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From Wikipedia, the free encyclopedia Polychlorinated dibenzodioxins

Polychlorinated dibenzodioxins

See also: Irish pork crisis of 2008

General structure of PCDDs where n and m can range from 0 to 4

Polychlorinated dibenzodioxins (PCDDs), or simply dioxins, are a group of polyhalo- The skeletal formula and substituent number- genated compounds which are significant be- ing scheme of the parent compound diben- cause they act as environmental pollutants. zo-p-dioxin They are commonly referred to as dioxins for simplicity in scientific publications because which is stabilized by the two flanking ben- every PCDD molecule contains a dioxin zene rings. skeletal structure. Typically, the p-dioxin In PCDDs, chlorine atoms are attached to skeleton is at the core of a PCDD molecule, this structure at any of 8 different places on giving the molecule a dibenzo-p-dioxin ring the molecule, at positions 1–4 and 6–9. There system. Members of the PCDD family have are 75 different types of PCDD congeners been shown to bioaccumulate in humans and (that is: related dioxin compounds).[3] The wildlife due to their lipophilic properties, and toxicity of PCDDs depends on the number are known teratogens, mutagens, and sus- and positions of the chlorine atoms. Congen- pected human . They are organic ers that have chlorines in the 2, 3, 7, and 8 compounds. positions have been found to be significantly Dioxins occur as by-products in the manu- toxic. In fact, 7 congeners have chlorine facture of , in the incinera- atoms in the relevant positions which were tion of chlorine-containing substances such considered toxic by the NATO Committee on as PVC (polyvinyl chloride), in the bleaching the Challenges to Modern Society (NATO/ of paper, and from natural sources such as CCMS) international toxic equivalent (I-TEQ) volcanoes and forest fires.[1] There have been scheme. many incidents of dioxin resulting from industrial emissions and accidents; the earliest such incidents were in the mid 18th Historical perspective century during the Industrial Revolution.[2] The word "dioxins" may also refer to a similar but unrelated compound, the poly- chlorinated dibenzofurans (PCDFs) of like en- vironmental importance. Chemical structure of Structure of 2,3,7,8-tetrachlorodibenzo-p-di- dibenzo-p-dioxins oxin (TCDD) The structure of dibenzo-p-dioxin comprises Low concentrations of dioxins existed in two rings joined by two oxygen nature prior to industrialization due to natur- bridges. This makes the compound an aro- al combustion and geological processes.[4][5] matic diether. The name dioxin formally Dioxins were first unintentionally produced refers to the central dioxygenated ring, as by-products from 1848 onwards as

1 From Wikipedia, the free encyclopedia Polychlorinated dibenzodioxins

Leblanc process plants started operating in Germany.[2] The first intentional synthesis of chlorinated dibenzodioxin was in 1872. Today, concentrations of dioxins are found in all humans, with higher levels commonly found in persons living in more industrialized countries. The most toxic dioxin, 2,3,7,8-tet- rachlorodibenzo-p-dioxin (TCDD), became well known as a contaminant of , an used in the .[6] Later, dioxins were found in Times Beach, Missouri[7] and Love Canal, [8] and Seveso, Italy.[9] More recently, dioxins have been in the news with the pois- oning of President Viktor Yushchenko of Ukraine in 2004,[10] the Naples Mozzarella Crisis[11] and the Irish pork crisis of 2008. Sources of dioxins The Environmental Protection Agency Dioxin Reassessment Report is pos- sibly the most comprehensive review of diox- ins, but other countries now have substantial research. Australia, New Zealand and the Un- ited Kingdom all have substantial research into body burdens and sources. Tolerable daily, monthly or annual intakes have been Concentration profile of PCDD in a dated sed- set by the World Health Organization and a iment core from Esthwaite Water, Cumbria, number of governments. Dioxins enter the UK. general population almost exclusively from ingestion of food, specifically through the Children are passed substantial body bur- consumption of fish, meat, and dairy dens by their mothers, and breastfeeding in- products since dioxins are fat-soluble and creases the child’s body burden. Children’s [12] readily climb the food chain. body burdens are often many times above the Occupational exposure is an issue for amount implied by tolerable intakes which some in the chemical industry, or in the ap- are based on body weight. Breast fed chil- plication of chemicals, notably . In- dren usually have substantially higher dioxin halation has been a problem for people living body burdens than non breast fed children near substantial point sources where emis- until they are about 8 to 10 years old. The sions are not adequately controlled. In many WHO still recommends breast feeding for its developed nations there are now emissions other benefits. regulations which have alleviated some con- Dioxins are produced in small concentra- cerns, although the lack of continuous tions when organic material is burned in the sampling of dioxin emissions causes concern presence of chlorine, whether the chlorine is about the understatement of emissions. In present as chloride ions or as organochlorine Belgium, through the introduction of a pro- compounds, so they are widely produced in cess called AMESA, continuous sampling many contexts. According to the most recent showed that periodic sampling understated US EPA data, the major sources of dioxins emissions by a factor of 30 to 50 times. Few are: facilities have continuous sampling. • Coal fired utilities Most controversial is the United States • Municipal waste incinerators[1] Environmental Protection Agency (US EPA) • Metal smelting assessment’s (draft) finding that any refer- • Diesel trucks ence dose that were to be set would be far • Land application of sewage sludge below current average intakes.

