Rotenone

• (2R,6aS,12aS)-1,2,6,6a,12,12a-Hexahydro-2-isopropenyl-8,9-dimethoxychromeno[3,4-b]furo(2,3-h)chromen-6-on
• (2R -6a, 12a ) -1,2 -dihydro-2 -isopropenyl -8 ,9- dimethoxychromano [3,4- b] furo [2,3- h] chroman- 6-one
• Barbasco
• Canex
• Derrin
• Dri- Kil
• Fish -Tox
• Noxfire
• Rotacide
• Rotocide
• Synpren
• Tubatoxin and more

Crystalline, orthorhombic plates

Fixed

165-166 ° C

Very soluble in water, insoluble in ethanol, benzene, acetone, well, in chloroform

Risk

Template: Infobox chemical / molecular formula search available

Rotenone is a furocoumarin derivative. It is the most famous representative of the rotenoids. Rotenone is widely used in the Fabaceae family, such as Derris eliptica ( Tubawurzel ) Pachyrrhizus erosus, as well as in Lonchocarpus and Tephrosia species. Rotenone is used as an insecticide and acaricide, but also for fish very toxic ( less toxic to mammals and bees).

Origin

Rotenone is derived from the root of barbasco ( Deguelia utilis ) or Tubawurzel ( Derris elliptica ), a native to Borneo Schmetterlingsblütler won. The effect of these plants (and thus the poison ) has been known since the 17th century.

Effect

The toxic effect of the substance based on a blockade of the localized on the inner membrane of the mitochondria respiratory chain, where it attaches to the complex I, thus preventing electron transfer. Thus, the cell can not produce more ATP and metabolism eventually comes to a halt. Not only the fishermen of the Trobriand Islands made ​​use of this property when fishing to-use - with the Rotenone extracted from crushed Derriswurzeln fish were anesthetized and then impaled. Also in Mexico, Ecuador, and Brazil is the plant use in fishing.

Outdoors is rotenone decomposes relatively quickly, but is still dangerous because it penetrates through the skin or as dust in the lungs. According to some studies, rotenone is suspected of causing Parkinson 's disease. The Technical University of Dresden showed the triggering and amplifying effect of rotenone on the protein alpha-synuclein in the intestine in mice, which cause many kinds Parkinson. Rotenone is currently not approved in Germany, according to BBA as an insecticide (but in Switzerland, Spain and some other countries ). In Norway, an attempt was made, a parasite ( Gyrodactylus salaris ) that threatens the salmon in some rivers to fight with rotenone. However, except for the parasites are killed and the entire fish stocks in the rivers, which is specifically used in some places (USA) to clean lakes of fish to there to attract new fish stocks.

Swell

• Burkhard Fugmann: Rompp lexicon natural substances; Thieme, New York, 1997
• M. Wink: Handbook of poisonous and psychoactive plants; Scientific. VerlagsG. mbH 2008