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Wikipedia

Rotenone

January 10, 2024

Rotenone is an odorless, colorless, crystalline isoflavone 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, and in the roots of several other members of the Fabaceae. It was the first-described member of the family of chemical compounds known as rotenoids.

Rotenone
Names
IUPAC name
(5′′R)-4′,5′-Dimethoxy-5′′-(prop-1-en-2-yl)-4′′,5′′-dihydrofuro[2′′,3′′:7,8]rotenan-4-one
Systematic IUPAC name
(2R,6aS,12aS)-8,9-Dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydro[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one
Other names
Tubatoxin, Paraderil
Identifiers
  • 83-79-4 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:28201 N
ChEMBL
  • ChEMBL429023 N
ChemSpider
  • 6500 N
ECHA InfoCard 100.001.365
KEGG
  • C07593 Y
MeSH Rotenone
  • 6758
UNII
  • 03L9OT429T Y
  • DTXSID6021248
  • InChI=1/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3/t16-,20-,21+/m1/s1
  • CC(=C)[C@H]1Cc2c(O1)ccc3c2O[C@@H]4COc5cc(OC)c(OC)cc5[C@@H]4C3=O
Properties
C23H22O6
Molar mass 394.423 g·mol−1
Appearance Colorless to red crystalline solid[1]
Odor odorless[1]
Density 1.27 g/cm3 @ 20 °C
Melting point 165 to 166 °C (329 to 331 °F; 438 to 439 K)
Boiling point 210 to 220 °C (410 to 428 °F; 483 to 493 K) at 0.5 mmHg
Solubility Soluble in ether and acetone, slightly soluble in ethanol
Vapor pressure <0.00004 mmHg (20°C)[1]
Hazards
Lethal dose or concentration (LD, LC):
60 mg/kg (oral, rat)
132 mg/kg (oral, rat)
25 mg/kg (oral, rat)
2.8 mg/kg (oral, mouse)[2]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 5 mg/m3[1]
REL (Recommended)
 TWA 5 mg/m3[1]
IDLH (Immediate danger)
 2500 mg/m3[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Discovery edit

The earliest written record of the now-known rotenone-containing plants used for killing leaf-eating caterpillars was in 1848; for centuries, these same plants had been used to poison fish.[3] The active chemical component was first isolated in 1895 by a French botanist, Emmanuel Geoffroy, who called it nicouline, from a specimen of Robinia nicou, now called Deguelia utilis, while traveling in French Guiana.[4] He wrote about this research in his thesis, published in 1895 after his death from a parasitic disease.[5] In 1902 Kazuo Nagai, Japanese chemical engineer of the Government-General of Taiwan, isolated a pure crystalline compound from Derris elliptica which he called rotenone, after the Taiwanese name of the plant 蘆藤 (Min Nan Chinese: lôo-tîn) translated into Japanese rōten (ローテン).[6] By 1930, nicouline and rotenone were established to be chemically the same.[7]

Uses edit

Rotenone is used as a pesticide, insecticide, and as a nonselective piscicide (fish killer).[8] Rotenone has historically been used by indigenous peoples to catch fish. Typically, rotenone-containing plants in the legume family, Fabaceae, 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.

In modern times it is frequently used as a tool to remove alien fish species,[9] as it has a relatively short half-life (days) and is gone from rivers in the course of days and from lakes within a few months, depending on (seasonal) stirring, organic content, availability of sunlight and temperature.[10] Rotenone has been used by government agencies to kill fish in rivers and lakes in the United States since 1952,[11] and in Canada[12] and Norway[13] since the 1980s. It is less frequently used in EU countries, due to strict regulations, but has seen some use in selected countries such as the UK (Topmouth gudgeon), Sweden (pike and pumpkinseed), Spain (Topmouth gudgeon, Gambusia) and Hungary (Prussian carp).

Rotenone decays through metabolites and its final product is reduced to water and carbon dioxide.[10] Furthermore, its use is more benign for the environment (as compared to other piscicides) as most species are seen to recolonize aquatic systems within weeks to a year after application.[14][15][16] Thus, it has also seen some use in other field studies in the marine environment needing only small quantities. 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, since it has only minor and transient environmental side effects.[17]

It is commercialized as cubé, tuba, or derris, in single preparation or in synergistic combination with other insecticides.[18] In the United States and Canada, all uses of rotenone except as a piscicide are being phased out.[19][20] It is currently banned in the United States for any use in organic farming.[21] In the UK, rotenone insecticides (sold under the trade name Derris) were banned for sale in 2009.[22]

Rotenone is also used in powdered form to treat scabies and head lice on humans, and parasitic mites on chickens, livestock, and pet animals.

In agriculture it is also unselective in action and kills potato beetles, cucumber beetles, flea beetles, cabbage worms, raspberry beetles, and asparagus beetles, as well as most other arthropods. It biodegrades rapidly in soil, with 90% degraded after 1–3 months at 20 °C (68 °F) and three times faster at 30 °C (86 °F).[23]

Mechanism of action edit

Rotenone works by interfering with the electron transport chain within complex I in mitochondria, which places it in IRAC MoA class 21 (by itself in 21B).[24] 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).[18] Complex I is unable to pass off its electron to CoQ, creating a back-up of electrons within the mitochondrial matrix. Cellular oxygen is reduced to the radical, creating reactive oxygen species, which can damage DNA and other components of the mitochondria.[25]

Rotenone also inhibits microtubule assembly.[26]

Presence in plants edit

Rotenone is produced by extraction from the roots and stems of several tropical and subtropical plant species, especially those belonging to the genera Lonchocarpus and Derris.

