View source for Chemistry:Chlordecone

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 415672056
| ImageFile = Chlordecone.png
| ImageSize = 120px
| ImageFile2 = Chlordecone Kepone 3D.png
| ImageSize2 = 120px
| IUPACName = decachloropentacyclo[5.3.0.0<sup>2.6</sup>.0<sup>3.9</sup>.0<sup>4.8</sup>]decan-5-one<ref>[https://archive.today/20121223055440/http://sitem.herts.ac.uk/aeru/iupac/1293.htm IUPAC Agrochemical information.]</ref>
| OtherNames = Chlordecone<br>Clordecone<br>Merex<br />
CAS name: <small>1,1a,3,3a,4,5,5,5a,5b,6-decachlorooctahydro-1,3,4-metheno-2H-cyclobuta[cd]pentalen-2-one</small>
|Section1={{Chembox Identifiers
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C01792
| InChI = 1/C10Cl10O/c11-2-1(21)3(12)6(15)4(2,13)8(17)5(2,14)7(3,16)9(6,18)10(8,19)20
| InChIKey = LHHGDZSESBACKH-UHFFFAOYAM
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 462576
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10Cl10O/c11-2-1(21)3(12)6(15)4(2,13)8(17)5(2,14)7(3,16)9(6,18)10(8,19)20
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LHHGDZSESBACKH-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 143-50-0
| PubChem = 299
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 293
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = RG5XJ88UDF
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 16548
| EINECS = 205-601-3
| SMILES = ClC54C(=O)C1(Cl)C2(Cl)C5(Cl)C3(Cl)C4(Cl)C1(Cl)C2(Cl)C3(Cl)Cl
}}
|Section2={{Chembox Properties
| C=10 | Cl=10 | O=1
| MolarMass = 490.633 g/mol
| Appearance = tan to white crystalline solid
| Odor = odorless
| Density = 1.6 g/cm<sup>3</sup>
| MeltingPtC = 349
| MeltingPt_notes = (decomposes)
| BoilingPt = 
| Solubility = 0.27&nbsp;g/100&nbsp;mL
| SolubleOther = soluble in [[Chemistry:Acetone|acetone]], [[Chemistry:Ketone|ketone]], [[Chemistry:Acetic acid|acetic acid]] <br> slightly soluble in [[Chemistry:Benzene|benzene]], [[Chemistry:Hexane|hexane]]
| LogP = 5.41
| VaporPressure = 3.10<sup>−7</sup> kPa
  }}
|Section4={{Chembox Thermochemistry
| DeltaHf = -225.9 kJ/mol
| Entropy = 764 J/K mol
  }}
|Section7={{Chembox Hazards
| MainHazards = carcinogen<ref name=PGCH/>
| FlashPt_notes = Non-flammable<ref name=PGCH/>
| AutoignitionPtC = 
| LD50 = 95 mg/kg (rat, oral)
| PEL = none<ref name=PGCH>{{PGCH|0365}}</ref>
| IDLH = N.D.<ref name=PGCH/>
| REL = Ca TWA 0.001 mg/m<sup>3</sup><ref name=PGCH/>
  }}
}}

'''Chlordecone''', better known in the United States under the brand name '''Kepone''', is an [[Chemistry:Organochlorine compound|organochlorine compound]] and a colourless solid. It is an obsolete [[Biology:Insecticide|insecticide]], now prohibited in the western world, but only after many thousands of tonnes had been produced and used.<ref name=Ullmann2>Robert L. Metcalf "Insect Control" in ''Ullmann's Encyclopedia of Industrial Chemistry'' Wiley-VCH, Wienheim, 2002. {{doi|10.1002/14356007.a14_263}}</ref> Chlordecone is a known persistent organic pollutant (POP) that was banned globally by the [[Chemistry:Stockholm Convention on Persistent Organic Pollutants|Stockholm Convention on Persistent Organic Pollutants]] in 2009.<ref name="COP4, 2009 Press release">[http://chm.pops.int/Convention/Pressrelease/COP4Geneva8May2009/tabid/542/ Press Release – COP4 – Geneva, 8 May 2009: Governments unite to step-up reduction on global DDT reliance and add nine new chemicals under international treaty], 2009.</ref>

==Synthesis==
Chlordecone is made by dimerizing [[Chemistry:Hexachlorocyclopentadiene|hexachlorocyclopentadiene]] and hydrolyzing to a [[Chemistry:Ketone|ketone]].<ref>Survey of Industrial Chemistry by Philip J. Chenier (2002), p. 484.</ref>