2 From Wikipedia, the free encyclopedia Polychlorinated dibenzodioxins

• Burning treated wood levels of chlorination require higher reaction • Trash burn barrels temperatures and greater dioxin production. These sources together account for nearly See Agent Orange for more on contamination 80% of dioxin emissions. problems in the 1960s. Dioxins may also be When the original US EPA inventory of di- formed during the photochemical breakdown oxin sources was done in 1987, incineration of the common antimicrobial compound represented over 80% of known dioxin triclosan.[14] sources. As a result, US EPA implemented Dioxins are also in typical cigarette new emissions requirements. These regula- smoke.[15] Dioxin in cigarette smoke was tions have been very successful in reducing noted as "understudied" by the US EPA in its dioxin stack emissions from incinerators. In- "Re-Evaluating Dioxin" (1995). In that same cineration of municipal solid waste, medical document, the US EPA acknowledged that di- waste, sewage sludge, and hazardous waste oxin in cigarettes is "anthropogenic" (man- together now produce less than 3% of all di- made, "not likely in nature"). Nevertheless, oxin emissions. the use of chlorine-containing tobacco pesti- In incineration, dioxins can also reform or cides and chlorine-bleached cigarette papers form de novo in the atmosphere above the remains legal. stack as the exhaust gases cool through a Dioxins are present in minuscule amounts temperature window of 600 to 200 °C. The in a wide range of materials used by hu- most common method of reducing the quant- mans — including practically all substances ity of dioxins reforming or forming de novo is manufactured using plastics, resins, or through rapid (30 millisecond) quenching of bleaches. Such materials include tampons, the exhaust gases through that 400 °C win- and a wide variety of food packaging sub- dow.[13] Incinerator emissions of dioxins stances. The use of these materials means have been reduced by over 90% as a result of that all Western humans receive at least a new emissions control requirements. Inciner- very small daily dose of dioxin—however, it is ation in developed countries is now a very disputed whether such exceptionally tiny ex- minor contributor to dioxin emissions. posures have any clinical relevance. It is even controversially discussed whether dioxins might have a non-linear dose-response curve with beneficial health effects in a certain lower dose range, a phenomenon called hormesis.[16] Dietary sources of dioxin in the United States have been analyzed by the EPA and scientists from other organizations. Toxicity Dioxins are absorbed primarily through diet- ary intake of fat, as this is where they accu- A chart illustrating how much dioxin the av- mulate in animals and humans. In humans, erage American consumes per day. (Note: pg the highly chlorinated dioxins are stored in = picogram, or one trillionth of a gram, or fatty tissues and are neither readily metabol- 10−12 g) [12]. ized nor excreted. The estimated elimination half-life for highly chlorinated dioxins (4-8 Dioxins are also generated in reactions chlorine atoms) in humans ranges from 7.8 to that do not involve burning — such as bleach- 132 years.[17] ing fibers for paper or textiles, and in the The persistence of a particular dioxin con- manufacture of chlorinated phenols, particu- gener in an animal is thought to be a con- larly when reaction temperature is not well sequence of its structure. It is believed that controlled. Affected compounds include the dioxins with few chlorines, which thus con- wood preservative pentachlorophenol, and tain hydrogen atoms on adjacent pairs of car- also herbicides such as 2,4-dichlorophenoxy- bons, can more readily be oxidized by cyto- acetic acid (or 2,4-D) and 2,4,5-tri- chromes P450. The oxidized dioxins can then chlorophenoxyacetic acid (2,4,5-T). Higher

