Knowledge (XXG)

2,3,7,8-Tetrachlorodibenzodioxin

Source 📝

1432:, two women were poisoned at their workplace in 1997, and the measured concentrations in one of them were the highest ever measured in a human being, 144,000 pg/g of fat. This is about 100,000 times the concentrations in most people today and about 10,000 times the sum of all dioxin-like compounds in young people today. They survived but suffered from difficult chloracne for several years. The poisoning likely happened in October 1997 but was not discovered until April 1998. At the institute where the women worked as secretaries, high concentrations of TCDD were found in one of the labs, suggesting that the compound had been produced there. The police investigation failed to find clear evidence of crime, and no one was ever prosecuted. Aside from malaise and 46: 1174:). In the occupational cohort studies available for the classification, the risk was weak and borderline detectable, even at very high exposures. Therefore, the classification was, in essence, based on animal experiments and mechanistic considerations. This was criticized as a deviation from IARC's 1997 classification rules. The main problem with IARC classification is that it only assesses qualitative hazard, i.e. carcinogenicity at any dose, and not the quantitative risk at different doses. According to a 2006 1053:
of various organs and the immune systems or other regulatory functions. The AH receptor is phylogenetically highly conserved, with a history of at least 600 million years, and is found in all vertebrates. Its ancient analogs are important regulatory proteins even in more primitive species. In fact, knock-out animals with no AH receptor are prone to illness and developmental problems. Taken together, this implies the necessity of a basal degree of AH receptor activation to achieve normal physiological function.
332: 237: 573: 578: 563: 55: 568: 769: 1284:. Development of some organs may be even more sensitive: very low doses perturb the development of sexual organs in rodents, and the development of teeth in rats. The latter is important in that tooth deformities were also seen after the Seveso accident and possibly after a long breast-feeding of babies in the 1970s and 1980s when the dioxin concentrations in Europe were about ten times higher than at present. 1358: 64: 774: 892: 1293:
there is a threshold below which it seems to cause no cancer. TCDD is not mutagenic or genotoxic, in other words, it is not able to initiate cancer, and the cancer risk is based on promotion of cancer initiated by other compounds or on indirect effects such as disturbing defense mechanisms of the body e.g. by preventing
773: 1304:
that is metabolized in two steps, oxidation and conjugation. Oxidation produces epoxide carcinogens that are rapidly detoxified by conjugation, but some molecules may escape to the nucleus of the cell and bind to DNA causing a mutation, resulting in cancer initiation. When TCDD increases the activity
1240:
has determined that levels higher than 1,000 ppt TEq in soil require intervention, including research, surveillance, health studies, community and physician education, and exposure investigation. The EPA is considering reducing these limits to 72 ppt TEq. This change would significantly increase the
1052:
The physiological function of the AH receptor has been the subject of continuous research. One obvious function is to increase the activity of enzymes breaking down foreign chemicals or normal chemicals of the body as needed. There seem to be many other functions, however, related to the development
1263:
atrophy is very typical in several animal species. TCDD also affects the balance of several hormones. In some species, but not in all, severe liver toxicity is seen. Taking into account the low doses of dioxins in the present human population, only two types of toxic effects have been considered to
1258:
and wasting, and even after a huge dose animals die only 1 to 6 weeks after the TCDD administration. Seemingly similar species have varying sensitivities to acute effects: lethal dose for a guinea pig is about 1 μg/kg, but to a hamster it is more than 1,000 μg/kg. A similar difference can
1048:
These polycyclic hydrocarbons also activate the AH receptor, but less than TCDD and only temporarily. Even many natural compounds present in vegetables cause some activation of the AH receptor. This phenomenon can be viewed as adaptive and beneficial, because it protects the organism from toxic and
3255:
Saracci, R.; Kogevinas, M.; Winkelmann, R.; Bertazzi, P. A.; Bueno De Mesquita, B. H.; Coggon, D.; Green, L. M.; Kauppinen, T.; l'Abbé, K. A.; Littorin, M.; Lynge, E.; Mathews, J. D.; Neuberger, M.; Osman, J.; Pearce, N. (1991). "Cancer mortality in workers exposed to chlorophenoxy herbicides and
1292:
Cancers can be induced in animals at many sites. At sufficiently high doses, TCDD has caused cancer in all animals tested. The most sensitive is liver cancer in female rats, and this has long been a basis for risk assessment. Dose-response of TCDD in causing cancer does not seem to be linear, and
1180:
article, there were debates on whether TCDD was carcinogenic only at high doses which also cause toxic damage of tissues. A 2011 review concluded that, after 1997, further studies did not support an association between TCDD exposure and cancer risk. One of the problems is that in all occupational
1194:
provided some direct epidemiological evidence that TCDD or other dioxins are not causing soft-tissue sarcoma at low doses, although this cancer has been considered typical for dioxins. There was in fact a trend of cancer to decrease. This is called a J-shape dose-response, low doses decrease the
772: 1385:
of several kilograms of TCDD from a pressure tank. Many animals died, and high concentrations of TCDD, up to 56,000 pg/g of fat, were noted especially in children playing outside and eating local food. The acute effects were limited to about 200 cases of
1447:
was poisoned with a large dose of TCDD. His blood TCDD concentration was measured 108,000 pg/g of fat, which is the second highest ever measured. This concentration implies a dose exceeding 2 mg, or 25 μg/kg of body weight. He suffered from
3299:
Harnly, M.; Stephens, R.; McLaughlin, C.; Marcotte, J.; Petreas, M.; Goldman, L. (1995). "Polychlorinated Dibenzo-p-dioxin and Dibenzofuran Contamination at Metal Recovery Facilities, Open Burn Sites, and a Railroad Car Incineration Facility".
1398:, as well as some developmental effects such as disturbed development of teeth and excess of girls born to fathers who were exposed as children. Several other long-term effects have been suspected, but the evidence is not very strong. 2974:
T.A. Mably; D.L. Bjerke; R.W. Moore; A. Gendron-Fitzpatrick; R.E. Peterson (1992). "In utero and lactational exposure of male rats to 2,3,7,8-tetrachlorodibenzo-pdioxin. 3. Effects on spermatogenesis and reproductive capability".
1409:, several hundred people were poisoned by extremely high concentrations of TCDD by Russell Martin Bliss, who sprayed TCDD-contaminated waste oil on dusty roads to avoid large dust clouds. Bliss himself obtained the waste oil from 2352:
Kogevinas M, Becher H, Benn T, Bertazzi PA, Boffetta P, Bueno-de-Mesquita HB, Coggon D, Colin D, Flesch-Janys D, Fingerhut M, Green L, Kauppinen T, Littorin M, Lynge E, Mathews JD, Neuberger M, Pearce N, Saracci R (1997).
586: 543: 1340:
The greatest production occurs from waste incineration, metal production, and fossil-fuel and wood combustion. Dioxin production can usually be reduced by increasing the combustion temperature. Total U.S. emissions of
708: 1150:
and the subsequent oxygen damage to DNA. There are other explanations such as endocrine disruption or altered signal transduction. The endocrine disrupting activities seem to be dependent on life stage, being
1065:
considered developmental toxicity as the most pertinent risk of dioxins to human beings. Because people are usually exposed simultaneously to several dioxin-like chemicals, a more detailed account is given at
5852: 4345: 1146:. Its main action is cancer promotion; it promotes the carcinogenicity initiated by other compounds. Very high doses may, in addition, cause cancer indirectly; one of the proposed mechanisms is 4426: 1413:, a company that produced Agent Orange. No one was ever charged in relation to the incident, and the city of Times Beach was abandoned and disincorporated following an investigation by the 1185:, had concluded that after 30 years the results did not provide evidence of disease. On the other hand, the latest studies on Seveso population support TCDD carcinogenicity at high doses. 1126:
and decreased sperm quality have been noted. Various developmental effects have been clearly shown after high mixed exposures to dioxins and dioxin-like compounds, the most dramatic in
1957:
DeGroot, Danica; He, Guochun; Fraccalvieri, Domenico; Bonati, Laura; Pandini, Allesandro; Denison, Michael S. (2011). "AHR Ligands: Promiscuity in Binding and Diversity in Response".
1181:
studies the subjects have been exposed to a large number of chemicals, not only TCDD. By 2011, it was reported that studies that include the update of Vietnam veteran studies from
1922:
Mandlekar S, Hong JL, Kong AN (August 2006). "Modulation of metabolic enzymes by dietary phytochemicals: a review of mechanisms underlying beneficial versus unfavorable effects".
4183: 3342: 1508: 819: 1329:. It may also be formed along with other polychlorinated dibenzodioxins and dibenzofuranes in any burning of hydrocarbons where chlorine is present, especially if certain metal 905: 704: 5845: 1313:
intermediates may increase, increasing the possibility of cancer initiation. Thus, a beneficial activation of detoxifying enzymes may lead to deleterious side effects.
1585:
Tuomisto, Jouko (2019) Dioxins and dioxin-like compounds: toxicity in humans and animals, sources, and behaviour in the environment. WikiJournal of Medicine 6(1): 8 |
1321:
TCDD has never been produced commercially except as a pure chemical for scientific research. It is, however, formed as a synthesis side product when producing certain
1237: 1210: 775: 5838: 1418: 1218: 2901:
R. Pohjanvirta; J. Tuomisto (1994). "Short-term toxicity of 2,3,7,8-tetrachlorodibenzop-dioxin in laboratory animals: effects, mechanisms, and animal models".
381: 3349: 1790:
J. Lindén; S. Lensu; J. Tuomisto; R. Pohjanvirta. (2010). "Dioxins, the aryl hydrocarbon receptor and the central regulation of energy balance. A review".
1163: 1414: 146: 1993:
Rothhammer, V; Quintana, FJ (March 2019). "The aryl hydrocarbon receptor: an environmental sensor integrating immune responses in health and disease".
5940: 3730: 1833:
Tijet N, Boutros PC, Moffat ID, et al. (2006). "Hydrocarbon receptor regulates distinct dioxin-dependent and dioxin-independent gene batteries".
2129:
Y.P. Dragan; D. Schrenk (2000). "Animal studies addressing the carcinogenicity of TCDD (or related compounds) with an emphasis on tumour promotion".
1259:
be seen even between two different rat strains. Various hyperplastic (overgrowth) or atrophic (wasting away) responses are seen in different organs,
3369: 2472:"Comparison of chronic toxicity and carcinogenicity of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in 2-year bioassays in female Sprague-Dawley rats" 1297:
or programmed death of altered cells. Carcinogenicity is associated with tissue damage, and it is often viewed now as secondary to tissue damage.
1118:
were the most statistically significant defects. Later some tooth defects and borderline neurodevelopmental effects have been reported. After the
3553:
Sorg, O.; Zennegg, M.; Schmid, P.; Fedosyuk, R.; Valikhnovskyi, R.; Gaide, O.; Kniazevych, V.; Saurat, J.-H. (2009). "2,3,7,8-tetrachlorodibenzo-
797: 3635: 1176: 656: 3688: 3239: 2319: 4942: 4558: 790: 1333:
such as copper are also present. Usually a mixture of dioxin-like compounds is produced, therefore a more thorough treatise is under
6072: 4573: 4563: 1974: 1469: 1334: 1067: 346: 31: 2036:"Consultation on assessment of the health risk of dioxins: re-evaluation of the tolerable daily intake (TDI): Executive summary". 1883:"An aryl hydrocarbon receptor odyssey to the shores of toxicology: the Deichmann Lecture, International Congress of Toxicology-XI" 1026:; it has been shown that high doses of TCDD either increase or decrease the expression of several hundred genes in rats. Genes of 963:. Pure TCDD is a colorless solid with no distinguishable odor at room temperature. It is usually formed as an unwanted product in 4401: 1236:
TEq in soils and 100 ppt in sediment. Most industrialized countries have dioxin concentrations in soils of less than 12 ppt. The
1171: 1049:
carcinogenic substances. Excessive and persistent stimulation of AH receptor, however, leads to a multitude of adverse effects.
