Citizendia

Rotenone
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
Other namesRotenone, Tubatoxin, Paraderil
Identifiers
CAS number[83-79-4]
PubChem6758
MeSHRotenone
SMILESC[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 formulaC23H22O6
Molar mass394. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component Medical Subject Headings ( MeSH) is a huge Controlled vocabulary (or metadata system for the purpose of indexing journal articles and books A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 41
AppearanceColorless to red
Density1. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 27 g/cm3 @ 20°C
Melting point

165-166°C

Boiling point

210-220°C at 0. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid 5 mmHg

SolubilitySoluble in ether and acetone, slightly soluble in ethanol
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Rotenone is an odorless chemical that is used as a broad-spectrum insecticide, piscicide, and pesticide. Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. Ether is a class of Organic compounds which contain an ether group — an Oxygen Atom connected to two (substituted Alkyl Acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is a colorless mobile flammable In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly An insecticide is a Pesticide used against Insects in all developmental forms A piscicide is a Chemical substance which is Poisonous to Fish. A pesticide is a substance or mixture of substances used to kill a pest. It occurs naturally in the roots and stems of several plants. It causes Parkinson's disease if injected into rats. Parkinson's disease (also known as Parkinson disease or PD) is a degenerative disorder of the Central nervous system that often impairs the sufferer's

Contents

History

Emmanuel Geoffroy first isolated rotenone from a specimen of Robinia nicou, now called Lonchocarpus nicou, while traveling in French Guiana. Emmanuel Geoffroy (1862 December 12 Saintes –1894 was a French Botanist and Explorer. French Guiana (Guyane française officially fr ''Guyane'' is an Overseas department (French département d'outre-mer, or DOM) of France [1] This research, which was to be the subject of his thesis, had to be published posthumously in 1895 after his death from a parasitic disease,[2] and it was later still that researchers determined that the substance which Geoffroy termed nicouline was identically rotenone. A parasitic disease is an Infectious disease caused or transmitted by a parasite.

Uses

Rotenone is used in solution as a pesticide and insecticide.

It is commonly used in powdered or emulsified liquid form in fisheries management to remove unwanted fish species[3] (such as to eradicate exotic fish from their non-native habitats). People have been known to catch fish by extracting rotenone from plants and releasing it into water. The fish then come to the surface and are easily caught. The initial such usage was by various indigenous tribes[4] who simply smashed the roots. Fish caught in this manner can be eaten by humans because rotenone is very poorly absorbed by the gastrointestinal tract, whereas it is lethal to fish because it readily enters the blood stream of the fish though the gills.

Small-scale sampling with rotenone is used by researchers studying the biodiversity of marine fishes to collect cryptic (hidden) fishes, which represent an important component of shoreline fish communities. Rotenone is the most effective tool available for such sampling, which, because only small quantities are used, has only minor and transient environmental side-effects. [5]

Rotenone is also used in powdered form to reduce parasitic mites on chickens and other fowl. Parasitism is a type of symbiotic relationship between Organisms of different Species. Mites, along with Ticks belong to the subclass Acarina (also known as Acari and the class Arachnida Mites are among the most diverse and successful The chicken ( Gallus gallus, sometimes G gallus domesticus) is a domesticated Fowl which is traditionally believed to have descended from Most or all Birds collectively referred to as fowl belong to one of two orders namely the gamefowl or landfowl ( Galliformes) and the waterfowl

Method of action

Rotenone works by interfering with the electron transport chain in mitochondria. An electron transport chain couples a chemical reaction between an electron donor (such as NADH) and an electron acceptor (such as O2) to the transfer In Cell biology, a mitochondrion (plural mitochondria) is a membrane-enclosed Organelle found in most eukaryotic cells. Specifically, it inhibits the transfer of electrons from iron-sulfur centers in complex I to ubiquinone. NADH dehydrogenase ( is an Enzyme located in the inner mitochondrial membrane that catalyzes the transfer of Electrons from NADH to Coenzyme Coenzyme Q10 (also known as ubiquinone ubidecarenone coenzyme Q and abbreviated at times to CoQ10 CoQ Q10 or Q is a Benzoquinone, where Q This prevents NADH from being converted into usable cellular energy (ATP). Nicotinamide adenine dinucleotide, abbreviated NAD+, is a Coenzyme found in all living cells The compound is a dinucleotide since it consists Adenosine-5'-triphosphate ( ATP) is a multifunctional Nucleotide that is most important as a " molecular currency" of intracellular Energy

Presence in plants

Rotenone is produced by extraction from the roots and stems of several tropical and subtropical plant species, especially those belonging to the genus Lonchocarpus or Derris. Lonchocarpus is a Plant Genus in the legume family ( Fabaceae) Derris is a climbing leguminous plant of Southeast Asia and the southwest Pacific islands including New Guinea.