3 From Wikipedia, the free encyclopedia Polychlorinated dibenzodioxins be more readily excreted rather than stored exposures may eventually reach dangerous for long time. levels. In 1994, the US EPA reported that di- oxins are a probable , but noted that non- effects (reproduction and sexual development, immune system) may pose an even greater threat to human health. TCDD, the most toxic of the dibenzodioxins, is classified as a Group 1 carcinogen by the International Agency for Research on Cancer (IARC). TCDD has a half-life of approximately 8 years in humans, although at high concen- trations, the elimination rate is enhanced by metabolism.[19] The health effects of dioxins Space-filling model of 2,3,7,8- tetrachlorod- are mediated by their action on a cellular re- ibenzo-p-dioxin. ceptor, the aryl hydrocarbon receptor (AhR).[20] 2,3,7,8-tetrachlorodibenzo-p-dioxin Exposure to high levels of dioxins in hu- (TCDD) is the most toxic of the congeners. mans causes a severe form of persistent Other dioxin congeners (or mixtures thereof) acne, known as chloracne.[21] A case-control are given a toxicity rating from 0 to 1, where study has shown an elevated risk of sarcoma TCDD = 1. This toxicity rating is called the (a type of cancer) associated with low-level Toxic Equivalence Factor, or TEF. TEFs are exposure (4.2 fg/m3) to dioxins from incinera- consensus values and, because of the strong tion plants.[22] High levels of exposures to di- species dependence for toxicity, are listed oxins have been shown by epidemiological separately for mammals, fish, and birds. studies to lead to an increased risk of tu- TEFs for mammalian species are generally mours at all sites.[22] Other effects in humans applicable to human risk calculations. The may include: TEFs have been developed from detailed as- • Developmental abnormalities in the sessment of literature data to facilitate both enamel of children’s teeth.[23][24] risk assessment and regulatory control.[18] • Central and peripheral nervous system Many other compounds may also have dioxin- pathology[25] like properties, particularly non-ortho PCBs, • Thyroid disorders[26] some of which can have TEFs as high as 0.1. • Damage to the immune systems.[27] The total dioxin toxic equivalence (TEQ) • Endometriosis[28] value expresses the toxicity as if the mixture • Diabetes[29] were pure TCDD. The TEQ approach and cur- Recent studies have shown that exposure to rent TEFs have been adopted internationally dioxins changes the ratio of male to female as the most appropriate way to estimate the births among a population such that more fe- potential health risks of mixture of dioxins. males are born than males.[30] Recent data suggest that this type of linear Dioxins accumulate in food chains in a scaling factor may not be the most appropri- fashion similar to other chlorinated com- ate treatment for complex mixtures of diox- pounds (bioaccumulation). This means that ins; further research into non-linear toxicity even small concentrations in contaminated models is required to substantiate this water can be concentrated up a food chain to hypothesis. dangerous levels due to the long biological Dioxins and other persistent organic pol- half life and low water solubility of dioxins. lutants (POPs) are subject to the Stockholm Convention. The treaty obliges signatories to take measures to eliminate where possible, Health effects in other and minimize where not possible to elimin- ate, all sources of dioxin. animals While it has been difficult to establish specif- Health effects in humans ic health effects in humans due to the lack of controlled dose experiments, studies in anim- Dioxins build up primarily in fatty tissues als have shown that dioxin causes a wide over time (bioaccumulate), so even small variety of toxic effects. In particular, TCDD

4 From Wikipedia, the free encyclopedia Polychlorinated dibenzodioxins has been shown to be teratogenic, mutagen- levels of approximately 1 to 2 ppt of TCDD. In ic, carcinogenic, immunotoxic, and hepato- Vietnam, TCDD levels up to 1,000,000 ppt toxic. Furthermore, alterations in multiple have been found in soil and sediments from endocrine and growth factor systems have Agent Orange contaminated areas, three to been reported. The most sensitive effects, ob- four decades after spraying. In addition, elev- served in multiple species, appear to be de- ated levels have been measured in food and velopmental, including effects on the devel- wildlife in Vietnam.[44] oping immune, nervous, and reproductive The most recent study, paid for by the Na- systems.[31] These effects are caused at body tional Academy of Sciences, was released in burdens close to those reported in humans. an April 2003 report. This report is currently Among the animals for which TCDD tox- (March 2007) being revised for release again icity has been studied, there is strong evid- later in 2007. ence for the following effects: The Centers for Disease Control and Pre- • Birth defects (teratogenicity) vention found that dioxin levels in Vietnam In rodents, including rats,[32] mice,[33] veterans[45] were in no way atypical when hamsters and guinea pigs,[34] birds,[35] compared against the rest of the population. and fish.[36] The only exception existed for those who dir- ectly handled Agent Orange. These were • Cancer (including neoplasms in the members of Operation Ranch Hand. Long- mammalian lung, oral/nasal cavities, term studies of the members of Ranch Hand thyroid and adrenal glands, and liver, have thus far uncovered a possibility of elev- squamous cell carcinoma, and various ated risks of diabetes. animal hepatocarcinomas) [32][37] [38] In rodents and fish Dioxin exposure • Hepatotoxicity (liver toxicity) In rodents,[37] chickens,[39] and fish[40] incidents • In 1949, in a herbicide production plant • Endocrine disruption for 2,4,5-T in Nitro, West Virginia, 240 [41] In rodents and fish people were affected when a relief valve opened.[46] • Immunosuppression • In 1963, a dioxin cloud escapes after an In rodents[42] and fish.[43] explosion in a Philips-Duphar plant (now [2] • Learning[31] Solvay Group) near Amsterdam. In the 1960s, Philips-Duphar produced 2250 tonnes of ’Agent Orange’ for the US Army. Studies of dioxins’ ef- • Between 1965 and 1968 production of fects in Vietnam 2,4,5-trichlorophenol in Spolana Neratovice plant in Czechoslovakia US veterans’ groups and Vietnamese groups, seriously poisoned about 60 workers with including the Vietnamese government, have dioxins; after 3 years of investigation of convened scientific studies to explore their reasons of health problems of workers belief that dioxins were responsible for a host Spolana stopped manufacture of 2,4,5-T of disorders, including tens of thousands of (most of which was supplied to the US birth defects in children, that have affected military in Vietnam). Several buildings of Vietnam veterans as well as an estimated one the Spolana chemical plant were heavily million Vietnamese, due to their exposure contaminated by dioxins.[47] Unclear during the Vietnam War to Agent Orange, a amount of dioxins were flushed into the defoliant chemical which was widely sprayed Elbe and Mulde rivers during the 2002 over Vietnamese land and which was found European flood, contaminating the to be highly contaminated with TCDD. Sever- soils.[48] Analysis of eggs and ducks find al exposure studies showed that some US Vi- 15-time higher level of dioxins then EU etnam Veterans who were exposed to Agent limit and high concentrations of dioxin-like Orange had serum TCDD levels up to 600 ppt PCBs in village Libiš. [49] In 2004 (parts per trillion) many years after they left published State Health Authority study, Vietnam, compared to general population which analysed the level of toxic

