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Revision as of 11:52, 21 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,044 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL').← Previous edit		Latest revision as of 11:18, 2 December 2024 edit undoBosula (talk | contribs)Extended confirmed users601 edits →Rotenone degradation and ecosystem impact: changes subsection headings to subsubsection headingsTag: Visual edit
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	{{chembox		{{Chembox
	| Verifiedfields = changed		| Verifiedfields = changed
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 431968369		| verifiedrevid = 456665070
	| ImageFile1=rotenone.png		| ImageFile1 = Rotenone Structural Formula V.1.svg
	| ImageSize1 = 200px		| ImageSize1 = 200
			| ImageAlt1 = Skeletal formula of rotenone
	<!--| ImageFile2=rotenone.jpg doesn't appear to match connectivity or stereochemistry of skeletal -->
			| ImageFile2 = rotenone-3D-spacefill.png
	| ImageSize2 = 200px
			| ImageSize2 = 200
	| IUPACName = {{{IUPAC|(2''R'',6a''S'',12a''S'')-1,2,6,6a,12,12a-<br>hexahydro-2-isopropenyl-8,9-<br>dimethoxychromeno<br>furo(2,3-h)chromen-6-one}}}
			| ImageAlt2 = Space-filling model of the rotenone molecule
			| IUPACName = (5′′''R'')-4′,5′-Dimethoxy-5′′-(prop-1-en-2-yl)-4′′,5′′-dihydrofurorotenan-4-one
			| SystematicName = (2''R'',6a''S'',12a''S'')-8,9-Dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrobenzopyranofurobenzopyran-6(6a''H'')-one
	| OtherNames = Tubatoxin, Paraderil		| OtherNames = Tubatoxin, Paraderil
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 83-79-4		| CASNo = 83-79-4
	| PubChem = 6758		| PubChem = 6758
			| ChEBI_Ref = {{ebicite|changed|EBI}}
			| ChEBI = 28201
	| ChEMBL_Ref = {{ebicite|changed|EBI}}		| ChEMBL_Ref = {{ebicite|changed|EBI}}
	| ChEMBL = <!-- blanked - oldvalue: 429023 -->		| ChEMBL = 429023
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
			| ChemSpiderID = 6500
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = C07593		| KEGG = C07593
	| UNII_Ref = {{fdacite|changed|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 03L9OT429T		| UNII = 03L9OT429T
	| SMILES = CC(=C)1CC2=C(O1)C=CC3=C2O4COC5=CC(=C(C=C54C3=O)OC)OC		| SMILES = CC(=C)1Cc2c(O1)ccc3c2O4COc5cc(OC)c(OC)cc54C3=O
	| InChI = 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		| 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
	| MeSHName = Rotenone		| MeSHName = Rotenone
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
			| C=23
	| Formula = C<sub>23</sub>H<sub>22</sub>O<sub>6</sub>
			| H=22
	| MolarMass = 394.41
			| O=6
	| ExactMass = 394.14164
	| Appearance = Colorless to red		| Appearance = Colorless to red crystalline solid<ref name=PGCH />
			| Odor = odorless<ref name=PGCH />
	| Density = 1.27 g/cm<sup>3</sup> @ 20°C
			| Density = 1.27 g/cm<sup>3</sup> @ 20&nbsp;°C
	| MeltingPt = 165-166°C
			| MeltingPtC = 165 to 166
	| BoilingPt = 210-220°C at 0.5 mmHg
			| BoilingPtC = 210 to 220
	| SolubleOther = Soluble in ] and ], slightly soluble in ]
			| BoilingPt_notes = at 0.5 mmHg
	}}
			| SolubleOther = Soluble in ] and ], slightly soluble in ]
	| Section3 = {{Chembox Hazards
			| VaporPressure = <0.00004 mmHg (20°C)<ref name=PGCH />
	| Solubility =
			}}
	| MainHazards =
			|Section3={{Chembox Hazards
	| FlashPt =
	| Autoignition =		| MainHazards =
			| FlashPt =
	}}
			| AutoignitionPt =
			| IDLH = 2500 mg/m<sup>3</sup><ref name=PGCH>{{PGCH|0548}}</ref>
			| REL = TWA 5 mg/m<sup>3</sup><ref name=PGCH />
			| PEL = TWA 5 mg/m<sup>3</sup><ref name=PGCH />
			| LD50 = 60 mg/kg (oral, rat)<br />132 mg/kg (oral, rat)<br />25 mg/kg (oral, rat)<br />2.8 mg/kg (oral, mouse)<ref>{{IDLH|83794|Rotenone}}</ref>
			}}
	}}		}}
	'''Rotenone''' is an odorless chemical that is used as a broad-spectrum ], ], and ]. It occurs naturally in the roots and stems of several plants such as the ] vine plant. In mammals, including humans, it is linked to the development of ].<ref name="Tanner 2011">{{Cite journal
	| doi = 10.1289/ehp.1002839
	| issn = 0091-6765
	| last = Tanner
	| first = Caroline M.
