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Rotenone

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924:. It oxidizes to rotenolone, which is about an order of magnitude less toxic than rotenone. In water, the rate of decomposition depends upon several factors, including temperature, pH, water hardness and sunlight. The half-life in natural waters ranges from half a day at 24 °C to 3.5 days at 0 °C. Furthermore, its use is more benign for the environment (as compared to other piscicides) as most species are seen to recolonize aquatic systems within weeks to a year after application. Thus, it has also seen some use in other field studies in the marine environment needing only small quantities. Small-scale sampling with rotenone is used by fish researchers studying the biodiversity of marine fishes to collect cryptic, or hidden, fishes, which represent an important component of shoreline fish communities, since it has only minor and transient environmental side effects. 24: 327: 218: 33: 603: 1394:
that die in Parkinson's disease. Another study has also described toxic action of rotenone at low concentrations (5 nM) in dopaminergic neurons from acute rat brain slices. This toxicity was exacerbated by an additional cell stressor – elevated intracellular calcium concentration – adding support to
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content, availability of sunlight and temperature. Rotenone has been used by government agencies to kill fish in rivers and lakes in the United States since 1952, and in Canada and Norway since the 1980s. It is less frequently used in EU countries, due to strict regulations, but has seen some use in
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The lowest lethal dose for a child is not known, but death occurred in a 3.5-year-old child who had ingested 40 mg/kg rotenone solution. Human deaths from rotenone poisoning are rare because its irritating action causes vomiting. Deliberate ingestion of rotenone can be fatal.
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In 2010, a study was published detailing the progression of Parkinson's-like symptoms in mice following chronic intragastric ingestion of low doses of rotenone. The concentrations in the central nervous system were below detectable limits, yet still induced PD pathology.
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Huang B, Wu S, Wang Z, Ge L, Rizak JD, Wu J, Li J, Xu L, Lv L, Yin Y, Hu X (2018-05-21). "Phosphorylated α-Synuclein Accumulations and Lewy Body-like Pathology Distributed in Parkinson's Disease-Related Brain Areas of Aged Rhesus Monkeys Treated with MPTP".
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from MPTP. Therefore, the mechanism behind MPTP as it relates to Parkinson's disease is not fully understood. Because of these developments, rotenone was investigated as a possible Parkinson-causing agent. Both MPTP and rotenone are
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Tanner CM, Kamel F, Ross GW, Hoppin JA, Goldman SM, Korell M, Marras C, Bhudhikanok GS, Kasten M, Chade AR, Comyns K, Richards MB, Meng C, Priestley B, Fernandez HH, Cambi F, Umbach DM, Blair A, Sandler DP, Langston JW (2011).
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Freestone PS, Chung KK, Guatteo E, Mercuri NB, Nicholson LF, Lipski J (November 2009). "Acute action of rotenone on nigral dopaminergic neurons--involvement of reactive oxygen species and disruption of Ca2+ homeostasis".
1324:; that is, that rotenone exposure in the developing fetus may impede proper human brain development, with potentially profound consequences later in life. The study found that rotenone was particularly damaging to 2748:
Pamies, David; Block, Katharina; Lau, Pierre; Gribaldo, Laura; Pardo, Carlos A.; Barreras, Paula; Smirnova, Lena; Wiersma, Daphne; Zhao, Liang; Harris, Georgina; Hartung, Thomas; Hogberg, Helena T. (2018-09-01).
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had been known earlier to cause PD-like symptoms (in humans and other primates, though not in rats) by interfering with complex I in the electron transport chain and killing dopaminergic neurons in the
841:, as well as most other arthropods. It biodegrades rapidly in soil, with 90% degraded after 1–3 months at 20 °C (68 °F) and three times faster at 30 °C (86 °F). The compound 135: 2215: 1807: 6024: 3739: 1507: 1485: 543: 616: 1320:
A 2018 study, which examined the effects of rotenone administration on cell cultures that mimicked properties of developing brains, found that rotenone may be a developmental
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Cavoski, Ivana; Caboni, Pierluigi; Sarais, Giorgia; Miano, Teodoro (2008-08-06). "Degradation and Persistence of Rotenone in Soils and Influence of Temperature Variations".
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Divakaruni AS, Rogers GW, Murphy AN (2014). "Measuring Mitochondrial Function in Permeabilized Cells Using the Seahorse XF Analyzer or a Clark-Type Oxygen Electrode".
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InChI=1/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3/t16-,20-,21+/m1/s1
997:, a reservoir in the southeastern portion of the U.S. state of Utah, was treated with rotenone, to potentially eradicate and control the invasive population of 2814:
Caboni P, Sherer T, Zhang N, Taylor G, Na H, Greenamyre J, Casida J (2004). "Rotenone, deguelin, their metabolites, and the rat model of Parkinson's disease".
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study showed a link between rotenone use and Parkinson's disease in farm workers, suggesting a link between neural damage and pulmonary uptake by not using
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Rotenone is produced by extraction from the roots and stems of several tropical and subtropical plant species, especially those belonging to the genera
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Lupescu, Adrian; Jilani, Kashif; Zbidah, Mohanad; Lang, Florian (October 2012). "Induction of apoptotic erythrocyte death by rotenone".
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Rytwinski T, Taylor JJ, Donaldson LA, Britton JR, Browne DR, Gresswell RE, Lintermans M, Prior KA, Pellatt MG, Vis C, Cooke SJ (2018).
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combination with other insecticides. All insecticidal uses were banned In the United States and Canada, in the UK, and in Switzerland.
8594: 4161: 2407:"Mechanistic Investigations of the Mitochondrial Complex I Inhibitor Rotenone in the Context of Pharmacological and Safety Evaluation" 8523: 8579: 4390: 3601: 3449: 3406: 3075:
Pan-Montojo F, Anichtchik O, Dening Y, Knels L, Pursche S, Jung R, Jackson S, Gille G, Spillantini MG (2010). Kleinschnitz C (ed.).
1098: 341: 5173: 5572: 4477: 4440: 4235: 4166: 3611: 3591: 3269: 2253: 1352:. The study does not directly suggest rotenone exposure is responsible for PD in humans, but is consistent with the belief that 8604: 8589: 7481: 4395: 3502: 3308: 3245: 2005: 1780: 8599: 6732: 3925: 3596: 3201: 1990: 1566: 1525: 1369: 5163: 1288:, but extremely toxic to insects and aquatic life, including fish. This higher toxicity in fish and insects is because the 880:(days) and is gone from rivers in the course of days and from lakes within a few months, depending on (seasonal) stirring, 8574: 8559: 8554: 3832: 3812: 3586: 3581: 3459: 1361: 2553: 623: 8318: 8082: 6632: 6192: 6167: 5971: 5941: 5506: 4800: 4661: 4188: 4014: 3827: 3678: 1109:, creating a back-up of electrons within the mitochondrial matrix. Cellular oxygen is reduced to the radical, creating 719: 284: 8417: 2465:
Fang N, Casida J (1999). "Cubé resin insecticide: identification and biological activity of 29 rotenoid constituents".
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of the same chemical makeup as that which makes up Lewy bodies with similar pathology to Parkinson's disease in aged
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Vinson, V; Dinger, EC; Vinson, DK (2010). "Piscicides and invertebrates: after 70 years, does anyone really know?".
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Rotenone is used in biomedical research to study the oxygen consumption rate of cells, usually in combination with
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In 2000, injecting rotenone into rats was reported to cause the development of symptoms similar to those of
1110: 1027:, in order to rid it of invasive species introduced since the migration of European settlers to the region. 1023:
In 2014, rotenone was used to kill all remaining fish in San Francisco's Mountain Lake, which is located in
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Planning and Standard Operating Procedures for the Use of Rotenone in Fish Management – Rotenone SOP Manual
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due to invasive pike destroying native species, which were reintroduced once the treatment was concluded.
842: 3507: 175: 7730: 7555: 7493: 7019: 6563: 6526: 6514: 6382: 5213: 4701: 4551: 4445: 4110: 3792: 3621: 3551: 1877: 1560: 1075: 59: 45: 8120: 6292: 6267: 6242: 6227: 6162: 6102: 6097: 3487: 3424: 1526:"The effectiveness of non-native fish removal techniques in freshwater ecosystems: A systematic review" 251: 3323: 1353: 869:, the affected fish rise to the surface in an attempt to gulp air, where they are more easily caught. 8564: 8412: 7150: 6807: 6546: 6452: 6394: 6232: 6172: 6107: 6082: 5487: 5373: 4841: 4812: 4785: 4651: 4539: 4348: 4316: 4282: 4004: 3920: 3891: 3682: 3636: 3522: 3088: 2920:"Critical role for microglial NADPH oxidase in rotenone-induced degeneration of dopaminergic neurons" 2762: 2638: 2418: 2098: 1357: 1325: 1297: 1153: 1017: 866: 673:
The earliest written record of the now-known rotenone-containing plants used for killing leaf-eating
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Nellis, David N. (1994). Seashore plants of South Florida and the Caribbean. Pineapple Press. 160 p.
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population. Rotenone successfully achieved these aims, killing between 179,000–197,000 goldfish and
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Rotenone is used as a nonselective piscicide (fish killer). Rotenone has historically been used by
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The eradication of invasive species using rotenone and its impact on freshwater macroinvertebrates
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Finlayson B, Schnick R, Skaar D, Anderson J, Demong L, Duffield D, Horton W, Steinkjer J (2018).
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Summary of the article by Dr. Greenamyre on pesticides and Parkinson's Disease at ninds.nih.gov
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class 21 (by itself in 21B). It inhibits the transfer of electrons from iron-sulfur centers in
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La Forge FB, Haller HL, Smith LE (1933). "The Determination of the structure of rotenone".
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Peterson Field Guides to Medicinal Plants and Herbs of Eastern and Central North America
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Heinz S, Freyberger A, Lawrenz B, Schladt L, Schmuck G, Ellinger-Ziegelbauer H (2017).
2346: 1719: 1265: 994: 987: 921: 881: 706:. He wrote about this research in his thesis, published in 1895 after his death from a 594: 496: 3168: 2726: 1651:"魚籘有毒成分の研究 第一報 [First report of research on toxic ingredients in fish rattan]" 76:)-8,9-Dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrobenzopyranofurobenzopyran-6(6a 32: 8538: 7785: 7620: 7595: 7375: 7293: 7126: 7104: 6959: 6836: 6568: 6419: 6377: 5812: 5757: 5732: 5308: 4706: 4606: 3817: 3416: 3381: 3328: 3277: 3163: 2997: 2981: 1904:(2nd ed.). Bethesda, Maryland: American Fisheries Society (published May 2018). 1444: 1419: 1321: 1010: 906: 890: 845:
when exposed to sunlight and usually has an activity of six days in the environment.
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have shown low doses of rotenone (below 10 nM) induce oxidative damage and death of
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Cornell University. Rotenone. Resource Guide for Organic and Disease Management.
956:, and by 1994, jaguar cichlids had successfully established themselves throughout 653:. It was the first-described member of the family of chemical compounds known as 8349: 3101: 2288: 1755: 936:(FWC) officials used rotenone to eradicate an established population of invasive 681:. The active chemical component was first isolated in 1895 by a French botanist, 273: 8298: 8226: 8191: 8186: 8146: 8116: 8102: 8092: 8087: 7916: 7860: 7855: 7750: 7745: 7725: 7675: 7650: 7645: 7570: 7560: 7477: 7473: 7469: 7461: 7451: 7447: 7415: 7403: 7389: 7381: 7321: 7254: 7198: 7170: 7004: 6979: 6851: 6752: 6627: 6551: 6521: 6372: 6352: 6302: 6256: 6152: 5936: 5817: 5802: 5797: 5727: 5663: 5618: 5522: 5518: 5514: 5467: 5413: 5408: 5388: 5328: 5273: 5243: 5233: 5223: 5193: 5178: 5094: 5074: 4979: 4903: 4795: 4748: 4713: 4631: 4621: 4566: 4524: 4489: 4435: 4420: 4385: 4380: 4134: 4105: 3566: 3464: 3386: 3333: 3283: 1667: 1650: 1411: 1340:(PD). Rotenone was continuously applied over a period of five weeks, mixed with 1121: 1031: 949: 894: 826: 658: 639: 525: 6002: 3717: 2774: 2366:"Neuroprotective role of mitochondrial uncoupling protein 2 in cerebral stroke" 2126:"Rotenone: An Essential but Demonized Tool for Assessing Marine Fish Diversity" 8241: 8221: 8196: 8043: 7988: 7943: 7921: 7830: 7825: 7795: 7780: 7775: 7740: 7630: 7585: 7565: 7443: 7437: 7341: 7329: 7289: 7270: 7246: 7230: 7140: 7136: 7110: 7096: 7049: 7044: 7039: 7029: 6999: 6969: 6964: 6944: 6881: 6802: 6782: 6767: 6762: 6742: 6707: 6657: 6558: 6499: 6432: 6427: 6404: 6342: 6317: 6237: 5906: 5873: 5722: 5717: 5697: 5668: 5588: 5553: 5548: 5538: 5433: 5368: 5303: 5253: 5109: 5004: 4959: 4918: 4826: 4775: 4626: 4576: 4529: 4519: 4338: 4306: 4265: 4215: 4205: 4151: 4139: 4100: 3952: 3947: 3942: 3937: 3932: 3854: 3401: 3273: 3178: 3065:-- Basic Neurochemistry -- NCBI Bookshelf, American Society for Neurochemistry 2677:"Fatality after deliberate ingestion of the pesticide rotenone: a case report" 2650: 2177: 2110: 1481: 1424: 1399: 1289: 1094: 1039: 913: 751:. By 1930, nicouline and rotenone were established to be chemically the same. 642: 475: 414: 186: 3033: 2886: 2782: 2751:"Rotenone exerts developmental neurotoxicity in a human brain spheroid model" 2587:(UNEP); International Labour Organization; World Health Organization (2007). 2075: 8502: 8381: 8236: 8216: 8156: 8136: 7978: 7815: 7690: 7685: 7670: 7655: 7615: 7497: 7465: 7423: 7371: 7367: 7363: 7353: 7333: 7317: 7266: 7242: 7238: 7226: 7218: 7214: 7174: 7162: 7146: 7132: 7122: 7118: 7074: 6934: 6908: 6896: 6871: 6861: 6846: 6826: 6777: 6677: 6672: 6647: 6637: 6602: 6462: 6437: 6399: 6357: 5927: 5901: 5881: 5877: 5865: 5742: 5707: 5648: 5608: 5603: 5502: 5482: 5418: 5383: 5358: 5353: 5338: 5258: 5208: 5129: 5064: 5009: 4999: 4989: 4923: 4770: 4758: 4514: 4405: 4333: 4294: 4220: 4193: 4122: 3876: 3859: 3479: 3193: 3183: 1499: 1380: 1260: 1254: 1090: 1047: 1002: 998: 979: 877: 807: 796: 792: 678: 645:. It occurs naturally in the seeds and stems of several plants, such as the 6182: 3120: 3041: 2989: 2953: 2904: 2835: 2800: 2712: 2658: 2486: 2448: 2391: 2296: 1853: 3141: 8407: 8389: 8107: 8097: 7800: 7660: 7580: 7575: 7508: 7325: 7262: 7258: 7222: 7210: 7182: 7178: 7166: 7158: 7088: 6876: 6866: 6712: 6697: 6682: 6617: 6612: 6457: 6367: 5913: 5792: 5787: 5782: 5777: 5772: 5578: 5333: 5268: 5084: 5039: 5034: 5029: 5024: 5019: 4974: 4913: 4908: 4848: 4029: 3871: 3469: 3391: 3348: 3318: 3298: 2559: 2382: 2365: 2067: 1544: 1309: 975: 953: 902: 862: 803: 654: 650: 2878: 1695: 1614: 8262: 8008: 7820: 7720: 7710: 7705: 7485: 7429: 7419: 7311: 7186: 6994: 6989: 6891: 6856: 6787: 6687: 6536: 6504: 6442: 5869: 5658: 5598: 5398: 5283: 5124: 5099: 4954: 4696: 4646: 4586: 4247: 3293: 3288: 1387: 945: 788: 781: 691: 489: 485: 470:
210 to 220 °C (410 to 428 °F; 483 to 493 K) at 0.5 mmHg
445: 260: 53:)-4′,5′-Dimethoxy-5′′-(prop-1-en-2-yl)-4′′,5′′-dihydrofurorotenan-4-one 2827: 2478: 2430: 2158: 2055: 1845: 8181: 8176: 8033: 7297: 7285: 7100: 7069: 7064: 7059: 6792: 6447: 5920: 5861: 5846: 5752: 2519: 2208:"Mann Lake Gets a Second Round of Rotenone for Cutthroat Restoration" 1376: 1285: 1140: 858: 166: 2757:. Alternative Approaches to Developmental Neurotoxicity Evaluation. 2142: 2125: 1597:
Ambrose, Anthony M.; Harvey B. Haag (1936). "Toxicological study of
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which he called rotenone, after the Taiwanese name of the plant 蘆藤 (
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Except where otherwise noted, data are given for materials in their
3571: 3363: 3338: 2693: 2254:"Alien fish poisoned by the thousands to save S.F.'s Mountain Lake" 234: 8257: 8131: 8013: 7983: 7202: 7084: 6913: 5452: 5134: 5044: 3454: 3353: 1281: 917: 146: 134: 124: 8277: 7968: 7337: 7092: 5885: 5198: 3368: 2675:
Wood DM, Alsahaf H, Streete P, Dargan PI, Jones AL (June 2005).