5 From Wikipedia, the free encyclopedia Polychlorinated dibenzodioxins

substances in human blood near Spolana. Agency report dated October 2002 and According to study is dioxin level in blood released in December 2002 titled in Neratovice, Libiš and Tišice about twice "Exposure and Human Health Evaluation the level of those from the control group of Airborne Pollution from the World in Benesov. Quantity of dioxin chemicals Trade Center Disaster" authored by the near Spolana is significantly higher then EPA Office of Research and Development background level in another countries eg. in Washington states that dioxin levels USA, Japan or Spain. According to the recorded at a monitoring station on Park U.S.EPA even the background level can Row near City Hall Park in New York cause the risk of cancer 1:1000 up to 1: between October 12 and 29, 2001, 10000, i.e. about 100x higher than what is averaged 5.6 parts per trillion, or nearly considered as a risk acceptable in the six times the highest dioxin level ever society. [50] The consumption of local fish, recorded in the U.S. Dioxin levels in the eggs, poultry and some produce was rubble of the World Trade Centers were prohibited because of the post-flood much higher with concentrations ranging contamination. from 10 to 170 parts per trillion. The • In 1976, large amounts of dioxins were report did no measuring of the toxicity of released in an industrial accident at indoor air. Seveso, although no immediate human • In a 2001 case study [21], physicians fatalities or birth defects reported clinical changes in a 30 year old occurred.[51][52][53] woman who had been exposed to a • In 1978, dioxins were some of the massive dosage (144,000 pg/g blood fat) contaminants that forced the evacuation of dioxin equal to 16,000 times the normal of the Love Canal neighborhood of body level; the highest dose of dioxin ever Niagara Falls, New York. Dioxins also recorded in a human. She suffered from caused the 1983 evacuation of Times chloracne, nausea, vomiting, epigastric Beach, Missouri. pain, loss of appetite, leukocytosis, • From 1982 through to 1985, Times Beach, anemia, amenorrhoea and Missouri, was bought out and evacuated thrombocytopenia. However, other under order of the United States notable laboratory tests, such as immune Environmental Protection Agency due to function tests, were relatively normal. The high levels of dioxins in the soil.[54] The same study also covered a second subject town eventually disincorporated.[55] who had received a dosage equivalent to • In December 1991, an electrical explosion 2,900 times the normal level, who caused dioxins (created from the oxidation apparently suffered no notable negative of ) to spread effects other than chloracne. These through four residence halls and two other patients were provided with olestra to buildings on the college campus of SUNY accelerate dioxin elimination [56]. New Paltz. • In 2004, a notable individual case of • In May 1999, there was a dioxin crisis in dioxin poisoning, Ukrainian politician Belgium: quantities of dioxins had entered Viktor Yushchenko was exposed to the the food chain through contaminated second-largest measured dose of dioxins, animal feed. 7,000,000 chickens and according to the reports of the physicians 60,000 pigs had to be slaughtered. This responsible for diagnosing him. This is the scandal was followed by a landslide first known case of a single high dose of change in government in the elections one TCDD dioxin poisoning, and was month later. diagnosed only after a toxicologist • Explosions resulting from the terrorist recognized the symptoms of chloracne attacks on the US on September 11, 2001 while viewing television news coverage of released massive amounts of dust into the his condition.[10] air. The air was measured for dioxins from • In the early 2000s, residents of the city of September 23, 2001, to November 21, New Plymouth, New Zealand, report many 2001, and reported to be "likely the illnesses of people living around and highest ambient concentration that have working at the Dow Chemical plant. This ever been reported." [in history]. The plant ceased production of 2,4,5-T in United States Environmental Protection 1987.