	| coauthors = Freya Kamel, G. Webster Ross, Jane A. Hoppin, Samuel M. Goldman, Monica Korell, Connie Marras, Grace S. Bhudhikanok, Meike Kasten, Anabel R. Chade, Kathleen Comyns, Marie Barber Richards, Cheryl Meng, Benjamin Priestley, Hubert H. Fernandez, Franca Cambi, David M. Umbach, Aaron Blair, Dale P. Sandler, J. William Langston
	| title = Rotenone, Paraquat and Parkinson’s Disease
	| journal = Environmental Health Perspectives
	| accessdate = 2011-02-14
	| year = 2011
	| url = http://ehp03.niehs.nih.gov/article/fetchArticle.action?articleURI=info%3Adoi%2F10.1289%2Fehp.1002839
	| pmid=21269927
	}}</ref>
			'''Rotenone''' is an odorless, colorless, ] ]. It occurs naturally in the seeds and stems of several plants, such as the ] vine, and in the roots of several other members of the ]. It was the first-described member of the family of chemical compounds known as ]s. Rotenone is approved for use as a piscicide to remove ],<ref name=":12">{{Cite journal |vauthors=Rytwinski T, Taylor JJ, Donaldson LA, Britton JR, Browne DR, Gresswell RE, Lintermans M, Prior KA, Pellatt MG, Vis C, Cooke SJ |year=2018 |title=The effectiveness of non-native fish removal techniques in freshwater ecosystems: A systematic review |url=http://eprints.bournemouth.ac.uk/31355/1/Rytwinski%20et%20al_Fish%20removal%20SR_FINAL.pdf |journal=Environmental Reviews |language=English |volume=27 |issue=1 |pages=71–94 |doi=10.1139/er-2018-0049 |s2cid=92554010 |postscript=, summary in French}}</ref> see ''Uses.'' It has also been used as a broad-spectrum ], but its use as an insecticide has been banned in many countries.
	==History==
	] first isolated rotenone from a specimen of ''Robinia nicou'', now called '']'', while traveling in ].<ref>{{cite journal| last=Ambrose | first=Anthony M. | coauthors=Harvey B. Haag | year=1936 | title=Toxicological study of ''Derris'' | journal=Industrial & Engineering Chemistry | volume=28 | issue=7 | pages=815–821 | doi=10.1021/ie50319a017}}</ref> He wrote about this research in his thesis, published posthumously in 1895 after his death from a ].<ref>{{cite web| title=Useful tropical plants | publisher=ASNOM | url=http://www.asnom.org/en/730_plantes_tropicales_utiles.html | date=2008-01-02 | accessdate=2008-03-16}}</ref> Researchers later determined that the substance that Geoffroy termed ''nicouline'' was identically rotenone.