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in 2006; as of 2016, the lake's fish population has recovered.
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was in 1848; for centuries, these same plants had been used to
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Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)
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Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)
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Rotenone use in research on the biodiversity of marine fishes
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Vitax Safety Data Sheet for Derris dust, revised October 1998
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Immediately Dangerous to Life or Health Concentrations (IDLH)
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officials used rotenone to kill an established population of
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the 'multiple hit hypothesis' of dopaminergic neuron death.
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to catch fish. Typically, rotenone-containing plants in the
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Rotenone registration at US Environmental Protection Agency
1878:"Lake poisoning seems to have worked to kill invasive pike" 460:
165 to 166 °C (329 to 331 °F; 438 to 439 K)
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The WHO Recommended Classification of Pesticides by Hazard
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Har myndighetene lyktes i kampen mot Gyrodactylus salaris?
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Re-evaluation Note: Rotenone (REV2008-01, 29 January 2008)
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In modern times it is frequently used as a tool to remove
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In 2012, rotenone was used to kill all remaining fish in
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17α-Alkylated 5α-dihydro-19-nortestosterone derivatives:
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The root extract is referred to as derris or derris root
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The root extract is referred to as derris or derris root
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7α-Methyl-19-norandrostenedione (MENT dione, trestione)
2347:"IRAC Mode of Action Classification Scheme Version 9.4" 1360:
increases the likelihood of the disease. In 2011, a US
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In agriculture it was unselective in action and killed
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vine, and in the roots of several other members of the
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Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
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5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives:
2033:. Trondheim: Doctoral theses at NTNU. pp. 1–100. 1508:
National Institute for Occupational Safety and Health
1486:
National Institute for Occupational Safety and Health
1348:
to enhance tissue penetration, and injected into the
1058:
Rotenone can be deactivated in water with the use of
5942: 3063:
Neurotransmitters and Disorders of the Basal Ganglia
2124:
Robertson, D. Ross; Smith-Vaniz, William F. (2008).
1105:). Complex I is unable to pass off its electron to 657:. Rotenone was used in the past as a broad-spectrum 8516: 8388: 8286: 8250: 8070: 8056: 7869: 7522: 6057: 6043: 5854: 5845: 5143: 4932: 4290:
Normethandrone (methylestrenolone, normethisterone)
3772: 3758: 3645: 3478: 3415: 3231: 2345:IRAC International MoA Working Group (March 2020). 4502:17α-Alkylated 5α-dihydrotestosterone derivatives: 2062:(in Norwegian). LFI, University of Bergen: 1–60. 1781:"RHS advice for the garden - Rotenone withdrawal" 1372:procedure in modern application of the chemical. 1217:) – southeast Asia and southwest Pacific islands 1203:) – southeast Asia and southwest Pacific islands 1001:, which were probably introduced accidentally by 948:; the cichlids had already spread throughout the 934:Florida Fish and Wildlife Conservation Commission 272: 4721:5α-Dihydro-17α-ethynyltestosterone derivatives: 1280:as moderately hazardous. It is mildly toxic to 1101:during the creation of usable cellular energy ( 737: 110: 7532:Tooltip Selective estrogen receptor modulators 6887:Furostilbestrol (diethylstilbestrol difuroate) 6248:16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 4172:11β-Methyl-19-nortestosterone dodecylcarbonate 2166:Reviews in Fisheries Science & Aquaculture 1812:Environmental Protection Agency of New Zealand 1760:Cornell Law School Legal Information Institute 744: 371:CC(=C)1Cc2c(O1)ccc3c2O4COc5cc(OC)c(OC)cc54C3=O 8365: 6078:3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol 6018: 4939:Tooltip Selective androgen receptor modulator 4584:17α-Alkylated 19-nortestosterone derivatives: 3733: 3209: 2370:Journal of Cerebral Blood Flow and Metabolism 1192:The root extract is referred to as cubé resin 1178:The root extract is referred to as cubé resin 661:, and is still used as a piscicide to remove 8: 6188:10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED) 4990:Enobosarm (ostarine, MK-2866, GTx-024, S-22) 3179:CDC – NIOSH Pocket Guide to Chemical Hazards 2863:"Rotenone, Paraquat and Parkinson's Disease" 2583:International Programme on Chemical Safety; 2327:, American Fisheries Society, archived from 1300:, but not as easily through the skin or the 787:Rotenone was used in powdered form to treat 722:, isolated a pure crystalline compound from 8524:6'-O-β-D-glucopyranosyl-12a-hydroxydalpanol 8063:Tooltip G protein-coupled estrogen receptor 6882:Fosfestrol (diethylstilbestrol diphosphate) 4741:17α-Ethynyl-19-nortestosterone derivatives: 3159:Rotenone. ARS Pesticide Properties Database 1586:. National Research Council, Washington DC. 8372: 8358: 8350: 8067: 7025:Triphenylmethylethylene (triphenylpropene) 6349:, many others; via estrogenic metabolites) 6273:17α-Epiestriol (16α-hydroxy-17α-estradiol) 6054: 6025: 6011: 6003: 5851: 4463:Methylclostebol (chloromethyltestosterone) 4358:5α-Dihydro-19-nortestosterone derivatives: 3769: 3740: 3726: 3718: 3216: 3202: 3194: 1834:Journal of Agricultural and Food Chemistry 1583:The Mode of Action of Organic Insecticides 1117:and other components of the mitochondria. 325: 216: 194: 15: 6045: 4684:17α-Vinyl-19-nortestosterone derivatives: 4300:Oxabolone cipionate (oxabolone cypionate) 3916:DHEA (androstenolone, prasterone; 5-DHEA) 3760: 3110: 3100: 2943: 2894: 2790: 2702: 2692: 2438: 2381: 2141: 1666: 292: 4391:Chlorodehydromethylandrostenediol (CDMA) 2555:Comprehensive Natural Products Chemistry 1745:, Consumer Product Safety, Health Canada 1480:NIOSH Pocket Guide to Chemical Hazards. 1292:rotenone is easily taken up through the 1147:Some of the plants containing rotenone: 1062:to lower toxicity to acceptable levels. 5992:List of androgens and anabolic steroids 4378:17α-Alkylated testosterone derivatives: 3142:Molecule of the Month at chm.bris.ac.uk 2670: 2668: 2460: 2458: 2351:Insecticide Resistance Action Committee 2157:Shafland, Paul L. (23 December 2008) . 1965:Mo, TO; Holthe, E; Andersen, O (2022). 1707: 1705: 1461: 1070:Rotenone works by interfering with the 368: 346: 321: 250: 4396:Chlorodehydromethyltestosterone (CDMT) 4152:Testifenon (testiphenon, testiphenone) 1982: 1603:Industrial & Engineering Chemistry 1558: 1475: 1473: 1471: 1469: 1467: 1465: 969:Oregon Department of Fish and Wildlife 207: 4677:Norvinisterone (vinylnortestosterone) 4211:Bolmantalate (nandrolone adamantoate) 4206:Bolandione (19-nor-4-androstenedione) 3921:DHEA enanthate (prasterone enanthate) 1895: 1893: 1375:Studies with primary cultures of rat 1009:. The lake was restocked with 20,000 174: 154: 7: 5947:Tooltip Sex hormone-binding globulin 4694:17α-Ethynyltestosterone derivatives: 3973:Polytestosterone phloretin phosphate 2970:The European Journal of Neuroscience 2918:Gao HM, Liu B, Hong JS (July 2003). 2585:United Nations Environment Programme 2237:Fish population booms in Stormy Lake 2172:(2). Taylor & Francis: 101–122. 1808:"How safe are natural insecticides?" 1519: 1517: 1036:electron transport chain Complex III 928:Notable administrations as piscicide 916:and its final product is reduced to 4617:Methylhydroxynandrolone (MOHN, MHN) 4322:Trenbolone hexahydrobenzylcarbonate 3982:5α-Dihydrotestosterone derivatives: 3850:Androstenedione (4-androstenedione) 2755:Toxicology and Applied Pharmacology 2252:Fimrite, Peter (12 November 2014). 2218:from the original on April 24, 2011 1925:Schmidt, Peter (28 February 2010). 885:selected countries such as the UK ( 430:Colorless to red crystalline solid 263: 233: 4674:17α-Vinyltestosterone derivatives: 4436:Methandriol (methylandrostenediol) 3026:10.1016/j.neuroscience.2018.03.026 2936:10.1523/JNEUROSCI.23-15-06181.2003 2187:from the original on 24 April 2024 1328:, consistent with prior findings. 14: 8550:Aldehyde dehydrogenase inhibitors 8418:12-deoxo-12alpha-methoxyelliptone 7424:taleranol (teranol, β-zearalanol) 6339:metandienone (methandrostenolone) 4714:Ethisterone (ethynyltestosterone) 4431:Metandienone (methandrostenolone) 4261:Methoxydienone (methoxygonadiene) 3872:Boldione (1,4-androstadienedione) 3823:Androstenediol (5-androstenediol) 3788:4-Dehydroepiandrosterone (4-DHEA) 2867:Environmental Health Perspectives 2503:(2nd ed.). pp. 130–131. 2206:Monroe, Bill (December 3, 2010). 