6 From Wikipedia, the free encyclopedia Polychlorinated dibenzodioxins

• In December 2008 in Ireland dioxin levels in Pork were disclosed to have been between 80 and 200 times the legal limit. All Irish pork products were withdrawn from sale both nationally and internationally. For more see Irish pork crisis of 2008 • According to the last available data[60], in 2005 the production of dioxin by the steel industry ILVA in Taranto (Italy) accounted for 90.3 per cent of the overall Italian emissions, and 8.8 per cent of the Viktor Yushchenko with acne after his PCDD European emissions. poisoning incident See also • The following paragraph has been edited • Polychlorinated dibenzofurans (PCDFs) - by DuPont associates: DuPont has been an unrelated compound with similar sued by 1,995 people who claim dioxin environmental concerns emissions from DuPont’s plant in DeLisle, • Dioxin (chemical) - the basic building Mississippi, caused their , illnesses block of dioxins or loved one’s death, of these only 850 are • Chemetco - this former copper smelter is pending as of June 2008. In August 2005, cited in an academic study as one of the Glen Strong, an oyster fisherman with the 10 highest ranking sources of dioxin rare blood cancer multiple myeloma, was pollution reaching Nunavut in the awarded $14 million from DuPont – this Canadian Arctic. ruling was overturned June 5, 2008 by a Mississippi jury who found DuPont’s plant had no connection to Mr. Strong’s References disease.[57] In another case, parents claim [1] ^ Beychok, Milton R. (January 1987). "A dioxin from pollution caused the death of data base for dioxin and furan emissions their 8 year old daughter; the trial took from refuse incinerators". Atmospheric place in the summer of 2007, and a jury Environment 21 (1): 29–36. doi:10.1016/ wholly rejected the family’s claims as no 0004-6981(87)90267-8. scientific connection could be proven [2] ^ Weber R, Tysklind M, and Gaus C between DuPont and the family’s tragic (2008). "Dioxin — Contemporary and loss.[58] DuPont’s DeLisle plant is one of future challenges of historical legacies three titanium dioxide facilities (including (Editorial, dedicated to Otto Hutzinger)". Edgemoor, DE, and New Johnsonville, TN) Env Sci Pollut Res 15 (2): 96–100 (p.97). that are the largest producers of dioxin in doi:10.1065/espr2008.01.473. the country, according to the US EPA’s [3] Nomenclature and physico-chemical Toxic Release Inventory. DuPont properties of PCDDs and PCDFs maintains its operations are safe and [4] "Compilation of EU Dioxin Exposure and environmentally responsible. Health Data" (PDF). http://ec.europa.eu/ • In 2007 in Italy thousands of tonnes of environment/dioxin/pdf/task6.pdf. foul-smelling refuse are piled up in Naples Retrieved on 2007-06-04. and its surrounding villages, defacing [5] "FDA/CFSAN — Questions and Answers entire neighbourhoods. Polychlorinated about Dioxins". http://www.cfsan.fda.gov/ dibenzodioxins are found in animals and ~lrd/dioxinqa.html#g9. Retrieved on humans over lethal dose[59].Sources of 2007-06-04. Polychlorinated dibenzodioxins was [6] Schecter A, Birnbaum L, Ryan JJ, identified in refuse and pvc combustion Constable JD (2006). "Dioxins: an and industrial refuse disposal in overview". Environ. Res. 101 (3): uncontrolled industrial waste disposal. In 419–28. doi:10.1016/ numbers animals and humans was found j.envres.2005.12.003. PMID 16445906. lethal dose.