	==Uses==		== Discovery ==
			The earliest written record of the now-known rotenone-containing plants used for killing leaf-eating ] was in 1848; for centuries, these same plants had been used to ].<ref name="Metcalf">{{cite book |title=The Mode of Action of Organic Insecticides |publisher=National Research Council, Washington DC |year=1948 |url=https://books.google.com/books?id=PmcrAAAAYAAJ&q=rotenone+isolated&pg=PA29 |author=Metcalf, R. L.}}</ref> The active chemical component was first isolated in 1895 by a French botanist, ], who called it ''nicouline'', from a specimen of ''] nicou'', now called '']'', while traveling in ].<ref>{{cite journal| last1=Ambrose | first1=Anthony M. |author2=Harvey B. Haag | year=1936 | title=Toxicological study of ''Derris'' | journal=Industrial & Engineering Chemistry | volume=28 | issue=7 | pages=815–821 | doi=10.1021/ie50319a017}}</ref> He wrote about this research in his thesis, published in 1895 after his death from a ].<ref>{{cite web| title=Useful tropical plants | publisher=ASNOM | url=http://www.asnom.org/en/730_plantes_tropicales_utiles.html | date=2008-01-02 | access-date=2008-03-16}}</ref> In 1902 ], Japanese ] of the ], isolated a pure crystalline compound from '']'' which he called rotenone, after the Taiwanese name of the plant 蘆藤 ({{Langx|nan|lôo-tîn}}) translated into Japanese {{Nihongo|2=ローテン|3=rōten}}.<ref name="Nagai1902">{{cite journal
	Rotenone is used in solution as a pesticide and insecticide, or in emulsified liquid form as a piscicide.<ref>
			| author = Nagai, Kazuo
	{{cite web
			| title = 魚籘有毒成分の研究 第一報
			| journal = 東京化學會誌
			| volume = 23
			| number = 7
			| pages = 744–777
			| doi = 10.1246/nikkashi1880.23.744
			| doi-access = free
			| year = 1902
			| language = ja
			}}</ref> By 1930, nicouline and rotenone were established to be chemically the same.<ref>{{cite journal |year=1933 |title=The Determination of the structure of rotenone |journal=Chemical Reviews |volume=18 |issue=2 |pages=181–213 |doi=10.1021/cr60042a001| vauthors=La Forge FB, Haller HL, Smith LE}}</ref>
			== Uses ==
			=== Use as piscicide in fisheries management ===
			When absorbed through the gills, rotenone disrupts cellular respiration in fish, and may lead to their death, depending on the concentration used. Due to this, it has become a key tool in managing ecosystems affected by invasive or unwanted fish species, and as of 2024 there are no viable options that can replace its versatile value in fish removal actions.
			Its value in ecosystem restoration is appreciated due to its rapid degradation, when exposed to light and warm temperatures, making it a temporary measure with minimal long-term environmental effects, see ''Rotenone and Ecosystem Impact''.
			Rotenone is used as a nonselective piscicide (fish killer).<ref>{{cite news
	|url=http://sfgate.com/cgi-bin/article.cgi?f=/c/a/2007/10/02/BAOHSI41V.DTL		|url=http://sfgate.com/cgi-bin/article.cgi?f=/c/a/2007/10/02/BAOHSI41V.DTL
	|title=Lake poisoning seems to have worked to kill invasive pike		|title=Lake poisoning seems to have worked to kill invasive pike
	|author=Peter Fimrite		|author=Peter Fimrite
	|publisher=]		|newspaper=]
	|date=2007-10-02		|date=2007-10-02
			}}</ref> Rotenone has historically been used by ] to catch fish. Typically, rotenone-containing plants in the ] family, ], are crushed and introduced into a body of water, and as rotenone interferes with ], the affected fish rise to the surface in an attempt to gulp air, where they are more easily caught.
	}}</ref>
			In modern times it is frequently used as a tool to remove ],<ref name=":1">{{Cite journal |vauthors=Rytwinski T, Taylor JJ, Donaldson LA, Britton JR, Browne DR, Gresswell RE, Lintermans M, Prior KA, Pellatt MG, Vis C, Cooke SJ |title=The effectiveness of non-native fish removal techniques in freshwater ecosystems: A systematic review |journal=Environmental Reviews |year=2018 |volume=27 |pages=71–94 |language=English |postscript=, summary in French |doi=10.1139/er-2018-0049 |issue=1|s2cid=92554010 |url=http://eprints.bournemouth.ac.uk/31355/1/Rytwinski%20et%20al_Fish%20removal%20SR_FINAL.pdf }}</ref> as it has a relatively short ] (days) and is gone from rivers in the course of days and from lakes within a few months, depending on (seasonal) stirring, ] content, availability of sunlight and temperature.<ref name=":0">{{Cite book |title=Planning and Standard Operating Procedures for the Use of Rotenone in Fish Management – Rotenone SOP Manual |vauthors=Finlayson B, Schnick R, Skaar D, Anderson J, Demong L, Duffield D, Horton W, Steinkjer J |publisher=American Fisheries Society |year=2018 |isbn=978-1-934874-49-3 |edition=2nd |location=Bethesda, Maryland |publication-date=May 2018 |pages= |language=English}}</ref> Rotenone has been used by government agencies to kill fish in rivers and lakes in the United States since 1952,<ref>{{cite journal |last=Schmidt |first=Peter |date=28 February 2010 |title=One Strange Fish Tale |journal=The Chronicle of Higher Education |url=http://chronicle.com/article/One-Strange-Fish-Tale/64348/ |access-date=24 September 2015}}</ref> and in Canada<ref>{{Cite web |title=Invasive Goldfish management |date=10 January 2023 |url=https://www.rmwb.ca/en/parks-and-recreation/invasive-goldfish-management.aspx#Why-are-we-using-Rotenone}}</ref> and Norway<ref>{{Cite book |last1=Mo |first1=TO |title=Har myndighetene lyktes i kampen mot Gyrodactylus salaris? |last2=Holthe |first2=E |last3=Andersen |first3=O |publisher=Norsk institutt for naturforskning, NINA rapport |year=2022 |isbn=978-82-426-4950-8 |issue=2157 |pages=1–62 |language=Norwegian |postscript=, summary in English |type=Report}}</ref> 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 (]), Sweden (] and ]), Spain (], ]) and Hungary (]).