Some of the plants containing rotenone:

Human toxicity edit

Rotenone is classified by the World Health Organization as moderately hazardous.[32] 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.[33]

The lowest lethal dose for a child is not known, but death occurred in a 3.5-year-old child who had ingested 40 mg/kg rotenone solution.[34] Human deaths from rotenone poisoning are rare because its irritating action causes vomiting.[35] Deliberate ingestion of rotenone can be fatal.[34]

The compound decomposes when exposed to sunlight and usually has an activity of six days in the environment.[36] It oxidizes to rotenolone, which is about 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.[37]

A 2018 study, which examined the effects of rotenone administration on cell cultures that mimicked properties of developing brains, found that rotenone may be a developmental neurotoxicant; that is, that rotenone exposure in the developing fetus may impede proper human brain development, with potentially profound consequences later in life. The study found that rotenone was particularly damaging to dopaminergic neurons, consistent with prior findings.[38]

Parkinson's disease edit

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.[39] 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.[40] In 2011, a US National Institutes of Health study showed a link between rotenone use and Parkinson's disease in farm workers, suggesting a link between neural damage and pulmonary uptake by not using protective gear.[41] Exposure to the chemical in the field can be avoided by wearing a gas mask with filter, which is standard HSE procedure in modern application of the chemical.

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,[42] 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.[43] 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. Further studies involving MPTP have failed to show development of Lewy bodies, a key component to PD pathology. However at least one study recently has found evidence of protein aggregation of the same chemical makeup as that which makes up Lewy bodies with similar pathology to Parkinson's disease in aged Rhesus monkeys from MPTP.[44] Therefore, the mechanism behind MPTP as it relates to Parkinson's disease is not fully understood.[45] 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.[46]

Notable administrations edit

Rotenone was implemented in 2010 to kill an invasive goldfish population present in eastern Oregon's 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.[47]

Beginning May 1, 2006, Panguitch Lake, a reservoir in the southeastern portion of the U.S. state of Utah, was treated with rotenone, to potentially eradicate and control the invasive population of Utah chub, which were probably introduced accidentally by anglers who used them as live bait. The lake was restocked with 20,000 rainbow trout in 2006; as of 2016, the lake's fish population has recovered.

In 2012 rotenone was used to kill all remaining fish in Stormy Lake (Alaska) due to invasive pike destroying native species, which were reintroduced once the treatment was concluded.[48]

In 2014, rotenone was used to kill all remaining fish in San Francisco's Mountain Lake, which is located in Mountain Lake Park, in order to rid it of invasive species introduced since the migration of European settlers to the region.[49]

Rotenone is used in biomedical research to study the oxygen consumption rate of cells, usually in combination with antimycin A (an electron transport chain Complex III inhibitor), oligomycin (an ATP synthase inhibitor) and FCCP (a mitochondrial uncoupler).[50]

Deactivation edit

Rotenone can be deactivated in water with the use of potassium permanganate to lower toxicity to acceptable levels.[51]