2159:"Exotic fishes of Florida — 1994" 1931:The Chronicle of Higher Education 1390:, and it is these neurons in the 8468:6-Methoxy-6a,12a-dehydrodeguelin 8453:6-Hydroxy-6a,12a-dehydrodeguelin 8334:Progesterone receptor modulators 8088:Afimoxifene (4-hydroxytamoxifen) 6970:Prinaberel (ERB-041, WAY-202041) 5987:Progesterone receptor modulators 4478:Methyltestosterone 3-hexyl ether 4441:Methandriol bisenanthoyl acetate 4401:Chloromethylandrostenediol (CMA) 4236:Dimethandrolone dodecylcarbonate 3995:1-Androsterone (1-andro, 1-DHEA) 2982:10.1111/j.1460-9568.2009.06990.x 1042:(an ATP synthase inhibitor) and 601: 398: 31: 22: 8031:Coregulator-binding modulators: 6298:17β-Methyl-17α-dihydroequilenin 4159:19-Nortestosterone derivatives: 3707:Monoamine metabolism modulators 2514:Coates Palgrave, Keith (2002). 2321:Rotenone Neutralization Methods 1806:Dowle, Joanna (2 August 2024). 1249:) – southern Florida, Caribbean 876:, as it has a relatively short 764:Rotenone was commercialized as 597:(at 25 °C , 100 kPa). 6862:Erteberel (SERBA-1, LY-500307) 5174:15β-Hydroxycyproterone acetate 5065:OPK-88004 (LY-2452473, TT-701) 2552:Barton D, Meth-Cohn O (1999). 1952:"Invasive Goldfish management" 1276:Rotenone is classified by the 780:, in single preparation or in 404: 392: 1: 8570:NADH dehydrogenase inhibitors 8458:6aα,12aα-12a-Hydroxyelliptone 8319:Receptor/signaling modulators 6283:17α-Ethynyl-3β-androstanediol 6278:17α-Ethynyl-3α-androstanediol 5972:Receptor/signaling modulators 4729:17α-Ethynyl-3β-androstanediol 4724:17α-Ethynyl-3α-androstanediol 4167:11β-Methyl-19-nortestosterone 3699:Monoamine reuptake inhibitors 3679:Receptor/signaling modulators 1362:National Institutes of Health 548:(US health exposure limits): 8473:6-Oxo-6a,12a-dehydrodeguelin 8329:Androgen receptor modulators 6633:Lynestrenol phenylpropionate 5982:Estrogen receptor modulators 5429:Trimethyltrienolone (R-2956) 4801:Lynestrenol phenylpropionate 4189:19-Nordehydroepiandrosterone 3102:10.1371/journal.pone.0008762 2289:10.1002/0471140856.tx2502s60 1876:Peter Fimrite (2007-10-02). 978:present in eastern Oregon's 720:Government-General of Taiwan 8324:Estrogens and antiestrogens 7974:Oxabicycloheptene sulfonate 7661:Etacstil (GW-5638, DPC-974) 6837:Doisynoestrol (fenocycline) 6581:Ethinylestradiol 3-benzoate 6093:3β,5α-Dihydrolevonorgestrel 6088:3α,5α-Dihydrolevonorgestrel 5977:Androgens and antiandrogens 5748:Ralaniten acetate (EPI-506) 5164:7α-Thiomethylspironolactone 4879:Medroxyprogesterone acetate 4241:Dimethandrolone undecanoate 4052:Dihydromethylandrostenediol 3843:Androstenediol dipropionate 2924:The Journal of Neuroscience 1668:10.1246/nikkashi1880.23.744 738: 736:) translated into Japanese 638:is an odorless, colorless, 514:or concentration (LD, LC): 8621: 8041:Noncompetitive inhibitors: 7666:Ethamoxytriphetol (MER-25) 6827:Dimestrol (dianisylhexene) 6586:Ethinylestradiol sulfonate 4067:Dihydrotestosterone esters 4020:11-Ketodihydrotestosterone 3833:Androstenediol 17β-acetate 3813:11β-Hydroxyandrostenedione 3798:4,17α-Dimethyltestosterone 3703:Monoamine releasing agents 2775:10.1016/j.taap.2018.02.003 1989:: CS1 maint: postscript ( 1565:: CS1 maint: postscript ( 733: 8595:Monoaminergic neurotoxins 8311: 8083:7β-Hydroxyepiandrosterone 7641:Desmethylchlorotrianisene 6820:Diethylstilbestrol esters 6773:Bisdehydrodoisynolic acid 6193:11β-Chloromethylestradiol 6168:7β-Hydroxyepiandrosterone 6050:Tooltip Estrogen receptor 5964: 4871:Progesterone derivatives: 4662:5α-Dihydronorethandrolone 4231:Dimethandrolone buciclate 4061:androstanolone, stanolone 4057:Dihydrotestosterone (DHT) 4015:7β-Hydroxyepiandrosterone 3904:Cloxotestosterone acetate 3828:Androstenediol 3β-acetate 3780:Testosterone derivatives: 3765:Tooltip Androgen receptor 3671: 3225:Monoaminergic neurotoxins 2651:10.1016/j.tox.2012.06.007 2595:World Health Organization 2178:10.1080/10641269609388581 2111:10.1577/1548-8446-35.2.61 1278:World Health Organization 1243:Florida fishpoison tree ( 1169:Cubé plant or lancepod ( 1151:Hoary pea or goat's rue ( 745: 591: 542: 510: 505: 379: 359: 337: 94: 86: 58: 44: 39: 30: 21: 8580:Plant toxin insecticides 8147:Fulvestrant (ICI-182780) 7964:Methylpiperidinopyrazole 7917:Fulvestrant (ICI-182780) 7400:Resorcylic acid lactones 6623:Hydroxyestrone diacetate 6559:Etamestrol (eptamestrol) 5677:-Butylbenzenesulfonamide 4864:5α-Dihydronorethisterone 4859:5α-Dihydrolevonorgestrel 4821:norethisterone enanthate 4790:levonorgestrel butanoate 4667:5α-Dihydronormethandrone 4520:Mebolazine (dimethazine) 4510:Desoxymethyltestosterone 4451:Methandriol dipropionate 4248:LS-1727 (nandrolone 17β- 4184:19-Nor-5-androstenedione 4042:Dihydroethyltestosterone 3838:Androstenediol diacetate 2516:Trees of Southern Africa 2318:Donald L Archer (2001), 2029:Kjærstad, Gaute (2022). 1629:"Useful tropical plants" 1266:South-east Asian regions 1072:electron transport chain 990:, and only three trout. 984:Lahontan cutthroat trout 912:Rotenone decays through 538:2.8 mg/kg (oral, mouse) 501:<0.00004 mmHg (20°C) 8428:9-Demethylclitoriacetal 7458:Synthetic xenoestrogens 7015:Triphenylchloroethylene 6950:Methestrol dipropionate 6478:Polyestradiol phosphate 5808:Topilutamide (fluridil) 5169:11α-Hydroxyprogesterone 4179:19-Nor-5-androstenediol 4079:Drostanolone propionate 1927:"One Strange Fish Tale" 1883:San Francisco Chronicle 1580:Metcalf, R. L. (1948). 1331: 1304:. Rotenone is toxic to 1120:Rotenone also inhibits 1111:reactive oxygen species 1097:. This interferes with 993:Beginning May 1, 2006, 450:1.27 g/cm @ 20 °C 8590:Microtubule inhibitors 8423:6a,12a-dehydrodeguelin 7551:4'-Hydroxynorendoxifen 7546:2-Phenylbenzothiophene 7420:zeranol (α-zearalanol) 7123:phlorizin (phloridzin) 7010:Triphenylbromoethylene 6909:ICI-85966 (Stilbostat) 6490:Estramustine phosphate 6363:Bolandiol dipropionate 5693:-Desmethylenzalutamide 5399:SC-5233 (spirolactone) 4817:norethisterone acetate 4456:Methandriol propionate 4327:Trenbolone undecanoate 4199:Bolandiol dipropionate 4047:Dihydrofluoxymesterone 4010:5α-Androst-2-en-17-one 3865:Boldenone undecylenate 2364:Mehta, Suresh (2009). 2054:Fjellheim, A. (2004). 1715:Handbook on Pesticides 1302:gastrointestinal tract 1060:potassium permanganate 488:, slightly soluble in 8600:Isopropenyl compounds 8438:11-Deoxyclitoriacetal 7731:Miproxifene phosphate 7556:27-Hydroxycholesterol 7020:Triphenyliodoethylene 6564:Ethinylandrostenediol 6527:Estrogenic substances 6515:Polyestriol phosphate 6383:Cloxestradiol acetate 5685:-Desmethylapalutamide 5214:Chlormadinone acetate 5159:7α-Thiospironolactone 5030:LGD-2941 (LGD-122941) 5020:LG121071 (LGD-121071) 4894:3-Keto-5α-abiraterone 4874:6α-Methylprogesterone 4813:Norethisterone esters 4786:Levonorgestrel esters 4702:Ethinylandrostenediol 4552:Methyl-1-testosterone 4472:+esterified estrogens 4446:Methandriol diacetate 4111:Mesterolone cipionate 3793:4-Hydroxytestosterone 3602:MDMA (midomafetamine) 1649:Nagai, Kazuo (1902). 1533:Environmental Reviews 1082:, which places it in 940:from a small pond in 702:, while traveling in 689:, from a specimen of 534:132 mg/kg (oral, rat) 60:Systematic IUPAC name 8575:Mitochondrial toxins 8560:Hydroxyquinol ethers 8555:Aromatase inhibitors 8463:12a-hydroxyelliptone 8433:6-Deoxyclitoriacetal 8380:Rotenoids and their 7045:WAY-204688 (SIM-688) 6857:ERB-196 (WAY-202196) 6808:Dienestrol diacetate 6547:Estrone methyl ether 6453:Esterified estrogens 6395:Conjugated estrogens 6288:17β-Dihydroequilenin 6263:17α-Dihydroequilenin 6203:15α-Hydroxyestradiol 6198:11β-Methoxyestradiol 6173:8,9-Dehydroestradiol 5374:Potassium canrenoate 4842:Quingestanol acetate 4652:Tetrahydrogestrinone 4540:Metenolone enanthate 4366:5α-Dihydrotrestolone 4361:5α-Dihydronandrolone 4349:Trestolone enanthate 4317:Trenbolone enanthate 4283:Norclostebol acetate 3892:Clostebol propionate 3465:Oxidopamine (6-OHDA) 3387:Oxidopamine (6-OHDA) 3377:-Methylnorsalsolinol 3189:Chemical Description 3184:Rotenone at Bioblast 2383:10.1038/jcbfm.2009.4 1979:, summary in English 1712:Hayes W. J. (1991). 1545:10.1139/er-2018-0049 1358:environmental toxins 1326:dopaminergic neurons 1154:Tephrosia virginiana 1018:Stormy Lake (Alaska) 867:cellular respiration 536:25 mg/kg (oral, rat) 532:60 mg/kg (oral, rat) 89:Tubatoxin, Paraderil 8605:Parkinson's disease 8212:Propylpyrazoletriol 8127:Diarylpropionitrile 6975:Propylpyrazoletriol 6832:Dimethylstilbestrol 6798:Diarylpropionitrile 6608:Etynodiol diacetate 6308:Abiraterone acetate 6218:16α-Fluoroestradiol 5897:Dihydrotestosterone 5892:Dehydroandrosterone 5743:Ralaniten (EPI-002) 5624:Inocoterone acetate 5349:Nomegestrol acetate 5249:Delmadinone acetate 5239:Cyproterone acetate 5184:Abiraterone acetate 5154:7α-Thioprogesterone 4764:Etynodiol diacetate 3968:Testosterone esters 3911:Dehydroandrosterone 3808:11-Ketotestosterone 3587:MDA (tenamfetamine) 3518:4-CAB (α-ethyl-PCA) 3460:MDA (tenamfetamine) 3093:2010PLoSO...5.8762P 2879:10.1289/ehp.1002839 2767:2018ToxAP.354..101P 2643:2012Toxgy.300..132L 2423:2017NatSR...745465H 2277:Curr Protoc Toxicol 2214:. Oregon Live LLC. 2103:2010Fish...35...61V 1785:Telegraph Gardening 1696:10.1021/cr60042a001 1631:. ASNOM. 