It is also the main degradation product of [[Chemistry:Mirex|mirex]].<ref name=Ullmann2/>

== History ==
In the U.S., chlordecone, commercialized under the brand name "Kepone", was produced by Allied Signal Company and LifeSciences Product Company in Hopewell, Virginia. The improper handling and dumping of the substance (including the waste materials generated in its manufacturing process) into the nearby James River (U.S.) in the 1960s and 1970s drew national attention to its toxic effects on humans and wildlife.  After two physicians, Dr. Yi-nan Chou and Dr. Robert S. Jackson of the Virginia Health Department, notified the Centers for Disease Control that employees of the company had been found to have toxic chemical poisoning, LifeSciences voluntarily closed its plant on July 4, 1975, and cleanup of the contamination began and a 100-mile section of the James River was closed to fishing while state health officials looked for other persons who might have been injured. <ref name=McAllister>"Two young doctors stopped the spread of Kepone poisoning", by Bill McAllister, L.A. Times-Washington Post Service, reprinted in ''Courier-Journal'' (Louisville KY), January 5, 1976, p. 1</ref>  At least 29 people in the area were hospitalized as a result of their exposure to Kepone. <ref name=McAllister/>

The product is made in a Diels-Alder reaction shared with pesticides like [[Chemistry:Chlordane|chlordane]] and [[Chemistry:Endosulfan|endosulfan]].<ref name=Ullmann2/> Chlordecone was not federally regulated until after the Hopewell disaster, in which 29 factory workers were hospitalized with various ailments, including neurological.<ref name=foster05>Richard Foster, [https://richmondmagazine.com/news/kepone-disaster-pesticide/ Kepone: The 'Flour' Factory], ''Richmond Magazine'' (July 8, 2005).</ref> Chlordecone is cited amongst a handful of other noxious substances as the driver for Gerald Ford's half-hearted approval in 1976 of the Toxic Substances Control Act, which "remains one of the most controversial regulatory bills ever passed".<ref name="hanson07">{{cite journal |last1=Hanson |first1=David J. |title=Those Were The Days |journal=Chemical & Engineering News |date=15 January 2007 |volume=85 |issue=3 |url=https://cen.acs.org/articles/85/i3/Those-Days.html |publisher=American Chemical Society|doi=10.1021/cen-v085n003.p044 }}</ref>

In 2009, chlordecone was included in the [[Chemistry:Stockholm Convention on Persistent Organic Pollutants|Stockholm Convention on Persistent Organic Pollutants]], which bans its production and use worldwide.<ref name= "COP4, 2009 Press release"/>

== Toxicology ==
Chlordecone can accumulate in the liver and the distribution in the human body is regulated by binding of the pollutant or its metabolites to [[Biology:Lipoprotein|lipoproteins]] like [[Medicine:Low-density lipoprotein|LDL]] and [[Medicine:High-density lipoprotein|HDL]].<ref>{{cite journal |last1=Delannoy |first1=Matthieu |last2=Girardet |first2=Jean-Michel |last3=Djelti |first3=Fathia |last4=Yen |first4=Frances T. |last5=Cakir-Kiefer |first5=Céline |title=Affinity of chlordecone and chlordecol for human serum lipoproteins |journal=Environmental Toxicology and Pharmacology |date=1 November 2020 |volume=80 |pages=103486 |doi=10.1016/j.etap.2020.103486 |pmid=32891758 |s2cid=221523766 |url=https://hal.univ-lorraine.fr/hal-02925906/file/Delannoy%20et%20al.%20draft%20sent%20to%20editorial%20preprint%281%29.pdf }}</ref> The LC<sub>50</sub> (LC = lethal concentration) is 35 μg/ L for ''Etroplus maculatus'',<ref>{{cite journal |last1=Asifa |first1=K. P. |last2=Chitra |first2=K. C. |year=2013 |title=Determination of median lethal concentration (LC50) and behavioral effects of chlordecone in the cichlid fish, Etroplus maculatus |journal=International Journal of Science and Research |volume=4 |issue=3 |pages=1473–1475 |url=https://www.ijsr.net/archive/v4i3/SUB152402.pdf }}</ref> 22–95&nbsp;μg/kg for blue gill and [[Biology:Trout|trout]]. Chlordecone bioaccumulates in animals by factors up to a million-fold.

