Rotenone

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Rotenone
Image:Rotenone.png
Chemical 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	Rotenone Canex
Chemical formula	C₂₃H₂₂O₆
Molecular mass	394.41 g/mol
CAS number	[83-79-4]
Density	1.27 g/cm³ @ 20°C
Melting point	165-166 °C
Boiling point	210-220 °C at 0.5 mmHg
SMILES	C[C@@]([C@@H]4OC3=CC=C(C(O5) =C3C4)C([C@@]([C@]5([H])CO2) ([H])C1=C2C=C(OC)C(OC)=C1)=O)=C
Disclaimer and references

Rotenone is a colorless-to-red, odorless solid. In solution it is used as a broad-spectrum insecticide that works by inhibiting the transfer of electrons from Fe-S centers in Complex I to ubiquinone (see electron transfer chain). This prevents NADH from being converted into usable cellular energy (ATP).

Rotenone is commonly used in powdered form to reduce parasitic mites on chickens and other fowl. It also stuns or kills fish and is used to eradicate exotic fish from their non-native habitats.

Rotenone is toxic to humans and other mammals. However, the compound breaks down when exposed to sunlight and usually has a short lifetime (two weeks or less) in the environment. In water rotenone may last six months.

Rotenone is produced by extraction from the roots and stems of several tropical and subtropical plant species belonging to the genus Lonchocarpus or Derris. People have been known to catch fish by extracting rotenone from plants and releasing it into water. The initial such usage was by various indigenous tribes who simply smashed the roots.

Some of the plants containing rotenone [Order Fabales; Family Fabaceae (or Leguminosae) – Pea family]:

Hoary Pea or Goat’s Rue (Tephrosia virginiana) - North America
Cubé Plant or Lancepod (Lonchocarpus utilis) - South America
- The root extract is referred to as Cubé resin
Barbasco (Lonchocarpus urucu) - South America
- The root extract is referred to as Cubé resin
Tuba Plant (Derris elliptica) - southeast Asia & southwest Pacific islands
- The root extract is referred to as Derris or Derris root
Jewel Vine (Derris involuta) - southeast Asia & southwest Pacific islands
- The root extract is referred to as Derris or Derris root

[edit] Rotenone and Parkinson's disease

Research has shown a correlation between intravenous rotenone and Parkinson's disease in rats. The study does not suggest that rotenone exposure is responsible for Parkinson's disease in humans, but is consistent with the belief that chronic exposure to environmental toxins can increase the likelihood of the disease.