Rotenone

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Rotenone
200px
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
Identifiers
CAS number 83-79-4
MeSH Rotenone
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
Properties
Molecular formula C23H22O6
Molar mass 394.41
Density 1.27 g/cm3 @ 20°C
Melting point

165-166 °C

Boiling point

210-220 °C at 0.5 mmHg

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

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[1] (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.[2] 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.[citation needed]

Rotenone is classified by the USDA National Organic Program as a nonsynthetic and is allowed to be used to grow "organic" produce.[3]

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[4] 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[5]
    • The root extract is referred to as Cubé resin
  • Barbasco (Lonchocarpus urucu) - South America[5]
    • 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.[6]

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.[7]

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.[8]

References

  1. Peter Fimrite (2007-10-02). Lake poisoning seems to have worked to kill invasive pike. San Francisco Chronicle.
  2. http://www.pan-uk.org/pestnews/Actives/rotenone.htm Factsheet - Rotenone
  3. http://www.nysaes.cornell.edu/pp/resourceguide/mfs/11rotenone.php Cornell University. Rotenone. Resource Guide for Organic and Disease Management.
  4. National Toxicology Program - Rotenone at ntp.niehs.nih.gov
  5. 5.0 5.1 Fang N, Casida J (1999). "Cubé resin insecticide: identification and biological activity of 29 rotenoid constituents". J Agric Food Chem 47 (5): 2130-6. PMID 10552508.
  6. Caboni P, Sherer T, Zhang N, Taylor G, Na H, Greenamyre J, Casida J (2004). "Rotenone, deguelin, their metabolites, and the rat model of Parkinson's disease". Chem Res Toxicol 17 (11): 1540-8. PMID 15540952.
  7. Summary of the article by Dr. Greenamyre on pesticides and Parkinson's Disease at ninds.nih.gov
  8. Gao HM, Liu B, Hong JS (2003). "Critical role for microglial NADPH oxidase in rotenone-induced degeneration of dopaminergic neurons". The Journal of Neuroscience 23 (15): 6181-7. PMID 12915048.

See also

External links

no:Rotenon sv:Rotenon


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