5950: 5814: 4032: 3187:
R.J. Kociba; et al. (1978). "Results of a two-year chronic toxicity and oncogenicity study of 2,3,7,8- tetrachlorodibenzo-
3144:
S. Alaluusua; P.L. Lukinmaa; J. Torppa; J. Tuomisto; T. Vartiainen (1999). "Developing teeth as biomarker of dioxin exposure".
1190: 3227: 2568:
Buffler PA, Ginevan ME, Mandel JS, Watkins DK (September 2011). "The Air Force health study: an epidemiologic retrospective".
5290: 5099: 4853: 3698: 1342: 936: 520: 5922: 5285: 4533: 3723: 2812: 1346: 1221:(EPA) established an oral reference dose (RfD) of 0.7 pg/kg b.w. per day for TCDD (see discussion on the differences in). 696: 912: 652: 6040: 4885: 4431: 999: 700: 642: 535: 289: 45: 4502: 577: 572: 4667: 4611: 4605: 4527: 4396: 3959: 310: 736: 2206:
Knerr S, Schrenk D (October 2006). "Carcinogenicity of 2,3,7,8-tetrachlorodibenzo-p-dioxin in experimental models".
5801: 5506: 4974: 4553: 4300: 1250:
By far most information on toxicity of dioxin-like chemicals is based on animal studies utilizing TCDD. Almost all
843: 830: 3346: 1094:
that contained TCDD as an impurity out of the production process. However, there has been some uncertainty on the
5872: 5861: 5769: 5172: 4969: 3012:"A dose-response analysis of the reproductive effects of a single gestational dose of 2,3,7,8-tetrachlorodibenzo- 1736:
Mandal PK (May 2005). "Dioxin: a review of its environmental effects and its aryl hydrocarbon receptor biology".
1456: 1062: 1011: 626: 3438: 2787:"EPA's Reanalysis of Key Issues Related to Dioxin Toxicity and Response to NAS Comments (External Review Draft)" 2432:
Cole P, Trichopoulos D, Pastides H, Starr T, Mandel JS (December 2003). "Dioxin and cancer: a critical review".
5481: 5466: 5074: 4984: 4818: 4631: 4456: 3716: 1214: 668: 2338:
2,3,7,8-tetrachlorodibenzopara-dioxin, 2,3,4,7,8-pentachlorodibenzofuran, and 3,3',4,4',5-pentachlorobiphenyl
2248:"Cancer incidence in the population exposed to dioxin after the "Seveso accident": twenty years of follow-up" 783: 724: 720: 562: 6067: 5945: 5029: 5024: 4599: 3708: 3665: 1038: 712: 232: 5054: 4808: 4636: 3987: 3977: 3824: 1265: 1102:
indicated large amount of heterogeneity between studies and emphasized a lack of consensus on the issue.
3366: 2246:
Angela Cecilia Pesatori; Dario Consonni; Maurizia Rubagotti; Paolo Grillo; Pier Alberto Bertazzi (2009).
676: 6077: 6062: 5426: 4953: 4754: 4662: 600: 567: 555: 491: 194: 6013: 1254:
are affected by high doses of TCDD. In short-term toxicity studies in animals, the typical effects are
5954: 5918: 5758: 5586: 5501: 5275: 5162: 5089: 5044: 5009: 4989: 4538: 4037: 3907: 3901: 3839: 3748: 3403: 3309: 2751: 2259: 1610: 1535: 1182: 1015: 975: 76: 3643: 3557:-dioxin (TCDD) poisoning in Victor Yushchenko: identification and measurement of TCDD metabolites". 634: 6023: 5994: 5970: 5791: 5446: 5214: 5142: 5137: 5069: 4994: 4677: 4626: 4497: 4487: 4257: 4068: 3895: 3869: 3859: 3829: 3689:
U.S. National Library of Medicine: Hazardous Substances Databank – 2,3,7,8-Tetrachlorodibenzodioxin
1452:
for many years, but after initial malaise, other symptoms or abnormal laboratory findings were few.
1111: 622: 327: 112: 2859:-dioxin and related halogenated aromatic hydrocarbons: examination of the mechanism of toxicity". 2742:
Malisch R, Kotz A (2014). "Dioxins and PCBs in feed and food – review from European perspective".
1300:
TCDD may in some conditions potentiate the carcinogenic effects of other compounds. An example is
1030:
activating the breakdown of foreign and often toxic compounds are classic examples of such genes (
664: 5864: 5819: 5677: 5632: 5591: 5486: 4964: 4931: 4858: 4672: 4466: 3834: 3582: 3479: 3281: 3169: 2956: 2154: 2061: 2018: 1858: 1815: 1761: 1715: 1672: 1551: 1326: 1255: 1233: 740: 2397:
Schwarz M, Appel KE (October 2005). "Carcinogenic risks of dioxin: mechanistic considerations".
2175:
M. Viluksela; et al. (2000). "Liver tumor-promoting activity of 2,3,7,8-tetrachlorodibenzo-
680: 6018: 2786: 688: 5637: 5491: 5411: 5059: 5019: 4979: 4833: 4652: 4647: 4593: 4588: 4568: 4522: 3782: 3617: 3574: 3532: 3471: 3419: 3325: 3273: 3235: 3208: 3161: 3126: 3074: 3035: 2992: 2948: 2910: 2876: 2767: 2724: 2675: 2634: 2585: 2550: 2501: 2449: 2414: 2376: 2315: 2287: 2223: 2188: 2146: 2102: 2053: 2010: 1970: 1939: 1904: 1850: 1807: 1753: 1707: 1664: 1626: 1440: 1395: 1362: 968: 868: 5899: 5888: 5774: 5601: 5476: 5039: 5014: 5004: 4682: 4548: 4492: 4247: 4229: 4198: 4193: 4188: 4178: 4173: 4168: 4120: 4109: 3969: 3809: 3788: 3777: 3743: 3609: 3600:
Senior, K; Mazza, A (September 2004). "Italian "Triangle of death" linked to waste crisis".
3566: 3522: 3514: 3461: 3453: 3411: 3317: 3265: 3200: 3153: 3116: 3108: 3066: 3027: 2984: 2940: 2868: 2759: 2714: 2706: 2665: 2624: 2616: 2603:
Warner, M; Mocarelli, P; Samuels, S; Needham, L; Brambilla, P; Eskenazi, B (December 2011).
2577: 2540: 2532: 2491: 2483: 2441: 2406: 2366: 2277: 2267: 2215: 2138: 2092: 2045: 2002: 1962: 1931: 1894: 1842: 1799: 1745: 1699: 1656: 1618: 1543: 1474: 1391: 1306: 1147: 944: 728: 610: 480: 404: 2652:
J.T. Tuomisto; J. Pekkanen; H. Kiviranta; E. Tukiainen; T. Vartiainen; J. Tuomisto (2004).
2309: 1647:
M.H. Sweeney; P. Mocarelli (2000). "Human health effects after exposure to 2,3,7,8- TCDD".
298: 214: 5657: 5431: 5147: 4900: 4823: 4803: 4725: 3819: 3799: 3373: 3353: 2314:. Monographs on the Evaluation of Carcinogenic Risks to Humans. Vol. 69. Lyon: IARC. 1382: 1251: 1225: 1195:
risk, and only higher doses increase the risk, according to a 2005 article in the journal
1152: 1119: 1019: 995: 122: 54: 2081:"Association between Agent Orange and birth defects: Systematic review and meta-analysis" 1369:
There have been numerous incidents where people have been exposed to high doses of TCDD.
3407: 3313: 2872: 2755: 2263: 1614: 1539: 174: 17: 5962: 5958: 5830: 5576: 5511: 5436: 5375: 5109: 5049: 4798: 4239: 4010: 3935: 3849: 3527: 3498: 3390:
P. Mocarelli; et al. (1991). "Serum concentrations of 2,3,7,8- tetrachlorodibenzo-
3121: 3096: 2719: 2694: 2629: 2604: 2545: 2520: 2496: 2471: 2371: 2355:"Cancer mortality in workers exposed to phenoxy herbicides, chlorophenols, and dioxins" 2354: 2282: 2247: 1301: 1281: 1277: 1042: 1031: 883: 874: 648: 504: 331: 236: 3613: 3570: 3457: 3157: 6056: 5780: 5727: 5722: 5652: 5596: 5456: 5441: 5395: 5220: 5183: 5152: 4999: 4848: 4731: 4657: 4583: 3954: 3879: 3804: 3670: 3269: 3204: 2988: 2838: 2710: 2065: 1422: 1197: 1127: 1099: 1083: 1010:
TCDD and dioxin-like compounds act via a specific receptor present in all cells: the
979: 469: 225: 3586: 3285: 3173: 3053:
H. Kattainen; et al. (2001). "In utero/lactational 2,3,7,8- tetrachlorodibenzo-
2960: 2763: 2581: 2158: 2022: 1819: 1765: 1719: 1690:
L. Poellinger (2000). "Mechanistic aspects—the dioxin (aryl hydrocarbon) receptor".
1676: 1555: 1459:, is contaminated with TCDD from years of illegal waste disposal by organized crime. 748: 5966: 5930: 5732: 5682: 5461: 5451: 5406: 5400: 5370: 5365: 5123: 5034: 4936: 4880: 4843: 4792: 4771: 4720: 4687: 4616: 4578: 4517: 4482: 4380: 4002: 3982: 3854: 3753: 3483: 1862: 1421:. This is marked as the single largest contamination of a civilian area by TCDD in 1322: 1115: 1107: 1087: 987: 684: 2931:
L.S. Birnbaum; J. Tuomisto (2000). "Non-carcinogenic effects of TCDD in animals".
1522:
Shiu WY; et al. (1988). "Physical-chemical properties of chlorinated dibenzo-
606: 278: 3497:
A. Geusau; K. Abraham; K. Geissler; M.O. Sator; G. Stingl; E. Tschachler (2001).
2536: 1622: 692: 618: 5981: 5742: 5717: 5672: 5535: 5496: 5360: 5355: 5320: 5315: 5310: 5305: 5300: 5280: 5199: 5188: 5178: 4890: 4621: 4512: 4507: 4441: 4150: 4140: 4125: 4097: 4079: 4060: 4051: 3943: 3764: 2445: 2410: 2341:. Vol. 100F. International Agency for Research on Cancer. pp. 339–378. 2336: 1803: 1402: 1079: 991: 809: 1935: 1357: 1213:(JECFA) derived in 2001 a provisional tolerable monthly intake (PTMI) of 70 pg 5998: 5991: 5905: 5895: 5891: 5692: 5687: 5667: 5662: 5647: 5642: 5555: 5550: 5526: 5345: 5330: 5325: 5270: 5265: 4947: 4828: 4787: 4781: 4765: 4748: 4742: 4709: 4701: 4642: 4436: 4208: 4114: 4103: 3925: 3919: 3703: 3415: 2006: 1966: 1749: 1601:
Schecter A, Birnbaum L, Ryan JJ, Constable JD (2006). "Dioxins: an overview".
1504: 1433: 1167: 1156: 1103: 1035: 660: 438: 355:
InChI=1S/C12H4Cl4O2/c13-5-1-9-10(2-6(5)14)18-12-4-8(16)7(15)3-11(12)17-9/h1-4H
205: 1276:
Developmental effects occur at very low doses in animals. They include frank
365:
InChI=1/C12H4Cl4O2/c13-5-1-9-10(2-6(5)14)18-12-4-8(16)7(15)3-11(12)17-9/h1-4H
6002: 5985: 5976: 5910: 5787: 5737: 5712: 5702: 5627: 5350: 5340: 5335: 5255: 5235: 5209: 5194: 5132: 5079: 4838: 4776: 4759: 4737: 4714: 4451: 4292: 4085: 3949: 3888: 3814: 2944: 2335:
IARC Working Group on the Evaluation of Carcinogenic Risk to Humans (2012).