7 From Wikipedia, the free encyclopedia Polychlorinated dibenzodioxins

[7] "Times Beach Record of Decision Response 3 (3): 332–341. doi:10.2203/ Signed". United States Environmental dose-response.003.03.004. PMID Protection Agency. http://www.epa.gov/ 18648613. history/topics/times/03.htm. Retrieved on http://www.pubmedcentral.nih.gov/ 2007-06-04. articlerender.fcgi?tool=pubmed&pubmedid=18648613. [8] "Love Canal Record of Decision Signed". [17] Geyer HJ, Schramm KW, Feicht EA, et al United States Environmental Protection (2002). "Half-lives of tetra-, penta-, Agency. http://www.epa.gov/history/ hexa-, hepta-, and octachlorodibenzo-p- topics/lovecanal/04.htm. Retrieved on dioxin in rats, monkeys, and humans—a 2007-06-04. critical review". Chemosphere 48 (6): [9] "4 Seveso: A paradoxical classic 631–44. doi:10.1016/ disaster". http://www.unu.edu/unupress/ S0045-6535(02)00030-9. PMID unupbooks/uu21le/uu21le09.htm. 12143938. Retrieved on 2007-06-04. [18] Van den Berg M, Birnbaum LS, Denison [10] ^ "Yushchenko’s acne points to dioxin M, et al (2006). "The 2005 World Health poisoning". http://www.nature.com/news/ Organization reevaluation of human and 2004/041122/full/news041122-8.html. Mammalian toxic equivalency factors for Retrieved on 2009-01-14. dioxins and dioxin-like compounds". [11] "Italy’s toxic waste crisis, the Mafia – Toxicol. Sci. 93 (2): 223–41. doi:10.1093/ and the scandal of Europe’s mozzarella". toxsci/kfl055. PMID 16829543. http://www.independent.co.uk/news/ [19] Geusau A, Schmaldienst S, Derfler K, europe/italys-toxic-waste-crisis-the- Päpke O, Abraham K (2002). "Severe mafia-ndash-and-the-scandal-of-europes- 2,3,7,8-tetrachlorodibenzo- p-dioxin mozzarella-799289.html?service=Print. (TCDD) intoxication: kinetics and trials Retrieved on 2008-03-28. to enhance elimination in two patients". [12] ^ Schecter A, Cramer P, Boggess K, et al Arch. Toxicol. 76 (5-6): 316–25. (2001). "Intake of dioxins and related doi:10.1007/s00204-002-0345-7. PMID compounds from food in the U.S. 12107649. population". J. Toxicol. Environ. Health [20] Bock KW, Köhle C (2006). "Ah receptor: Part A 63 (1): 1–18. doi:10.1080/ dioxin-mediated toxic responses as hints 152873901750128326. PMID 11346131. to deregulated physiologic functions". [13] Cheung WH, Lee VK, McKay G (2007). Biochem. Pharmacol. 72 (4): 393–404. "Minimizing dioxin emissions from doi:10.1016/j.bcp.2006.01.017. PMID integrated MSW thermal treatment". 16545780. Environ. Sci. Technol. 41 (6): 2001–7. [21] ^ Geusau A, Abraham K, Geissler K, doi:10.1021/es061989d. PMID Sator MO, Stingl G, Tschachler E (2001). 17410797. "Severe 2,3,7,8-tetrachlorodibenzo-p- [14] Latch DE, Packer JL, Stender BL, dioxin (TCDD) intoxication: clinical and VanOverbeke J, Arnold WA, McNeill K laboratory effects". Environ. Health (2005). "Aqueous photochemistry of Perspect. 109 (8): 865–9. doi:10.2307/ triclosan: formation of 3454832. PMID 11564625. 2,4-dichlorophenol, 2,8-dichlorodibenzo- [22] ^ Zambon P, Ricci P, Bovo E, Casula A, p-dioxin, and oligomerization products". Gattolin M, Fiore AR, Chiosi F, and Environ. Toxicol. Chem. 24 (3): 517–25. Guzzinati S (2007). "Sarcoma risk and doi:10.1897/04-243R.1. PMID dioxin emissions from incinerators and 15779749. industrial plants: a population-based [15] Ball M, Paepke O, Lis A (1990). case-control study (Italy)". Environ. "Polychlordibenzodioxine und Health 6 (19): 1–19. doi:10.1186/ Polychlordibenzofurane in 1476-069X-6-19. PMID 1948886. Cigarettenrauch" (PDF). Beitr. [23] Alaluusua S, Calderara P, Gerthoux PM, Tabakforsch. Int. 14 (6): 393–402. et al (2004). "Developmental dental http://www.itrust.de/btfi/pdf/ aberrations after the dioxin accident in 1990-14-06-393.pdf. Seveso". Environ. Health Perspect. 112 [16] Tuomisto J, Pekkanen J, Kiviranta H, (13): 1313–8. PMID 15345345. Tuomisto J (2005). "Dioxin Cancer [24] Peterson RE, Theobald HM, Kimmel GL Risk — Example of Hormesis?". Dose (1993). "Developmental and reproductive