	People catch fish by extracting rotenone from plants and releasing it into water. Poisoned fish come to the surface and are easily caught. This method was first practiced by various indigenous tribes<ref></ref> who smashed the roots. Fish caught this way can be eaten because rotenone is very poorly absorbed by the gastrointestinal tract of humans, whereas it is lethal to fish because it readily enters the blood stream of the fish through the gills.
	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.<ref>{{cite journal |doi=10.1641/B580211 |title=Rotenone: An Essential but Demonized Tool for Assessing Marine Fish Diversity |year=2008 |last1=Robertson |first1=D. Ross |last2=Smith-Vaniz |first2=William F. |journal=BioScience |volume=58 |pages=165 |issue=2}}</ref>		Rotenone 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, local and transient environmental side effects.<ref>{{cite journal |last1=Robertson |first1=D. Ross |last2=Smith-Vaniz |first2=William F. |year=2008 |title=Rotenone: An Essential but Demonized Tool for Assessing Marine Fish Diversity |journal=BioScience |volume=58 |issue=2 |pages=165 |doi=10.1641/B580211 |doi-access=free}}</ref>
			==== Rotenone degradation and ecosystem impact ====
	Rotenone is also used in powdered form to reduce ] ]s on ] and other ]. In the United States and in Canada, all uses of rotenone except as a piscicide (fish killer) are being phased out.<ref>, EPA 738-R-07-005, March 2007, United States Environmental Protection Agency</ref><ref>, Consumer Product Safety, Health Canada</ref>
			Rotenone primarily affects gilled organisms such as fish and aquatic invertebrates. Terrestrial animals such as birds, mammals, and amphibians (except tadpoles/larvae) are much less affected by rotenone.<ref>{{cite web |last1=Skaar |first1=Donald R. |display-authors=etal |title=Effects of Rotenone on Amphibians and Macroinvertebrates in Yellowstone |url=https://www.nps.gov/articles/effects-of-rotenone-on-amphibians-and-macroinvertebrates-in-yellowstone.htm |publisher=U.S. National Park Service |access-date=29 September 2024 |language=en}}</ref> When applied in freshwater systems, the treatment dose kills the target fish and usually other gilled species like tadpoles and zooplankton are affected, depending on dosage. However, timing treatments in the fall or winter, when many species are less active, can reduce these impacts. Some taxa may also recover through natural life cycles, such as resting eggs. Its use is more benign for the environment (as compared to drying ponds, or using other piscicides), and studies show that most ecosystems naturally recover within one or two years after rotenone application- with aquatic invertebrates repopulating affected areas,<ref>{{Cite book |last=Kjærstad |first=Gaute |title=The eradication of invasive species using rotenone and its impact on freshwater macroinvertebrates |publisher=Doctoral theses at NTNU |year=2022 |isbn=978-82-326-6270-8 |location=Trondheim |pages=1–100 |language=English}}</ref><ref>{{Cite journal |last=Fjellheim |first=A. |year=2004 |title=Virkning av rotenonbehandling på bunndyrsamfunnene I et område ved Stigstu, Hardangervidda |url=http://hdl.handle.net/11250/2630458 |journal=Lfi-122 |language=Norwegian |publisher=LFI, University of Bergen |pages=1–60 |issn=0801-9576 |hdl=11250/2630458}}</ref><ref>{{Cite journal |last1=Vinson |first1=V |last2=Dinger |first2=EC |last3=Vinson |first3=DK |year=2010 |title=Piscicides and invertebrates: after 70 years, does anyone really know? |journal=Fisheries |volume=35 |issue=2 |pages=61–71 |bibcode=2010Fish...35...61V |doi=10.1577/1548-8446-35.2.61}}</ref> thus restoring initial local biodiversity to its status prior to the introduction of the invasive species.
