus). | 2002 |
|
Persistent chlorinated pesticides and polychlorinated biphenyls in selected fish species from Lake Tanganyika, Burundi, Africa. | 2002 |
|
Intraspecific variation in trophic feeding levels and organochlorine concentrations in glaucous gulls (Larus hyperboreus) from Bjørnøya, the Barents Sea. | 2002 Apr |
|
Differential expression and induction of two Drosophila cytochrome P450 genes near the Rst(2)DDT locus. | 2002 Aug |
|
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 |
|
Dichlorodiphenyltrichloroethane in soil, river sediment, and fish in the Amazon in Brazil. | 2002 Feb |
|
A molecular motif required for the activation of rat neutrophil phospholipase A(2) by organochlorine compounds. | 2002 Feb |
|
Hair analysis: another approach for the assessment of human exposure to selected persistent organochlorine pollutants. | 2002 Jan |
|
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 |
|
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 |
|
Residuals of beta-hexachlorocyclohexane, dichlorodiphenyltrichloroethane, and hexachlorobenzene in serum, and relations with consumption of dietary components in rural residents in Japan. | 2002 Mar 8 |
|
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 |
|
Development of a fish reporter gene system for the assessment of estrogenic compounds and sewage treatment plant effluents. | 2002 Sep |
|
Evidence for a stabilizer element in the untranslated regions of Drosophila glutathione S-transferase D1 mRNA. | 2002 Sep 20 |
|
Great tit (Parus major) nestlings as biomonitors of organochlorine pollution. | 2003 Jan |
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 15:52:50 GMT 2023
by
admin
on
Sat Dec 16 15:52:50 GMT 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
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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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METABOLITE -> PARENT |
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ACTIVE MOIETY |