Editing Rotenone (section)

{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 456665070
| ImageFile1 = Rotenone Structural Formula V.1.svg
| ImageSize1 = 200
| ImageAlt1 = Skeletal formula of rotenone
| ImageFile2 = rotenone-3D-spacefill.png
| ImageSize2 = 200
| ImageAlt2 = Space-filling model of the rotenone molecule
| IUPACName = (5′′''R'')-4′,5′-Dimethoxy-5′′-(prop-1-en-2-yl)-4′′,5′′-dihydrofuro[2′′,3′′:7,8]rotenan-4-one
| SystematicName = (2''R'',6a''S'',12a''S'')-8,9-Dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydro[1]benzopyrano[3,4-''b'']furo[2,3-''h''][1]benzopyran-6(6a''H'')-one
| OtherNames = Tubatoxin, Paraderil, nicouline 
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 83-79-4
| PubChem = 6758
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 28201
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 429023
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 6500
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C07593
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 03L9OT429T
| SMILES = CC(=C)[C@H]1Cc2c(O1)ccc3c2O[C@@H]4COc5cc(OC)c(OC)cc5[C@@H]4C3=O
| 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
| MeSHName = Rotenone
 }}
|Section2={{Chembox Properties
| C=23
| H=22
| O=6
| Appearance = Colorless to red crystalline solid<ref name=PGCH />
| Odor = odorless<ref name=PGCH />
| Density = 1.27 g/cm<sup>3</sup> @ 20&nbsp;°C
| MeltingPtC = 165 to 166
| BoilingPtC = 210 to 220
| BoilingPt_notes = at 0.5 mmHg
| SolubleOther = Soluble in [[diethyl ether|ether]] and [[acetone]], slightly soluble in [[ethanol]]
| VaporPressure = <0.00004 mmHg (20°C)<ref name=PGCH />
 }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
| IDLH = 2500 mg/m<sup>3</sup><ref name=PGCH>{{PGCH|0548}}</ref>
| REL = TWA 5 mg/m<sup>3</sup><ref name=PGCH />
| PEL = TWA 5 mg/m<sup>3</sup><ref name=PGCH />
| LD50 = 60 mg/kg (oral, rat)<br />132 mg/kg (oral, rat)<br />25 mg/kg (oral, rat)<br />2.8 mg/kg (oral, mouse)<ref>{{IDLH|83794|Rotenone}}</ref>
 }}
}}

'''Rotenone''' is an odorless, colorless, [[crystalline]] [[isoflavone]]. It occurs naturally in the seeds and stems of several plants, such as the [[Pachyrhizus erosus|jicama]] vine, and in the roots of several other members of the [[Fabaceae]]. It was the first-described member of the family of chemical compounds known as [[rotenoid]]s. Rotenone is approved for use as a piscicide to remove [[Introduced species|alien fish species]],<ref name=":12">{{Cite journal |vauthors=Rytwinski T, Taylor JJ, Donaldson LA, Britton JR, Browne DR, Gresswell RE, Lintermans M, Prior KA, Pellatt MG, Vis C, Cooke SJ |year=2018 |title=The effectiveness of non-native fish removal techniques in freshwater ecosystems: A systematic review |url=http://eprints.bournemouth.ac.uk/31355/1/Rytwinski%20et%20al_Fish%20removal%20SR_FINAL.pdf |journal=Environmental Reviews |language=English |volume=27 |issue=1 |pages=71–94 |doi=10.1139/er-2018-0049 |s2cid=92554010 |postscript=, summary in French}}</ref> see ''Uses.'' It has also been used as a broad-spectrum [[insecticide]], but its use as an insecticide has been banned in many countries.