Rotenone

Synonyms and keywords: Tubatoxin, paraderil

Overview

Rotenone is a colorless-to-red, odorless solid. In solution it is used as a broad-spectrum insecticide and piscicide 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 or emulsified liquid form in fisheries management to remove unwanted fish species (such as to eradicate exotic fish from their non-native habitats). Rotenone is also used in powdered form to reduce parasitic mites on chickens and other fowl.

Rotenone is classified by the World Health Organization as a moderately hazardous and is mildly toxic to humans and other mammals. The lowest lethal dose for a child is 143 mg/kg. However, human deaths attributed to Rotenone are rare because its irritating action causes vomiting in cases where it could be fatal. 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 classified by the USDA National Organic Program as a nonsynthetic and is allowed to be used to grow "organic" produce.

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.

Plants containing rotenone

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
• Among the Mizo tribes of India (Derris walchii/D. thyrsiflora) the tender root is eaten as vegetable
  • The root extract is referred to as Derris or Derris root
• Duboisia - This shrub grows in Australia and bears white clusters of flowers and berry like fruit. The crushed plants were used by the Aboriginals for poisoning fish for food.

Rotenone and Parkinson's disease

Research has shown a correlation between intravenous rotenone and Parkinson's disease in rats.

The study does not directly 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.

In addition, 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.

See also

• NADH dehydrogenase

External links

• Rotenone, Molecule of the Month at chm.bris.ac.uk
• Wood D, Alsahaf H, Streete P, Dargan P, Jones A (2005). "Fatality after deliberate ingestion of the pesticide rotenone: a case report". Crit Care. 9 (3): R280–4. PMID 15987402.CS1 maint: Multiple names: authors list (link)
• Compendium of Pesticide Common Names at alanwood.net
• Cornell University. Rotenone. Resource Guide for Organic and Disease Management.
• Rotenone. ARS Pesticide Properties Database