Rotenone

Rotenone

Names
IUPAC name (2R,6aS,12aS)-1,2,6,6a,12,12a-hexahydro-2-isopropenyl-8,9-dimethoxychromeno[3,4-b]furo(2,3-h)chromen-6-one
Other names Tubatoxin, Paraderil
Identifiers
CAS Number	83-79-4 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:28201 N
ChEMBL	ChEMBL429023 N
ChemSpider	6500 N
ECHA InfoCard	100.001.365
KEGG	C07593 Y
MeSH	Rotenone
PubChem	6758
UNII	03L9OT429T Y
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	394.42 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)
US health exposure limits (NIOSH):
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).
N  (what is YN ?)
Infobox references

Rotenone is an odorless, colorless, crystalline isoflavone used as a broad-spectrum insecticide, piscicide, and pesticide. It occurs naturally in the seeds and stems of several plants, such as the jicama vine plant, and the roots of several members of Fabaceae. It was the first described member of the family of chemical compounds known as rotenoids.

The earliest record of the now-known rotenone-containing plants used for killing leaf-eating caterpillars was in 1848, and for centuries, the same plants were used to poison fish. The active chemical component was first isolated in 1895 by a French botanist, Emmanuel Geoffroy, who called it nicouline, from a specimen of Robinia nicou, now called Lonchocarpus nicou, while traveling in French Guiana. He wrote about this research in his thesis, published posthumously in 1895 after his death from a parasitic disease. In 1902 Japanese chemist Nagai Nagayoshi isolated a pure crystalline compound from Derris elliptica which he called rotenone, after the Japanese name of the plant, roten. By 1930, nicouline and rotenone were established to be chemically the same.

Rotenone is used as a pesticide, insecticide, and as a nonselective piscicide (fish killer).

It is commercialized as cubé, tuba, or derris, in single preparation or in synergistic combination with other insecticides. In the United States and Canada, all uses of rotenone except as a piscicide are being phased out.

Rotenone has historically been used by indigenous peoples to catch fish. Typically, rotenone-containing plants in the Fabaceae family of legumes are crushed and introduced into a body of water, and as rotenone interferes with cellular respiration, the affected fish rise to the surface in an attempt to gulp air, where they are more easily caught.