2142: 1899: 1882: 1703: 1660: 1449: 1387: 1365:
after he was poisoned by TCDD. TCDD often causes disfiguring facial swelling
1294: 1143: 1139: 1123: 672: 3621: 3578: 3536: 3475: 3329: 3130: 3078: 3070: 3031: 2952: 2771: 2728: 2679: 2638: 2589: 2554: 2505: 2487: 2453: 2418: 2291: 2272: 2227: 2219: 2192: 2150: 2106: 2057: 2014: 1943: 1908: 1854: 1846: 1811: 1757: 1711: 1668: 1630: 63: 3423: 3277: 3165: 3039: 2996: 2914: 2880: 2380: 2079:
Ngo, Anh D; Taylor, Richard; Roberts, Christine L; Nguyen, Tuan V (2006).
5934: 5796: 5697: 5606: 5571: 5516: 5471: 5385: 5295: 5245: 5128: 5117: 5094: 5084: 5064: 4959: 4926: 4920: 4910: 4310: 4282: 4277: 4272: 3913: 3772: 3518: 3212: 2097: 2080: 1406: 1349:
were reduced from ca. 14 kg TEq in 1987 to 1.4 kg TEq in 2000.
1330: 796: 789: 782: 755: 3321: 2620: 1586: 1547: 943:(sometimes shortened, though inaccurately, to simply 'dioxin') with the 5915: 5545: 5540: 5250: 5240: 5230: 5225: 4915: 4543: 4461: 4446: 4421: 4416: 4411: 4406: 4375: 4370: 4365: 4360: 4355: 4325: 4320: 4315: 4305: 4213: 4203: 4163: 4158: 4135: 4130: 3864: 3666:"Discariche piene di rifiuti tossici quello è il triangolo della morte" 3466: 1444: 1410: 1310: 1091: 964: 716: 459: 265: 3097:"Developmental dental aberrations after the dioxin accident in Seveso" 2670: 2653: 2311:
Polychlorinated dibenzo-para-dioxins and polychlorinated dibenzofurans
2049: 614: 5763: 5421: 5416: 5204: 4350: 4340: 4335: 4330: 3992: 3794: 3112: 1429: 1374: 1260: 1155:
when estrogen is present (or in high concentration) in the body, and
1095: 1027: 983: 630: 185: 3394:-dioxin and test results from selected residents of Seveso, Italy". 3011: 2605:"Dioxin exposure and cancer risk in the Seveso Women's Health Study" 882:
Except where otherwise noted, data are given for materials in their
2793:. US EPA National Center for Environmental Assessment,Cincinnati Oh 2470:
Walker NJ, Wyde ME, Fischer LJ, Nyska A, Bucher JR (October 2006).
253: 5707: 5622: 5581: 4863: 4267: 4262: 4252: 4091: 4074: 4027: 2179:-dioxin (TCDD) in TCDD-sensitive and TCDD resistant rat strains". 1378: 1356: 165: 145: 135: 2519:
Boffetta P, Mundt KA, Adami HO, Cole P, Mandel JS (August 2011).
732: 4873: 4868: 1023: 856: 744: 244: 5834: 3712: 3232:
Casarett & Doull's Toxicology: the basic science of poisons
5260: 4813: 3439:"Paternal concentrations of dioxin and sex ratio of offspring" 3377: 1436:
there were few other symptoms or abnormal laboratory findings.
3503:-dioxin (TCDD) intoxication: clinical and laboratory effects" 2521:"TCDD and cancer: a critical review of epidemiologic studies" 1130:
and Yu-chen catastrophes, in Japan and Taiwan, respectively.
4346:
Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)
2855:
A. Poland; J.C. Knutson (1982). "2,3,7,8-Tetrachlorodibenzo-
315: 4427:
2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate
3693: 3057:-dioxin exposure impairs molar tooth development in rats". 1232:
The general environmental limit in most countries is 1,000
1241:
potential volume of contaminated soil requiring treatment.
3234:(6th ed.). New York: McGraw-Hill. pp. 201–267. 767: 1086:
were observed in children of people who were exposed to
1390:. Long-term effects seem to include a slight excess of 967:
processes of organic materials or as a side product in
900: 2654:"Soft-tissue sarcoma and dioxin: a case-control study" 1098:
link between Agent Orange/dioxin exposure. In 2006, a
1509:
National Institute for Occupational Safety and Health
2308:
International Agency for Research on Cancer (1997).
1238:
U.S. Agency for Toxic Substance and Disease Registry
5871: 5751: 5615: 5564: 5525: 5384: 5161: 5108: 4899: 4700: 4475: 4389: 4291: 4238: 4222: 4149: 4059: 4050: 4020: 4001: 3968: 3934: 3887: 3878: 3763: 1034:). TCDD increases the enzymes breaking down, e.g., 27:
Polychlorinated dibenzo-p-dioxin, chemical compound
5873: 3016:-dioxin in male Long Evans Hooded rat offspring" 2926: 2924: 1455:An area of polluted land in Italy, known as the 1211:Joint FAO/WHO Expert Committee on Food Additives 994:. TCDD was released into the environment in the 277: 3380:'s National Center for Environmental Assessment 1988: 1986: 1138:It is largely agreed that TCDD is not directly 771: 121: 2896: 2894: 2892: 2890: 1961:. John Wiley & Sons, Ltd. pp. 63–79. 1581: 1579: 1577: 1575: 1573: 1571: 1569: 1567: 1565: 5846: 3724: 3376:(accessed 2013-08-01), p.40; using data from 3347:Report on Carcinogens, Twelfth Edition (2011) 1219:United States Environmental Protection Agency 8: 3704:CDC – NIOSH Pocket Guide to Chemical Hazards 3090: 3088: 2170: 2168: 814:164.2 °C (327.6 °F; 437.3 K) 2241: 2239: 2237: 1164:International Agency for Research on Cancer 5853: 5839: 5831: 4056: 3884: 3731: 3717: 3709: 3010:L.E. Gray; J.S. Ostby; W.R. Kelce (1997). 2695:"Dioxin cancer risk –example of hormesis?" 2392: 2390: 1596: 1594: 389:ClC1=C(Cl)C=C2OC(C=C(C(Cl)=C3)Cl)=C3OC2=C1 330: 235: 213: 37: 3526: 3465: 3120: 2718: 2669: 2628: 2544: 2495: 2465: 2463: 2370: 2281: 2271: 2124: 2122: 2120: 2118: 2116: 2096: 1959:The AH Receptor in Biology and Toxicology 1898: 1642: 1640: 1006:Biological activity in humans and animals 297: 3226:Pitot III, H. C.; Dragan, Y. P. (2001). 1785: 1783: 1781: 1779: 1777: 1775: 1731: 1729: 1503:NIOSH Pocket Guide to Chemical Hazards. 3548: 3546: 2303: 2301: 1876: 1874: 1872: 1486: 1177:Molecular Nutrition & Food Research 986:) and became known as a contaminant in 386: 351: 326: 4612:Methylphosphonyl dichloride (dichloro) 4606:Methylphosphonyl difluoride (difluoro) 3302:Environmental Science & Technology 1498: 1496: 1494: 1492: 1490: 474:305 °C (581 °F; 578 K) 226: 4854:Tetramethylenedisulfotetramine (TETS) 2085:International Journal of Epidemiology 1587:https://doi.org/10.15347/wjm/2019.008 1373:In 1976, thousands of inhabitants of 1122:, tooth development defects, changed 454:Colorless to white crystalline solid 358:Key: HGUFODBRKLSHSI-UHFFFAOYSA-N 193: 173: 7: 2744:The Science of the Total Environment 4943:Dimethyl(trifluoromethylthio)arsine 3499:"Severe 2,3,7,8-tetrachlorodibenzo- 2873:10.1146/annurev.pa.22.040182.002505 1309:more than conjugation enzymes, the 368:Key: HGUFODBRKLSHSI-UHFFFAOYAA 268: 252: 4559:Dimethylamidophosphoric dichloride 3437:P. Mocarelli; et al. (2000). 3095:S. Alaluusua; et al. (2004). 2693:Tuomisto, J.; et al. (2005). 2372:10.1093/oxfordjournals.aje.a009069 1078:In Vietnam and the United States, 974:TCDD is the most potent compound ( 25: 5946:Modified low-density lipoproteins 5878:Tooltip Aryl hydrocarbon receptor 4574:Ethylphosphonoselenoic dichloride 4564:Dimethylamidophosphoric dicyanide 2609:Environmental Health Perspectives 2038:Food Additives & Contaminants 1470:Dioxins and dioxin-like compounds 1335:dioxins and dioxin-like compounds 1264:cause a relevant risk to humans: 1068:dioxins and dioxin-like compounds 1061:In 2000, the Expert Group of the 978:) of its series (polychlorinated 90:2,3,7,8-Tetrachlorodibenzodioxine 39:2,3,7,8-Tetrachlorodibenzodioxin 32:Dioxins and dioxin-like compounds 5951:Polycyclic aromatic hydrocarbons 4402:Dicyclohexyl phosphorofluoridate 3845:2,3,7,8-Tetrachlorodibenzodioxin 2711:10.2203/dose-response.003.03.004 1439:In 2004, presidential candidate 890: 576: 571: 566: 561: 422: 416: 62: 53: 44: 5815:List of chemical warfare agents 4033:Dibutylchloromethyltin chloride 2764:10.1016/j.scitotenv.2014.03.022 2582:10.1016/j.annepidem.2011.02.001 2131:Food Additives and Contaminants 1792:Frontiers in Neuroendocrinology 1692:Food Additives and Contaminants 1191:International Journal of Cancer 886:(at 25 °C , 100 kPa). 5923:polychlorinated dibenzodioxins 1381:were exposed to TCDD after an 1012:aryl hydrocarbon (AH) receptor 521:Occupational safety and health 428: 410: 1: 6041:Receptor/signaling modulators 3614:10.1016/s1470-2045(04)01561-x 3571:10.1016/S0140-6736(09)60912-0 3458:10.1016/S0140-6736(00)02290-X 3158:10.1016/S0140-6736(05)77214-7 2861:Annu. Rev. Pharmacol. Toxicol 1327:chlorophenoxy acid herbicides 824:(US health exposure limits): 81:2,3,7,8-Tetrachlorooxanthrene 4886:Trimethylolpropane phosphite 4432:Neopentylene fluorophosphate 3642:. March 2007. Archived from 3367:Synopsis on Dioxins and PCBs 3270:10.1016/0140-6736(91)91898-5 3230:. In Klaassen, C. D. (ed.). 