			Rotenone decays through ]s and its final product is reduced to ] and ].<ref name=":0" /> 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&nbsp;°C to 3.5 days at 0&nbsp;°C.<ref>{{cite web |author=Kevin C. Ott |title=Rotenone. A Brief Review of its Chemistry, Environmental Fate, and the Toxicity of Rotenone Formulations |url=http://www.newmexicotu.org/Rotenone%20summary.pdf |url-status=dead |archive-url=https://web.archive.org/web/20120904171741/http://www.newmexicotu.org/Rotenone%20summary.pdf |archive-date=2012-09-04}}</ref>
	Rotenone is sold as an organic pesticide dust for the garden. Unselective in action, it kills potato beetles, cucumber beetles, flea beetles, cabbage worms, raspberry bugs, and asparagus bugs, as well as most other arthropods. Rotenone rapidly bio-degrades under warm conditions so there is minimal harmful residue. A light dusting on the leaves of plants will control insects for several days. It is not known to be harmful to humans when used properly.
	However, a recent report from the National Institutes of Health finds statistically significant associations between use of either rotenone or paraquat with Parkinson's disease.<ref>http://www.nih.gov/news/health/feb2011/niehs-11.htm</ref>
			==== Notable administrations as piscicide ====
	Use of Rotenone is controversial as it is not a selective piscicide (kills all species of fish), and in general is not able to kill 100% of the fish from a body of water, thus resulting in eventual return of the species targeted for killing.
			Norwegian authorities have been using rotenone since the mid-1980s to eradicate the salmon fluke ],<ref>{{Cite journal |last=Adolfsen |first=Pål |last2=Bardal |first2=Helge |last3=Aune |first3=Svein |date=2021 |title=Fighting an invasive fish parasite in subarctic Norwegian rivers – The end of a long story? |url=http://dx.doi.org/10.3391/mbi.2021.12.3 |journal=Management of Biological Invasions |volume=12 |issue=1 |pages=49–65 |doi=10.3391/mbi.2021.12.3 |issn=1989-8649|doi-access=free }}</ref> and as of 2024 48 out of 54 affected river catchments have been treated. Additionally, many lakes and ponds have been rotenone treated in an effort to remove national or regional invasive species, such as ], ], ], ], ] and ].<ref>Bardal, H. 2019. Small- and large-scale eradication of invasive fish and fish parasites in freshwater systems in Norway. In: C.R. Veitch, M.N. Clout, A.R. Martin, J.C. Russell, and C.J. West (eds.). Island invasives: scaling up to meet the challenge, pp. 457-451. Occasional paper SSC no. 62. Gland, Switzerland: IUCN.</ref>
			In 1992, ] (FWC) officials used rotenone to eradicate an established population of invasive ] from a small pond in ]. Officials were successful in killing every jaguar cichlid (along with every other fish) in the pond, but unsuccessful in eradicating them from ]; the cichlids had already spread throughout the ] and its connected ]s, and by 1994, jaguar cichlids had successfully established themselves throughout ] and ].<ref name="Shaffland1996">{{cite journal |last=Shafland |first=Paul L. |date=23 December 2008 |orig-date=1996 |title=Exotic fishes of Florida — 1994 |url=https://files.catbox.moe/7mtmdp.pdf |url-status=live |journal=Reviews in Fisheries Science & Aquaculture |publisher=Taylor & Francis |volume=4 |issue=2 |pages=101–122 |doi=10.1080/10641269609388581 |archive-url=https://web.archive.org/web/20240424220601/https://files.catbox.moe/7mtmdp.pdf |archive-date=24 April 2024 |access-date=24 April 2024}}</ref>
	==Method of action==
	Rotenone works by interfering with the ] in ]. To be specific, it inhibits the transfer of electrons from iron-sulfur centers in ] to ]. This interferes with ] during the creation of usable cellular energy (]). This is much like the action of ].