2008-01-02 1615:10.1021/ie50319a017 1555:, summary in French 1429:blood–brain barrier 1416:protein aggregation 1338:Parkinson's disease 1332:Parkinson's disease 1252:Several species of 1240:) – southern Africa 1172:Lonchocarpus utilis 1113:, which can damage 1066:Mechanism of action 967:In September 2010, 422: g·mol 18: 8585:Respiratory toxins 8294:Diethylstilbestrol 8078:2-Methoxyestradiol 8009:TAS-108 (SR-16234) 7959:Methylepitiostanol 7897:EM-800 (SCH-57050) 7821:TAS-108 (SR-16234) 7541:2-Phenylbenzofuran 7155:8-prenylnaringenin 6815:Diethylstilbestrol 6473:Lipoidal estradiol 6448:ERA-63 (ORG-37663) 6390:Conjugated estriol 6335:methyltestosterone 6293:17β-Dihydroequilin 6268:17α-Dihydroequilin 6243:16β-Hydroxyestrone 6228:16α-Hydroxyestrone 6178:8,9-Dehydroestrone 6163:7α-Methylestradiol 6138:4-Methoxyestradiol 6128:4-Hydroxyestradiol 6103:3β-Hydroxytibolone 6098:3α-Hydroxytibolone 6068:2-Hydroxyestradiol 4734:Dihydroethisterone 4597:Dimethyltrienolone 4557:Methylepitiostanol 4535:Metenolone acetate 4468:Methyltestosterone 4371:19-Norandrosterone 4344:Trestolone acetate 4312:Trenbolone acetate 4256:-nitrosocarbamate) 4145:Stenbolone acetate 4035:Bolazine capronate 3887:Clostebol caproate 3255:-Cysteinyldopamine 3169:Rotenone Factsheet 3152:2007-06-09 at the 2411:Scientific Reports 1954:. 10 January 2023. 1450:NADH dehydrogenase 1427:and can cross the 1272:Mammalian toxicity 1246:Piscidia piscipula 1189:) – South America 1186:Lonchocarpus urucu 1175:) – South America 1163:Pachyrhizus erosus 1128:Presence in plants 1025:Mountain Lake Park 952:and its connected 874:alien fish species 855:indigenous peoples 760:Use as insecticide 663:alien fish species 624:Infobox references 583:(Immediate danger) 16: 8532: 8531: 8347: 8346: 8339:List of estrogens 8307: 8306: 8052: 8051: 7892:Cytestrol acetate 7115:isoliquiritigenin 7057:Unknown/unsorted: 6743:β-LGND2 (GTx-878) 6323:Anabolic steroids 6233:16α-Iodoestradiol 6123:4-Fluoroestradiol 6118:4-Androstenedione 6108:3β-Androstanediol 6083:3α-Androstanediol 6034:Estrogen receptor 6000: 5999: 5960: 5959: 5930: 5923: 5916: 5909: 5841: 5840: 5364:Osaterone acetate 5324:Megestrol acetate 5189:Allyltestosterone 4965:Acetothiolutamide 4884:Megestrol acetate 4687:Vinyltestosterone 4592:Dimethyldienolone 4411:Ethyltestosterone 4339:Trestolone (MENT) 4271:Nandrolone esters 4252:-(2-chloroethyl)- 4128:Nisterime acetate 4005:3α-Androstanediol 3990:1-Androstenedione 3899:Cloxotestosterone 3882:Clostebol acetate 3803:5-Androstenedione 3749:Androgen receptor 3715: 3714: 3710: 3547:-Dimethyldopamine 3538:α-Me-DA (3,4-DHA) 2828:10.1021/tx049867r 2604:978-92-4-154663-8 2569:978-0-08-091283-7 2529:978-0-86977-081-8 2479:10.1021/jf981188x 2467:J Agric Food Chem 2431:10.1038/srep45465 2256:. SFGate / Hearst 2240:Peninsula Clarion 2235:Earl, Elizabeth, 2040:978-82-326-6270-8 1976:978-82-426-4950-8 1911:978-1-934874-49-3 1846:10.1021/jf801461h 1840:(17): 8066–8073. 1729:978-0-12-334161-7 1228:Verbascum thapsus 1166:) – North America 1157:) – North America 1046:(a mitochondrial 1005:who used them as 942:Miami-Dade County 839:asparagus beetles 835:raspberry beetles 716:chemical engineer 708:parasitic disease 683:Emmanuel Geoffroy 632:Chemical compound 630: 629: 306:CompTox Dashboard 136:Interactive image 8612: 8374: 8367: 8360: 8351: 8206:2,2',5'-PCB-4-OH 8142:Ethinylestradiol 8068: 8064: 8060: 7801:Rimostil (P-081) 7611:Chlorotrianisene 7533: 7529: 7308:Metalloestrogens 7087:-related (e.g., 6902:Hexestrol esters 6576:Ethinylestradiol 6468:Estradiol esters 6223:16α-Hydroxy-DHEA 6208:16-Ketoestradiol 6148:5-Androstenediol 6143:4-Methoxyestrone 6133:4-Hydroxyestrone 6113:4-Androstenediol 6073:2-Hydroxyestrone 6055: 6051: 6047: 6027: 6020: 6013: 6004: 5948: 5944: 5928: 5921: 5914: 5907: 5852: 5634:Ketodarolutamide 5614:Hydroxyflutamide 5571:(via metabolite 4940: 4936: 4891:Others/unsorted: 4562:Methylstenbolone 4426:Hydroxystenozole 3985:1-Androstenediol 3783:4-Androstenediol 3770: 3766: 3762: 3742: 3735: 3728: 3719: 3673: 3324:Dopamine quinone 3218: 3211: 3204: 3195: 3125: 3124: 3114: 3104: 3072: 3066: 3060: 3054: 3053: 3008: 3002: 3001: 2964: 2958: 2957: 2947: 2915: 2909: 2908: 2898: 2857: 2851: 2846: 2840: 2839: 2816:Chem Res Toxicol 2811: 2805: 2804: 2794: 2745: 2739: 2738: 2723: 2717: 2716: 2706: 2696: 2672: 2663: 2662: 2626: 2620: 2619: 2617: 2616: 2607:. Archived from 2580: 2574: 2573: 2549: 2543: 2540: 2534: 2533: 2511: 2505: 2504: 2497: 2491: 2490: 2462: 2453: 2452: 2442: 2402: 2396: 2395: 2385: 2361: 2355: 2354: 2342: 2336: 2335: 2333: 2326: 2315: 2309: 2308: 2272: 2266: 2265: 2263: 2261: 2249: 2243: 2233: 2227: 2226: 2224: 2223: 2203: 2197: 2196: 2194: 2192: 2186: 2163: 2154: 2148: 2147: 2145: 2121: 2115: 2114: 2086: 2080: 2079: 2051: 2045: 2044: 2026: 2020: 2019: 2017: 2011:. Archived from 2010: 2001: 1995: 1994: 1988: 1980: 1962: 1956: 1955: 1948: 1942: 1941: 1939: 1937: 1922: 1916: 1915: 1897: 1888: 1887: 1873: 1867: 1864: 1858: 1857: 1829: 1823: 1822: 1820: 1818: 1803: 1797: 1796: 1794: 1792: 1787:. 2 October 2008 1777: 1771: 1770: 1768: 1766: 1752: 1746: 1740: 1734: 1733: 1709: 1700: 1699: 1684:Chemical Reviews 1679: 1673: 1672: 1670: 1646: 1640: 1639: 1637: 1636: 1625: 1619: 1618: 1594: 1588: 1587: 1577: 1571: 1570: 1564: 1556: 1530: 1521: 1512: 1511: 1496: 1490: 1489: 1477: 1408:substantia nigra 1392:substantia nigra 1354:chronic exposure 1237:Mundulea sericea 1225:Common Mullein ( 1200:Derris elliptica 899:Topmouth gudgeon 887:Topmouth gudgeon 849:Use as piscicide 823:cucumber beetles 750: 748: 747: 741: 735: 725:Derris elliptica 685:, who called it 614: 608: 605: 604: 421: 406: 400: 394: 387:Chemical formula 330: 329: 314: 312: 296: 276: 265: 254: 237: 220: 209: 198: 178: 158: 138: 114: 35: 26: 19: 8620: 8619: 8615: 8614: 8613: 8611: 8610: 8609: 8535: 8534: 8533: 8528: 8512: 8413:Dehydrodeguelin 8384: 8378: 8348: 8343: 8303: 8282: 8246: 8062: 8048: 7882:7β-Hydroxy-DHEA 7865: 7701:Levormeloxifene 7531: 7524: 7518: 7434:deoxymiroestrol 7302:-hinokiresinol) 6940:Methallenestril 6842:Doisynolic acid 6643:Methylestradiol 6158:7α-Hydroxy-DHEA 6049: 6039: 6031: 6001: 5996: 5956: 5946: 5837: 5559:Cyanonilutamide 5488:Bavdegalutamide 5299:Epitestosterone 5139: 4970:Acetoxolutamide 4938: 4928: 4637:Norethandrolone 4612:Methyldienolone 4416:Fluoxymesterone 4226:Dimethandrolone 4086:Epiandrosterone 3764: 3754: 3746: 3716: 3711: 3667: 3641: 3617:Norfenfluramine 3607:Methamphetamine 3474: 3411: 3364:MPP (cyperquat) 3359:Methamphetamine 3270:ALDH inhibitors 3227: 3222: 3154:Wayback Machine 3134: 3129: 3128: 3074: 3073: 3069: 3061: 3057: 3010: 3009: 3005: 2976:(10): 1849–59. 2966: 2965: 2961: 2917: 2916: 2912: 2859: 2858: 2854: 2847: 2843: 2813: 2812: 2808: 2747: 2746: 2742: 2731:Pesticides News 2725: 2724: 2720: 2674: 2673: 2666: 2628: 2627: 2623: 2614: 2612: 2611:on July 8, 2004 2605: 2582: 2581: 2577: 2570: 2551: 2550: 2546: 2541: 2537: 2530: 2513: 2512: 2508: 2499: 2498: 2494: 2464: 2463: 2456: 2404: 2403: 2399: 2363: 2362: 2358: 2344: 2343: 2339: 2331: 2324: 2317: 2316: 2312: 2274: 2273: 2269: 2259: 2257: 2251: 2250: 2246: 2234: 2230: 2221: 2219: 2205: 2204: 2200: 2190: 2188: 2184: 2161: 2156: 2155: 2151: 2143:10.1641/B580211 2123: 2122: 2118: 2088: 2087: 2083: 2053: 2052: 2048: 2041: 2028: 2027: 2023: 2015: 2008: 2003: 2002: 1998: 1981: 1977: 1964: 1963: 1959: 1950: 1949: 1945: 1935: 1933: 1924: 1923: 1919: 1912: 1899: 1898: 1891: 1875: 1874: 1870: 1865: 1861: 1831: 1830: 1826: 1816: 1814: 1805: 1804: 1800: 1790: 1788: 1779: 1778: 1774: 1764: 1762: 1754: 1753: 1749: 1741: 1737: 1730: 1718:. Vol. 1. 1711: 1710: 1703: 1681: 1680: 1676: 1657:(in Japanese). 1648: 1647: 1643: 1634: 1632: 1627: 1626: 1622: 1596: 1595: 1591: 1579: 1578: 1574: 1557: 1528: 1523: 1522: 1515: 1498: 1497: 1493: 1479: 1478: 1463: 1458: 1441: 1366:protective gear 1334: 1274: 1214:Derris involuta 1130: 1068: 1056: 988:fathead minnows 962:Central Florida 938:jaguar cichlids 930: 905:) and Hungary ( 851: 795:on humans, and 762: 757: 742: 730:Min Nan Chinese 699:Deguelia utilis 671: 633: 626: 621: 620: 619:  ?) 610: 606: 602: 598: 584: 571: 558: 537: 535: 533: 529: 523: 419: 409: 403: 397: 389: 375: 372: 367: 366: 355: 352: 351: 345: 344: 333: 315: 308: 299: 279: 266: 240: 201: 181: 161: 141: 128: 117: 104: 90: 82: 81: 54: 12: 11: 5: 8618: 8616: 8608: 8607: 8602: 8597: 8592: 8587: 8582: 8577: 8572: 8567: 8562: 8557: 8552: 8547: 8537: 8536: 8530: 8529: 8527: 8526: 8520: 8518: 8514: 8513: 8511: 8510: 8505: 8500: 8495: 8490: 8485: 8480: 8475: 8470: 8465: 8460: 8455: 8450: 8445: 8440: 8435: 8430: 8425: 8420: 8415: 8410: 8405: 8400: 8394: 8392: 8386: 8385: 8379: 8377: 8376: 8369: 8362: 8354: 8345: 8344: 8342: 8341: 8336: 8331: 8326: 8321: 8316: 8312: 8309: 8308: 8305: 8304: 8302: 8301: 8296: 8290: 8288: 8284: 8283: 8281: 8280: 8275: 8270: 8265: 8260: 8254: 8252: 8248: 8247: 8245: 8244: 8239: 8234: 8229: 8224: 8219: 8214: 8209: 8199: 8194: 8189: 8184: 8179: 8174: 8172:Hydroxytyrosol 8169: 8164: 8159: 8154: 8149: 8144: 8139: 8134: 8129: 8124: 8110: 8105: 8100: 8095: 8090: 8085: 8080: 8074: 8072: 8065: 8054: 8053: 8050: 8049: 8047: 8046: 8037: 8036: 8027: 8026: 8021: 8016: 8011: 8006: 8001: 7996: 7991: 7986: 7981: 7976: 7971: 7966: 7961: 7956: 7951: 7946: 7941: 7919: 7914: 7909: 7904: 7899: 7894: 7889: 7887:Chloroindazole 7884: 7879: 7873: 7871: 7867: 7866: 7864: 7863: 7858: 7853: 7848: 7843: 7838: 7833: 7828: 7823: 7818: 7813: 7808: 7806:Spironolactone 7803: 7798: 7793: 7788: 7783: 7778: 7773: 7768: 7763: 7758: 7753: 7748: 7743: 7738: 7733: 7728: 7723: 7718: 7713: 7708: 7703: 7698: 7693: 7688: 7683: 7678: 7673: 7668: 7663: 7658: 7653: 7648: 7643: 7638: 7633: 7628: 7623: 7618: 7613: 7608: 7603: 7598: 7593: 7588: 7583: 7578: 7573: 7568: 7563: 7558: 7553: 7548: 7543: 7537: 7535: 7520: 7519: 7517: 7516: 7507:Others (e.g., 7505: 7455: 7441: 7427: 7397: 7379: 7357: 7315: 7305: 7283: 7278: 7235:liquiritigenin 7144: 7130: 7108: 7082:Xenoestrogens: 7078: 7077: 7072: 7067: 7062: 7053: 7052: 7047: 7042: 7037: 7032: 7027: 7022: 7017: 7012: 7007: 7002: 6997: 6992: 6987: 6982: 6977: 6972: 6967: 6962: 6957: 6955:Paroxypropione 6952: 6947: 6942: 6937: 6932: 6924: 6916: 6911: 6906: 6905: 6904: 6894: 6889: 6884: 6879: 6874: 6869: 6867:Estrobin (DBE) 6864: 6859: 6854: 6849: 6844: 6839: 6834: 6829: 6824: 