3205:10.1016/0041-008X(78)90075-3 2989:10.1016/0041-008X(92)90103-Y 2537:10.3109/10408444.2011.560141 1623:10.1016/j.envres.2005.12.003 1159:in the absence of estrogen. 1000:persistent organic pollutant 536:persistent organic pollutant 4668:3,3,5-Trimethylcyclohexanol 4528:N,N-Diisopropylaminoethanol 4397:Diisopropyl fluorophosphate 3396:J. Toxicol. Environ. Health 2446:10.1016/j.yrtph.2003.08.002 2411:10.1016/j.yrtph.2005.05.008 1804:10.1016/j.yfrne.2010.07.002 1188:In 2004, an article in the 1162:TCDD was classified by the 990:, an herbicide used in the 982:, known as PCDDs or simply 925:2,3,7,8-Tetrachlorodibenzo- 6094: 5507:Hexamethylene diisocyanate 4975:Phenylcarbylamine chloride 4301:Dimethylcarbamoyl fluoride 3636:"Il triangolo della morte" 1995:Nature Reviews. Immunology 1936:10.2174/138920006778017795 29: 6032: 5862:Aryl hydrocarbon receptor 5810: 5770:Fluoroethyl fluoroacetate 4970:Perchloromethyl mercaptan 4381:4-686-293-01 (Agent 1-10) 3416:10.1080/15287399109531490 3372:27 September 2011 at the 3365:Jouko Tuomisto &al.: 3228:"Chemical carcinogenesis" 2839:"Toxic Substances Portal" 2434:Regul. Toxicol. Pharmacol 2399:Regul. Toxicol. Pharmacol 2007:10.1038/s41577-019-0125-8 1967:10.1002/9781118140574.ch4 1750:10.1007/s00360-005-0483-3 1280:such as cleft palate and 1063:World Health Organization 1018:which is involved in the 880: 818: 542: 518: 513: 397: 377: 342: 105: 87: 75: 70: 61: 52: 43: 6073:IARC Group 1 carcinogens 5482:Chloroacetophenone oxime 5467:Bromomethyl ethyl ketone 5075:Trifluoroacetyl chloride 4985:Tetrachlorodinitroethane 4632:Phosphorus pentachloride 4457:Methanesulfonyl fluoride 3507:Environ. Health Perspect 3352:17 February 2013 at the 3193:Toxicol. Appl. Pharmacol 3101:Environ. Health Perspect 3059:Toxicol. Appl. Pharmacol 3020:Toxicol. Appl. Pharmacol 2977:Toxicol. Appl. Pharmacol 643:Precautionary statements 94:Tetrachlorodibenzodioxin 18:Tetrachlorodibenzodioxin 5766:(variants and mixtures) 5030:Trichloronitrosomethane 5025:Trifluoronitrosomethane 4600:Methyldichlorophosphine 2945:10.1080/026520300283351 2143:10.1080/026520300283360 1704:10.1080/026520300283333 1661:10.1080/026520300283379 1039:polycyclic hydrocarbons 937:polychlorinated dibenzo 5977:Tapinarof (benvitimod) 5565:Cornea-clouding agents 5055:Phosphorus trichloride 4637:Phosphorus trichloride 4371:Miotine (AR-28/T-1843) 3825:Phosphorus trifluoride 3071:10.1006/taap.2001.9216 3032:10.1006/taap.1997.8223 2488:10.1002/mnfr.200600031 2273:10.1186/1476-069X-8-39 2220:10.1002/mnfr.200600006 1847:10.1124/mol.105.018705 1835:Molecular Pharmacology 1366: 1243: 1205:Safety recommendations 778: 534:Potent carcinogen and 5919:aromatic hydrocarbons 4954:Disulfur decafluoride 4755:Chlorophenylsilatrane 4663:2,4,5-Trichlorophenol 3356:(accessed 2013-08-01) 1900:10.1093/toxsci/kfm096 1881:Okey AB (July 2007). 1360: 1272:Developmental effects 1266:developmental effects 1230: 1217:/kg body weight. The 1074:Developmental effects 1014:. This receptor is a 777: 5955:3-methylcholanthrene 5759:Methyl fluoroacetate 5587:Methyl cyanoacrylate 5502:Allyl isothiocyanate 5090:Uranium hexafluoride 5045:Dinitrogen tetroxide 4990:Chlorine trifluoride 4038:Selenium oxychloride 3908:Phenyldichloroarsine 3902:Methyldichloroarsine 3840:Nickel tetracarbonyl 3519:10.1289/ehp.01109865 2252:Environmental Health 2044:(4): 223–240. 2000. 1183:Operation Ranch Hand 1016:transcription factor 760:(fire diamond) 77:Preferred IUPAC name 6024:Cyproterone acetate 5906:Dietary carotenoids 5447:Bromobenzyl cyanide 5215:Dimethylheptylpyran 5143:Diphenylcyanoarsine 5138:Diphenylchlorarsine 5070:Methyl vinyl ketone 4995:Perchloryl fluoride 4859:Bicyclic phosphates 4678:Trimethyl phosphite 4627:Phosphoryl chloride 3896:Ethyldichloroarsine 3870:Chloral cyanohydrin 3860:Acetone cyanohydrin 3830:Methyl cyanoformate 3646:on 15 February 2009 3565:(9696): 1179–1185. 3452:(9218): 1858–1863. 3408:1991JTEHA..32..357M 3322:10.1021/es00003a015 3314:1995EnST...29..677H 3264:(8774): 1027–1032. 2817:The Aspen Institute 2756:2014ScTEn.491....2M 2621:10.1289/ehp.1103720 2264:2009EnvHe...8...39P 1738:J. Comp. Physiol. B 1615:2006ER....101..419S 1548:10.1021/es00171a006 1540:1988EnST...22..651S 1528:Environ Sci Technol 1112:neural tube defects 481:Solubility in water 446: g·mol 96:Tetrachlorodibenzo- 40: 5820:CB military symbol 5678:Enterotoxin type B 5633:Cyclopiazonic acid 5592:N-Methylmorpholine 5487:Ethyl bromoacetate 4965:Ethyl bromoacetate 4932:Perfluoroisobutene 4673:Triethyl phosphite 3944:Levinstein mustard 3835:Iron pentacarbonyl 3191:-dioxin in rats". 2933:Food Addit. Contam 2525:Crit. Rev. Toxicol 2098:10.1093/ije/dyl038 1649:Food Addit. Contam 1383:accidental release 1367: 1057:Toxicity in humans 913:Infobox references 859:(Immediate danger) 779: 38: 6050: 6049: 6014:7-Ketocholesterol 5828: 5827: 5638:Histrionicotoxins 5616:Biological toxins 5492:Ethyl iodoacetate 5060:Methyl isocyanate 5020:Selenoyl fluoride 5010:Mercuric chloride 4980:Tetranitromethane 4834:Sulfuryl fluoride 4819:HN3 hydrochloride 4814:HN2 hydrochloride 4809:HN1 hydrochloride 4696: 4695: 4653:Phenacyl chloride 4648:Pinacolyl alcohol 4594:Isopropyl alcohol 4589:4-Hydroxycoumarin 4523:1,8-Dibromooctane 4046: 4045: 3970:Nitrogen mustards 3783:Cyanogen chloride 3674:. 31 August 2004. 3241:978-0-07-134721-1 3107:(13): 1313–1318. 2671:10.1002/ijc.11635 2615:(12): 1700–1705. 2476:Mol Nutr Food Res 2365:(12): 1061–1075. 2321:978-92-832-1269-0 2208:Mol Nutr Food Res 2050:10.1080/713810655 1475:Toxic Equivalency 1457:Triangle of Death 1441:Viktor Yushchenko 1396:myeloid leukaemia 1363:Viktor Yushchenko 1353:Cases of exposure 1307:oxidative enzymes 1246:Animal toxicology 1224:According to the 969:organic synthesis 921:Chemical compound 919: 918: 869:Safety data sheet 601:Hazard statements 311:CompTox Dashboard 147:Interactive image 16:(Redirected from 6085: 5971:β-naphthoflavone 5900:prostaglandin G2 5889:Arachidonic acid 5879: 5875: 5855: 5848: 5841: 5832: 5802:White phosphorus 5779:post-combustion 5775:Depleted uranium 5602:Osmium tetroxide 5477:Phenacyl bromide 5040:Nitrogen dioxide 5015:Selenium dioxide 5005:Cadmium chloride 4462:Dimefox (TL-792) 4057: 3885: 3810:Hydrogen sulfide 3789:Hydrogen cyanide 3778:Cyanogen bromide 3744:chemical warfare 3733: 3726: 3719: 3710: 3676: 3675: 3662: 3656: 3655: 3653: 3651: 3632: 3626: 3625: 3597: 3591: 3590: 3550: 3541: 3540: 3530: 3494: 3488: 3487: 3469: 3443: 3434: 3428: 3427: 3387: 3381: 3363: 3357: 3340: 3334: 3333: 3296: 3290: 3289: 3256:chlorophenols". 3252: 3246: 3245: 3223: 3217: 3216: 3184: 3178: 3177: 3141: 3135: 3134: 3124: 3113:10.1289/ehp.6920 3092: 3083: 3082: 3050: 3044: 3043: 3007: 3001: 3000: 2971: 2965: 2964: 2928: 2919: 2918: 2898: 2885: 2884: 2852: 2846: 2845: 2843: 2835: 2829: 2828: 2826: 2824: 2813:"Health Effects" 2809: 2803: 2802: 2800: 2798: 2782: 2776: 2775: 2739: 2733: 2732: 2722: 2690: 2684: 2683: 2673: 2649: 2643: 2642: 2632: 2600: 2594: 2593: 2565: 2559: 2558: 2548: 2516: 2510: 2509: 2499: 2467: 2458: 2457: 2429: 2423: 2422: 2394: 2385: 2384: 2374: 2349: 2343: 2342: 2332: 2326: 2325: 2305: 2296: 2295: 2285: 2275: 2243: 2232: 2231: 2203: 2197: 2196: 2187:(24): 6911–620. 2172: 2163: 2162: 2126: 2111: 2110: 2100: 2091:(5): 1220–1230. 