See also edit

References edit

  1. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0548". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ "Rotenone". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. ^ Metcalf, R. L. (1948). The Mode of Action of Organic Insecticides. National Research Council, Washington DC.
  4. ^ Ambrose, Anthony M.; Harvey B. Haag (1936). "Toxicological study of Derris". Industrial & Engineering Chemistry. 28 (7): 815–821. doi:10.1021/ie50319a017.
  5. ^ "Useful tropical plants". ASNOM. 2008-01-02. Retrieved 2008-03-16.
  6. ^ Nagai, Kazuo (1902). Journal of the Chemical Society of Tokyo. 23: 744. {{cite journal}}: Missing or empty |title= (help)
  7. ^ La Forge FB, Haller HL, Smith LE (1933). "The Determination of the structure of rotenone". Chemical Reviews. 18 (2): 181–213. doi:10.1021/cr60042a001.
  8. ^ Peter Fimrite (2007-10-02). "Lake poisoning seems to have worked to kill invasive pike". San Francisco Chronicle.
  9. ^ Rytwinski T, Taylor JJ, Donaldson LA, Britton JR, Browne DR, Gresswell RE, Lintermans M, Prior KA, Pellatt MG, Vis C, Cooke SJ (2018). "The effectiveness of non-native fish removal techniques in freshwater ecosystems: A systematic review" (PDF). Environmental Reviews. 27 (1): 71–94. doi:10.1139/er-2018-0049. S2CID 92554010, summary in French{{cite journal}}: CS1 maint: postscript (link)
  10. ^ a b Finlayson B, Schnick R, Skaar D, Anderson J, Demong L, Duffield D, Horton W, Steinkjer J (2010). Planning and Standard Operating Procedures for the Use of Rotenone in Fish Management – Rotenone SOP Manual. Bethesda, Maryland: American Fisheries Society. pp. 1–200.
  11. ^ Schmidt, Peter (28 February 2010). "One Strange Fish Tale". The Chronicle of Higher Education. Retrieved 24 September 2015.
  12. ^ "Invasive Goldfish management". 10 January 2023.
  13. ^ Mo, TO; Holthe, E; Andersen, O (2022). Har myndighetene lyktes i kampen mot Gyrodactylus salaris? (Report) (in Norwegian). Norsk institutt for naturforskning, NINA rapport. pp. 1–62. ISBN 978-82-426-4950-8, summary in English{{cite book}}: CS1 maint: postscript (link)
  14. ^ Kjærstad, Gaute (2022). The eradication of invasive species using rotenone and its impact on freshwater macroinvertebrates. Trondheim: Doctoral theses at NTNU. pp. 1–100. ISBN 978-82-326-6270-8.
  15. ^ Fjellheim, A. (2004). "Virkning av rotenonbehandling på bunndyrsamfunnene I et område ved Stigstu, Hardangervidda". Lfi-122 (in Norwegian). LFI, University of Bergen: 1–60. hdl:11250/2630458. ISSN 0801-9576.
  16. ^ Vinson, V; Dinger, EC; Vinson, DK (2010). "Piscicides and invertebrates: after 70 years, does anyone really know?". Fisheries. 35 (2): 61–71. doi:10.1577/1548-8446-35.2.61.
  17. ^ Robertson, D. Ross; Smith-Vaniz, William F. (2008). "Rotenone: An Essential but Demonized Tool for Assessing Marine Fish Diversity". BioScience. 58 (2): 165. doi:10.1641/B580211.
  18. ^ a b Hayes W. J. (1991). Handbook on Pesticides. Vol. 1. Academic Press. ISBN 978-0-12-334161-7.
  19. ^ ,[dead link] EPA 738-R-07-005, March 2007, United States Environmental Protection Agency
  20. ^ ,[dead link] Consumer Product Safety, Health Canada
  21. ^ "7 CFR § 205.602 - Nonsynthetic substances prohibited for use in organic crop production". Cornell Law School Legal Information Institute. Retrieved 20 May 2021.
  22. ^ "RHS advice for the garden - Rotenone withdrawal". Telegraph Gardening. 2 October 2008. Retrieved 20 October 2019.
  23. ^ Cavoski, Ivana; Caboni, Pierluigi; Sarais, Giorgia; Miano, Teodoro (2008-08-06). "Degradation and Persistence of Rotenone in Soils and Influence of Temperature Variations". Journal of Agricultural and Food Chemistry. 56 (17): 8066–8073. doi:10.1021/jf801461h. PMID 18681442.
  24. ^ IRAC International MoA Working Group (March 2020). "IRAC Mode of Action Classification Scheme Version 9.4". Insecticide Resistance Action Committee.
  25. ^ Mehta, Suresh (2009). "Neuroprotective role of mitochondrial uncoupling protein 2 in cerebral stroke". Journal of Cerebral Blood Flow and Metabolism. 29 (6): 1069–78. doi:10.1038/jcbfm.2009.4. PMID 19240738.
  26. ^ Heinz S, Freyberger A, Lawrenz B, Schladt L, Schmuck G, Ellinger-Ziegelbauer H (2017). "Mechanistic Investigations of the Mitochondrial Complex I Inhibitor Rotenone in the Context of Pharmacological and Safety Evaluation". Scientific Reports. 7: 45465. Bibcode:2017NatSR...745465H. doi:10.1038/srep45465. PMC 5379642. PMID 28374803.
  27. ^ 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. PMID 10552508.
  28. ^ Peterson Field Guides to Medicinal Plants and Herbs of Eastern and Central North America (2nd ed.). pp. 130–131.