6823: 6822: 6812: 6811: 6810: 6800: 6795: 6790: 6785: 6780: 6775: 6770: 6765: 6760: 6758:Allenolic acid 6755: 6750: 6745: 6740: 6735: 6730: 6725: 6716: 6715: 6710: 6705: 6700: 6695: 6690: 6685: 6680: 6675: 6670: 6665: 6663:Norethisterone 6660: 6655: 6653:Mytatrienediol 6650: 6645: 6640: 6635: 6630: 6625: 6620: 6615: 6610: 6605: 6600: 6598:Ethylestradiol 6595: 6593:Ethinylestriol 6590: 6589: 6588: 6583: 6573: 6572: 6571: 6561: 6556: 6555: 6554: 6549: 6544: 6542:Estrone esters 6534: 6529: 6524: 6519: 6518: 6517: 6512: 6510:Estriol esters 6502: 6497: 6495:Estrapronicate 6492: 6487: 6482: 6481: 6480: 6475: 6470: 6460: 6455: 6450: 6445: 6440: 6435: 6430: 6425: 6417: 6412: 6407: 6402: 6397: 6392: 6387: 6386: 6385: 6375: 6370: 6365: 6360: 6355: 6350: 6320: 6315: 6313:Alestramustine 6310: 6305: 6300: 6295: 6290: 6285: 6280: 6275: 6270: 6265: 6260: 6250: 6245: 6240: 6235: 6230: 6225: 6220: 6215: 6213:16-Ketoestrone 6210: 6205: 6200: 6195: 6190: 6185: 6180: 6175: 6170: 6165: 6160: 6155: 6150: 6145: 6140: 6135: 6130: 6125: 6120: 6115: 6110: 6105: 6100: 6095: 6090: 6085: 6080: 6075: 6070: 6061: 6059: 6052: 6041: 6040: 6032: 6030: 6029: 6022: 6015: 6007: 5998: 5997: 5995: 5994: 5989: 5984: 5979: 5974: 5969: 5965: 5962: 5961: 5958: 5957: 5955: 5954: 5949: 5939: 5934: 5910:-α-Amino acids 5904: 5899: 5894: 5889: 5858: 5856: 5849: 5843: 5842: 5839: 5838: 5836: 5835: 5830: 5825: 5820: 5815: 5810: 5805: 5800: 5795: 5790: 5785: 5780: 5775: 5770: 5765: 5760: 5755: 5750: 5745: 5740: 5735: 5730: 5725: 5720: 5715: 5710: 5705: 5700: 5695: 5687: 5679: 5671: 5666: 5661: 5656: 5651: 5646: 5641: 5636: 5631: 5626: 5621: 5616: 5611: 5606: 5601: 5596: 5591: 5586: 5581: 5576: 5566: 5561: 5556: 5551: 5546: 5541: 5536: 5531: 5526: 5500: 5495: 5490: 5485: 5480: 5475: 5470: 5465: 5460: 5455: 5450: 5437: 5436: 5431: 5426: 5421: 5416: 5411: 5406: 5404:Spironolactone 5401: 5396: 5391: 5386: 5381: 5376: 5371: 5366: 5361: 5356: 5351: 5346: 5341: 5336: 5331: 5326: 5321: 5316: 5311: 5306: 5301: 5296: 5291: 5286: 5281: 5276: 5271: 5266: 5261: 5256: 5251: 5246: 5241: 5236: 5231: 5229:Cyproheptadine 5226: 5221: 5216: 5211: 5206: 5204:Canrenoic acid 5201: 5196: 5191: 5186: 5181: 5176: 5171: 5166: 5161: 5156: 5147: 5145: 5141: 5140: 5138: 5137: 5132: 5127: 5122: 5113: 5112: 5107: 5102: 5097: 5092: 5087: 5082: 5077: 5072: 5067: 5062: 5057: 5052: 5047: 5042: 5037: 5032: 5027: 5022: 5017: 5012: 5007: 5002: 4997: 4992: 4987: 4982: 4977: 4972: 4967: 4962: 4957: 4952: 4943: 4941: 4930: 4929: 4927: 4926: 4921: 4916: 4911: 4906: 4901: 4896: 4887: 4886: 4881: 4876: 4867: 4866: 4861: 4852: 4851: 4846: 4845: 4844: 4834: 4832:Norgestrienone 4829: 4824: 4810: 4808:Norethisterone 4805: 4804: 4803: 4793: 4783: 4781:Levonorgestrel 4778: 4773: 4768: 4767: 4766: 4756: 4751: 4746: 4737: 4736: 4731: 4726: 4717: 4716: 4711: 4710: 4709: 4699: 4690: 4689: 4680: 4679: 4670: 4669: 4664: 4655: 4654: 4649: 4644: 4639: 4634: 4629: 4624: 4619: 4614: 4609: 4604: 4602:Ethyldienolone 4599: 4594: 4589: 4580: 4579: 4574: 4569: 4564: 4559: 4554: 4549: 4544: 4543: 4542: 4537: 4527: 4522: 4517: 4512: 4507: 4505:Androisoxazole 4498: 4497: 4492: 4487: 4482: 4481: 4480: 4465: 4460: 4459: 4458: 4453: 4448: 4443: 4433: 4428: 4423: 4418: 4413: 4408: 4403: 4398: 4393: 4388: 4383: 4374: 4373: 4368: 4363: 4354: 4353: 4352: 4351: 4346: 4336: 4331: 4330: 4329: 4324: 4319: 4314: 4304: 4303: 4302: 4292: 4287: 4286: 4285: 4275: 4274: 4273: 4263: 4258: 4245: 4244: 4243: 4238: 4233: 4223: 4218: 4213: 4208: 4203: 4202: 4201: 4191: 4186: 4181: 4176: 4175: 4174: 4164: 4155: 4154: 4149: 4148: 4147: 4137: 4132: 4131: 4130: 4120: 4118:Methyldiazinol 4115: 4114: 4113: 4103: 4098: 4093: 4088: 4083: 4082: 4081: 4071: 4070: 4069: 4054: 4049: 4044: 4039: 4038: 4037: 4027: 4022: 4017: 4012: 4007: 4002: 4000:1-Testosterone 3997: 3992: 3987: 3978: 3977: 3976: 3975: 3970: 3955: 3950: 3945: 3940: 3935: 3930: 3929: 3928: 3923: 3913: 3908: 3907: 3906: 3896: 3895: 3894: 3889: 3884: 3874: 3869: 3868: 3867: 3857: 3852: 3847: 3846: 3845: 3840: 3835: 3830: 3820: 3815: 3810: 3805: 3800: 3795: 3790: 3785: 3776: 3774: 3767: 3756: 3755: 3747: 3745: 3744: 3737: 3730: 3722: 3713: 3712: 3672: 3669: 3668: 3666: 3665: 3660: 3655: 3649: 3647: 3643: 3642: 3640: 3639: 3634: 3629: 3624: 3619: 3614: 3609: 3604: 3599: 3594: 3589: 3584: 3579: 3574: 3569: 3564: 3559: 3554: 3549: 3540: 3535: 3530: 3525: 3520: 3515: 3510: 3505: 3500: 3495: 3490: 3484: 3482: 3476: 3475: 3473: 3472: 3467: 3462: 3457: 3452: 3447: 3442: 3437: 3432: 3427: 3421: 3419: 3413: 3412: 3410: 3409: 3404: 3399: 3394: 3389: 3384: 3379: 3371: 3366: 3361: 3356: 3351: 3346: 3341: 3336: 3331: 3326: 3321: 3316: 3311: 3306: 3301: 3296: 3291: 3286: 3281: 3267: 3265:6-OHDA quinone 3262: 3257: 3248: 3243: 3237: 3235: 3229: 3228: 3223: 3221: 3220: 3213: 3206: 3198: 3192: 3191: 3186: 3181: 3176: 3171: 3166: 3161: 3156: 3144: 3133: 3132:External links 3130: 3127: 3126: 3067: 3055: 3003: 2959: 2930:(15): 6181–7. 2910: 2852: 2841: 2822:(11): 1540–8. 2806: 2740: 2737:: 20–21. 2001. 2718: 2694:10.1186/cc3528 2664: 2621: 2603: 2575: 2568: 2544: 2535: 2528: 2506: 2492: 2454: 2397: 2376:(6): 1069–78. 2356: 2337: 2310: 2267: 2244: 2228: 2198: 2149: 2116: 2081: 2046: 2039: 2021: 2018:on 2012-09-04. 2004:Kevin C. Ott. 1996: 1975: 1957: 1943: 1917: 1910: 1889: 1868: 1859: 1824: 1798: 1772: 1747: 1735: 1728: 1720:Academic Press 1701: 1690:(2): 181–213. 1674: 1661:(7): 744–777. 1641: 1620: 1609:(7): 815–821. 1589: 1572: 1513: 1491: 1460: 1459: 1457: 1454: 1453: 1452: 1447: 1440: 1437: 1420:rhesus monkeys 1333: 1330: 1273: 1270: 1269: 1268: 1250: 1241: 1232: 1223: 1222: 1221: 1209: 1208: 1207: 1195: 1194: 1193: 1181: 1180: 1179: 1167: 1158: 1129: 1126: 1067: 1064: 1055: 1052: 995:Panguitch Lake 929: 926: 922:carbon dioxide 850: 847: 819:potato beetles 761: 758: 756: 753: 670: 667: 631: 628: 627: 622: 600: 599: 595:standard state 592: 589: 588: 585: 579: 576: 575: 572: 566: 563: 562: 559: 553: 550: 549: 540: 539: 530: 521: 519: 516: 515: 508: 507: 503: 502: 499: 497:Vapor pressure 493: 492: 478: 472: 471: 468: 462: 461: 458: 452: 451: 448: 442: 441: 438: 432: 431: 428: 424: 423: 417: 411: 410: 407: 401: 395: 390: 385: 382: 381: 377: 376: 374: 373: 370: 362: 361: 360: 357: 356: 354: 353: 349: 348: 340: 339: 338: 335: 334: 332: 331: 318: 316: 304: 301: 300: 298: 297: 289: 287: 281: 280: 278: 277: 269: 267: 259: 256: 255: 248: 242: 241: 239: 238: 230: 228: 222: 221: 211: 203: 202: 200: 199: 191: 189: 183: 182: 180: 179: 171: 169: 163: 162: 160: 159: 151: 149: 143: 142: 140: 139: 131: 129: 122: 119: 118: 116: 115: 107: 105: 100: 97: 96: 92: 91: 88: 84: 83: 63: 62: 56: 55: 48: 42: 41: 37: 36: 28: 27: 13: 10: 9: 6: 4: 3: 2: 8617: 8606: 8603: 8601: 8598: 8596: 8593: 8591: 8588: 8586: 8583: 8581: 8578: 8576: 8573: 8571: 8568: 8566: 8563: 8561: 8558: 8556: 8553: 8551: 8548: 8546: 8543: 8542: 8540: 8525: 8522: 8521: 8519: 8515: 8509: 8506: 8504: 8501: 8499: 8496: 8494: 8491: 8489: 8486: 8484: 8481: 8479: 8476: 8474: 8471: 8469: 8466: 8464: 8461: 8459: 8456: 8454: 8451: 8449: 8446: 8444: 8441: 8439: 8436: 8434: 8431: 8429: 8426: 8424: 8421: 8419: 8416: 8414: 8411: 8409: 8406: 8404: 8403:Clitoriacetal 8401: 8399: 8396: 8395: 8393: 8391: 8387: 8383: 8375: 8370: 8368: 8363: 8361: 8356: 8355: 8352: 8340: 8337: 8335: 8332: 8330: 8327: 8325: 8322: 8320: 8317: 8314: 8313: 8310: 8300: 8297: 8295: 8292: 8291: 8289: 8285: 8279: 8276: 8274: 8271: 8269: 8266: 8264: 8261: 8259: 8256: 8255: 8253: 8249: 8243: 8240: 8238: 8235: 8233: 8230: 8228: 8225: 8223: 8220: 8218: 8215: 8213: 8210: 8207: 8203: 8200: 8198: 8195: 8193: 8190: 8188: 8185: 8183: 8180: 8178: 8175: 8173: 8170: 8168: 8165: 8163: 8160: 8158: 8155: 8153: 8150: 8148: 8145: 8143: 8140: 8138: 8135: 8133: 8130: 8128: 8125: 8122: 8118: 8114: 8111: 8109: 8106: 8104: 8101: 8099: 8096: 8094: 8091: 8089: 8086: 8084: 8081: 8079: 8076: 8075: 8073: 8069: 8066: 8061: 8055: 8045: 8042: 8039: 8038: 8035: 8032: 8029: 8028: 8025: 8022: 8020: 8017: 8015: 8012: 8010: 8007: 8005: 8002: 8000: 7997: 7995: 7992: 7990: 7987: 7985: 7982: 7980: 7977: 7975: 7972: 7970: 7967: 7965: 7962: 7960: 7957: 7955: 7952: 7950: 7947: 7945: 7942: 7939: 7935: 7931: 7927: 7923: 7920: 7918: 7915: 7913: 7910: 7908: 7905: 7903: 7900: 7898: 7895: 7893: 7890: 7888: 7885: 7883: 7880: 7878: 7875: 7874: 7872: 7868: 7862: 7859: 7857: 7854: 7852: 7849: 7847: 7844: 7842: 7839: 7837: 7834: 7832: 7829: 7827: 7824: 7822: 7819: 7817: 7814: 7812: 7809: 7807: 7804: 7802: 7799: 7797: 7794: 7792: 7789: 7787: 7786:Pipendoxifene 7784: 7782: 7779: 7777: 7774: 7772: 7769: 7767: 7764: 7762: 7759: 7757: 7754: 7752: 7749: 7747: 7744: 7742: 7739: 7737: 7734: 7732: 7729: 7727: 7724: 7722: 7719: 7717: 7714: 7712: 7709: 7707: 7704: 7702: 7699: 7697: 7694: 7692: 7689: 7687: 7684: 7682: 7679: 7677: 7674: 7672: 7669: 7667: 7664: 7662: 7659: 7657: 7654: 7652: 7649: 7647: 7644: 7642: 7639: 7637: 7634: 7632: 7629: 7627: 7624: 7622: 7621:Clomifenoxide 7619: 7617: 7614: 7612: 7609: 7607: 7604: 7602: 7599: 7597: 7596:Brilanestrant 7594: 7592: 7589: 7587: 7584: 7582: 7579: 7577: 7574: 7572: 7569: 7567: 7564: 7562: 7559: 7557: 7554: 7552: 7549: 7547: 7544: 7542: 7539: 7538: 7536: 7530: 7521: 7514: 7510: 7506: 7503: 7499: 7495: 7491: 7487: 7483: 7479: 7475: 7471: 7467: 7463: 7459: 7456: 7453: 7449: 7445: 7442: 7439: 7435: 7432:-like (e.g., 7431: 7428: 7425: 7421: 7417: 7413: 7409: 7405: 7401: 7398: 7395: 7391: 7387: 7383: 7380: 7377: 7376:guggulsterone 7373: 7369: 7365: 7361: 7360:Phytosteroids 7358: 7355: 7351: 7347: 7343: 7339: 7335: 7331: 7327: 7323: 7319: 7316: 7313: 7309: 7306: 7303: 7301: 7295: 7294:enterolactone 7291: 7287: 7284: 7282: 7279: 7276: 7272: 7268: 7264: 7260: 7256: 7252: 