2076: 2070: 2069: 2033: 2027: 2026: 1990: 1981: 1980: 1954: 1948: 1947: 1924:Curr. Drug Metab 1919: 1913: 1912: 1902: 1878: 1867: 1866: 1830: 1824: 1823: 1787: 1770: 1769: 1733: 1724: 1723: 1687: 1681: 1680: 1644: 1635: 1634: 1598: 1589: 1583: 1560: 1559: 1519: 1513: 1512: 1500: 1392:multiple myeloma 1361:A photograph of 1148:oxidative stress 1032:enzyme induction 945:chemical formula 903: 897: 894: 893: 799: 792: 785: 770: 750: 746: 742: 738: 734: 730: 726: 722: 718: 714: 710: 706: 702: 698: 694: 690: 686: 682: 678: 674: 670: 666: 662: 658: 654: 650: 636: 632: 628: 624: 620: 616: 612: 608: 580: 575: 570: 565: 445: 430: 424: 418: 412: 405:Chemical formula 335: 334: 319: 317: 301: 281: 270: 256: 239: 228: 217: 197: 177: 149: 125: 66: 57: 48: 41: 21: 6093: 6092: 6088: 6087: 6086: 6084: 6083: 6082: 6053: 6052: 6051: 6046: 6028: 5963:benzanthracenes 5877: 5867: 5859: 5829: 5824: 5806: 5747: 5658:Botulinum toxin 5611: 5560: 5521: 5432:Benzyl chloride 5387: 5380: 5164: 5157: 5148:Cacodyl cyanide 5110:Vomiting agents 5104: 4902: 4895: 4804:Dimethylmercury 4726:Botulinum toxin 4692: 4471: 4385: 4287: 4240:Novichok agents 4234: 4218: 4145: 4042: 4016: 3997: 3964: 3936:Sulfur mustards 3930: 3874: 3820:Carbon monoxide 3800:Cacodyl cyanide 3759: 3758: 3742:Agents used in 3737: 3694:Dioxin synopsis 3685: 3680: 3679: 3664: 3663: 3659: 3649: 3647: 3634: 3633: 3629: 3599: 3598: 3594: 3552: 3551: 3544: 3496: 3495: 3491: 3441: 3436: 3435: 3431: 3389: 3388: 3384: 3374:Wayback Machine 3364: 3360: 3354:Wayback Machine 3341: 3337: 3298: 3297: 3293: 3254: 3253: 3249: 3242: 3225: 3224: 3220: 3186: 3185: 3181: 3143: 3142: 3138: 3094: 3093: 3086: 3052: 3051: 3047: 3009: 3008: 3004: 2973: 2972: 2968: 2930: 2929: 2922: 2900: 2899: 2888: 2854: 2853: 2849: 2841: 2837: 2836: 2832: 2822: 2820: 2811: 2810: 2806: 2796: 2794: 2784: 2783: 2779: 2741: 2740: 2736: 2692: 2691: 2687: 2651: 2650: 2646: 2602: 2601: 2597: 2567: 2566: 2562: 2518: 2517: 2513: 2482:(10): 934–944. 2469: 2468: 2461: 2431: 2430: 2426: 2396: 2395: 2388: 2351: 2350: 2346: 2334: 2333: 2329: 2322: 2307: 2306: 2299: 2245: 2244: 2235: 2214:(10): 897–907. 2205: 2204: 2200: 2174: 2173: 2166: 2128: 2127: 2114: 2078: 2077: 2073: 2035: 2034: 2030: 1992: 1991: 1984: 1977: 1956: 1955: 1951: 1921: 1920: 1916: 1880: 1879: 1870: 1832: 1831: 1827: 1789: 1788: 1773: 1735: 1734: 1727: 1689: 1688: 1684: 1646: 1645: 1638: 1600: 1599: 1592: 1584: 1563: 1521: 1520: 1516: 1502: 1501: 1488: 1483: 1466: 1355: 1319: 1290: 1274: 1248: 1226:Aspen Institute 1207: 1153:anti-estrogenic 1136: 1120:Seveso accident 1076: 1059: 1008: 996:Seveso disaster 962: 958: 954: 950: 922: 915: 910: 909: 908:  ?) 899: 895: 891: 887: 860: 847: 834: 804: 803: 802: 801: 794: 787: 780: 776: 768: 645: 603: 589: 558: 531: 483: 443: 433: 427: 421: 415: 407: 393: 390: 385: 384: 373: 370: 369: 366: 360: 359: 356: 350: 349: 338: 320: 313: 304: 284: 271: 259: 220: 200: 180: 152: 139: 128: 115: 101: 95: 93: 91: 83: 82: 34: 28: 23: 22: 15: 12: 11: 5: 6091: 6089: 6081: 6080: 6075: 6070: 6068:Dibenzodioxins 6065: 6055: 6054: 6048: 6047: 6045: 6044: 6037: 6033: 6030: 6029: 6027: 6026: 6021: 6016: 6007: 6006: 5989: 5979: 5974: 5948: 5943: 5938: 5913: 5908: 5903: 5882: 5880: 5869: 5868: 5860: 5858: 5857: 5850: 5843: 5835: 5826: 5825: 5823: 5822: 5817: 5811: 5808: 5807: 5805: 5804: 5799: 5794: 5785: 5784: 5783: 5781:uranium oxides 5772: 5767: 5761: 5755: 5753: 5749: 5748: 5746: 5745: 5740: 5735: 5730: 5725: 5720: 5715: 5710: 5705: 5700: 5695: 5690: 5685: 5680: 5675: 5670: 5665: 5660: 5655: 5650: 5645: 5640: 5635: 5630: 5625: 5619: 5617: 5613: 5612: 5610: 5609: 5604: 5599: 5594: 5589: 5584: 5579: 5574: 5568: 5566: 5562: 5561: 5559: 5558: 5553: 5548: 5543: 5538: 5532: 5530: 5523: 5522: 5520: 5519: 5514: 5512:Crotonaldehyde 5509: 5504: 5499: 5494: 5489: 5484: 5479: 5474: 5469: 5464: 5459: 5454: 5449: 5444: 5439: 5437:Benzyl bromide 5434: 5429: 5424: 5419: 5414: 5409: 5404: 5398: 5392: 5390: 5382: 5381: 5379: 5378: 5376:Chlorpromazine 5373: 5368: 5363: 5358: 5353: 5348: 5343: 5338: 5333: 5328: 5323: 5318: 5313: 5308: 5303: 5298: 5293: 5288: 5283: 5278: 5273: 5268: 5263: 5258: 5253: 5248: 5243: 5238: 5233: 5228: 5223: 5218: 5212: 5207: 5202: 5197: 5192: 5186: 5181: 5176: 5169: 5167: 5163:Incapacitating 5159: 5158: 5156: 5155: 5150: 5145: 5140: 5135: 5126: 5121: 5114: 5112: 5106: 5105: 5103: 5102: 5097: 5092: 5087: 5082: 5077: 5072: 5067: 5062: 5057: 5052: 5050:Sulfur dioxide 5047: 5042: 5037: 5032: 5027: 5022: 5017: 5012: 5007: 5002: 4997: 4992: 4987: 4982: 4977: 4972: 4967: 4962: 4957: 4951: 4945: 4940: 4934: 4929: 4924: 4918: 4913: 4907: 4905: 4903:choking agents 4897: 4896: 4894: 4893: 4888: 4883: 4878: 4877: 4876: 4871: 4866: 4856: 4851: 4846: 4841: 4836: 4831: 4826: 4821: 4816: 4811: 4806: 4801: 4799:Tetraethyllead 4796: 4790: 4785: 4779: 4774: 4769: 4763: 4757: 4752: 4746: 4740: 4735: 4729: 4723: 4718: 4712: 4706: 4704: 4698: 4697: 4694: 4693: 4691: 4690: 4685: 4680: 4675: 4670: 4665: 4660: 4655: 4650: 4645: 4640: 4634: 4629: 4624: 4619: 4614: 4609: 4603: 4597: 4591: 4586: 4581: 4576: 4571: 4566: 4561: 4556: 4551: 4546: 4541: 4536: 4531: 4525: 4520: 4515: 4510: 4505: 4503:A.P.C. complex 4500: 4495: 4490: 4485: 4479: 4477: 4473: 4472: 4470: 4469: 4464: 4459: 4454: 4449: 4444: 4439: 4434: 4429: 4424: 4419: 4414: 4409: 4404: 4399: 4393: 4391: 4387: 4386: 4384: 4383: 4378: 4373: 4368: 4363: 4358: 4353: 4348: 4343: 4338: 4333: 4328: 4323: 4318: 4313: 4308: 4303: 4297: 4295: 4289: 4288: 4286: 4285: 4280: 4275: 4270: 4265: 4260: 4255: 4250: 4244: 4242: 4236: 4235: 4233: 4232: 4226: 4224: 4220: 4219: 4217: 4216: 4214:V-sub x (GD-7) 4211: 4206: 4201: 4196: 4191: 4186: 4181: 4176: 4171: 4166: 4161: 4155: 4153: 4147: 4146: 4144: 4143: 4138: 4133: 4128: 4123: 4118: 4112: 4107: 4101: 4095: 4089: 4083: 4077: 4072: 4065: 4063: 4054: 4048: 4047: 4044: 4043: 4041: 4040: 4035: 4030: 4024: 4022: 4018: 4017: 4015: 4014: 4011:Phosgene oxime 4007: 4005: 3999: 3998: 3996: 3995: 3990: 3985: 3980: 3974: 3972: 3966: 3965: 3963: 3962: 3957: 3952: 3947: 3940: 3938: 3932: 3931: 3929: 3923: 3917: 3911: 3905: 3899: 3893: 3891: 3882: 3880:Blister agents 3876: 3875: 3873: 3872: 3867: 3862: 3857: 3852: 3850:Glycolonitrile 3847: 3842: 3837: 3832: 3827: 3822: 3817: 3812: 3807: 3802: 3797: 3792: 3786: 3780: 3775: 3769: 3767: 3761: 3760: 3757: 3756: 3751: 3749:incapacitation 3746: 3739: 3738: 3736: 3735: 3728: 3721: 3713: 3707: 3706: 3701: 3696: 3691: 3684: 3683:External links 3681: 3678: 3677: 3657: 3627: 3608:(9): 525–527. 3592: 3542: 3513:(8): 865–869. 3489: 3429: 3402:(4): 357–366. 3382: 3358: 3335: 3308:(3): 677–684. 3291: 3247: 3240: 3218: 3199:(2): 279–303. 3179: 3136: 3084: 3065:(3): 216–224. 3045: 3002: 2983:(1): 118–126. 2966: 2939:(4): 275–288. 2920: 2909:(4): 483–549. 2903:Pharmacol. Rev 2886: 2867:(1): 517–554. 2847: 2830: 2804: 2777: 2734: 2705:(3): 332–341. 2685: 2664:(6): 893–900. 2658:Int. J. Cancer 2644: 2595: 2576:(9): 673–687. 2560: 2531:(7): 622–636. 2511: 2459: 2440:(3): 378–388. 2424: 2386: 2359:Am J Epidemiol 2344: 2327: 2320: 2297: 2233: 2198: 2164: 2137:(4): 289–302. 2112: 2071: 2028: 2001:(3): 184–197. 1982: 1975: 1949: 1914: 1868: 1841:(1): 140–153. 1825: 1798:(4): 452–478. 1771: 1725: 1682: 1655:(4): 303–316. 1636: 1590: 1561: 1534:(6): 651–658. 1514: 1485: 1484: 1482: 1479: 1478: 1477: 1472: 1465: 1462: 1461: 1460: 1453: 1437: 1426: 1399: 1354: 1351: 1318: 1315: 1302:benzo(a)pyrene 1289: 1286: 1282:hydronephrosis 1278:teratogenicity 1273: 1270: 1247: 1244: 1206: 1203: 1135: 1132: 1075: 1072: 1058: 1055: 1043:benzo(a)pyrene 1007: 1004: 980:dibenzodioxins 960: 956: 952: 948: 920: 917: 916: 911: 889: 888: 884:standard state 881: 878: 877: 872: 865: 864: 861: 855: 852: 851: 848: 842: 839: 838: 835: 829: 826: 825: 816: 815: 812: 806: 805: 795: 788: 781: 766: 765: 764: 763: 761: 752: 751: 709:P304+P340+P312 705:P303+P361+P353 646: 641: 638: 637: 604: 599: 596: 595: 590: 585: 582: 581: 559: 554: 551: 550: 540: 539: 532: 529: 526: 525: 516: 515: 511: 510: 509:1.5 × 10 mmHg 507: 505:Vapor pressure 501: 500: 497: 488: 487: 484: 479: 476: 475: 472: 466: 465: 462: 456: 455: 452: 448: 447: 441: 435: 434: 431: 425: 419: 413: 408: 403: 400: 399: 395: 394: 392: 391: 388: 380: 379: 378: 375: 374: 372: 371: 367: 364: 363: 361: 357: 354: 353: 345: 344: 343: 340: 339: 337: 336: 323: 321: 309: 306: 305: 303: 302: 294: 292: 286: 285: 283: 282: 274: 272: 264: 261: 260: 258: 257: 249: 247: 241: 240: 230: 222: 221: 219: 218: 210: 208: 202: 201: 199: 198: 190: 188: 182: 181: 179: 178: 170: 168: 162: 161: 158: 157:Abbreviations 154: 153: 151: 150: 142: 140: 133: 130: 129: 127: 126: 118: 116: 111: 108: 107: 103: 102: 