  29. ^ Coates Palgrave, Keith (2002). Trees of Southern Africa. Struik. ISBN 978-0-86977-081-8.
  30. ^ Nellis, David N. (1994). Seashore plants of South Florida and the Caribbean. Pineapple Press. 160 p.
  31. ^ Barton D, Meth-Cohn O (1999). Comprehensive Natural Products Chemistry. Pergamon. ISBN 978-0-08-091283-7.
  32. ^ International Programme on Chemical Safety; United Nations Environment Programme (UNEP); International Labour Organization; World Health Organization (2007). . World Health Organization. ISBN 978-92-4-154663-8. Archived from the original on July 8, 2004. Retrieved 2007-12-02.
  33. ^ Lupescu, Adrian; Jilani, Kashif; Zbidah, Mohanad; Lang, Florian (October 2012). "Induction of apoptotic erythrocyte death by rotenone". Toxicology. 300 (3): 132–7. doi:10.1016/j.tox.2012.06.007. PMID 22727881.
  34. ^ a b Wood DM, Alsahaf H, Streete P, Dargan PI, Jones AL (June 2005). "Fatality after deliberate ingestion of the pesticide rotenone: a case report". Critical Care. 9 (3): R280–4. doi:10.1186/cc3528. PMC 1175899. PMID 15987402.
  35. ^ "Rotenone". Pesticides News. 54: 20–21. 2001.
  36. ^ Vitax Safety Data Sheet for Derris dust, revised October 1998
  37. ^ Kevin C. Ott. (PDF). Archived from the original (PDF) on 2012-09-04.
  38. ^ Pamies, David; Block, Katharina; Lau, Pierre; Gribaldo, Laura; Pardo, Carlos A.; Barreras, Paula; Smirnova, Lena; Wiersma, Daphne; Zhao, Liang; Harris, Georgina; Hartung, Thomas; Hogberg, Helena T. (2018-09-01). "Rotenone exerts developmental neurotoxicity in a human brain spheroid model". Toxicology and Applied Pharmacology. Alternative Approaches to Developmental Neurotoxicity Evaluation. 354: 101–114. doi:10.1016/j.taap.2018.02.003. ISSN 0041-008X. PMC 6082736. PMID 29428530.
  39. ^ 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. PMID 15540952.
  40. ^ Summary of the article by Dr. Greenamyre on pesticides and Parkinson's Disease at ninds.nih.gov
  41. ^ Tanner CM, Kamel F, Ross GW, Hoppin JA, Goldman SM, Korell M, Marras C, Bhudhikanok GS, Kasten M, Chade AR, Comyns K, Richards MB, Meng C, Priestley B, Fernandez HH, Cambi F, Umbach DM, Blair A, Sandler DP, Langston JW (2011). "Rotenone, Paraquat and Parkinson's Disease". Environmental Health Perspectives. 119 (6): 866–72. doi:10.1289/ehp.1002839. ISSN 0091-6765. PMC 3114824. PMID 21269927.
  42. ^ Gao HM, Liu B, Hong JS (July 2003). "Critical role for microglial NADPH oxidase in rotenone-induced degeneration of dopaminergic neurons". The Journal of Neuroscience. 23 (15): 6181–7. doi:10.1523/JNEUROSCI.23-15-06181.2003. PMC 6740554. PMID 12867501.
  43. ^ Freestone PS, Chung KK, Guatteo E, Mercuri NB, Nicholson LF, Lipski J (November 2009). "Acute action of rotenone on nigral dopaminergic neurons--involvement of reactive oxygen species and disruption of Ca2+ homeostasis". The European Journal of Neuroscience. 30 (10): 1849–59. doi:10.1111/j.1460-9568.2009.06990.x. PMID 19912331. S2CID 205515222.
  44. ^ Huang B, Wu S, Wang Z, Ge L, Rizak JD, Wu J, Li J, Xu L, Lv L, Yin Y, Hu X (2018-05-21). "Phosphorylated α-Synuclein Accumulations and Lewy Body-like Pathology Distributed in Parkinson's Disease-Related Brain Areas of Aged Rhesus Monkeys Treated with MPTP". Neuroscience. 379: 302–315. doi:10.1016/j.neuroscience.2018.03.026. ISSN 0306-4522. PMID 29592843. S2CID 4969894.
  45. ^ Neurotransmitters and Disorders of the Basal Ganglia -- Basic Neurochemistry -- NCBI Bookshelf, American Society for Neurochemistry
  46. ^ Pan-Montojo F, Anichtchik O, Dening Y, Knels L, Pursche S, Jung R, Jackson S, Gille G, Spillantini MG (2010). Kleinschnitz C (ed.). "Progression of Parkinson's Disease Pathology Is Reproduced by Intragastric Administration of Rotenone in Mice". PLOS ONE. 5 (1): e8762. Bibcode:2010PLoSO...5.8762P. doi:10.1371/journal.pone.0008762. PMC 2808242. PMID 20098733.
  47. ^ Monroe, Bill (December 3, 2010). "Mann Lake Gets a Second Round of Rotenone for Cutthroat Restoration". The Oregonian. Oregon Live LLC. from the original on April 24, 2011. Retrieved 2012-12-20.
  48. ^ Earl, Elizabeth, Fish population booms in Stormy Lake Peninsula Clarion, 10/7/2015
  49. ^ Fimrite, Peter (12 November 2014). "Alien fish poisoned by the thousands to save S.F.'s Mountain Lake". SFGate / Hearst. Retrieved 24 September 2015.
  50. ^ Divakaruni AS, Rogers GW, Murphy AN (2014). "Measuring Mitochondrial Function in Permeabilized Cells Using the Seahorse XF Analyzer or a Clark-Type Oxygen Electrode". Curr Protoc Toxicol. 60: 25.2.1–16. doi:10.1002/0471140856.tx2502s60. PMID 24865646. S2CID 21195854.
  51. ^ Donald L Archer (2001), (PDF), American Fisheries Society, archived from the original (PDF) on 2017-11-07