7248: 7244: 7240: 7236: 7232: 7228: 7224: 7220: 7216: 7212: 7208: 7204: 7200: 7196: 7192: 7188: 7184: 7180: 7176: 7172: 7168: 7164: 7160: 7156: 7152: 7148: 7145: 7142: 7138: 7134: 7131: 7128: 7127:wedelolactone 7124: 7120: 7116: 7112: 7109: 7106: 7105:photoanethole 7102: 7098: 7094: 7090: 7086: 7083: 7080: 7079: 7076: 7073: 7071: 7068: 7066: 7063: 7061: 7058: 7055: 7054: 7051: 7048: 7046: 7043: 7041: 7038: 7036: 7033: 7031: 7028: 7026: 7023: 7021: 7018: 7016: 7013: 7011: 7008: 7006: 7003: 7001: 6998: 6996: 6993: 6991: 6988: 6986: 6983: 6981: 6978: 6976: 6973: 6971: 6968: 6966: 6963: 6961: 6960:Pentafluranol 6958: 6956: 6953: 6951: 6948: 6946: 6943: 6941: 6938: 6936: 6933: 6931: 6929: 6925: 6923: 6921: 6917: 6915: 6912: 6910: 6907: 6903: 6900: 6899: 6898: 6895: 6893: 6890: 6888: 6885: 6883: 6880: 6878: 6875: 6873: 6870: 6868: 6865: 6863: 6860: 6858: 6855: 6853: 6850: 6848: 6845: 6843: 6840: 6838: 6835: 6833: 6830: 6828: 6825: 6821: 6818: 6817: 6816: 6813: 6809: 6806: 6805: 6804: 6801: 6799: 6796: 6794: 6791: 6789: 6786: 6784: 6781: 6779: 6776: 6774: 6771: 6769: 6766: 6764: 6761: 6759: 6756: 6754: 6751: 6749: 6746: 6744: 6741: 6739: 6736: 6734: 6731: 6729: 6726: 6724: 6721: 6720:Nonsteroidal: 6718: 6717: 6714: 6711: 6709: 6706: 6704: 6701: 6699: 6696: 6694: 6691: 6689: 6686: 6684: 6681: 6679: 6676: 6674: 6671: 6669: 6666: 6664: 6661: 6659: 6656: 6654: 6651: 6649: 6646: 6644: 6641: 6639: 6636: 6634: 6631: 6629: 6626: 6624: 6621: 6619: 6616: 6614: 6611: 6609: 6606: 6604: 6601: 6599: 6596: 6594: 6591: 6587: 6584: 6582: 6579: 6578: 6577: 6574: 6570: 6569:Ethandrostate 6567: 6566: 6565: 6562: 6560: 6557: 6553: 6550: 6548: 6545: 6543: 6540: 6539: 6538: 6535: 6533: 6530: 6528: 6525: 6523: 6520: 6516: 6513: 6511: 6508: 6507: 6506: 6503: 6501: 6498: 6496: 6493: 6491: 6488: 6486: 6483: 6479: 6476: 6474: 6471: 6469: 6466: 6465: 6464: 6461: 6459: 6456: 6454: 6451: 6449: 6446: 6444: 6441: 6439: 6436: 6434: 6431: 6429: 6426: 6424: 6422: 6418: 6416: 6413: 6411: 6408: 6406: 6403: 6401: 6398: 6396: 6393: 6391: 6388: 6384: 6381: 6380: 6379: 6378:Cloxestradiol 6376: 6374: 6371: 6369: 6366: 6364: 6361: 6359: 6356: 6354: 6351: 6348: 6344: 6340: 6336: 6332: 6328: 6324: 6321: 6319: 6316: 6314: 6311: 6309: 6306: 6304: 6301: 6299: 6296: 6294: 6291: 6289: 6286: 6284: 6281: 6279: 6276: 6274: 6271: 6269: 6266: 6264: 6261: 6258: 6254: 6253:17α-Estradiol 6251: 6249: 6246: 6244: 6241: 6239: 6236: 6234: 6231: 6229: 6226: 6224: 6221: 6219: 6216: 6214: 6211: 6209: 6206: 6204: 6201: 6199: 6196: 6194: 6191: 6189: 6186: 6184: 6181: 6179: 6176: 6174: 6171: 6169: 6166: 6164: 6161: 6159: 6156: 6154: 6151: 6149: 6146: 6144: 6141: 6139: 6136: 6134: 6131: 6129: 6126: 6124: 6121: 6119: 6116: 6114: 6111: 6109: 6106: 6104: 6101: 6099: 6096: 6094: 6091: 6089: 6086: 6084: 6081: 6079: 6076: 6074: 6071: 6069: 6066: 6063: 6062: 6060: 6056: 6053: 6048: 6042: 6038: 6035: 6028: 6023: 6021: 6016: 6014: 6009: 6008: 6005: 5993: 5990: 5988: 5985: 5983: 5980: 5978: 5975: 5973: 5970: 5967: 5966: 5963: 5953: 5950: 5945: 5940: 5938: 5935: 5932: 5925: 5918: 5911: 5905: 5903: 5900: 5898: 5895: 5893: 5890: 5887: 5883: 5879: 5875: 5871: 5867: 5863: 5860: 5859: 5857: 5853: 5850: 5848: 5844: 5834: 5831: 5829: 5826: 5824: 5821: 5819: 5816: 5814: 5813:Valproic acid 5811: 5809: 5806: 5804: 5801: 5799: 5796: 5794: 5791: 5789: 5786: 5784: 5781: 5779: 5776: 5774: 5771: 5769: 5766: 5764: 5761: 5759: 5758:Rezvilutamide 5756: 5754: 5751: 5749: 5746: 5744: 5741: 5739: 5736: 5734: 5733:Proxalutamide 5731: 5729: 5726: 5724: 5721: 5719: 5716: 5714: 5711: 5709: 5706: 5704: 5701: 5699: 5696: 5694: 5692: 5688: 5686: 5684: 5680: 5678: 5676: 5672: 5670: 5667: 5665: 5662: 5660: 5657: 5655: 5652: 5650: 5647: 5645: 5642: 5640: 5637: 5635: 5632: 5630: 5627: 5625: 5622: 5620: 5617: 5615: 5612: 5610: 5607: 5605: 5602: 5600: 5597: 5595: 5592: 5590: 5587: 5585: 5582: 5580: 5577: 5574: 5570: 5567: 5565: 5562: 5560: 5557: 5555: 5552: 5550: 5547: 5545: 5542: 5540: 5537: 5535: 5532: 5530: 5527: 5524: 5520: 5516: 5512: 5508: 5504: 5501: 5499: 5496: 5494: 5491: 5489: 5486: 5484: 5481: 5479: 5476: 5474: 5471: 5469: 5466: 5464: 5461: 5459: 5456: 5454: 5451: 5449: 5448:-Bicalutamide 5447: 5442: 5441:Nonsteroidal: 5439: 5438: 5435: 5432: 5430: 5427: 5425: 5422: 5420: 5417: 5415: 5412: 5410: 5407: 5405: 5402: 5400: 5397: 5395: 5392: 5390: 5387: 5385: 5382: 5380: 5377: 5375: 5372: 5370: 5367: 5365: 5362: 5360: 5357: 5355: 5352: 5350: 5347: 5345: 5342: 5340: 5337: 5335: 5332: 5330: 5327: 5325: 5322: 5320: 5317: 5315: 5312: 5310: 5309:Guggulsterone 5307: 5305: 5302: 5300: 5297: 5295: 5292: 5290: 5287: 5285: 5282: 5280: 5277: 5275: 5272: 5270: 5267: 5265: 5262: 5260: 5257: 5255: 5252: 5250: 5247: 5245: 5242: 5240: 5237: 5235: 5232: 5230: 5227: 5225: 5222: 5220: 5217: 5215: 5212: 5210: 5207: 5205: 5202: 5200: 5197: 5195: 5192: 5190: 5187: 5185: 5182: 5180: 5177: 5175: 5172: 5170: 5167: 5165: 5162: 5160: 5157: 5155: 5152: 5149: 5148: 5146: 5142: 5136: 5133: 5131: 5128: 5126: 5123: 5121: 5118: 5115: 5114: 5111: 5108: 5106: 5103: 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: 4998: 4996: 4993: 4991: 4988: 4986: 4983: 4981: 4978: 4976: 4973: 4971: 4968: 4966: 4963: 4961: 4958: 4956: 4953: 4951: 4948: 4947:Nonsteroidal: 4945: 4944: 4942: 4937: 4931: 4925: 4922: 4920: 4917: 4915: 4912: 4910: 4907: 4905: 4902: 4900: 4899:5α-Androstane 4897: 4895: 4892: 4889: 4888: 4885: 4882: 4880: 4877: 4875: 4872: 4869: 4868: 4865: 4862: 4860: 4857: 4854: 4853: 4850: 4847: 4843: 4840: 4839: 4838: 4835: 4833: 4830: 4828: 4825: 4822: 4818: 4814: 4811: 4809: 4806: 4802: 4799: 4798: 4797: 4794: 4791: 4787: 4784: 4782: 4779: 4777: 4774: 4772: 4769: 4765: 4762: 4761: 4760: 4757: 4755: 4752: 4750: 4747: 4745: 4742: 4739: 4738: 4735: 4732: 4730: 4727: 4725: 4722: 4719: 4718: 4715: 4712: 4708: 4707:Ethandrostate 4705: 4704: 4703: 4700: 4698: 4695: 4692: 4691: 4688: 4685: 4682: 4681: 4678: 4675: 4672: 4671: 4668: 4665: 4663: 4660: 4657: 4656: 4653: 4650: 4648: 4645: 4643: 4640: 4638: 4635: 4633: 4630: 4628: 4625: 4623: 4620: 4618: 4615: 4613: 4610: 4608: 4607:Ethylestrenol 4605: 4603: 4600: 4598: 4595: 4593: 4590: 4588: 4585: 4582: 4581: 4578: 4575: 4573: 4570: 4568: 4565: 4563: 4560: 4558: 4555: 4553: 4550: 4548: 4545: 4541: 4538: 4536: 4533: 4532: 4531: 4528: 4526: 4523: 4521: 4518: 4516: 4513: 4511: 4508: 4506: 4503: 4500: 4499: 4496: 4493: 4491: 4488: 4486: 4483: 4479: 4476: 4475: 4473: 4469: 4466: 4464: 4461: 4457: 4454: 4452: 4449: 4447: 4444: 4442: 4439: 4438: 4437: 4434: 4432: 4429: 4427: 4424: 4422: 4419: 4417: 4414: 4412: 4409: 4407: 4404: 4402: 4399: 4397: 4394: 4392: 4389: 4387: 4384: 4382: 4379: 4376: 4375: 4372: 4369: 4367: 4364: 4362: 4359: 4356: 4355: 4350: 4347: 4345: 4342: 4341: 4340: 4337: 4335: 4332: 4328: 4325: 4323: 4320: 4318: 4315: 4313: 4310: 4309: 4308: 4305: 4301: 4298: 4297: 4296: 4293: 4291: 4288: 4284: 4281: 4280: 4279: 4276: 4272: 4269: 4268: 4267: 4264: 4262: 4259: 4257: 4255: 4251: 4246: 4242: 4239: 4237: 4234: 4232: 4229: 4228: 4227: 4224: 4222: 4219: 4217: 4214: 4212: 4209: 4207: 4204: 4200: 4197: 4196: 4195: 4192: 4190: 4187: 4185: 4182: 4180: 4177: 4173: 4170: 4169: 4168: 4165: 4163: 4160: 4157: 4156: 4153: 4150: 4146: 4143: 4142: 4141: 4138: 4136: 4133: 4129: 4126: 4125: 4124: 4121: 4119: 4116: 4112: 4109: 4108: 4107: 4104: 4102: 4099: 4097: 4094: 4092: 4089: 4087: 4084: 4080: 4077: 4076: 4075: 4072: 4068: 4065: 4064: 4062: 4058: 4055: 4053: 4050: 4048: 4045: 4043: 4040: 4036: 4033: 4032: 4031: 4028: 4026: 4023: 4021: 4018: 4016: 4013: 4011: 4008: 4006: 4003: 4001: 3998: 3996: 3993: 3991: 3988: 3986: 3983: 3980: 3979: 3974: 3971: 3969: 3966: 3965: 3963: 3959: 3956: 3954: 3951: 3949: 3946: 3944: 3941: 3939: 3936: 3934: 3931: 3927: 3924: 3922: 3919: 3918: 3917: 3914: 3912: 3909: 3905: 3902: 3901: 3900: 3897: 3893: 3890: 3888: 3885: 3883: 3880: 3879: 3878: 3875: 3873: 3870: 3866: 3863: 3862: 3861: 3858: 3856: 3853: 3851: 3848: 3844: 3841: 3839: 3836: 3834: 3831: 3829: 3826: 3825: 3824: 3821: 3819: 3816: 3814: 3811: 3809: 3806: 3804: 3801: 3799: 3796: 3794: 3791: 3789: 3786: 3784: 3781: 3778: 3777: 3775: 3771: 3768: 3763: 3757: 3753: 3750: 3743: 3738: 3736: 3731: 3729: 3724: 3723: 3720: 3709: 3708: 3704: 3700: 3696: 3695:Serotonergics 3692: 3691:Melatonergics 3688: 3687:Dopaminergics 3684: 3680: 3677: 3670: 3664: 3661: 3659: 3656: 3654: 3651: 3650: 3648: 3644: 3638: 3635: 3633: 3630: 3628: 3625: 3623: 3620: 3618: 3615: 3613: 3610: 3608: 3605: 3603: 3600: 3598: 3595: 3593: 3590: 3588: 3585: 3583: 3580: 3578: 3575: 3573: 3570: 3568: 3565: 3563: 3560: 3558: 3555: 3553: 3550: 3548: 3546: 3541: 3539: 3536: 3534: 3531: 3529: 3526: 3524: 3521: 3519: 3516: 3514: 3511: 3509: 3506: 3504: 3501: 3499: 3496: 3494: 3491: 3489: 3488:2'-Amino-MPTP 3486: 3485: 3483: 3481: 3477: 3471: 3468: 3466: 3463: 3461: 3458: 3456: 3453: 3451: 3448: 3446: 3445:6-Hydroxydopa 3443: 3441: 3438: 3436: 3433: 3431: 3428: 3426: 3425:2'-Amino-MPTP 3423: 3422: 3420: 3418: 3417:Noradrenergic 3414: 3408: 3405: 3403: 3400: 3398: 3395: 3393: 3390: 3388: 3385: 3383: 3382:Norsalsolinol 3380: 3378: 3376: 3372: 3370: 3367: 3365: 3362: 3360: 3357: 3355: 3352: 3350: 3347: 3345: 3342: 3340: 3337: 3335: 3332: 3330: 3329:Fenpropathrin 3327: 3325: 3322: 3320: 3317: 3315: 3314:DOPAL quinone 3312: 3310: 3307: 3305: 3302: 3300: 3297: 3295: 3292: 3290: 3287: 3285: 3282: 3279: 3278:methylmercury 3275: 3271: 3268: 3266: 3263: 3261: 3258: 3256: 3254: 3249: 3247: 3244: 3242: 3239: 3238: 3236: 3234: 3230: 3226: 3219: 3214: 3212: 3207: 3205: 3200: 3199: 3196: 3190: 3187: 3185: 3182: 3180: 3177: 3175: 3172: 3170: 3167: 3165: 3162: 3160: 3157: 3155: 3151: 3148: 3145: 3143: 3139: 3136: 3135: 3131: 3122: 3118: 3113: 3108: 3103: 3098: 3094: 3090: 3086: 3082: 3078: 3071: 3068: 3064: 3059: 3056: 3051: 3047: 3043: 3039: 3035: 3031: 3027: 3023: 3019: 3015: 3007: 3004: 2999: 2995: 2991: 2987: 2983: 2979: 2975: 2971: 2963: 2960: 2955: 2951: 2946: 2941: 2937: 2933: 2929: 2925: 2921: 2914: 2911: 2906: 2902: 2897: 2892: 2888: 2884: 2880: 2876: 2873:(6): 866–72. 