89: 85: 84: 80: 79: 73: 72: 68: 67: 59: 58: 50: 49: 26: 24: 14: 13: 10: 9: 6: 4: 3: 2: 6090: 6079: 6076: 6074: 6071: 6069: 6066: 6064: 6061: 6060: 6058: 6043: 6042: 6038: 6035: 6034: 6031: 6025: 6022: 6020: 6017: 6015: 6012: 6009: 6008: 6004: 6000: 5996: 5993: 5990: 5987: 5983: 5980: 5978: 5975: 5972: 5968: 5967:benzoflavones 5964: 5960: 5956: 5952: 5949: 5947: 5944: 5942: 5939: 5936: 5932: 5931:dibenzofurans 5928: 5924: 5920: 5917: 5914: 5912: 5909: 5907: 5904: 5901: 5897: 5893: 5890: 5887: 5884: 5883: 5881: 5876: 5870: 5866: 5863: 5856: 5851: 5849: 5844: 5842: 5837: 5836: 5833: 5821: 5818: 5816: 5813: 5812: 5809: 5803: 5800: 5798: 5795: 5793: 5792:its compounds 5789: 5786: 5782: 5778: 5777: 5776: 5773: 5771: 5768: 5765: 5762: 5760: 5757: 5756: 5754: 5750: 5744: 5741: 5739: 5736: 5734: 5731: 5729: 5728:Tetanospasmin 5726: 5724: 5723:T-2 mycotoxin 5721: 5719: 5716: 5714: 5711: 5709: 5706: 5704: 5701: 5699: 5696: 5694: 5691: 5689: 5686: 5684: 5681: 5679: 5676: 5674: 5671: 5669: 5666: 5664: 5661: 5659: 5656: 5654: 5653:Batrachotoxin 5651: 5649: 5646: 5644: 5641: 5639: 5636: 5634: 5631: 5629: 5626: 5624: 5621: 5620: 5618: 5614: 5608: 5605: 5603: 5600: 5598: 5597:Allyl alcohol 5595: 5593: 5590: 5588: 5585: 5583: 5580: 5578: 5575: 5573: 5570: 5569: 5567: 5563: 5557: 5554: 5552: 5549: 5547: 5544: 5542: 5539: 5537: 5534: 5533: 5531: 5528: 5524: 5518: 5515: 5513: 5510: 5508: 5505: 5503: 5500: 5498: 5495: 5493: 5490: 5488: 5485: 5483: 5480: 5478: 5475: 5473: 5470: 5468: 5465: 5463: 5460: 5458: 5457:Chloroacetone 5455: 5453: 5450: 5448: 5445: 5443: 5442:Benzyl iodide 5440: 5438: 5435: 5433: 5430: 5428: 5425: 5423: 5420: 5418: 5415: 5413: 5410: 5408: 5405: 5402: 5399: 5397: 5396:Xylyl bromide 5394: 5393: 5391: 5389: 5383: 5377: 5374: 5372: 5369: 5367: 5364: 5362: 5359: 5357: 5354: 5352: 5349: 5347: 5344: 5342: 5339: 5337: 5334: 5332: 5329: 5327: 5324: 5322: 5319: 5317: 5314: 5312: 5309: 5307: 5304: 5302: 5299: 5297: 5294: 5292: 5289: 5287: 5284: 5282: 5279: 5277: 5274: 5272: 5269: 5267: 5264: 5262: 5259: 5257: 5254: 5252: 5249: 5247: 5244: 5242: 5239: 5237: 5234: 5232: 5229: 5227: 5224: 5222: 5219: 5216: 5213: 5211: 5208: 5206: 5203: 5201: 5198: 5196: 5193: 5190: 5187: 5185: 5184:Butyrophenone 5182: 5180: 5177: 5174: 5171: 5170: 5168: 5166: 5160: 5154: 5153:o-Dianisidine 5151: 5149: 5146: 5144: 5141: 5139: 5136: 5134: 5130: 5127: 5125: 5122: 5119: 5116: 5115: 5113: 5111: 5107: 5101: 5098: 5096: 5093: 5091: 5088: 5086: 5083: 5081: 5078: 5076: 5073: 5071: 5068: 5066: 5063: 5061: 5058: 5056: 5053: 5051: 5048: 5046: 5043: 5041: 5038: 5036: 5033: 5031: 5028: 5026: 5023: 5021: 5018: 5016: 5013: 5011: 5008: 5006: 5003: 5001: 5000:Cadmium oxide 4998: 4996: 4993: 4991: 4988: 4986: 4983: 4981: 4978: 4976: 4973: 4971: 4968: 4966: 4963: 4961: 4958: 4955: 4952: 4949: 4946: 4944: 4941: 4938: 4935: 4933: 4930: 4928: 4925: 4922: 4919: 4917: 4914: 4912: 4909: 4908: 4906: 4904: 4898: 4892: 4889: 4887: 4884: 4882: 4879: 4875: 4872: 4870: 4867: 4865: 4862: 4861: 4860: 4857: 4855: 4852: 4850: 4849:Batrachotoxin 4847: 4845: 4842: 4840: 4837: 4835: 4832: 4830: 4827: 4825: 4822: 4820: 4817: 4815: 4812: 4810: 4807: 4805: 4802: 4800: 4797: 4794: 4791: 4789: 4786: 4783: 4780: 4778: 4775: 4773: 4770: 4767: 4764: 4761: 4758: 4756: 4753: 4750: 4747: 4744: 4741: 4739: 4736: 4733: 4732:Tetanospasmin 4730: 4727: 4724: 4722: 4719: 4716: 4713: 4711: 4708: 4707: 4705: 4703: 4699: 4689: 4686: 4684: 4681: 4679: 4676: 4674: 4671: 4669: 4666: 4664: 4661: 4659: 4656: 4654: 4651: 4649: 4646: 4644: 4641: 4638: 4635: 4633: 4630: 4628: 4625: 4623: 4620: 4618: 4615: 4613: 4610: 4607: 4604: 4601: 4598: 4595: 4592: 4590: 4587: 4585: 4582: 4580: 4577: 4575: 4572: 4570: 4567: 4565: 4562: 4560: 4557: 4555: 4552: 4550: 4547: 4545: 4542: 4540: 4537: 4535: 4532: 4529: 4526: 4524: 4521: 4519: 4516: 4514: 4511: 4509: 4506: 4504: 4501: 4499: 4496: 4494: 4491: 4489: 4486: 4484: 4481: 4480: 4478: 4474: 4468: 4465: 4463: 4460: 4458: 4455: 4453: 4450: 4448: 4445: 4443: 4440: 4438: 4435: 4433: 4430: 4428: 4425: 4423: 4420: 4418: 4415: 4413: 4410: 4408: 4405: 4403: 4400: 4398: 4395: 4394: 4392: 4388: 4382: 4379: 4377: 4374: 4372: 4369: 4367: 4364: 4362: 4359: 4357: 4354: 4352: 4349: 4347: 4344: 4342: 4339: 4337: 4334: 4332: 4329: 4327: 4324: 4322: 4319: 4317: 4314: 4312: 4309: 4307: 4304: 4302: 4299: 4298: 4296: 4294: 4290: 4284: 4281: 4279: 4276: 4274: 4271: 4269: 4266: 4264: 4261: 4259: 4256: 4254: 4251: 4249: 4246: 4245: 4243: 4241: 4237: 4231: 4228: 4227: 4225: 4221: 4215: 4212: 4210: 4207: 4205: 4202: 4200: 4197: 4195: 4192: 4190: 4187: 4185: 4182: 4180: 4177: 4175: 4172: 4170: 4167: 4165: 4162: 4160: 4157: 4156: 4154: 4152: 4148: 4142: 4139: 4137: 4134: 4132: 4129: 4127: 4124: 4122: 4119: 4116: 4113: 4111: 4108: 4105: 4102: 4099: 4096: 4093: 4090: 4087: 4084: 4081: 4078: 4076: 4073: 4070: 4067: 4066: 4064: 4062: 4058: 4055: 4053: 4049: 4039: 4036: 4034: 4031: 4029: 4026: 4025: 4023: 4019: 4012: 4009: 4008: 4006: 4004: 4003:Nettle agents 4000: 3994: 3991: 3989: 3986: 3984: 3981: 3979: 3976: 3975: 3973: 3971: 3967: 3961: 3958: 3956: 3953: 3951: 3948: 3945: 3942: 3941: 3939: 3937: 3933: 3927: 3924: 3921: 3918: 3915: 3912: 3909: 3906: 3903: 3900: 3897: 3894: 3892: 3890: 3886: 3883: 3881: 3877: 3871: 3868: 3866: 3863: 3861: 3858: 3856: 3853: 3851: 3848: 3846: 3843: 3841: 3838: 3836: 3833: 3831: 3828: 3826: 3823: 3821: 3818: 3816: 3813: 3811: 3808: 3806: 3805:Cacodyl oxide 3803: 3801: 3798: 3796: 3793: 3790: 3787: 3784: 3781: 3779: 3776: 3774: 3771: 3770: 3768: 3766: 3762: 3755: 3752: 3750: 3747: 3745: 3741: 3740: 3734: 3729: 3727: 3722: 3720: 3715: 3714: 3711: 3705: 3702: 3700: 3697: 3695: 3692: 3690: 3687: 3686: 3682: 3673: 3672: 3671:la Repubblica 3667: 3661: 3658: 3645: 3641: 3637: 3631: 3628: 3623: 3619: 3615: 3611: 3607: 3603: 3596: 3593: 3588: 3584: 3580: 3576: 3572: 3568: 3564: 3560: 3556: 3549: 3547: 3543: 3538: 3534: 3529: 3524: 3520: 3516: 3512: 3508: 3504: 3502: 3493: 3490: 3485: 3481: 3477: 3473: 3468: 3463: 3459: 3455: 3451: 3447: 3440: 3433: 3430: 3425: 3421: 3417: 3413: 3409: 3405: 3401: 3397: 3393: 3386: 3383: 3379: 3375: 3371: 3368: 3362: 3359: 3355: 3351: 3348: 3344: 3339: 3336: 3331: 3327: 3323: 3319: 3315: 3311: 3307: 3303: 3295: 3292: 3287: 3283: 3279: 3275: 3271: 3267: 3263: 3259: 3251: 3248: 3243: 3237: 3233: 3229: 3222: 3219: 3214: 3210: 3206: 3202: 3198: 3194: 3190: 3183: 3180: 3175: 3171: 3167: 3163: 3159: 3155: 3152:(9148): 206. 3151: 3147: 3140: 3137: 3132: 3128: 3123: 3118: 3114: 3110: 3106: 3102: 3098: 3091: 3089: 3085: 3080: 3076: 3072: 3068: 3064: 3060: 3056: 3049: 3046: 3041: 3037: 3033: 3029: 3025: 3021: 3017: 3015: 3006: 3003: 2998: 2994: 2990: 2986: 2982: 2978: 2970: 2967: 2962: 2958: 2954: 2950: 2946: 2942: 2938: 2934: 2927: 2925: 2921: 2916: 2912: 2908: 2904: 2897: 2895: 2893: 2891: 2887: 2882: 2878: 2874: 2870: 2866: 2862: 2858: 2851: 2848: 2840: 2834: 2831: 2819:. August 2011 2818: 2814: 2808: 2805: 2792: 2791:cfpub.epa.gov 2788: 2785:Rice, Glenn. 2781: 2778: 2773: 2769: 2765: 2761: 2757: 2753: 2749: 2745: 2738: 2735: 2730: 2726: 2721: 2716: 2712: 2708: 2704: 2700: 2699:Dose-Response 2696: 2689: 2686: 2681: 2677: 2672: 2667: 2663: 2659: 2655: 2648: 2645: 2640: 2636: 2631: 2626: 2622: 2618: 2614: 2610: 2606: 2599: 2596: 2591: 2587: 2583: 2579: 2575: 2571: 2570:Ann Epidemiol 2564: 2561: 2556: 2552: 2547: 2542: 2538: 2534: 2530: 2526: 2522: 2515: 2512: 2507: 2503: 2498: 2493: 2489: 2485: 2481: 2477: 2473: 2466: 2464: 2460: 2455: 2451: 2447: 2443: 2439: 2435: 2428: 2425: 2420: 2416: 2412: 2408: 2404: 2400: 2393: 2391: 2387: 2382: 2378: 2373: 2368: 2364: 2360: 2356: 2348: 2345: 2340: 2339: 2331: 2328: 2323: 2317: 2313: 2312: 2304: 2302: 2298: 2293: 2289: 2284: 2279: 2274: 2269: 2265: 2261: 2257: 2253: 2249: 2242: 2240: 2238: 2234: 2229: 2225: 2221: 2217: 2213: 2209: 2202: 2199: 2194: 2190: 2186: 2182: 2178: 2171: 2169: 2165: 2160: 2156: 2152: 2148: 2144: 2140: 2136: 2132: 2125: 2123: 2121: 2119: 2117: 2113: 2108: 2104: 2099: 2094: 2090: 2086: 2082: 2075: 2072: 2067: 2063: 2059: 2055: 2051: 2047: 2043: 2039: 2032: 2029: 2024: 2020: 2016: 2012: 2008: 2004: 2000: 1996: 1989: 1987: 1983: 1978: 1976:9781118140574 1972: 1968: 1964: 1960: 1953: 1950: 1945: 1941: 1937: 1933: 1930:(6): 661–75. 