External links edit

  • Rotenone, Molecule of the Month at chm.bris.ac.uk
  • Cornell University. Rotenone. Resource Guide for Organic and Disease Management. 2007-06-09 at the Wayback Machine
  • Rotenone. ARS Pesticide Properties Database
  • Rotenone use in research on the biodiversity of marine fishes
  • Rotenone Factsheet
  • Rotenone registration at US Environmental Protection Agency
  • CDC – NIOSH Pocket Guide to Chemical Hazards
  • Rotenone at Bioblast
  • Chemical Description

January 10, 2024
rotenone, odorless, colorless, crystalline, isoflavone, used, broad, spectrum, insecticide, piscicide, pesticide, occurs, naturally, seeds, stems, several, plants, such, jicama, vine, roots, several, other, members, fabaceae, first, described, member, family, . Rotenone is an odorless colorless crystalline isoflavone 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 and in the roots of several other members of the Fabaceae It was the first described member of the family of chemical compounds known as rotenoids Rotenone NamesIUPAC name 5 R 4 5 Dimethoxy 5 prop 1 en 2 yl 4 5 dihydrofuro 2 3 7 8 rotenan 4 oneSystematic IUPAC name 2R 6aS 12aS 8 9 Dimethoxy 2 prop 1 en 2 yl 1 2 12 12a tetrahydro 1 benzopyrano 3 4 b furo 2 3 h 1 benzopyran 6 6aH oneOther names Tubatoxin ParaderilIdentifiersCAS Number 83 79 4 Y3D model JSmol Interactive imageChEBI CHEBI 28201 NChEMBL ChEMBL429023 NChemSpider 6500 NECHA InfoCard 100 001 365KEGG C07593 YMeSH RotenonePubChem CID 6758UNII 03L9OT429T YCompTox Dashboard EPA DTXSID6021248InChI InChI 1 C23H22O6 c1 11 2 16 8 14 15 28 16 6 5 12 22 24 21 13 7 18 25 3 19 26 4 9 17 13 27 10 20 21 29 23 12 14 h5 7 9 16 20 21H 1 8 10H2 2 4H3 t16 20 21 m1 s1SMILES CC C C H 1Cc2c O1 ccc3c2O C H 4COc5cc OC c OC cc5 C H 4C3 OPropertiesChemical formula C 23H 22O 6Molar mass 394 423 g mol 1Appearance Colorless to red crystalline solid 1 Odor odorless 1 Density 1 27 g cm3 20 CMelting point 165 to 166 C 329 to 331 F 438 to 439 K Boiling point 210 to 220 C 410 to 428 F 483 to 493 K at 0 5 mmHgSolubility Soluble in ether and acetone slightly soluble in ethanolVapor pressure lt 0 00004 mmHg 20 C 1 HazardsLethal dose or concentration LD LC LD50 median dose 60 mg kg oral rat 132 mg kg oral rat 25 mg kg oral rat 2 8 mg kg oral mouse 2 NIOSH US health exposure limits PEL Permissible TWA 5 mg m3 1 REL Recommended TWA 5 mg m3 1 IDLH Immediate danger 2500 mg m3 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Discovery 2 Uses 3 Mechanism of action 4 Presence in plants 5 Human toxicity 5 1 Parkinson s disease 6 Notable administrations 6 1 Deactivation 7 See also 8 References 9 External linksDiscovery editThe earliest written record of the now known rotenone containing plants used for killing leaf eating caterpillars was in 1848 for centuries these same plants had been used to poison fish 3 The active chemical component was first isolated in 1895 by a French botanist Emmanuel Geoffroy who called it nicouline from a specimen of Robinia nicou now called Deguelia utilis while traveling in French Guiana 4 He wrote about this research in his thesis published in 1895 after his death from a parasitic disease 5 In 1902 Kazuo Nagai Japanese chemical engineer of the Government General of Taiwan isolated a pure crystalline compound from Derris elliptica which he called rotenone after the Taiwanese name of the plant 蘆藤 Min Nan Chinese loo tin translated into Japanese rōten ローテン 6 By 1930 nicouline and rotenone were established to be chemically the same 7 Uses editRotenone is used as a pesticide insecticide and as a nonselective piscicide fish killer 8 Rotenone has historically been used by indigenous peoples to catch fish Typically rotenone containing plants in the legume family Fabaceae 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 In modern times it is frequently used as a tool to remove alien fish species 9 as it has a relatively short half life days and is gone from rivers in the course of days and from lakes within a few months depending on seasonal stirring organic content availability of sunlight and temperature 10 Rotenone has been used by government agencies to kill fish in rivers and lakes in the United States since 1952 11 and in Canada 12 and Norway 13 since the 1980s It is less frequently used in EU countries due to strict regulations but has seen some use in selected countries such as the UK Topmouth gudgeon Sweden pike and pumpkinseed Spain Topmouth gudgeon Gambusia and Hungary Prussian carp Rotenone decays through metabolites and its final product is reduced to water and carbon dioxide 10 Furthermore its use is more benign for the environment as compared to other piscicides as most species are seen to recolonize aquatic systems within weeks to a year after application 14 15 16 Thus it has also seen some use in other field studies in the marine environment needing only small quantities 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 since it has only minor and transient environmental side effects 17 It is commercialized as cube tuba or derris in single preparation or in synergistic combination with other