			In September 2010, ] officials used rotenone to kill an established population of ] ] present in eastern Oregon's ], with the intention of not disrupting the lake's native ] population. Rotenone successfully achieved these aims, killing between 179,000–197,000 goldfish and ]s, and only three trout.<ref>{{cite news |last=Monroe |first=Bill |date=December 3, 2010 |title=Mann Lake Gets a Second Round of Rotenone for Cutthroat Restoration |url=http://www.oregonlive.com/sports/oregonian/bill_monroe/index.ssf/2010/12/mann_lake_gets_a_second_round.html |url-status=live |archive-url=https://web.archive.org/web/20110424075200/http://www.oregonlive.com/sports/oregonian/bill_monroe/index.ssf/2010/12/mann_lake_gets_a_second_round.html |archive-date=April 24, 2011 |access-date=2012-12-20 |work=The Oregonian |publisher=Oregon Live LLC}}</ref>
	==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 '']'' or '']''.
			Beginning May 1, 2006, ], 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 ], which were probably introduced accidentally by ] who used them as ]. The lake was restocked with 20,000 ] in 2006; as of 2016, the lake's fish population has recovered.
	Some of the plants containing rotenone:
	*Hoary Pea or Goat’s Rue ('']'') – North America
	*Jícama ('']'') – North America
	*Cubé Plant or Lancepod ('']'') – South America<ref name="Fang">{{cite journal |author=Fang N, Casida J |title=Cubé resin insecticide: identification and biological activity of 29 rotenoid constituents |journal=J Agric Food Chem |volume=47 |issue=5 |pages=2130–6 |year=1999 |pmid=10552508 |doi= 10.1021/jf981188x }}</ref>
	**The root extract is referred to as Cubé resin
	*Barbasco ('']'') – South America<ref name="Fang" />
	**The root extract is referred to as Cubé resin
	*Tuba Plant ('']'') – southeast Asia & southwest Pacific islands
	**The root extract is referred to as Derris or Derris root
	*Jewel Vine ('']'') – southeast Asia & southwest Pacific islands
	*Among the Mizo tribes of India (''Derris walchii''/''D. thyrsiflora'') the tender root is eaten as vegetable {{Citation needed|date=October 2008}}
	**The root extract is referred to as Derris or Derris root
	*] – 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. {{Citation needed|date=October 2008}}
	*'']'' {{Citation needed|date=October 2008}}
	*Cork-Bush ('']'') – southern Africa<ref name="Palgrave">
	{{cite book | last = Coates Palgrave | first = Keith | title = Trees of Southern Africa | publisher = ] | year = 2002 | isbn = 0869770810}}</ref>
	*Florida fishpoison tree ('']'') – southern Florida, Caribbean<ref name=Nellis>Nellis, David N. (1994). Seashore plants of South Florida and the Caribbean. Pineapple Press. 160 p.</ref>
			In 2012, rotenone was used to kill all remaining fish in ] due to invasive pike destroying native species, which were reintroduced once the treatment was concluded.<ref>Earl, Elizabeth, ], 10/7/2015</ref>
	==Toxicity==
	Rotenone is classified by the ] as moderately hazardous.<ref name="who">{{cite book | title=The WHO Recommended Classification of Pesticides by Hazard | publisher=] | isbn=92-4-154663-8 | year=2007 | url=http://www.who.int/ipcs/publications/pesticides_hazard/en/ | accessdate=2007-12-02 | author=IPCS, International Programme on Chemical Safety; United Nations Environment Programme; International Labour Organization; World Health Organization.}}</ref> It is mildly toxic to ]s and other ]s, but extremely toxic to insects and aquatic life including fish. This higher toxicity in fish and insects is due to the fact that the ] rotenone is easily taken up through the ]s or ], but not as easily through the skin or through the ].