1929: 1925: 1918: 1915: 1910: 1906: 1901: 1896: 1892: 1888: 1884: 1877: 1875: 1873: 1869: 1864: 1860: 1856: 1852: 1848: 1844: 1840: 1836: 1829: 1826: 1821: 1817: 1813: 1809: 1805: 1801: 1797: 1793: 1786: 1784: 1782: 1780: 1778: 1776: 1772: 1767: 1763: 1759: 1755: 1751: 1747: 1744:(4): 221–30. 1743: 1739: 1732: 1730: 1726: 1721: 1717: 1713: 1709: 1705: 1701: 1697: 1693: 1686: 1683: 1678: 1674: 1670: 1666: 1662: 1658: 1654: 1650: 1643: 1641: 1637: 1632: 1628: 1624: 1620: 1616: 1612: 1609:(3): 419–28. 1608: 1604: 1597: 1595: 1591: 1588: 1582: 1580: 1578: 1576: 1574: 1572: 1570: 1568: 1566: 1562: 1557: 1553: 1549: 1545: 1541: 1537: 1533: 1529: 1525: 1518: 1515: 1510: 1506: 1499: 1497: 1495: 1493: 1491: 1487: 1480: 1476: 1473: 1471: 1468: 1467: 1463: 1458: 1454: 1451: 1446: 1442: 1438: 1435: 1431: 1427: 1424: 1423:United States 1420: 1416: 1412: 1408: 1404: 1400: 1397: 1393: 1389: 1384: 1380: 1376: 1372: 1371: 1370: 1364: 1359: 1352: 1350: 1348: 1344: 1338: 1336: 1332: 1328: 1324: 1323:chlorophenols 1316: 1314: 1312: 1308: 1303: 1298: 1296: 1287: 1285: 1283: 1279: 1271: 1269: 1267: 1262: 1257: 1253: 1245: 1242: 1239: 1235: 1229: 1227: 1222: 1220: 1216: 1212: 1204: 1202: 1200: 1199: 1198:Dose-Response 1193: 1192: 1186: 1184: 1179: 1178: 1173: 1169: 1165: 1160: 1158: 1154: 1149: 1145: 1141: 1133: 1131: 1129: 1125: 1121: 1117: 1113: 1109: 1105: 1101: 1100:meta-analysis 1097: 1093: 1089: 1085: 1084:birth defects 1081: 1073: 1071: 1069: 1064: 1056: 1054: 1050: 1046: 1044: 1040: 1037: 1033: 1029: 1025: 1021: 1017: 1013: 1005: 1003: 1001: 997: 993: 989: 985: 981: 977: 972: 970: 966: 946: 942: 940: 934: 930: 928: 914: 907: 902: 885: 879: 876: 873: 870: 867: 866: 862: 858: 854: 853: 849: 846:(Recommended) 845: 841: 840: 836: 833:(Permissible) 832: 828: 827: 823: 822: 817: 813: 811: 808: 807: 800: 793: 786: 762: 759: 758: 754: 753: 647: 644: 640: 639: 605: 602: 598: 597: 594: 591: 588: 584: 583: 579: 574: 569: 564: 560: 557: 553: 552: 548: 546: 541: 537: 533: 528: 527: 523: 522: 517: 512: 508: 506: 503: 502: 498: 496: 495: 490: 489: 485: 482: 478: 477: 473: 471: 470:Melting point 468: 467: 463: 461: 458: 457: 453: 450: 449: 442: 440: 437: 436: 409: 406: 402: 401: 396: 387: 383: 376: 362: 352: 348: 341: 333: 329: 328:DTXSID2021315 325: 324: 322: 312: 308: 307: 300: 296: 295: 293: 291: 288: 287: 280: 276: 275: 273: 267: 263: 262: 255: 251: 250: 248: 246: 243: 242: 238: 234: 231: 229: 227:ECHA InfoCard 224: 223: 216: 212: 211: 209: 207: 204: 203: 196: 192: 191: 189: 187: 184: 183: 176: 172: 171: 169: 167: 164: 163: 159: 156: 155: 148: 144: 143: 141: 137: 132: 131: 124: 120: 119: 117: 114: 110: 109: 104: 99: 86: 78: 74: 69: 65: 60: 56: 51: 47: 42: 36: 33: 19: 6078:Blood agents 6063:Chloroarenes 6039: 6011:Antagonists: 6010: 5982:Tetrapyroles 5926: 5885: 5733:Tetrodotoxin 5683:Grayanotoxin 5462:Bromoacetone 5452:Thiophosgene 5407:Mace (spray) 5401:Pepper spray 5386:Lachrymatory 5371:Fluphenazine 5366:Procarbazine 5276:Sleeping gas 5124:Chloropicrin 5035:Nitric oxide 4937:Chloropicrin 4881:Cloflubicyne 4844:Oxotremorine 4793:Antillatoxin 4772:Tetrodotoxin 4721:Bungarotoxin 4617:Nitromethane 4579:Formaldoxime 4518:Cyclohexanol 4483:Acetonitrile 4230:GV (EA-5365) 4052:Nerve agents 3855:Lactonitrile 3844: 3765:Blood agents 3754:riot control 3669: 3660: 3650:25 September 3648:. Retrieved 3644:the original 3639: 3630: 3605: 3602:Lancet Oncol 3601: 3595: 3562: 3558: 3554: 3510: 3506: 3500: 3492: 3449: 3445: 3432: 3399: 3395: 3391: 3385: 3361: 3338: 3305: 3301: 3294: 3261: 3257: 3250: 3231: 3221: 3196: 3192: 3188: 3182: 3149: 3145: 3139: 3104: 3100: 3062: 3058: 3054: 3048: 3026:(1): 11–20. 3023: 3019: 3013: 3005: 2980: 2976: 2969: 2936: 2932: 2906: 2902: 2864: 2860: 2856: 2850: 2833: 2823:23 September 2821:. Retrieved 2816: 2807: 2795:. Retrieved 2790: 2780: 2747: 2743: 2737: 2702: 2698: 2688: 2661: 2657: 2647: 2612: 2608: 2598: 2573: 2569: 2563: 2528: 2524: 2514: 2479: 2475: 2437: 2433: 2427: 2405:(1): 19–34. 2402: 2398: 2362: 2358: 2347: 2337: 2330: 2310: 2255: 2251: 2211: 2207: 2201: 2184: 2180: 2176: 2134: 2130: 2088: 2084: 2074: 2041: 2037: 2031: 1998: 1994: 1958: 1952: 1927: 1923: 1917: 1890: 1887:Toxicol. Sci 1886: 1838: 1834: 1828: 1795: 1791: 1741: 1737: 1698:(4): 261–6. 1695: 1691: 1685: 1652: 1648: 1606: 1603:Environ. Res 1602: 1531: 1527: 1523: 1517: 1368: 1339: 1320: 1299: 1291: 1275: 1268:and cancer. 1249: 1231: 1223: 1208: 1196: 1189: 1187: 1175: 1170:for humans ( 1166:(IARC) as a 1161: 1137: 1116:spina bifida 1108:cleft palate 1088:Agent Orange 1077: 1060: 1051: 1047: 1036:carcinogenic 1009: 988:Agent Orange 973: 938: 932: 926: 924: 923: 820: 756: 592: 544: 530:Main hazards 519: 493: 160:TCDD; TCDBD 106:Identifiers 97: 88:Other names 35: 5995:derivatives 5959:benzopyrene 5916:Halogenated 5892:metabolites 5743:Veratridine 5718:Shiga toxin 5673:Domoic acid 5536:Thioacetone 5497:Iodoacetone 5361:Pentazocine 5356:Sevoflurane 5321:CAR-302,668 5316:CAR-302,282 5311:CAR-302,196 5306:CAR-301,060 5301:CAR-226,086 5281:Carfentanil 5179:Apomorphine 5100:Green Cross 4891:Domoic acid 4702:Neurotoxins 4622:OPA mixture 4513:Chlorosoman 4508:Chlorosarin 4442:Phospholine 4141:Crotylsarin 4126:Fluorotabun 4098:Chlorosoman 4080:Chlorosarin 3640:rassegna.it 3467:10281/16136 2797:16 December 1893:(1): 5–38. 1526:-dioxins". 1403:Times Beach 1104:Stillbirths 1080:teratogenic 992:Vietnam War 810:Flash point 587:Signal word 524:(OHS/OSH): 451:Appearance 398:Properties 233:100.015.566 195:ChEMBL30327 175:CHEBI:28119 92:Tetradioxin 6057:Categories 5999:indigo dye 5992:Tryptophan 5896:lipoxin A4 5865:modulators 5693:Maitotoxin 5688:Guanitoxin 5668:Ciguatoxin 5663:Brevetoxin 5648:Anatoxin-a 5643:Aflatoxins 5556:Putrescine 5551:Cadaverine 5527:Malodorant 5346:Isoflurane 5331:Desflurane 5326:Benperidol 5271:Psilocybin 5266:PAVA spray 4948:Diphosgene 4901:Pulmonary/ 4829:Picrotoxin 4788:Strychnine 4782:Brevetoxin 4766:Maitotoxin 4749:Guanitoxin 4743:Ciguatoxin 4710:Anatoxin-a 4643:Pinacolone 4476:Precursors 4437:Selenophos 4293:Carbamates 4209:Chinese VX 4115:Cyclosarin 4104:Ethylsarin 4075:Sarin (GB) 3926:Lewisite 3 3920:Lewisite 2 3889:Arsenicals 3559:The Lancet 3258:The Lancet 2181:Cancer Res 1481:References 1434:amenorrhea 1228:, in 2011: 1168:carcinogen 1157:estrogenic 1020:expression 998:. It is a 556:Pictograms 439:Molar mass 299:DO80M48B6O 206:ChemSpider 134:3D model ( 113:CAS Number 30:See also: 6019:CH-223191 6003:indirubin 5986:bilirubin 5935:biphenyls 5911:Flutamide 5886:Agonists: 5788:Plutonium 5738:Volkensin 5713:Saxitoxin 5703:Palytoxin 5628:Aconitine 5351:Halothane 5341:Bufotenin 5336:Enflurane 5256:Kolokol-1 5236:Pethidine 5210:Etoxadrol 5195:Etorphine 5191:(CS-4640) 5175:(CS-4030) 5133:glycerine 5080:Salcomine 4839:Tremorine 4777:Aconitine 4760:Palytoxin 4738:Ryanodine 4715:Saxitoxin 4452:Ro 3-0422 4223:GV agents 4086:Thiosarin 3815:Phosphine 2258:(1): 39. 2066:216644694 1450:chloracne 1388:chloracne 1331:catalysts 1295:apoptosis 1144:genotoxic 1140:mutagenic 1124:sex ratio 741:P403+P235 737:P403+P233 729:P370+P378 725:P362+P364 721:P332+P313 713:P308+P313 701:P301+P310 547:labelling 486:0.2 μg/L 464:1.8 g/cm 123:1746-01-6 6036:See also 5797:Polonium 5698:Modeccin 5607:Acrolein 5572:Lewisite 5517:DRC-5593 5472:Acrolein 5296:CS-27349 5246:Ibogaine 5129:Litharge 5118:Adamsite 5095:Diborane 5085:Fluomine 5065:Ethenone 4960:Acrolein 4927:Fluorine 4921:Phosgene 4911:Chlorine 4311:EA-3887A 4283:C01-A042 4278:C01-A039 4273:C01-A035 4151:V-agents 4061:G-agents 3946:(EA-229) 3914:Lewisite 3773:Cyanogen 3622:15384216 3587:24761553 3579:19660807 3537:11564625 3476:10866441 3370:Archived 3350:Archived 3330:22200276 3286:23115128 3174:31562457 3131:15345345 3079:11485382 2961:45117354 2953:10912242 2772:24804623 2750:: 2–10. 