insecticides 18 In the United States and Canada all uses of rotenone except as a piscicide are being phased out 19 20 It is currently banned in the United States for any use in organic farming 21 In the UK rotenone insecticides sold under the trade name Derris were banned for sale in 2009 22 Rotenone is also used in powdered form to treat scabies and head lice on humans and parasitic mites on chickens livestock and pet animals In agriculture it is also unselective in action and kills potato beetles cucumber beetles flea beetles cabbage worms raspberry beetles and asparagus beetles as well as most other arthropods It biodegrades rapidly in soil with 90 degraded after 1 3 months at 20 C 68 F and three times faster at 30 C 86 F 23 Mechanism of action editRotenone works by interfering with the electron transport chain within complex I in mitochondria which places it in IRAC MoA class 21 by itself in 21B 24 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 18 Complex I is unable to pass off its electron to CoQ creating a back up of electrons within the mitochondrial matrix Cellular oxygen is reduced to the radical creating reactive oxygen species which can damage DNA and other components of the mitochondria 25 Rotenone also inhibits microtubule assembly 26 Presence in plants editRotenone is produced by extraction from the roots and stems of several tropical and subtropical plant species especially those belonging to the genera Lonchocarpus and Derris Some of the plants containing rotenone Hoary pea or goat s rue Tephrosia virginiana North America Jicama Pachyrhizus erosus North America Cube plant or lancepod Lonchocarpus utilis South America 27 The root extract is referred to as cube resin Barbasco Lonchocarpus urucu South America 27 The root extract is referred to as cube 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 Common Mullein Verbascum thapsus L 28 Cork bush Mundulea sericea southern Africa 29 Florida fishpoison tree Piscidia piscipula southern Florida Caribbean 30 Several species of Millettia and Tephrosia in South east Asian regions 31 Human toxicity editRotenone is classified by the World Health Organization as moderately hazardous 32 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 33 The lowest lethal dose for a child is not known but death occurred in a 3 5 year old child who had ingested 40 mg kg rotenone solution 34 Human deaths from rotenone poisoning are rare because its irritating action causes vomiting 35 Deliberate ingestion of rotenone can be fatal 34 The compound decomposes when exposed to sunlight and usually has an activity of six days in the environment 36 It oxidizes to rotenolone which is about 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 37 A 2018 study which examined the effects of rotenone administration on cell cultures that mimicked properties of developing brains found that rotenone may be a developmental neurotoxicant that is that rotenone exposure in the developing fetus may impede proper human brain development with potentially profound consequences later in life The study found that rotenone was particularly damaging to dopaminergic neurons consistent with prior findings 38 Parkinson s disease edit 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 39 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 40 In 2011 a US National Institutes of Health study showed a link between rotenone use and Parkinson s disease in farm workers suggesting a link between neural damage and pulmonary uptake by not using protective gear 41 Exposure to the chemical in the field can be avoided by wearing a gas mask with filter which is standard HSE procedure in modern application of the chemical 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 42 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 43 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 Further studies involving MPTP have failed to show development of Lewy bodies a key component to PD pathology However at least one study recently has found evidence of protein aggregation of the same chemical makeup as that which makes up Lewy bodies with similar pathology to Parkinson s disease in aged Rhesus monkeys from MPTP 44 Therefore the mechanism behind MPTP as it relates to Parkinson s disease is not fully understood 45 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 46 Notable administrations editRotenone was implemented in 2010 to kill an invasive goldfish population present in eastern Oregon s 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 47 Beginning May 1 2006 Panguitch Lake a reservoir in the southeastern portion of the U S state of Utah was treated with rotenone to potentially eradicate and control the invasive population of Utah chub which were probably introduced accidentally by anglers who used them as live bait The lake was restocked with 20 000 rainbow trout in 2006 as of 2016 the lake s fish population has recovered In 2012 rotenone was used to kill all remaining fish in Stormy Lake Alaska due to invasive pike destroying native species which were reintroduced once the treatment was concluded 48 In 2014 