|Jmol-3D images||Image 1|
|Appearance||Colorless to red|
|Density||1.27 g/cm3 @ 20 °C|
210−220 °C at 0.5 mmHg
|Solubility||Soluble in ether and acetone, slightly soluble in ethanol|
| (what is: / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Rotenone is an odourless, colourless, crystalline ketonic chemical compound 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.
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 by a French botanist Emmanuel Geoffroy in 1895 and 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, a Japanese chemist, Nagai isolated a pure crystalline compound from Derris elliptica which he called rotenone, after the Japanese name of the plant 'roten'. By 1930 it was established that nicouline and rotenone were chemically the same.
Rotenone is used as a pesticide, insecticide, and as a non-selective 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.
Small-scale sampling with rotenone is used by fish researchers studying the biodiversity of marine fishes to collect cryptic, or hidden, fishes, which represent an important component of shoreline fish communities. Rotenone is the most effective tool available because only small quantities are necessary. It has only minor and transient environmental side effects.
Rotenone is sold as an organic pesticide dust for gardens. Unselective in action, it kills potato beetles, cucumber beetles, flea beetles, cabbage worms, raspberry beetles, and asparagus beetles, as well as most other arthropods. It rapidly biodegrades under warm conditions, so harmful residues are minimal. A light dusting on the leaves of plants will control insects for several days.
Mode of action
Rotenone works by interfering with the electron transport chain in mitochondria. To be specific, it inhibits the transfer of electrons from iron-sulfur centers in complex I to ubiquinone. This interferes with NADH during the creation of usable cellular energy (ATP).
Presence in plants
Some of the plants containing rotenone:
- Hoary pea or goat’s rue (Tephrosia virginiana) – North America
- Jícama (Pachyrhizus erosus) – 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 and southwest Pacific islands
- The root extract is referred to as derris or derris root
- Jewel vine (Derris involuta) – southeast Asia and southwest Pacific islands
- 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.
- Verbascum thapsus
- Cork-bush (Mundulea sericea) – southern Africa
- Florida fishpoison tree (Piscidia piscipula) – southern Florida, Caribbean
- Several species of Millettia and Tephrosia in South-east Asian regions
Rotenone is classified by the World Health Organization as moderately hazardous. It is mildly toxic to humans and other mammals, but extremely toxic to insects and aquatic life, including fish. This higher toxicity in fish and insects is because the lipophilic rotenone is easily taken up through the gills or trachea, but not as easily through the skin or the gastrointestinal tract. Rotenone is toxic to erythrocytes in vitro.
The compound decomposes when exposed to sunlight and usually has a lifetime of six days in the environment. It oxidises to rotenolone which is approximately an order of magnitude less toxic than rotenone. In water the rate of decomposition depends upon several factors including temperature, pH, water hardness and sunlight. The half-life in natural waters ranges from half a day at 24°C to 3.5 days at 0°C.
In 2000, injecting rotenone into rats was reported to cause the development of symptoms similar to those of Parkinson's disease (PD). Rotenone was continuously applied over a period of five weeks, mixed with DMSO and PEG to enhance tissue penetration, and injected into the jugular vein. The study does not directly suggest rotenone exposure is responsible for PD in humans, but is consistent with the belief that chronic exposure to environmental toxins increases 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) induce oxidative damage and death of dopaminergic neurons, and it is these neurons in the substantia nigra that die in Parkinson's disease. Another study has also described toxic action of rotenone at low concentrations (5 nM) in dopaminergic neurons from acute rat brain slices. This toxicity was exacerbated by an additional cell stressor - elevated intracellular calcium concentration - adding support to the 'multiple hit hypothesis' of dopaminergic neuron death.
The neurotoxin MPTP had been known earlier to cause PD-like symptoms (in humans and other primates, though not in rats) by interfering with Complex I in the electron transport chain and killing dopaminergic neurons in the substantia nigra. However, further studies involving MPTP have failed to show development of Lewy bodies, a key component to PD pathology. Therefore, the mechanism behind MPTP as it relates to Parkinson's disease is not fully understood. Because of these developments, rotenone was investigated as a possible Parkinson-causing agent. Both MPTP and rotenone are lipophilic and can cross the blood–brain barrier.
In 2010, a study was published detailing the progression of Parkinson's-like symptoms in mice following chronic intragastric ingestion of low doses of rotenone. The concentrations in the central nervous system were below detectable limits, yet still induced PD pathology.
In 2011, a US National Institutes of Health study showed a link between rotenone use and Parkinson's disease in farm workers.
Rotenone was implemented in 2010 to kill an invasive goldfish population present in Mann Lake, with the intention of not disrupting the lake's trout population. Rotenone successfully achieved these aims, killing nearly 200,000 goldfish, and only three trout.
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- Chemical Description