Workers with repeated exposure suffer severe convulsions resulting from degradation of the synaptic junctions.<ref name=Ullmann2/>

Chronic low level exposure appears to cause [[Medicine:Prostate cancer|prostate cancer]] in men,<ref name="multigner16">{{cite journal |doi=10.1016/j.purol.2015.08.080|title=Exposition au chlordécone et cancer de la prostate. Interactions avec les gènes codants pour les œstrogènes|year=2015|last1=Brureau|first1=L.|last2=Emeville|first2=E.|last3=Ferdinand|first3=S.|last4=Thome|first4=J.|last5=Romana|first5=M.|last6=Blanchet|first6=P.|last7=Multigner|first7=L.|journal=Progrès en Urologie|volume=25|issue=13|page=755|pmid=26544275}}</ref> and "significant excesses of deaths were observed for [[Medicine:Stomach cancer|stomach cancer]] in women and [[Medicine:Pancreatic cancer|pancreatic cancer]] in women".<ref name="multigner20">{{cite journal |doi=10.1007/s11356-019-06481-4|title=A cohort study of banana plantation workers in the French West Indies: First mortality analysis (2000–2015)|year=2020|last1=Luce|first1=Danièle|last2=Dugas|first2=Julien|last3=Vaidie|first3=Amandine|last4=Michineau|first4=Léah|last5=El-Yamani|first5=Mounia|last6=Multigner|first6=Luc|journal=Environmental Science and Pollution Research|volume=27|issue=33|pages=41014–41022|pmid=31621027|s2cid=204707528|url=https://hal-univ-rennes1.archives-ouvertes.fr/hal-02355983/file/Luce2019_ESPR.pdf}}</ref>

Chlordecone has been found to act as an [[Biology:Agonist|agonist]] of the [[Biology:GPER|GPER]] (GPR30), which interacts strongly with the [[Biology:Estrogen|estrogen]] [[Biology:Sex hormone|sex hormone]] [[Chemistry:Estradiol|estradiol]].<ref name="ProssnitzBarton2014">{{cite journal |last1=Prossnitz |first1=Eric R. |last2=Barton |first2=Matthias |title=Estrogen biology: New insights into GPER function and clinical opportunities |journal=Molecular and Cellular Endocrinology |date=May 2014 |volume=389 |issue=1–2 |pages=71–83 |doi=10.1016/j.mce.2014.02.002 |pmid=24530924 |pmc=4040308 }}</ref>

==Incidents==
The history of chlordecone incidents are reviewed in ''Who's Poisoning America?: Corporate Polluters and Their Victims in the Chemical Age'' (1982).

=== James River estuary ===
In July 1975,<ref name="ssv">{{cite news |last1=SUGAWARA |first1=SANDRA |title=Virginia's James River Still Is Choked With Pesticide Contamination |url=https://www.latimes.com/archives/la-xpm-1985-10-25-mn-14199-story.html |agency=Washington Post |work=Los Angeles Times |date=25 October 1985}}</ref> Virginia Governor Mills Godwin Jr. shut down the James River to fishing for 100 miles, from Richmond to the Chesapeake Bay.<ref name=foster05/> This ban remained in effect for 13 years, until efforts to clean up the river began to show results.<ref name="Cooksey">[https://web.archive.org/web/20140520042033/http://www.richmondmagazine.com/articles/whats-in-the-water-11-09-2008.html Jack Cooksey, "What's in the Water?"], ''Richmond Magazine'', June 2007. Retrieved 13 June 2012.</ref>

Due to the pollution risks, many fishermen, marinas, seafood businesses, and restaurants, along with their employees along the river suffered economic losses. In 1981, a large group of these entities sued Allied Chemical in federal district court (Eastern District of Virginia), claiming special economic damages from Allied's negligent damage to the fish and wildlife.<ref>''Pruitt v. Allied Chemical Corp.'', [https://law.justia.com/cases/federal/district-courts/FSupp/523/975/2298321/ 523 F. Supp. 975] (E.D. Va. 1981).</ref> In a case that sometimes appears in law school courses on Remedies, the court rejected the traditional "economic-loss rule", which requires physical impact causing personal injury or property damage to receive economic damages, and instead allowed a limited group of the plaintiffs—the fishing boat owners, the marinas, and the bait and tackle shops—to recover economic damages from Allied Chemical.