			In 2014, rotenone was used to kill all remaining fish in San Francisco's Mountain Lake, which is located in ], in order to rid it of invasive species introduced since the migration of European settlers to the region.<ref>{{cite web |last=Fimrite |first=Peter |date=12 November 2014 |title=Alien fish poisoned by the thousands to save S.F.'s Mountain Lake |url=http://www.sfgate.com/bayarea/article/Workers-pour-poison-into-Mountain-Lake-begin-5888355.php |access-date=24 September 2015 |publisher=SFGate / Hearst}}</ref>
			==== Deactivation ====
	The lowest lethal dose for a child is 143&nbsp;mg/kg. Human deaths from rotenone poisoning are rare because its irritating action causes vomiting.<ref>{{cite journal|journal=Pesticides News |volume=54|year=2001|pages=20–21|title=Rotenone |url=http://www.pan-uk.org/pestnews/Actives/rotenone.htm}}</ref> Deliberate ingestion of rotenone can be fatal.<ref name="wood">{{cite journal |author=Wood DM, Alsahaf H, Streete P, Dargan PI, Jones AL |title=Fatality after deliberate ingestion of the pesticide rotenone: a case report |journal=Critical Care |volume=9 |issue=3 |pages=R280–4 |year=2005 |month=June |pmid=15987402 |pmc=1175899 |doi=10.1186/cc3528}}</ref>
			Rotenone can be deactivated in water with the use of ] to lower toxicity to acceptable levels.<ref>{{citation |author=Donald L Archer |title=Rotenone Neutralization Methods |date=2001 |url=http://www.fisheriessociety.org/rotenone/rewards/01archer.pdf |archive-url=https://web.archive.org/web/20171107024940/http://www.fisheriessociety.org/rotenone/rewards/01archer.pdf |archive-date=2017-11-07 |url-status=dead |publisher=American Fisheries Society}}</ref>
			=== Use as insecticide ===
	The compound ] when exposed to sunlight and usually has a lifetime of six days in the environment.<ref>Vitax Safety Data Sheet for Derris dust, revised October 1998</ref> In water rotenone may last six months.{{Citation needed|date=July 2007}}
			Rotenone was commercialized as '']'', ], in single preparation or in ] combination with other insecticides.<ref name="Hayes">{{cite book |author=Hayes W. J. |url=https://books.google.com/books?id=sUrLT9z9i3IC&q=rotenone+millettia&pg=PA135 |title=Handbook on Pesticides |publisher=] |year=1991 |isbn=978-0-12-334161-7 |volume=1}}</ref> It has high acute toxicity to mammals,<ref>{{Cite web |date=March 2007 |title=Reregistration Eligibility Decision for Rotenone |url=https://www3.epa.gov/pesticides/chem_search/reg_actions/reregistration/red_PC-071003_31-Mar-07.pdf |access-date=22 October 2024 |website=United States Environmental Protection Agency}}</ref> and all insecticidal uses were banned in the United States and Canada,<ref>,{{dead link|date=January 2020}} Consumer Product Safety, Health Canada</ref><ref>{{cite journal |last= |first= |date= |title=7 CFR § 205.602 - Nonsynthetic substances prohibited for use in organic crop production |url=https://www.law.cornell.edu/cfr/text/7/205.602 |journal=Cornell Law School Legal Information Institute |access-date=20 May 2021}}</ref> in the EU,<ref name=":3" /> in the UK,<ref>{{cite web |date=2 October 2008 |title=RHS advice for the garden - Rotenone withdrawal |url=https://www.telegraph.co.uk/gardening/gardeningadvice/3350291/RHS-advice-for-the-garden.html |access-date=20 October 2019 |website=Telegraph Gardening}}</ref> and in Switzerland.<ref name=":3">{{Cite web |last=Dowle |first=Joanna |date=2 August 2024 |title=How safe are natural insecticides? |url=https://www.epa.govt.nz/community-involvement/science-at-work/how-safe-is-natural-taking-a-look-at-four-plant-based-pesticides-from-natures-arsenal/ |access-date=4 August 2024 |website=Environmental Protection Agency of New Zealand}}</ref> It remains legal as a pesticide in a number of other countries, including Australia<ref>{{cite web |url=https://www.apvma.gov.au/chemicals-and-products/active-constituents/exempt |title=Active constituents exempt from the requirements of APVMA approval for use in agricultural or veterinary chemical products |access-date=2 December 2024 |website=Australian Pesticides and Veterinary Medicines Authority}}</ref> and New Zealand;<ref>{{cite web |url=https://www.epa.govt.nz/assets/RecordsAPI/Rotenone_HSR003076.pdf |title=Approval for Rotenone (HSR003076) |website=Environmental Protection Agency of New Zealand |date=30 April 2021 |access-date=2 December 2024}}</ref> the status and effective date of ban in select countries is provided in the table below.