8 From Wikipedia, the free encyclopedia Polychlorinated dibenzodioxins

toxicity of dioxins and related [33] Peters JM, Narotsky MG, Elizondo G, compounds: cross-species comparisons". Fernandez-Salguero PM, Gonzalez FJ, Crit. Rev. Toxicol. 23 (3): 283–335. Abbott BD (1999). "Amelioration of doi:10.3109/10408449309105013. PMID TCDD-induced teratogenesis in aryl 8260069. hydrocarbon receptor (AhR)-null mice". [25] Pelclová D, Urban P, Preiss J, et al Toxicol. Sci. 47 (1): 86–92. doi:10.1093/ (2006). "Adverse health effects in toxsci/47.1.86. PMID 10048156. humans exposed to [34] Kransler KM, McGarrigle BP, Olson JR 2,3,7,8-tetrachlorodibenzo-p-dioxin (2007). "Comparative developmental (TCDD)". Reviews on environmental toxicity of 2,3,7,8-tetrachlorodibenzo-p- health 21 (2): 119–38. PMID 16898675. dioxin in the hamster, rat and guinea [26] Pavuk M, Schecter AJ, Akhtar FZ, pig". Toxicology 229 (3): 214–25. Michalek JE (2003). "Serum doi:10.1016/j.tox.2006.10.019. PMID 2,3,7,8-tetrachlorodibenzo-p-dioxin 17126467. (TCDD) levels and thyroid function in Air [35] Bruggeman V, Swennen Q, De Ketelaere Force veterans of the Vietnam War". B, Onagbesan O, Tona K, Decuypere E Annals of epidemiology 13 (5): 335–43. (2003). "Embryonic exposure to doi:10.1016/S1047-2797(02)00422-2. 2,3,7,8-tetrachlorodibenzo-p-dioxin in PMID 12821272. chickens: effects of dose and embryonic [27] Baccarelli A, Mocarelli P, Patterson DG, stage on hatchability and growth". Comp. et al (2002). "Immunologic effects of Biochem. Physiol. C Toxicol. Pharmacol. dioxin: new results from Seveso and 136 (1): 17–28. doi:10.1016/ comparison with other studies". Environ. S1532-0456(03)00168-6. PMID Health Perspect. 110 (12): 1169–73. 14522596. PMID 12460794. [36] Carney SA, Prasch AL, Heideman W, [28] Eskenazi B, Mocarelli P, Warner M, et al Peterson RE (2006). "Understanding (2002). "Serum dioxin concentrations dioxin developmental toxicity using the and endometriosis: a cohort study in zebrafish model". Birth Defects Res. Part Seveso, Italy". Environ. Health Perspect. a Clin. Mol. Teratol. 76 (1): 7–18. 110 (7): 629–34. PMID 12117638. doi:10.1002/bdra.20216. PMID [29] Arisawa K, Takeda H, Mikasa H (2005). 16333842. "Background exposure to PCDDs/PCDFs/ [37] ^ Mann PC (1997). "Selected lesions of PCBs and its potential health effects: a dioxin in laboratory rodents". Toxicologic review of epidemiologic studies". J. Med. pathology 25 (1): 72–9. doi:10.1177/ Invest. 52 (1-2): 10–21. doi:10.2152/ 019262339702500114. PMID 9061855. jmi.52.10. PMID 15751269. [38] Grinwis GC, Vethaak AD, Wester PW, [30] "Dioxin pollution leads to more baby girls Vos JG (2000). "Toxicology of -study". http://www.reuters.com/article/ environmental chemicals in the flounder healthNews/ (Platichthys flesus) with emphasis on the idUSN1836384520071018?feedType=RSS&feedName=healthNewsimmune system: field,. semi-field Retrieved on 2007-10-22. (mesocosm) and laboratory studies". [31] ^ Birnbaum LS, Tuomisto J (2000). "Non- Toxicol. Lett. 112-113: 289–301. carcinogenic effects of TCDD in doi:10.1016/S0378-4274(99)00239-8. animals". Food additives and PMID 10720744. contaminants 17 (4): 275–88. [39] El-Sabeawy F, Enan E, Lasley B (2001). doi:10.1080/026520300283351. PMID "Biochemical and toxic effects of 10912242. 2,3,7,8-tetrachlorodibenzo-p-dioxin in [32] ^ "NTP technical report on the immature male and female chickens". toxicology and carcinogenesis studies of Comp. Biochem. Physiol. C Toxicol. 2,3,7,8-tetrachlorodibenzo-p-dioxin Pharmacol. 129 (4): 317–27. (TCDD) (CAS No. 1746-01-6) in female doi:10.1016/S1532-0456(01)00199-5. Harlan Sprague-Dawley rats (Gavage PMID 11489429. Studies)". National Toxicology Program [40] Zodrow JM, Stegeman JJ, Tanguay RL technical report series (521): 4–232. (2004). "Histological analysis of acute 2006. PMID 16835633. toxicity of 2,3,7,8-tetrachlorodibenzo-p- dioxin (TCDD) in zebrafish". Aquat.