Some of the plants containing rotenone:

Toxicity

Rotenone is classified by the World Health Organization as moderately hazardous. Verbascum thapsus ( Great or Common Mullein) is a species of Mullein native to Europe, northern Africa and Asia [7] It is mildly toxic to humans and other mammals, but extremely toxic to insects and aquatic life including fish. Human beings, humans or man (Origin 1590–1600 L homō man OL hemō the earthly one (see Humus Mammals ( class Mammalia) are a class of Vertebrate Animals characterized by the presence of Sweat glands, including sweat glands This higher toxicity in fish and insects is due to the fact that the lipophilic rotenone is easily taken up through the gills or trachea, but not as easily through the skin or through the gastrointestinal tract. Lipophilicity, fat-liking, refers to the ability of a Chemical compound to dissolve in fats oils lipids and non-polar solvents such as Hexane or A gill is an anatomical structure found in many aquatic organisms Many terrestrial Arthropods have evolved a closed Respiratory system composed of Spiracles, tracheae and Tracheoles to transport metabolic

The lowest lethal dose for a child is 143 mg/kg. Human deaths attributed to Rotenone are rare because its irritating action causes vomiting. [8] Deliberate ingestion of rotenone can be fatal. [9]

The compound breaks down when exposed to sunlight and usually has a short lifetime of six days in the environment. Chemical decomposition or analysis is the separation of a Chemical compound into elements or smaller compounds [10] 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. In the United States, the National Organic Program (NOP is the federal regulatory framework governing Organic food. Organic farming is a form of agriculture that relies on Crop rotation, Green manure, Compost, Biological pest control, and mechanical Cultivation [11]

Parkinson's disease

In 2000 it was reported that injecting rotenone into rats causes symptoms of Parkinson's disease to develop. Parkinson's disease (also known as Parkinson disease or PD) is a degenerative disorder of the Central nervous system that often impairs the sufferer's 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. Dimethyl sulfoxide (DMSO is the Chemical compound with the formula (CH32SO Poly( Ethylene glycol) (PEG also known as poly( Ethylene oxide) (PEO or polyoxyethylene (POE is the most commercially important type of polyether The jugular veins are Veins that bring deoxygenated blood from the Head back to the heart via the Superior vena cava. [12]

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 increases the likelihood of the disease. [13]

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[14] and it is these neurons in the substantia nigra that die in Parkinson's disease. Neurons (ˈnjuːɹɒn also known as neurones and nerve cells) are responsive cells in the Nervous system that process and transmit information Microglia are a type of Glial cell that acts as the first and main form of active immune defense in the Central nervous system (CNS Dopaminergic means "related to the Neurotransmitter Dopamine " Neurons (ˈnjuːɹɒn also known as neurones and nerve cells) are responsive cells in the Nervous system that process and transmit information The substantia nigra ( Latin for "black substance" Sömmering) or locus niger is a heterogeneous portion of the midbrain, separating

It had been known earlier that the neurotoxin MPTP causes Parkinson's disease (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. A neurotoxin is a Toxin that acts specifically on nerve cells ( Neurons, usually by interacting with Membrane proteins such as Ion channels MPTP (1- Methyl -4- Phenyl -1236-tetrahydro Pyridine) is a Neurotoxin that causes permanent symptoms of Parkinson's disease by Because of this, rotenone was investigated as a possible Parkinson-causing agent. Both MPTP and rotenone are lipophilic and can cross the blood-brain barrier. Lipophilicity, fat-liking, refers to the ability of a Chemical compound to dissolve in fats oils lipids and non-polar solvents such as Hexane or The blood-brain barrier (BBB is a metabolic or cellular structure in the Central nervous system (CNS that restricts the passage of various chemical substances and microscopic

References

  1. ^ Ambrose, Anthony M. ; Harvey B. Haag (1936). "Toxicological study of Derris". Industrial & Engineering Chemistry 28 (7): 815–821. doi:10.1021/ie50319a017. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.  
  2. ^ Useful tropical plants. ASNOM (2008-01-02). 2008 ( MMVIII) is the current year in accordance with the Gregorian calendar, a Leap year that started on Tuesday of the Common Events 366 - The Alamanni cross the frozen Rhine River in large numbers invading the Roman Empire. Retrieved on 2008-03-16. 2008 ( MMVIII) is the current year in accordance with the Gregorian calendar, a Leap year that started on Tuesday of the Common Events 597 BC - Babylonians capture Jerusalem, replace Jehoiachin with Zedekiah as king
  3. ^ Peter Fimrite (2007-10-02). Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 1187 - Siege of Jerusalem: Saladin captures Jerusalem after 88 years of Crusader rule Lake poisoning seems to have worked to kill invasive pike. San Francisco Chronicle. The San Francisco Chronicle was founded in 1865 as The Daily Dramatic Chronicle by teenage brothers Charles de Young and Michael H
  4. ^ National Toxicology Program - Rotenone at ntp.niehs.nih.gov
  5. ^ Robertson DR, Smith-Vaniz WF. (2008). Rotenone: an essential but demonized tool for assessing marine fish diversity.. Bioscience. 58:165-170.
  6. ^ a b Fang N, Casida J (1999). "Cubé resin insecticide: identification and biological activity of 29 rotenoid constituents". J Agric Food Chem 47 (5): 2130-6. doi:10.1021/jf981188x. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. PMID 10552508.  
  7. ^ (2007) The WHO Recommended Classification of Pesticides by Hazard. World Health Organization. ISBN 92-4-154663-8. Retrieved on 2007-12-02. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 1409 - The University of Leipzig opens 1755 - The second Eddystone Lighthouse is destroyed by fire  
  8. ^ Factsheet - Rotenone
  9. ^ 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. doi:10.1186/cc3528. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. PMID 15987402.  
  10. ^ Vitax Safety Data Sheet for Derris dust, revised October 1998
  11. ^ Rotenone. Resource Guide for Organic and Disease Management. Cornell University.
  12. ^ 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. doi:10.1021/tx049867r. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. PMID 15540952.  
  13. ^ Summary of the article by Dr. Greenamyre on pesticides and Parkinson's Disease at ninds.nih.gov
  14. ^ 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

Dictionary

rotenone

-noun

  1. an insecticide extracted from the roots of the plant derris; it is toxic to humans and other mammals
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