Dichlorodiphenyldichloroethane (DDD) is an

organochlorine An organochloride, organochlorine compound, chlorocarbon, or chlorinated hydrocarbon is an organic compound containing at least one covalently bonded atom of chlorine. The chloroalkane class (alkanes with one or more hydrogens substituted by chlo ...

insecticide that is slightly irritating to the skin.Merck Index, 11th ed, p482 DDD is a metabolite of

DDT Dichlorodiphenyltrichloroethane, commonly known as DDT, is a colorless, tasteless, and almost odorless crystalline chemical compound, an organochloride. Originally developed as an insecticide, it became infamous for its environmental impacts. ...

.“p,p'-Dichlorodiphenyl dichloroethane (DDD) (CASRN 72-54-8).” ''Integrated Risk Information System''. 25 Jan. 2007. United States Environmental Protection Agency. 23 Apr. 2007 . DDD is colorless and crystalline;Mish, Frederick C., Editor in Chief. “DDD.” ''Webster’s Ninth New Collegiate Dictionary''. 9th ed. Springfield, MA: Merriam-Webster Inc., 1985. it is closely related chemically and is similar in properties to DDT, but it is considered to be less toxic to animals than DDT.Guralnik, David B., Editor in Chief. “DDD.” ''Webster’s New World Dictionary of the American Language''. Second College Edition. New York, NY: Prentice Hall Press, 1986. The molecular formula for DDD is (ClC₆H₄)₂CHCHCl₂ or C₁₄H₁₀Cl₄, whereas the formula for DDT is (ClC₆H₄)₂CHCCl₃ or C₁₄H₉Cl₅. DDD is in the “ Group B2” classification, meaning that it is a probable

human Humans (''Homo sapiens'') are the most abundant and widespread species of primate, characterized by bipedalism and exceptional cognitive skills due to a large and complex brain. This has enabled the development of advanced tools, cultu ...

carcinogen A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive subs ...

. This is based on an increased incidence of

lung tumors Lung tumors are neoplastic lung nodules. These include: Primary tumors of the lung/pulmonary system: * Bronchial leiomyoma, a rare, benign tumor * Lung cancer, the term commonly used to refer to ''carcinoma of the lung'' * Pulmonary carcinoi ...

in male and female mice,

liver tumors Liver tumors (also known as hepatic tumors) are abnormal growth of liver cells on or in the liver. Several distinct types of tumors can develop in the liver because the liver is made up of various cell types. Liver tumors can be classified as beni ...

in male mice, and thyroid tumors in male rats. A further basis is that DDD is similar to and is a metabolite of DDT, another probable human carcinogen. DDD is no longer registered for agricultural use in the

United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country primarily located in North America. It consists of 50 states, a federal district, five major unincorporated territori ...

, but the general population continues to be exposed to it due to its long persistence time. The primary source of exposure is oral ingestion of food.“DDD.” ''Hazardous Substances Data Bank''. United States National Library of Medicine. 25 Apr. 2007 . 1946 is the date of the earliest recorded use in English of the abbreviation “DDD” to stand for dichlorodiphenyldichloroethane, as far as could be determined. Reductive dechlorination DDT DDD

Mitotane

If one of the ''p''-chlorines in DDD is switched to ''ortho''-position, the result is the chemotherapeutic agent

mitotane Mitotane, sold under the brand name Lysodren, is a steroidogenesis inhibitor and cytostatic antineoplastic medication which is used in the treatment of adrenocortical carcinoma and Cushing's syndrome. It is a derivative of the early insecticid ...

. This is an example of a

positional isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is another compound whose molecule has the same number of atoms of each element, but with logically distinct bonds between them. The term meta ...

Table of names

The following are synonyms for DDD:

References

*“Chemicals: Dichlorodiphenyldichloroethane.” ''The Comparative Toxicogenomics Database''.

MDI Biological Laboratory The MDI Biological Laboratory (MDIBL), formerly known as Mount Desert Island Biological Laboratory is an independent non-profit biomedical research institution founded in 1898 and located in Salisbury Cove, Maine, on Mount Desert Island. Its mi ...

, 11 Apr. 2007 . *“Data From SRC PhysProp Database.” ''SRC PhysProp Database''. Syracuse Research Corporation. 11 Apr. 2007 . *“DDD.” ''Hazardous Substances Data Bank''.

United States National Library of Medicine The United States National Library of Medicine (NLM), operated by the United States federal government, is the world's largest medical library. Located in Bethesda, Maryland, the NLM is an institute within the National Institutes of Health. Its ...

. 25 Apr. 2007 . *“DDD—RN: 72-54-8.” ''ChemIDplus Lite Record''. 9 Sept. 2004. United States National Library of Medicine Specialized Information Services. 11 Apr. 2007 . *Guralnik, David B., Editor in Chief. “DDD.” '' Webster’s New World Dictionary of the American Language''. Second College Edition. New York, NY:

Prentice Hall Press Prentice Hall was an American major educational publisher owned by Savvas Learning Company. Prentice Hall publishes print and digital content for the 6–12 and higher-education market, and distributes its technical titles through the Safari B ...

, 1986. (indexed), (plain edge), (pbk.), and (LeatherKraft). *Mish, Frederick C., Editor in Chief. “DDD.” '' Webster’s Ninth New Collegiate Dictionary''. 9th ed. Springfield, MA: Merriam-Webster Inc., 1985. , (indexed), and (deluxe). *“p,p'-DDD.” ''Substance Registry System''. 1 Feb. 2006.

United States Environmental Protection Agency The Environmental Protection Agency (EPA) is an independent executive agency of the United States federal government tasked with environmental protection matters. President Richard Nixon proposed the establishment of EPA on July 9, 1970; it ...

. 11 Apr. 2007 . *“p,p'-Dichlorodiphenyl dichloroethane (DDD) (CASRN 72-54-8).” ''Integrated Risk Information System''. 25 Jan. 2007. United States Environmental Protection Agency. 23 Apr. 2007 .

Notes

External links

TOXMAP Chemical Page for DDD
provided by the

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of the

University of Oxford , mottoeng = The Lord is my light , established = , endowment = £6.1 billion (including colleges) (2019) , budget = £2.145 billion (2019–20) , chancellor ...

{{insecticides Organochloride insecticides Chlorobenzenes