9 From Wikipedia, the free encyclopedia Polychlorinated dibenzodioxins

Toxicol. 66 (1): 25–38. doi:10.1016/ [50] Greenpeace: Carcinogens in human j.aquatox.2003.07.002. PMID 14687977. blood near Spolana can cause serious [41] Heiden TK, Carvan MJ, Hutz RJ (2006). health problems "Inhibition of follicular development, [51] "Seveso – 30 Years After" (PDF). vitellogenesis, and serum 17beta- http://www.roche.com/com_his_sev-e.pdf. estradiol concentrations in zebrafish Retrieved on 2007-06-04. following chronic, sublethal dietary [52] "Icmesa chemical company, Seveso, exposure to 2,3,7,8-tetrachlorodibenzo-p- Italy. 9th July 1976". dioxin". Toxicol. Sci. 90 (2): 490–9. http://www.hse.gov.uk/comah/sragtech/ doi:10.1093/toxsci/kfj085. PMID caseseveso76.htm. Retrieved on 16387744. 2007-06-04. [42] Holladay SD (1999). "Prenatal [53] "Seveso". http://www.chm.bris.ac.uk/ immunotoxicant exposure and postnatal motm/245t/245th/seveso.htm. Retrieved autoimmune disease". Environ. Health on 2007-06-04. Perspect. 107 Suppl 5: 687–91. [54] "AROUND THE NATION; Times Beach, doi:10.2307/3434328. PMID 10502532. Mo., Board Moves to Seal Off Town — [43] Spitsbergen JM, Schat KA, Kleeman JM, New York Times". Peterson RE (1986). "Interactions of http://query.nytimes.com/gst/ 2,3,7,8-tetrachlorodibenzo-p-dioxin fullpage.html?res=9403E0D71438F934A15757C0A965948260. (TCDD) with immune responses of Retrieved on 2007-06-04. rainbow trout". Vet. Immunol. [55] "AROUND THE NATION; Times Beach, Immunopathol. 12 (1-4): 263–80. Mo., Votes Itself Out of Existence — New doi:10.1016/0165-2427(86)90130-3. York Times". http://query.nytimes.com/ PMID 3765346. gst/ [44] Schecter A, Dai LC, Thuy LT, et al fullpage.html?res=9E02E4DF1238F930A35757C0A963948260. (1995). "Agent Orange and the Retrieved on 2007-06-04. Vietnamese: the persistence of elevated [56] Geusau A, Tschachler E, Meixner M, et al dioxin levels in human tissues". (1999). "Olestra increases faecal American journal of 85 (4): excretion of 2,3,7,8-tetrachlorodibenzo- 516–22. doi:10.2105/AJPH.85.4.516. p-dioxin". Lancet 354 (9186): 1266–7. PMID 7702115. doi:10.1016/S0140-6736(99)04271-3. [45] "Veterans Health — Vietnam Studies" PMID 10520643. (PDF). http://www.cdc.gov/nceh/ [57] "Miss. jury rules for DuPont in $14m veterans/vet_hlth_actvy.pdf. Retrieved on dioxin case". 2007-06-04. http://money.netscape.cnn.com/ [46] Collins JJ, Strauss ME, Levinskas GJ, news_story.jsp?idq=/ff/story/0001/ Conner PR (1993). "The mortality 20080605/ experience of workers exposed to 1630797316.htm&TickerSymbols=DD. 2,3,7,8-tetrachlorodibenzo-p-dioxin in a Retrieved on 2008-08-22. trichlorophenol process accident". [58] "Jury Finds DuPont Dioxins Not Epidemiology (Cambridge, Mass.) 4 (1): Responsible for Child’s Death". 7–13. PMID 8420584. http://www.insurancejournal.com/news/ [47] Miroslav Šuta: Spolana — časovaná national/2007/06/12/80735.htm. bomba na břehu Labe, Sedmá generace, Retrieved on 2008-08-22. 10/2002 [59] "Italy’s toxic waste crisis, the Mafia – [48] Christoph EH, Umlauf GCK, Bidoglio G and the scandal of Europe’s mozzarella". (September 2004). "PCDD/Fs and Dioxin- http://www.independent.co.uk/news/ like PCBs in Soils after the Flooding of europe/italys-toxic-waste-crisis-the- River Elbe and Mulde in 2002". DIOXIN mafia-ndash-and-the-scandal-of-europes- 2004 - 24th Intern. Symposium on mozzarella-799289.html?service=Print. Halogenated Environmental Organic Retrieved on 2008-03-28. Pollutants and POPs, 6-10 September [60] "Peacelink" (PDF). 2004. http://www.tarantosociale.org/ [49] Miroslav Šuta: Dioxinové kachny „made tarantosociale/docs/2000.pdf. Retrieved in Spolana“, Sedmá generace, 3/2003 on 2009-01-31.

10 From Wikipedia, the free encyclopedia Polychlorinated dibenzodioxins

• "Researcher Dispels Myth of Dioxins and External links Plastic Water Bottles" Johns Hopkins • What is Dioxin? Researcher explains the facts about • "Dioxin Homepage at Environmental Dioxins Justice Advocates" • "Health Risks from Dioxin and Related • "EPA: Exposure and Human Health Compounds: Evaluation of the EPA Reassessment of Reassessment" Includes discussion of 2,3,7,8-Tetrachlorodibenzo-p-Dioxin methods of evaluating risk of low (TCDD) and Related Compounds National concentrations, and Toxic Equivalency Academy Sciences (NAS) Review Draft" • "Dioxins in Cigarette Smoke". • "Dioxins and Dioxin-like Compounds in the • residues that are legal Food Supply: Strategies to Decrease contaminants of tobacco Exposure", a 2003 report by the National • Health effects of dioxins Academy of Sciences • "Assessment of the Health Risks of • National Pollutant Inventory - Dioxin and Dioxins", a 1998 report by the World Furan Fact Sheet Health Organisation. • "Rhodes Remediation" Website about • New Zealand Ministry of Health page on remediation of dioxin contaminated dioxins Homebush Bay and land in Rhodes, a • IARC monograph: "Polychlorinated suburb of Sydney, NSW, Australia. Union Dibenzo-para-dioxins" Carbide was the polluter.

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Categories: Organochlorides, IARC Group 1 carcinogens, IARC Group 3 carcinogens, Incinera- tion, Persistent organic pollutants, Immunotoxins, Oxygen heterocycles

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