2872: 2868: 2864: 2856: 2853: 2850: 2845: 2842: 2837: 2833: 2829: 2825: 2821: 2817: 2810: 2807: 2802: 2798: 2793: 2788: 2784: 2780: 2776: 2772: 2768: 2764: 2760: 2756: 2752: 2744: 2741: 2736: 2732: 2728: 2722: 2719: 2714: 2710: 2705: 2700: 2695: 2690: 2687:(3): R280–4. 2686: 2682: 2681:Critical Care 2678: 2671: 2669: 2665: 2660: 2656: 2652: 2648: 2644: 2640: 2636: 2632: 2625: 2622: 2610: 2606: 2600: 2596: 2592: 2591: 2586: 2579: 2576: 2571: 2565: 2561: 2557: 2556: 2548: 2545: 2539: 2536: 2531: 2525: 2521: 2517: 2510: 2507: 2502: 2496: 2493: 2488: 2484: 2480: 2476: 2473:(5): 2130–6. 2472: 2468: 2461: 2459: 2455: 2450: 2446: 2441: 2436: 2432: 2428: 2424: 2420: 2416: 2412: 2408: 2401: 2398: 2393: 2389: 2384: 2379: 2375: 2371: 2367: 2360: 2357: 2352: 2348: 2341: 2338: 2334:on 2017-11-07 2330: 2323: 2322: 2314: 2311: 2306: 2302: 2298: 2294: 2290: 2286: 2283:: 25.2.1–16. 2282: 2278: 2271: 2268: 2255: 2248: 2245: 2241: 2238: 2232: 2229: 2217: 2213: 2212:The Oregonian 2209: 2202: 2199: 2183: 2179: 2175: 2171: 2167: 2160: 2153: 2150: 2144: 2139: 2135: 2131: 2127: 2120: 2117: 2112: 2108: 2104: 2100: 2096: 2092: 2085: 2082: 2077: 2073: 2069: 2068:11250/2630458 2065: 2061: 2057: 2050: 2047: 2042: 2036: 2032: 2025: 2022: 2014: 2007: 2000: 1997: 1992: 1986: 1978: 1972: 1968: 1961: 1958: 1953: 1947: 1944: 1932: 1928: 1921: 1918: 1913: 1907: 1903: 1896: 1894: 1890: 1885: 1884: 1879: 1872: 1869: 1863: 1860: 1855: 1851: 1847: 1843: 1839: 1835: 1828: 1825: 1813: 1809: 1802: 1799: 1786: 1782: 1776: 1773: 1761: 1757: 1751: 1748: 1744: 1739: 1736: 1731: 1725: 1721: 1717: 1716: 1708: 1706: 1702: 1697: 1693: 1689: 1685: 1678: 1675: 1669: 1664: 1660: 1656: 1652: 1645: 1642: 1630: 1624: 1621: 1616: 1612: 1608: 1604: 1600: 1593: 1590: 1585: 1584: 1576: 1573: 1568: 1562: 1554: 1550: 1546: 1542: 1538: 1534: 1527: 1520: 1518: 1514: 1509: 1505: 1501: 1495: 1492: 1487: 1483: 1476: 1474: 1472: 1470: 1468: 1466: 1462: 1455: 1451: 1448: 1446: 1445:Fenpropathrin 1443: 1442: 1438: 1436: 1432: 1430: 1426: 1421: 1417: 1413: 1409: 1404: 1401: 1396: 1393: 1389: 1386: 1382: 1378: 1373: 1371: 1367: 1363: 1359: 1355: 1351: 1347: 1343: 1339: 1329: 1327: 1323: 1322:neurotoxicant 1318: 1314: 1312: 1311: 1307: 1303: 1299: 1295: 1291: 1287: 1283: 1279: 1271: 1267: 1263: 1262: 1257: 1256: 1251: 1248: 1247: 1242: 1239: 1238: 1233: 1231: 1229: 1224: 1219: 1218: 1216: 1215: 1210: 1205: 1204: 1202: 1201: 1196: 1191: 1190: 1188: 1187: 1182: 1177: 1176: 1174: 1173: 1168: 1165: 1164: 1159: 1156: 1155: 1150: 1149: 1148: 1145: 1143: 1142: 1137: 1136: 1127: 1125: 1123: 1118: 1116: 1112: 1108: 1104: 1100: 1096: 1092: 1088: 1085: 1081: 1077: 1073: 1065: 1063: 1061: 1053: 1051: 1049: 1045: 1041: 1037: 1033: 1028: 1026: 1021: 1019: 1014: 1012: 1011:rainbow trout 1008: 1004: 1000: 996: 991: 989: 985: 981: 977: 974: 970: 965: 963: 959: 955: 951: 947: 943: 939: 935: 927: 925: 923: 919: 915: 910: 908: 907:Prussian carp 904: 900: 896: 892: 888: 883: 879: 875: 870: 868: 864: 860: 856: 848: 846: 844: 840: 836: 832: 831:cabbage worms 828: 824: 820: 815: 813: 809: 805: 801: 798: 794: 790: 785: 783: 779: 778: 774: 769: 768: 759: 754: 752: 740: 731: 727: 726: 721: 717: 713: 709: 705: 704:French Guiana 701: 700: 696:, now called 695: 693: 688: 684: 680: 676: 668: 666: 664: 660: 656: 652: 648: 644: 641: 637: 625: 618: 613: 596: 590: 586: 582: 578: 577: 573: 570:(Recommended) 569: 565: 564: 560: 557:(Permissible) 556: 552: 551: 547: 546: 541: 531: 527: 518: 517: 513: 509: 504: 500: 498: 495: 494: 491: 487: 483: 479: 477: 474: 473: 469: 467: 466:Boiling point 464: 463: 459: 457: 456:Melting point 454: 453: 449: 447: 444: 443: 439: 437: 434: 433: 429: 426: 425: 418: 416: 413: 412: 391: 388: 384: 383: 378: 369: 365: 358: 347: 343: 336: 328: 324: 323:DTXSID6021248 320: 319: 317: 307: 303: 302: 295: 291: 290: 288: 286: 283: 282: 275: 271: 270: 268: 262: 258: 257: 253: 249: 247: 244: 243: 236: 232: 231: 229: 227: 224: 223: 219: 215: 212: 210: 208:ECHA InfoCard 205: 204: 197: 193: 192: 190: 188: 185: 184: 177: 173: 172: 170: 168: 165: 164: 157: 153: 152: 150: 148: 145: 144: 137: 133: 132: 130: 126: 121: 120: 113: 109: 108: 106: 103: 99: 98: 93: 85: 79: 75: 71: 67: 61: 57: 52: 47: 43: 38: 34: 29: 25: 20: 8488:Stemonacetal 8482: 8040: 8030: 7954:Mepitiostane 7902:Epitiostanol 7771:Ormeloxifene 7696:Lasofoxifene 7606:Camizestrant 7601:Broparestrol 7591:Bazedoxifene 7513:rotundifuran 7462:alkylphenols 7412:β-zearalenol 7408:α-zearalenol 7394:stigmasterol 7386:β-sitosterol 7382:Phytosterols 7350:triclocarban 7346:methoxychlor 7299: 7281:Lavender oil 7275:tectorigenin 7207:formononetin 7081: 7056: 6927: 6919: 6719: 6703:Quinestradol 6693:Promestriene 6668:Noretynodrel 6532:Estromustine 6485:Estramustine 6420: 6327:testosterone 6064: 5952:Testosterone 5738:Pyrilutamide 5690: 5682: 5674: 5639:Lavender oil 5629:Ketoconazole 5594:Enzalutamide 5564:Darolutamide 5498:Bicalutamide 5473:Atraric acid 5445: 5440: 5424:Trimegestone 5379:Promegestone 5344:Mifepristone 5319:Medrogestone 5264:Drospirenone 5219:Clascoterone 5150: 5116: 5060:JNJ-37654032 5055:JNJ-28330835 5050:JNJ-26146900 4946: 4890: 4870: 4855: 4837:Quingestanol 4754:Etonogestrel 4740: 4720: 4693: 4683: 4673: 4658: 4642:Propetandrol 4583: 4572:Oxymetholone 4547:Methasterone 4501: 4495:Tiomesterone 4485:Oxymesterone 4377: 4357: 4278:Norclostebol 4253: 4249: 4158: 4096:Mepitiostane 4091:Epitiostanol 4074:Drostanolone 4025:Androsterone 3981: 3962:+dutasteride 3958:Testosterone 3926:DHEA sulfate 3779: 3675: 3674: 3562:Fenfluramine 3544: 3480:Serotonergic 3396: 3374: 3304:DOPA quinone 3252: 3233:Dopaminergic 3087:(1): e8762. 3084: 3080: 3070: 3058: 3017: 3014:Neuroscience 3013: 3006: 2973: 2969: 2962: 2927: 2923: 2913: 2870: 2866: 2855: 2844: 2819: 2815: 2809: 2758: 2754: 2743: 2734: 2730: 2721: 2684: 2680: 2637:(3): 132–7. 2634: 2630: 2624: 2613:. 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Retrieved 1623: 1606: 1602: 1598: 1592: 1582: 1575: 1561:cite journal 1539:(1): 71–94. 1536: 1532: 1503: 1494: 1433: 1397: 1385:dopaminergic 1374: 1350:jugular vein 1335: 1319: 1315: 1308: 1306:erythrocytes 1275: 1259: 1253: 1244: 1235: 1226: 1212: 1211:Jewel vine ( 1198: 1197:Tuba plant ( 1184: 1170: 1161: 1152: 1146: 1139: 1135:Lonchocarpus 1133: 1131: 1119: 1080:mitochondria 1069: 1057: 1054:Deactivation 1038:inhibitor), 1029: 1022: 1015: 992: 966: 931: 911: 871: 852: 827:flea beetles 816: 786: 776: 772: 765: 763: 723: 697: 690: 686: 675:caterpillars 672: 635: 634: 544: 511: 176:ChEMBL429023 95:Identifiers 87:Other names 77: 73: 69: 65: 50: 8565:Isoflavones 8299:Zearalenone 8251:Antagonists 8227:Resveratrol 8192:Nonylphenol 8187:Niacinamide 8103:Bisphenol A 8093:Aldosterone 7922:Glyceollins 7870:Antagonists 7861:Zuclomifene 7856:Zindoxifene 7766:NNC 45-1506 7761:NNC 45-0781 7756:NNC 45-0320 7751:NNC 45-0095 7746:Nitromifene 7726:Miproxifene 7676:Fispemifene 7651:Enclomifene 7646:Droloxifene 7626:CN-55945-27 7571:Afimoxifene 7561:Acefluranol 7452:rhaponticin 7448:resveratrol 7444:Stilbenoids 7416:zearalenone 7404:zearalanone 7390:campesterol 7322:alternariol 7255:pinocembrin 7199:epicatechin 7171:biochanin A 7111:Chalconoids 7005:Terfluranol 6980:Quadrosilan 6852:Elacestrant 6753:Allenestrol 6628:Lynestrenol 6552:Estropipate 6522:Estrofurate 6373:Clomestrone 6353:Atrimustine 6303:Abiraterone 6257:alfatradiol 5937:Osteocalcin 5818:Vinclozolin 5803:Thalidomide 5798:Seviteronel 5728:Procymidone 5664:Masofaniten 5619:Inocoterone 5523:bisphenol S 5519:bisphenol F 5515:bisphenol A 5493:BAY-1024767 5468:Apalutamide 5414:Spiroxasone 5409:Spirorenone 5389:Rosterolone 5329:Mespirenone 5274:Edogestrone 5244:Delanterone 5234:Cyproterone 5224:Clometerone 5194:Benorterone 5179:Abiraterone 5144:Antagonists 5075:PF-06260414 4980:BMS-564,929 4904:Alternariol 4796:Lynestrenol 4749:Desogestrel 4632:Norboletone 4622:Metribolone 4567:Oxandrolone 4525:Mestanolone 4490:Penmesterol 4421:Formebolone 4386:Calusterone 4381:Bolasterone 4135:Prostanozol 4106:Mesterolone 3683:Adrenergics 3567:Haloperidol 3334:Haloperidol 3284:Amphetamine 3020:: 302–315. 2761:: 101–114. 2242:, 10/7/2015 1412:Lewy bodies 1234:Cork-bush ( 1122:microtubule 1032:antimycin A 950:Miami Canal 914:metabolites 895:pumpkinseed 889:), Sweden ( 782:synergistic 714:, Japanese 712:Kazuo Nagai 679:poison fish 659:insecticide 640:crystalline 574:TWA 5 mg/m 561:TWA 5 mg/m 526:median dose 512:Lethal dose 480:Soluble in 427:Appearance 380:Properties 214:100.001.365 156:CHEBI:28201 8539:Categories 8517:Glycosides 8382:glycosides 8242:Tectoridin 8222:Raloxifene 8197:Oleuropein 8044:Trilostane 7989:Prochloraz 7949:MDL-101906 7944:ICI-164384 7831:Trioxifene 7826:Toremifene 7796:Raloxifene 7781:Panomifene 7776:Ospemifene 7741:Nafoxidine 7631:Cyclofenil 7586:Arzoxifene 7566:Acolbifene 7498:phthalates 7466:bisphenols 7438:miroestrol 7342:methiocarb 7330:endosulfan 7318:Pesticides 7290:enterodiol 7271:tectoridin 7251:penduletin 7247:naringenin 7231:kaempferol 7147:Flavonoids 7141:psoralidin 7137:coumestrol 7133:Coumestans 7097:dianethole 7050:WAY-214156 7040:WAY-200070 7035:WAY-169916 7030:WAY-166818 7000:SKF-82,958 6965:Phenestrol 6945:Methestrol 6930:-Hexestrol 6922:-Butestrol 6803:Dienestrol 6783:Carbestrol 6768:Bifluranol 6763:Benzestrol 6708:Quinestrol 6658:Nilestriol 6500:Estrazinol 6433:Epimestrol 6423:-Estradiol 6405:Cyclotriol 6343:nandrolone 6318:Almestrone 6153:7-Oxo-DHEA 6065:Steroidal: 6037:modulators 5931:-ornithine 5874:gadolinium 5723:Prochloraz 5718:Phenothrin 5698:Nilutamide 5669:Methiocarb 5589:Endosulfan 5554:Cioteronel 5549:Cimetidine 5539:BMS-641988 5534:BMS-570511 5529:BMS-501949 5503:Bisphenols 5458:Antarlides 5434:Zanoterone 5369:Oxendolone 5314:Ludaterone 5304:Galeterone 5254:Dicirenone 5151:Steroidal: 5117:Steroidal: 5110:Vosilasarm 5005:GSK2881078 4960:AC-262,536 4919:Trilostane 4827:Norgestrel 4776:Gestrinone 4744:Δ-Tibolone 4627:Mibolerone 4577:Stanozolol 4530:Metenolone 4307:Trenbolone 4266:Nandrolone 4216:Dienedione 4140:Stenbolone 4101:Mesabolone 3953:Silandrone 3948:Quinbolone 3943:Plomestane 3938:Formestane 3933:Exemestane 3855:Atamestane 3752:modulators 3503:2,4,5-THMA 3402:Salsolinol 3274:disulfiram 3246:2,4,5-THMA 2727:"Rotenone" 2631:Toxicology 2615:2007-12-02 2222:2012-12-20 2136:(2): 165. 