=== French Antilles ===
The French islands of Martinique and Guadeloupe are heavily contaminated with chlordecone,<ref>{{cite journal | author = Durimel A.|display-authors=0 | year = 2013 | title = pH dependence of chlordecone adsorption on activated carbons and role of adsorbent physico-chemical properties | journal = Chemical Engineering Journal | volume = 229 | pages = 239–349 | doi=10.1016/j.cej.2013.03.036}}</ref> following years of its massive and unrestricted use on banana plantations.<ref>{{cite journal |last1=Wong |first1=Alfred |last2=Ribero |first2=Christine |title=Alternative Agricultural Cropping Options for Chlordecone-Polluted Martinique |journal=Études Caribéennes |date=26 March 2014 |issue=26 |doi=10.4000/etudescaribeennes.6710|doi-access=free }}{{open access}}</ref><ref>{{Cite journal|title = Bodies in the System|journal =Small Axe|date = 1 November 2013 |pages = 182–192|volume = 17|issue = 3(42)|doi = 10.1215/07990537-2378991|first = Vanessa|last = Agard-Jones|s2cid =145642259}}</ref> Despite a 1990 ban on the substance in mainland France, the economically powerful banana planters lobbied intensively to obtain a waiver to keep using Kepone until 1993. They argued that no alternative pesticide was available, which has since been disputed. After the 1993 ban, the banana planters were discreetly granted derogations to use their remaining stocks, and a 2005 report prepared by the French National Assembly states that after the 1993 ban was imposed, the chemical was illegally imported to the islands under the name Curlone, and continued to be used for many years.<ref>[https://www.assemblee-nationale.fr/12/rap-info/i2430.asp Rapport d'information (...) sur l'utilisation du chlordécone et des autres pesticides dans l'agriculture martiniquaise et guadeloupéenne.]</ref> Since 2003, local authorities in the two islands have restricted the cultivation of various food crops because the [[Chemistry:Soil contamination|soil is badly contaminated]] by chlordecone. A 2018 large-scale study by the French public health agency, ''Santé publique France'', shows that 95% of the inhabitants of Guadeloupe and 92% of those of Martinique are contaminated by the chemical.<ref>[https://www.lemonde.fr/planete/article/2018/06/06/chlordecone-les-antilles-empoisonnees-pour-sept-siecles_5310192_3244.html Chlordécone : les Antilles empoisonnées pour des générations], Le Monde, 6 June 2018.</ref> Guadeloupe has one of the highest [[Medicine:Prostate cancer|prostate cancer]] diagnosis rates in the world.<ref>{{cite news |title=France: Island Paradise With Contaminated Drinking Water |url=http://www.dw-world.de/dw/episode/0,,5542822,00.html |work=European Journal |publisher=Deutsche Welle |date=26 May 2010 |archiveurl=https://web.archive.org/web/20100527120102/http://www.dw-world.de/dw/episode/0,,5542822,00.html |archivedate=27 May 2010}}</ref>

== In popular culture ==
* Kepone was the name of an American indie rock band from Richmond, Virginia formed in 1991.
* The Dead Kennedys recorded a song named "Kepone Factory", a satire of the controversy surrounding Allied Signal and their negligence regarding employee safety, for their 1981 album ''In God We Trust, Inc.''.
==References==
{{reflist}}

==External links==
*[http://www.terradaily.com/reports/Pesticide_blamed_for_health_disaster_in_French_Caribbean_999.html Terradaily: Pesticide blamed for 'health disaster' in French Caribbean]
*[http://cfpub.epa.gov/ncea/cfm/iris/recordisplay.cfm?deid=178123 EPA releases a Toxicological Review of Kepone (External Review Draft) for public comment – 01/2008]
*[https://www.cdc.gov/niosh/npg/npgd0365.html CDC – NIOSH Pocket Guide to Chemical Hazards]

{{Insecticides}}
{{Xenoestrogens}}
{{Estrogen receptor modulators}}

[[Category:Obsolete pesticides]]
[[Category:Carcinogens]]
[[Category:GPER agonists]]
[[Category:Ketones]]
[[Category:Organochloride insecticides]]
[[Category:Endocrine disruptors]]
[[Category:IARC Group 2B carcinogens]]
[[Category:Xenoestrogens]]
[[Category:Cyclobutanes]]
[[Category:Neurotoxins]]

{{Sourceattribution|Chlordecone}}