801 Rotenone Rotenone is found in jicama. Rotenone is widely distributed in the Leguminosae (Papilionoideae) e.g. Pachyrrhizus erosus (yam bean).Rotenone is an odorless chemical that is used as a broad-spectrum insecticide, piscicide, and pesticide. It occurs naturally in the roots and stems of several plants such as the jicama vine plant. In mammals, including humans, it is linked to the development of Parkinson's disease. (Wikipedia) Rotenone has been shown to exhibit apoptotic, neuroprotectant and neuroprotective functions (A7776, A7777, A7777). Rotenone belongs to the family of Rotenoids. These are phenolic compounds containing aA cis-fused tetrahydrochromeno[3,4-b]chromenenucleus. Many rotenoids contain an additional ring, e.g rotenone[1]. (Reference: [1] IUPAC. Compendium of Chemical Terminology, 2nd ed. (the Gold Book). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: http://goldbook.iupac.org (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. doi:10.1351/goldbook. (PAC, 1995, 67, 1307 (Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995)) on page 1364)). 83-79-4 6758 C20H18O6 394.141640 White powder. 163°C 0.0002 mg/mL at 20°C Rotenone works by interfering with the electron transport chain in mitochondria. Specifically, it inhibits the transfer of electrons from iron-sulfur centers in complex I to ubiquinone. This prevents NADH from being converted into usable cellular energy (ATP). (L1274) No indication of carcinogenicity to humans (not listed by IARC). Rotenone is used in solution as a pesticide and insecticide. It is commonly used in powdered or emulsified liquid form in fisheries management to remove unwanted fish species, such as the eradication of exotic fish from non-native habitats. People catch fish by extracting rotenone from plants and releasing it into water. Poisoned fish come to the surface and are easily caught. This method was first practiced by various indigenous tribes who smashed the roots. Fish caught this way can be eaten because rotenone is very poorly absorbed by the gastrointestinal tract of humans, whereas it is lethal to fish because it readily enters the blood stream of the fish through the gills. 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. Rotenone is the most effective tool available because only small quantities are necessary. It has only minor and transient environmental side-effects. Rotenone is also used in powdered form to reduce parasitic mites on chickens and other fowl. In the United States and in Canada, all uses of Rotenone except as a piscicide are being phased out. (L1274) Studies with primary cultures of rat neurons and microglia have shown low doses of rotenone (below 10 nM) to induce oxidative damage and death of dopaminergic neurons and it is these neurons in the substantia nigra that die in Parkinson's disease. Injecting rotenone into rats causes symptoms of Parkinson's disease to develop. The study does not directly suggest that rotenone exposure is responsible for Parkinson's disease in humans. (L1274) Rotenone dust is highly irritating to the eyes (causing conjunctivitis), skin (causing contact dermatitis), upper respiratory tract (causing rhinitis), and throat (linked with pharyngitis) (T10) Acute poisoning in animals is characterized by an initial respiratory stimulation followed by respiratory depression, ataxia, convulsions, and death from respiratory arrest. (T10) Since rotenone is unstable in light and heat, its toxicity can be lost after 2 or 3 days. (T10) 2009-06-02T15:21:19Z 2014-12-24T20:22:50Z http://en.wikipedia.org/wiki/Rotenone C07593 28201 CPD-5741 D012402 Rotenone 1279 true [H][C@@]12COC3=CC(OC)=C(OC)C=C3[C@]1([H])C(=O)C1=C(O2)C2=C(OCC2)C=C1 C20H18O6 InChI=1S/C20H18O6/c1-22-15-7-12-14(8-16(15)23-2)25-9-17-18(12)19(21)11-3-4-13-10(5-6-24-13)20(11)26-17/h3-4,7-8,17-18H,5-6,9H2,1-2H3/t17-,18+/m1/s1 InChIKey=NZVPMEQJVQAGNB-MSOLQXFVSA-N 354.3533 354.110338308 Exogenous Solid 4.1 HMDB34436 6500