Rotenone

Rotenone
Names
	IUPAC name (5′′R)-4′,5′-Dimethoxy-5′′-(prop-1-en-2-yl)-4′′,5′′-dihydrofuro[2′′,3′′:7,8]rotenan-4-one
	Systematic IUPAC name (2R,6aS,12aS)-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(6aH)-one
	Other names Tubatoxin, Paraderil
Identifiers
CAS Number	83-79-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28201 ;
ChEMBL	ChEMBL429023 ;
ChemSpider	6500 ;
ECHA InfoCard	100.001.365
KEGG	C07593 ;
MeSH	Rotenone
PubChem CID	6758;
UNII	03L9OT429T ;
CompTox Dashboard (EPA)	DTXSID6021248 ;
	InChI 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;
	SMILES CC(=C)[C@H]1Cc2c(O1)ccc3c2O[C@@H]4COc5cc(OC)c(OC)cc5[C@@H]4C3=O;
Properties
Chemical formula	C23H22O6
Molar mass	394.423 g·mol−1
Appearance	Colorless to red crystalline solid
Odor	odorless
Density	1.27 g/cm3 @ 20 °C
Melting point	165 to 166 °C (329 to 331 °F; 438 to 439 K)
Boiling point	210 to 220 °C (410 to 428 °F; 483 to 493 K) at 0.5 mmHg
Solubility	Soluble in ether and acetone, slightly soluble in ethanol
Vapor pressure	<0.00004 mmHg (20°C)
Hazards
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	60 mg/kg (oral, rat); 132 mg/kg (oral, rat); 25 mg/kg (oral, rat); 2.8 mg/kg (oral, mouse)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 5 mg/m3
REL (Recommended)	TWA 5 mg/m3
IDLH (Immediate danger)	2500 mg/m3
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Rotenone is an odorless, colorless, crystalline isoflavone. It occurs naturally in the seeds and stems of several plants, such as the 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 rotenoids. Rotenone is used as a piscicide to remove remove alien fish species,^[3] see Uses. It has also been used as a broad-spectrum insecticide, but due to its high mammalian toxicity its use as an insecticide has been banned in several countries.

^ ^a ^b ^c ^d ^e ^f NIOSH Pocket Guide to Chemical Hazards. "#0548". National Institute for Occupational Safety and Health (NIOSH).
^ "Rotenone". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ Rytwinski T, Taylor JJ, Donaldson LA, Britton JR, Browne DR, Gresswell RE, Lintermans M, Prior KA, Pellatt MG, Vis C, Cooke SJ (2018). "The effectiveness of non-native fish removal techniques in freshwater ecosystems: A systematic review" (PDF). Environmental Reviews. 27 (1): 71–94. doi:10.1139/er-2018-0049. S2CID 92554010, summary in French{{cite journal}}: CS1 maint: postscript (link)

[PGCH-1] ^ ^a ^b ^c ^d ^e ^f NIOSH Pocket Guide to Chemical Hazards. "#0548". National Institute for Occupational Safety and Health (NIOSH).

[2] "Rotenone". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[:12-3] Rytwinski T, Taylor JJ, Donaldson LA, Britton JR, Browne DR, Gresswell RE, Lintermans M, Prior KA, Pellatt MG, Vis C, Cooke SJ (2018). "The effectiveness of non-native fish removal techniques in freshwater ecosystems: A systematic review" (PDF). Environmental Reviews. 27 (1): 71–94. doi:10.1139/er-2018-0049. S2CID 92554010, summary in French{{cite journal}}: CS1 maint: postscript (link)

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