2130:BioScience 1791:20 October 1635:2008-03-16 1500:"Rotenone" 1456:References 1425:lipophilic 1400:neurotoxin 1290:lipophilic 1284:and other 1183:Barbasco ( 1124:assembly. 1095:ubiquinone 1040:oligomycin 897:), Spain ( 843:decomposes 710:. In 1902 643:isoflavone 587:2500 mg/m 476:Solubility 415:Molar mass 294:03L9OT429T 187:ChemSpider 123:3D model ( 102:CAS Number 46:IUPAC name 8545:Rotenoids 8508:Toxicarol 8503:Tephrosin 8448:Elliptone 8390:Rotenoids 8237:Tamoxifen 8217:Quercetin 8157:Genistein 8137:Estradiol 8121:o',p'-DDE 8024:ZK-191703 8019:ZK-164015 7979:Phenytoin 7877:(R,R)-THC 7816:Tamoxifen 7791:Promensil 7716:LY-117018 7691:Idoxifene 7686:ICI-55548 7671:Femarelle 7656:Endoxifen 7616:Clomifene 7372:diosgenin 7368:digitalis 7364:digitoxin 7354:triclosan 7334:fenarimol 7267:quercetin 7243:myricetin 7239:mirificin 7227:glycitein 7219:genistein 7215:glabridin 7175:calycosin 7163:baicalein 7119:phloretin 7075:ZK-283197 6935:Mestilbol 6897:Hexestrol 6872:Fenestrel 6847:Efavirenz 6778:Butestrol 6733:2,8-DHHHC 6728:(S,S)-THC 6723:(R,R)-THC 6678:Pentolame 6673:Orestrate 6648:Moxestrol 6638:Mestranol 6603:Etynodiol 6463:Estradiol 6438:Equilenin 6400:Cyclodiol 6358:Bolandiol 5917:-arginine 5902:Estradiol 5882:strontium 5878:magnesium 5866:aluminium 5833:YM-175735 5768:Ro 5-2537 5763:Ro 2-7239 5713:PF-998425 5708:Pentomone 5649:LG-120907 5609:Flutamide 5604:Fenarimol 5544:CH5137291 5483:Bakuchiol 5419:Topterone 5384:Prorenone 5359:Osaterone 5354:Nordinone 5339:Mexrenone 5259:Dienogest 5209:Canrenone 5130:TFM-4AS-1 5070:ORM-11984 5010:GSK-4336A 5000:GLPG-0492 4924:ZM-182345 4771:Gestodene 4759:Etynodiol 4515:Furazabol 4406:Enestebol 4334:Trendione 4295:Oxabolone 4221:Dienolone 4194:Bolandiol 4123:Nisterime 3877:Clostebol 3860:Boldenone 3676:See also: 3498:2,4,5-THA 3430:2,4,5-THA 3241:2,4,5-THA 3034:0306-4522 2998:205515222 2887:0091-6765 2783:0041-008X 2417:: 45465. 2091:Fisheries 2076:0801-9576 1985:cite book 1381:microglia 1261:Tephrosia 1255:Millettia 1091:complex I 1076:complex I 1048:uncoupler 1007:live bait 999:Utah chub 980:Mann Lake 954:waterways 932:In 1992, 878:half-life 814:animals. 808:livestock 797:parasitic 793:head lice 687:nicouline 669:Discovery 655:rotenoids 440:odorless 17:Rotenone 8498:Sumatrol 8493:Stemonal 8483:Rotenone 8443:Elliptol 8408:Deguelin 8398:Amorphol 8315:See also 8117:p,p'-DDT 8108:Daidzein 8098:Atrazine 8071:Agonists 7999:RU-58668 7994:RU-39411 7841:U-11555A 7836:TZE-5323 7581:Anordrin 7576:Anordiol 7509:agnuside 7486:parabens 7326:dieldrin 7298:nyasol ( 7263:puerarin 7259:prunetin 7223:genistin 7211:glabrene 7183:daidzein 7179:catechin 7167:baicalin 7159:apigenin 7089:anethole 6877:FERb 033 6713:Tibolone 6698:RU-16117 6683:Prodiame 6618:Hippulin 6613:Hexolame 6458:Estetrol 6368:Butolame 6058:Agonists 5968:See also 5855:Agonists 5828:YM-92088 5793:RU-58841 5788:RU-58642 5783:RU-57073 5778:RU-56187 5773:RU-22930 5703:ONC1-13B 5654:LGD-1331 5579:Dieldrin 5573:p,p’-DDE 5478:AZD-3514 5463:Arabilin 5394:RU-15328 5334:Metogest 5269:DU-41165 5105:S-101479 5085:RU-59063 5040:LGD-4033 5035:LGD-3303 5025:LGD-2226 5015:GSK-8698 4914:Drupanol 4909:Cl-4AS-1 4849:Tibolone 4030:Bolazine 3773:Agonists 3646:Unsorted 3470:Xylamine 3397:Rotenone 3392:Paraquat 3349:Mancozeb 3319:Dopamine 3299:Dieldrin 3150:Archived 3138:Rotenone 3121:20098733 3081:PLOS ONE 3042:29592843 2990:19912331 2954:12867501 2905:21269927 2836:15540952 2801:29428530 2713:15987402 2659:22727881 2560:Pergamon 2487:10552508 2449:28374803 2392:19240738 2305:21195854 2297:24865646 2216:Archived 2191:24 April 2182:Archived 1854:18681442 1817:4 August 1553:92554010 1510:(NIOSH). 1488:(NIOSH). 1439:See also 1310:in vitro 1160:Jícama ( 976:goldfish 973:invasive 958:Southern 903:Gambusia 863:Fabaceae 861:family, 804:chickens 651:Fabaceae 636:Rotenone 506:Hazards 252:Rotenone 8478:Rotenol 8287:Unknown 8263:Estriol 8167:GPER-L2 8162:GPER-L1 7846:U-11634 7721:Menerba 7711:LN-2299 7706:LN-1643 7681:GW-7604 7636:D-15413 7468:(e.g., 7460:(e.g., 7446:(e.g., 7430:Steroid 7402:(e.g., 7384:(e.g., 7362:(e.g., 7320:(e.g., 7312:cadmium 7310:(e.g., 7288:(e.g., 7286:Lignans 7187:daidzin 7151:7,8-DHF 7149:(incl. 7135:(e.g., 7113:(e.g., 6995:SERBA-2 6990:SC-4289 6985:SC-3296 6892:GTx-758 6788:D-15414 6738:β-LGND1 6688:Prolame 6537:Estrone 6505:Estriol 6443:Equilin 6325:(e.g., 6238:16α-LE2 5924:-lysine 5912:(incl. 5870:calcium 5864:(incl. 5862:Cations 5659:Linuron 5599:EPI-001 5505:(e.g., 5294:EM-6537 5289:EM-5855 5284:EM-5854 5279:EM-4350 5125:MK-0773 5120:EM-9017 5100:S-40503 4955:ACP-105 4950:198RL26 4815:(e.g., 4788:(e.g., 4697:Danazol 4647:RU-2309 4587:Bolenol 3533:5,7-DHT 3528:5,6-DHT 3513:3,4-DCA 3493:2,4-DCA 3450:DOPEGAL 3440:5,7-DHT 3435:5,6-DHT 3294:Daidzin 3289:Benomyl 3272:(e.g., 3260:5,6-DHT 3112:2808242 3089:Bibcode 3050:4969894 2945:6740554 2896:3114824 2792:6082736 2763:Bibcode 2704:1175899 2639:Bibcode 2440:5379642 2419:Bibcode 2099:Bibcode 2060:Lfi-122 1655:東京化學會誌 1482:"#0548" 1388:neurons 1377:neurons 1298:trachea 1286:mammals 1074:within 1003:anglers 946:Florida 882:organic 789:scabies 734:lôo-tîn 718:of the 692:Robinia 617:what is 615: ( 490:ethanol 486:acetone 446:Density 420:394.423 261:PubChem 112:83-79-4 8182:Niacin 8177:Kepone 8034:ERX-11 8004:SS1020 7912:ERB-88 7907:ERA-90 7811:SS1010 7736:MRL-37 7101:dianol 7070:ERB-79 7065:ERA-45 7060:ERB-26 6793:DCW234 6748:AC-186 6415:DHEA-S 6347:esters 6331:esters 6183:8β-VE2 5847:GPRC6A 5823:YM-580 5753:RD-162 5644:LG-105 4995:FTBU-1 3653:5-HIAL 3119:  3109:  3048:  3040:  3032:  2996:  2988:  2952:  2942:  2903:  2893:  2885:  2834:  2799:  2789:  2781:  2711:  2701:  2657:  2601:  2566:  2526:  2520:Struik 2485:  2447:  2437:  2390:  2303:  2295:  2074:  2037:  1973:  1908:  1852:  1765:20 May 1726:  1599:Derris 1551:  1282:humans 1141:Derris 859:legume 837:, and 810:, and 777:derris 647:jicama 612:verify 609:  364:SMILES 235:C07593 167:ChEMBL 40:Names 8258:CCL18 8132:Equol 8014:ZB716 7984:PHTPP 7851:Y-134 7528:SERMs 7523:Mixed 7203:equol 7085:Anise 6914:M2613 5511:BFDGE 5507:BADGE 5453:AA560 5135:YK-11 5045:LY305 4935:SARMs 3663:RHPTP 3523:5-IAI 3455:DSP-4 3407:Ziram 3354:Maneb 3309:DOPAL 3046:S2CID 2994:S2CID 2332:(PDF) 2325:(PDF) 2301:S2CID 2185:(PDF) 2162:(PDF) 2016:(PDF) 2009:(PDF) 1549:S2CID 1529:(PDF) 1294:gills 918:water 800:mites 775:, or 739:rōten 694:nicou 545:NIOSH 482:ether 342:InChI 147:ChEBI 125:JSmol 80:)-one 8278:MIBE 8273:G-36 8268:G-15 8202:PCBs 8059:GPER 7969:MIBE 7502:PCBs 7494:PHBA 7490:PBBs 7338:HPTE 7195:EGCG 7093:anol 6928:meso 6920:meso 6410:DHEA 6345:and 6329:and 5943:SHBG 5886:zinc 5584:DIMP 5199:BOMT 5095:S-23 4985:DTIB 3658:RHPP 3632:PCMA 3612:MMAI 3597:MDEA 3592:MDAI 3582:MBDB 3577:HPTP 3508:3-CA 3369:MPTP 3344:HPTP 3117:PMID 3038:PMID 3030:ISSN 2986:PMID 2950:PMID 2901:PMID 2883:ISSN 2832:PMID 2797:PMID 2779:ISSN 2709:PMID 2655:PMID 2599:ISBN 2564:ISBN 2524:ISBN 2483:PMID 2445:PMID 2388:PMID 2293:PMID 2262:2015 2193:2024 2072:ISSN 2035:ISBN 1991:link 1971:ISBN 1938:2015 1906:ISBN 1850:PMID 1819:2024 1793:2019 1767:2021 1724:ISBN 1567:link 1403:MPTP 1398:The 1379:and 1344:and 1342:DMSO 1258:and 1138:and 1099:NADH 1084:IRAC 1044:FCCP 1034:(an 960:and 920:and 909:). 893:and 891:pike 791:and 773:tuba 767:cubé 755:Uses 746:ローテン 581:IDLH 484:and 436:Odor 285:UNII 274:6758 246:MeSH 226:KEGG 196:6500 72:,12a 49:(5′′ 8232:STX 8152:G-1 8113:DDT 7934:III 7482:DDT 7480:), 7478:BPS 7474:BPF 7470:BPA 7370:), 7300:cis 7191:ECG 6421:ent 5569:DDT 5090:S-1 5080:R-1 3637:PIA 3627:PCA 3622:PBA 3572:HPP 3557:DCA 3552:αET 3339:HPP 3107:PMC 3097:doi 3022:doi 3018:379 2978:doi 2940:PMC 2932:doi 2891:PMC 2875:doi 2871:119 2824:doi 2787:PMC 2771:doi 2759:354 2699:PMC 2689:doi 2647:doi 2635:300 2475:doi 2435:PMC 2427:doi 2378:doi 2285:doi 2174:doi 2138:doi 2107:doi 2064:hdl 1842:doi 1692:doi 1663:doi 1611:doi 1601:". 1541:doi 1370:HSE 1356:to 1346:PEG 1296:or 1264:in 1230:L.) 1115:DNA 1107:CoQ 1103:ATP 1093:to 1087:MoA 1078:in 1050:). 812:pet 802:on 568:REL 555:PEL 311:EPA 264:CID 68:,6a 8541:: 8119:, 7938:IV 7936:, 7932:, 7930:II 7928:, 7511:, 7500:, 7496:, 7492:, 7488:, 7484:, 7476:, 7472:, 7464:, 7450:, 7436:, 7422:, 7418:, 7414:, 7410:, 7406:, 7392:, 7388:, 7374:, 7352:, 7348:, 7344:, 7340:, 7336:, 7332:, 7328:, 7324:, 7296:, 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Index

Skeletal formula of rotenone
Space-filling model of the rotenone molecule
IUPAC name
Systematic IUPAC name
CAS Number
83-79-4
JSmol
Interactive image
ChEBI
CHEBI:28201
ChEMBL
ChEMBL429023
ChemSpider
6500
ECHA InfoCard
100.001.365
Edit this at Wikidata
KEGG
C07593
MeSH
Rotenone
PubChem
6758
UNII
03L9OT429T
CompTox Dashboard
DTXSID6021248
Edit this at Wikidata
InChI
SMILES

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