rotenone was used to kill all remaining fish in San Francisco s Mountain Lake which is located in Mountain Lake Park in order to rid it of invasive species introduced since the migration of European settlers to the region 49 Rotenone is used in biomedical research to study the oxygen consumption rate of cells usually in combination with antimycin A an electron transport chain Complex III inhibitor oligomycin an ATP synthase inhibitor and FCCP a mitochondrial uncoupler 50 Deactivation edit Rotenone can be deactivated in water with the use of potassium permanganate to lower toxicity to acceptable levels 51 See also editFenpropathrin NADH dehydrogenaseReferences edit a b c d e f NIOSH Pocket Guide to Chemical Hazards 0548 National Institute for Occupational Safety and Health NIOSH Rotenone Immediately Dangerous to Life or Health Concentrations IDLH National Institute for Occupational Safety and Health NIOSH Metcalf R L 1948 The Mode of Action of Organic Insecticides National Research Council Washington DC Ambrose Anthony M Harvey B Haag 1936 Toxicological study of Derris Industrial amp Engineering Chemistry 28 7 815 821 doi 10 1021 ie50319a017 Useful tropical plants ASNOM 2008 01 02 Retrieved 2008 03 16 Nagai Kazuo 1902 Journal of the Chemical Society of Tokyo 23 744 a href Template Cite journal html title Template Cite journal cite journal a Missing or empty title help La Forge FB Haller HL Smith LE 1933 The Determination of the structure of rotenone Chemical Reviews 18 2 181 213 doi 10 1021 cr60042a001 Peter Fimrite 2007 10 02 Lake poisoning seems to have worked to kill invasive pike San Francisco Chronicle Rytwinski T Taylor JJ Donaldson LA Britton JR Browne DR Gresswell RE Lintermans M Prior KA Pellatt MG Vis C Cooke SJ 2018 The effectiveness of non native fish removal techniques in freshwater ecosystems A systematic review PDF Environmental Reviews 27 1 71 94 doi 10 1139 er 2018 0049 S2CID 92554010 summary in French a href Template Cite journal html title Template Cite journal cite journal a CS1 maint postscript link a b Finlayson B Schnick R Skaar D Anderson J Demong L Duffield D Horton W Steinkjer J 2010 Planning and Standard Operating Procedures for the Use of Rotenone in Fish Management Rotenone SOP Manual Bethesda Maryland American Fisheries Society pp 1 200 Schmidt Peter 28 February 2010 One Strange Fish Tale The Chronicle of Higher Education Retrieved 24 September 2015 Invasive Goldfish management 10 January 2023 Mo TO Holthe E Andersen O 2022 Har myndighetene lyktes i kampen mot Gyrodactylus salaris Report in Norwegian Norsk institutt for naturforskning NINA rapport pp 1 62 ISBN 978 82 426 4950 8 summary in English a href Template Cite book html title Template Cite book cite book a CS1 maint postscript link Kjaerstad Gaute 2022 The eradication of invasive species using rotenone and its impact on freshwater macroinvertebrates Trondheim Doctoral theses at NTNU pp 1 100 ISBN 978 82 326 6270 8 Fjellheim A 2004 Virkning av rotenonbehandling pa bunndyrsamfunnene I et omrade ved Stigstu Hardangervidda Lfi 122 in Norwegian LFI University of Bergen 1 60 hdl 11250 2630458 ISSN 0801 9576 Vinson V Dinger EC Vinson DK 2010 Piscicides and invertebrates after 70 years does anyone really know Fisheries 35 2 61 71 doi 10 1577 1548 8446 35 2 61 Robertson D Ross Smith Vaniz William F 2008 Rotenone An Essential but Demonized Tool for Assessing Marine Fish Diversity BioScience 58 2 165 doi 10 1641 B580211 a b Hayes W J 1991 Handbook on Pesticides Vol 1 Academic Press ISBN 978 0 12 334161 7 Reregistration Eligibility Decision for Rotenone dead link EPA 738 R 07 005 March 2007 United States Environmental Protection Agency Re evaluation Note Rotenone REV2008 01 29 January 2008 dead link Consumer Product Safety Health Canada 7 CFR 205 602 Nonsynthetic substances prohibited for use in organic crop production Cornell Law School Legal Information Institute Retrieved 20 May 2021 RHS advice for the garden Rotenone withdrawal Telegraph Gardening 2 October 2008 Retrieved 20 October 2019 Cavoski Ivana Caboni Pierluigi Sarais Giorgia Miano Teodoro 2008 08 06 Degradation and Persistence of Rotenone in Soils and Influence of Temperature Variations Journal of Agricultural and Food Chemistry 56 17 8066 8073 doi 10 1021 jf801461h PMID 18681442 IRAC International MoA Working Group March 2020 IRAC Mode of Action Classification Scheme Version 9 4 Insecticide Resistance Action Committee Mehta Suresh 2009 Neuroprotective role of mitochondrial uncoupling protein 2 in cerebral stroke Journal of Cerebral Blood Flow and Metabolism 29 6 1069 78 doi 10 1038 jcbfm 2009 4 PMID 19240738 Heinz S Freyberger A Lawrenz B Schladt L Schmuck G Ellinger Ziegelbauer H 2017 Mechanistic Investigations of the Mitochondrial Complex I Inhibitor Rotenone in the Context of Pharmacological and Safety Evaluation Scientific Reports 7 45465 Bibcode 2017NatSR 745465H doi 10 1038 srep45465 PMC 5379642 PMID 28374803 a b Fang N Casida J 1999 Cube resin insecticide identification and biological activity of 29 rotenoid constituents J Agric Food Chem 47 5 2130 6 doi 10 1021 jf981188x PMID 10552508 