2729:18648613 2680:14712494 2639:21810551 2590:21441038 2555:21718216 2506:16977594 2454:14623487 2419:16054739 2292:19754930 2228:16977593 2193:11156390 2159:24500449 2151:10912243 2107:16543362 2058:10912238 2023:59603271 2015:30718831 1944:16918318 1909:17569696 1855:16214954 1820:34036181 1812:20624415 1766:20508397 1758:15900503 1720:22295283 1712:10912240 1677:11814994 1669:10912244 1631:16445906 1556:53459209 1511:(NIOSH). 1464:See also 1425:history. 1407:Missouri 1256:anorexia 1041:such as 976:congener 757:NFPA 704 514:Hazards 5997:(e.g., 5984:(e.g., 5969:(e.g., 5953:(e.g., 5925:(e.g., 5921:(e.g., 5894:(e.g., 5546:Skatole 5541:Allicin 5251:EA-3834 5241:EA-3580 5231:EA-3443 5226:EA-3167 5221:EA-2148 5205:CS-4297 5200:EA-2092 5189:EA-4941 4916:Bromine 4554:EA-1224 4534:EA-1250 4447:R-16661 4422:EA-2613 4417:EA-2098 4412:EA-2054 4407:EA-2012 4376:3152 CT 4366:TL-1317 4361:TL-1299 4356:TL-1238 4326:EA-4056 4321:EA-3990 4316:EA-3966 4306:EA-3887 4204:EA-1763 4164:EA-3148 4159:EA-2192 4136:EA-4352 4131:EA-1356 3865:Stibine 3699:Dioxins 3528:1240417 3484:6353869 3424:1826746 3404:Bibcode 3310:Bibcode 3278:1681353 3166:9923879 3122:1247522 3040:9299592 2997:1585364 2915:7899475 2881:6282188 2752:Bibcode 2720:2475943 2630:3261987 2546:3154583 2497:1934421 2381:9199536 2283:2754980 2260:Bibcode 1863:1913812 1611:Bibcode 1536:Bibcode 1505:"#0594" 1445:Ukraine 1411:NEPACCO 1317:Sources 1311:epoxide 1172:group 1 1114:, with 1092:2,4,5-T 1028:enzymes 984:dioxins 965:burning 935:) is a 906:what is 904: ( 460:Density 266:PubChem 100:-dioxin 5764:Napalm 5529:agents 5388:agents 5291:JB-336 5286:JB-318 5261:LSD-25 5217:(DMHP) 5165:agents 4824:A-8564 4784:(PbTX) 4734:(TeNT) 4351:TL-599 4341:T-1194 4336:T-1152 4331:T-1123 4100:(ClGD) 4082:(ClGB) 3993:TL-301 3795:Arsine 3620:  3585:  3577:  3535:  3525:  3482:  3474:  3446:Lancet 3422:  3328:  3284:  3276:  3238:  3213:734660 3211:  3172:  3164:  3146:Lancet 3129:  3119:  3077:  3038:  2995:  2959:  2951:  2913:  2879:  2770:  2727:  2717:  2678:  2637:  2627:  2588:  2553:  2543:  2504:  2494:  2452:  2417:  2379:  2318:  2290:  2280:  2226:  2191:  2157:  2149:  2105:  2064:  2056:  2021:  2013:  1973:  1942:  1907:  1861:  1853:  1818:  1810:  1764:  1756:  1718:  1710:  1675:  1667:  1629:  1554:  1430:Vienna 1375:Seveso 1288:Cancer 1261:thymus 1252:organs 1134:Cancer 1110:, and 1096:causal 941:dioxin 929:dioxin 901:verify 898:  871:(SDS) 593:Danger 444:321.96 382:SMILES 254:C07557 186:ChEMBL 71:Names 5752:Other 5708:Ricin 5623:Abrin 5582:KB-16 4864:IPTBO 4795:(ATX) 4768:(MTX) 4762:(PTX) 4751:(GTX) 4745:(CTX) 4728:(BTX) 4584:Nital 4390:Other 4268:A-262 4263:A-242 4258:A-234 4253:A-232 4248:A-208 4092:Soman 4088:(SGB) 4069:Tabun 4028:KB-16 4021:Other 3583:S2CID 3480:S2CID 3442:(PDF) 3282:S2CID 3170:S2CID 2957:S2CID 2842:(PDF) 2155:S2CID 2062:S2CID 2019:S2CID 1859:S2CID 1816:S2CID 1762:S2CID 1716:S2CID 1673:S2CID 1552:S2CID 1379:Italy 1128:Yusho 1024:genes 863:N.D. 837:none 821:NIOSH 347:InChI 279:15625 215:14865 166:ChEBI 136:JSmol 5927:TCDD 5790:and 5403:(OC) 5120:(DM) 4950:(DP) 4939:(PS) 4923:(CG) 4874:TBPS 4869:TBPO 4717:(TZ) 4639:(TH) 4608:(DF) 4602:(SW) 4596:(TB) 4569:DMHP 4549:DEHP 4539:DIHP 4530:(KB) 4467:MSPI 4117:(GF) 4106:(GE) 4094:(GD) 4071:(GA) 4013:(CX) 3960:CEES 3928:(L3) 3922:(L2) 3910:(PD) 3904:(MD) 3898:(ED) 3791:(AC) 3785:(CK) 3652:2014 3618:PMID 3575:PMID 3533:PMID 3472:PMID 3420:PMID 3343:DHHS 3326:PMID 3274:PMID 3236:ISBN 3209:PMID 3162:PMID 3127:PMID 3075:PMID 3036:PMID 2993:PMID 2949:PMID 2911:PMID 2877:PMID 2825:2019 2799:2019 2768:PMID 2725:PMID 2676:PMID 2635:PMID 2586:PMID 2551:PMID 2502:PMID 2450:PMID 2415:PMID 2377:PMID 2316:ISBN 2288:PMID 2224:PMID 2189:PMID 2147:PMID 2103:PMID 2054:PMID 2011:PMID 1971:ISBN 1940:PMID 1905:PMID 1851:PMID 1808:PMID 1754:PMID 1708:PMID 1665:PMID 1627:PMID 1417:and 1394:and 1343:PCCD 1209:The 933:TCDD 875:MSDS 857:IDLH 749:P501 745:P405 733:P391 717:P331 697:P280 693:P273 689:P271 685:P264 681:P260 677:P243 673:P242 669:P241 665:P240 661:P233 657:P210 653:P202 649:P201 635:H410 631:H401 627:H373 623:H361 619:H336 615:H315 611:H304 607:H225 499:6.8 492:log 290:UNII 245:KEGG 5941:ΙΤΕ 5929:), 5874:AhR 5427:CNS 4956:(Z) 4498:AlP 4493:ATO 3988:HN3 3983:HN2 3978:HN1 3916:(L) 3610:doi 3567:doi 3563:374 3523:PMC 3515:doi 3511:109 3462:hdl 3454:doi 3450:355 3412:doi 3378:EPA 3318:doi 3266:doi 3262:338 3201:doi 3154:doi 3150:353 3117:PMC 3109:doi 3105:112 3067:doi 3063:174 3028:doi 3024:146 2985:doi 2981:114 2941:doi 2869:doi 2760:doi 2748:491 2715:PMC 2707:doi 2666:doi 2662:108 2625:PMC 2617:doi 2613:119 2578:doi 2541:PMC 2533:doi 2492:PMC 2484:doi 2442:doi 2407:doi 2367:doi 2363:145 2278:PMC 2268:doi 2216:doi 2139:doi 2093:doi 2046:doi 2003:doi 1963:doi 1932:doi 1895:doi 1843:doi 1800:doi 1746:doi 1742:175 1700:doi 1657:doi 1619:doi 1607:101 1544:doi 1443:of 1428:In 1419:EPA 1415:CDC 1401:In 1325:or 1305:of 1234:ppt 1215:TEQ 1142:or 1090:or 1082:or 1022:of 939:-p- 850:Ca 844:REL 831:PEL 545:GHS 316:EPA 269:CID 6059:: 6001:, 5973:)) 5965:, 5961:, 5957:, 5933:, 5898:, 5577:CX 5422:CR 5417:CS 5412:CN 5173:BZ 4688:TG 4683:TC 4658:QL 4544:ZS 4488:AT 4199:VX 4194:VS 4189:VR 4184:VP 4179:VM 4174:VG 4169:VE 4121:GP 4110:GH 3668:. 3638:. 3616:. 3604:. 3581:. 3573:. 3561:. 3545:^ 3531:. 3521:. 3509:. 3505:. 3478:. 3470:. 3460:. 3448:. 3444:. 3418:. 3410:. 3400:32 3398:. 3345:: 3324:. 3316:. 3306:29 3304:. 3280:. 3272:. 3260:. 3207:. 3197:46 3195:. 3168:. 3160:. 3148:. 3125:. 3115:. 3103:. 3099:. 3087:^ 3073:. 3061:. 3034:. 3022:. 3018:. 2991:. 2979:. 2955:. 2947:. 2937:17 2935:. 2923:^ 2907:46 2905:. 2889:^ 2875:. 2865:22 2863:. 2815:. 2789:. 2766:. 2758:. 2746:. 2723:. 2713:. 2701:. 2697:. 2674:. 2660:. 2656:. 2633:. 2623:. 2611:. 2607:. 2584:. 2574:21 2572:. 2549:. 2539:. 2529:41 2527:. 2523:. 2500:. 2490:. 2480:50 2478:. 2474:. 2462:^ 2448:. 2438:38 2436:. 2413:. 2403:43 2401:. 2389:^ 2375:. 2361:. 2357:. 2300:^ 2286:. 2276:. 2266:. 2254:. 2250:. 2236:^ 2222:. 2212:50 2210:. 2185:60 2183:. 2167:^ 2153:. 2145:. 2135:17 2133:. 2115:^ 2101:. 2089:35 2087:. 2083:. 2060:. 2052:. 2042:17 2040:. 2017:. 2009:. 1999:19 1997:. 1985:^ 1969:. 1938:. 1926:. 1903:. 1891:98 1889:. 1885:. 1871:^ 1857:. 1849:. 1839:69 1837:. 1814:. 1806:. 1796:31 1794:. 1774:^ 1760:. 1752:. 1740:. 1728:^ 1714:. 1706:. 1696:17 1694:. 1671:. 1663:. 1653:17 1651:. 1639:^ 1625:. 1617:. 1605:. 1593:^ 1564:^ 1550:. 1542:. 1532:22 1530:. 1507:. 1489:^ 1405:, 1377:, 1347:Fs 1337:. 1201:. 1106:, 1070:. 1045:. 1002:. 971:. 955:Cl 949:12 927:p- 747:, 743:, 739:, 735:, 731:, 727:, 723:, 719:, 715:, 711:, 707:, 703:, 699:, 695:, 691:, 687:, 683:, 679:, 675:, 671:, 667:, 663:, 659:, 655:, 651:, 633:, 629:, 625:, 621:, 617:, 613:, 609:, 549:: 538:. 423:Cl 414:12 6005:) 5988:) 5937:) 5902:) 5854:e 5847:t 5840:v 5131:- 3955:Q 3950:T 3732:e 3725:t 3718:v 3654:. 3624:. 3612:: 3606:5 3589:. 3569:: 3555:p 3539:. 3517:: 3501:p 3486:. 3464:: 3456:: 3426:. 3414:: 3406:: 3392:p 3332:. 3320:: 3312:: 3288:. 3268:: 3244:. 3215:. 3203:: 3189:p 3176:. 3156:: 3133:. 3111:: 3081:. 3069:: 3055:p 3042:. 3030:: 3014:p 2999:. 2987:: 2963:. 2943:: 2917:. 2883:. 2871:: 2857:p 2844:. 2827:. 2801:. 2774:. 2762:: 2754:: 2731:. 2709:: 2703:3 2682:. 2668:: 2641:. 2619:: 2592:. 2580:: 2557:. 2535:: 2508:. 2486:: 2456:. 2444:: 2421:. 2409:: 2383:. 2369:: 2324:. 2294:. 2270:: 2262:: 2256:8 2230:. 2218:: 2195:. 2177:p 2161:. 2141:: 2109:. 2095:: 2068:. 2048:: 2025:. 2005:: 1979:. 1965:: 1946:. 1934:: 1928:7 1911:. 1897:: 1865:. 1845:: 1822:. 1802:: 1768:. 1748:: 1722:. 1702:: 1679:. 1659:: 1633:. 1621:: 1613:: 1558:. 1546:: 1538:: 1524:p 1345:/ 961:2 959:O 957:4 953:4 951:H 947:C 931:( 896:N 798:0 791:1 784:4 494:P 432:2 429:O 426:4 420:4 417:H 411:C 318:) 314:( 138:) 98:p 20:)

Index

Tetrachlorodibenzodioxin
Dioxins and dioxin-like compounds



Preferred IUPAC name
CAS Number
1746-01-6
JSmol
Interactive image
ChEBI
CHEBI:28119
ChEMBL
ChEMBL30327
ChemSpider
14865
ECHA InfoCard
100.015.566
Edit this at Wikidata
KEGG
C07557
PubChem
15625
UNII
DO80M48B6O
CompTox Dashboard
DTXSID2021315
Edit this at Wikidata
InChI
SMILES

Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.