Peterson Field Guides to Medicinal Plants and Herbs of Eastern and Central North America 2nd ed pp 130 131 Coates Palgrave Keith 2002 Trees of Southern Africa Struik ISBN 978 0 86977 081 8 Nellis David N 1994 Seashore plants of South Florida and the Caribbean Pineapple Press 160 p Barton D Meth Cohn O 1999 Comprehensive Natural Products Chemistry Pergamon ISBN 978 0 08 091283 7 International Programme on Chemical Safety United Nations Environment Programme UNEP International Labour Organization World Health Organization 2007 The WHO Recommended Classification of Pesticides by Hazard World Health Organization ISBN 978 92 4 154663 8 Archived from the original on July 8 2004 Retrieved 2007 12 02 Lupescu Adrian Jilani Kashif Zbidah Mohanad Lang Florian October 2012 Induction of apoptotic erythrocyte death by rotenone Toxicology 300 3 132 7 doi 10 1016 j tox 2012 06 007 PMID 22727881 a b Wood DM Alsahaf H Streete P Dargan PI Jones AL June 2005 Fatality after deliberate ingestion of the pesticide rotenone a case report Critical Care 9 3 R280 4 doi 10 1186 cc3528 PMC 1175899 PMID 15987402 Rotenone Pesticides News 54 20 21 2001 Vitax Safety Data Sheet for Derris dust revised October 1998 Kevin C Ott Rotenone A Brief Review of its Chemistry Environmental Fate and the Toxicity of Rotenone Formulations PDF Archived from the original PDF on 2012 09 04 Pamies David Block Katharina Lau Pierre Gribaldo Laura Pardo Carlos A Barreras Paula Smirnova Lena Wiersma Daphne Zhao Liang Harris Georgina Hartung Thomas Hogberg Helena T 2018 09 01 Rotenone exerts developmental neurotoxicity in a human brain spheroid model Toxicology and Applied Pharmacology Alternative Approaches to Developmental Neurotoxicity Evaluation 354 101 114 doi 10 1016 j taap 2018 02 003 ISSN 0041 008X PMC 6082736 PMID 29428530 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 PMID 15540952 Summary of the article by Dr Greenamyre on pesticides and Parkinson s Disease at ninds nih gov Tanner CM Kamel F Ross GW Hoppin JA Goldman SM Korell M Marras C Bhudhikanok GS Kasten M Chade AR Comyns K Richards MB Meng C Priestley B Fernandez HH Cambi F Umbach DM Blair A Sandler DP Langston JW 2011 Rotenone Paraquat and Parkinson s Disease Environmental Health Perspectives 119 6 866 72 doi 10 1289 ehp 1002839 ISSN 0091 6765 PMC 3114824 PMID 21269927 Gao HM Liu B Hong JS July 2003 Critical role for microglial NADPH oxidase in rotenone induced degeneration of dopaminergic neurons The Journal of Neuroscience 23 15 6181 7 doi 10 1523 JNEUROSCI 23 15 06181 2003 PMC 6740554 PMID 12867501 Freestone PS Chung KK Guatteo E Mercuri NB Nicholson LF Lipski J November 2009 Acute action of rotenone on nigral dopaminergic neurons involvement of reactive oxygen species and disruption of Ca2 homeostasis The European Journal of Neuroscience 30 10 1849 59 doi 10 1111 j 1460 9568 2009 06990 x PMID 19912331 S2CID 205515222 Huang B Wu S Wang Z Ge L Rizak JD Wu J Li J Xu L Lv L Yin Y Hu X 2018 05 21 Phosphorylated a Synuclein Accumulations and Lewy Body like Pathology Distributed in Parkinson s Disease Related Brain Areas of Aged Rhesus Monkeys Treated with MPTP Neuroscience 379 302 315 doi 10 1016 j neuroscience 2018 03 026 ISSN 0306 4522 PMID 29592843 S2CID 4969894 Neurotransmitters and Disorders of the Basal Ganglia Basic Neurochemistry NCBI Bookshelf American Society for Neurochemistry Pan Montojo F Anichtchik O Dening Y Knels L Pursche S Jung R Jackson S Gille G Spillantini MG 2010 Kleinschnitz C ed Progression of Parkinson s Disease Pathology Is Reproduced by Intragastric Administration of Rotenone in Mice PLOS ONE 5 1 e8762 Bibcode 2010PLoSO 5 8762P doi 10 1371 journal pone 0008762 PMC 2808242 PMID 20098733 Monroe Bill December 3 2010 Mann Lake Gets a Second Round of Rotenone for Cutthroat Restoration The Oregonian Oregon Live LLC Archived from the original on April 24 2011 Retrieved 2012 12 20 Earl Elizabeth Fish population booms in Stormy Lake Peninsula Clarion 10 7 2015 Fimrite Peter 12 November 2014 Alien fish poisoned by the thousands to save S F s Mountain Lake SFGate Hearst Retrieved 24 September 2015 Divakaruni AS Rogers GW Murphy AN 2014 Measuring Mitochondrial Function in Permeabilized Cells Using the Seahorse XF Analyzer or a Clark Type Oxygen Electrode Curr Protoc Toxicol 60 25 2 1 16 doi 10 1002 0471140856 tx2502s60 PMID 24865646 S2CID 21195854 Donald L Archer 2001 Rotenone Neutralization Methods PDF American Fisheries Society archived from the original PDF on 2017 11 07External links editRotenone Molecule of the Month at chm bris ac uk Cornell University Rotenone Resource Guide for Organic and Disease Management Archived 2007 06 09 at the Wayback Machine Rotenone ARS Pesticide Properties Database Rotenone use in research on the biodiversity of marine fishes Rotenone Factsheet Rotenone registration at US Environmental Protection Agency CDC NIOSH Pocket Guide to Chemical Hazards Rotenone at Bioblast Chemical Description Retrieved from https en wikipedia org w index php title Rotenone amp oldid 1185439838, wikipedia, wiki, book, books, library,

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