			{| class="wikitable"
	Rotenone is classified by the ] ] as a nonsynthetic and was allowed to be used to grow ] produce until 2005, when it was added to the list of prohibited substances due to concerns about its safety. However, it has since been re-approved.<ref>. List of substances approved by the National Organic Program (from the Electronic Code of Federal Regulations).</ref>
			|+ Legal status of rotenone as a pesticide, by country
			|-
			! Country !! Status !! Ban effective
			|-
			| Australia || legal || -
			|-
			| Canada || banned || 31 December 2012
			|-
			| EU || banned || 10 October 2008
			|-
			| New Zealand || legal || -
			|-
			| Switzerland || banned || 1 January 2014
			|-
			| United Kingdom || banned || 10 October 2008
			|-
			| United States || banned || 23 March 2011 (EPA); 28 January 2019 (USDA)
			|}
			Rotenone was used in powdered form to treat ] and ] on humans, and ] ]s on ], ], and ] animals.
	=== Parkinson's disease ===
	In 2000, it was reported that injecting rotenone into rats causes the development of symptoms similar to those of ] (PD). Rotenone was continuously applied over a period of five weeks, mixed with ] and ] to enhance tissue penetration, and injected into the ].<ref>{{cite journal |author=Caboni P, Sherer T, Zhang N, Taylor G, Na H, Greenamyre J, Casida J |title=Rotenone, deguelin, their metabolites, and the rat model of Parkinson's disease |journal=Chem Res Toxicol |volume=17 |issue=11 |pages=1540–8 |year=2004 |pmid=15540952 |doi= 10.1021/tx049867r }}</ref> The study does not directly suggest that 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.<ref></ref>
			In agriculture it was unselective in action and killed ]s, ]s, ]s, ]s, ]s, and ]s, as well as most other arthropods. It biodegrades rapidly in soil, with 90% degraded after 1–3 months at {{convert|20|C|F}} and three times faster at {{convert|30|C|F}}.<ref>{{Cite journal |last1=Cavoski |first1=Ivana |last2=Caboni |first2=Pierluigi |last3=Sarais |first3=Giorgia |last4=Miano |first4=Teodoro |date=2008-08-06 |title=Degradation and Persistence of Rotenone in Soils and Influence of Temperature Variations |journal=Journal of Agricultural and Food Chemistry |language=EN |volume=56 |issue=17 |pages=8066–8073 |doi=10.1021/jf801461h |pmid=18681442}}</ref> The compound ] when exposed to sunlight and usually has an activity of six days in the environment.<ref name=":2">Vitax Safety Data Sheet for Derris dust, revised October 1998</ref>
	In addition, studies with primary cultures of rat ]s and ] have shown that low doses of rotenone (below 10 nM) induce oxidative damage and death of ] ]<ref>{{cite journal |author=Gao HM, Liu B, Hong JS |title=Critical role for microglial NADPH oxidase in rotenone-induced degeneration of dopaminergic neurons |journal=The Journal of Neuroscience |volume=23 |issue=15 |pages=6181–7 |year=2003 |month=July |pmid=12867501 |url=http://www.jneurosci.org/cgi/pmidlookup?view=long&pmid=12867501}}</ref> and it is these neurons in the ] 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.<ref>{{cite journal |author=Freestone PS, Chung KK, Guatteo E, Mercuri NB, Nicholson LF, Lipski J |title=Acute action of rotenone on nigral dopaminergic neurons--involvement of reactive oxygen species and disruption of Ca2+ homeostasis |journal=The European Journal of Neuroscience |volume=30 |issue=10 |pages=1849–59 |year=2009 |month=November |pmid=19912331 |doi=10.1111/j.1460-9568.2009.06990.x}}</ref> This toxicity was exacerbated by an additional cell stressor - elevated intracellular calcium concentration - adding support to the 'multiple hit hypothesis' of dopaminergic neuron death.
			== Mechanism of action ==
	It had been known earlier that the ] ] causes 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 ], a key component to PD pathology. Therefore, the mechanism behind MPTP as it relates to Parkinson's Disease is not fully understood.<ref> -- Basic Neurochemistry -- NCBI Bookshelf, American Society for Neurochemistry</ref> Because of these developments, rotenone was investigated as a possible Parkinson-causing agent. Both MPTP and rotenone are ] and can cross the ].
			Rotenone works by interfering with the ] within ] in ], which places it in ] ] class 21 (by itself in 21B).<ref name="IRAC-MoAs">{{cite web|url=http://irac-online.org/documents/moa-classification/|date=March 2020|publisher=]|title=IRAC Mode of Action Classification Scheme Version 9.4|author=IRAC International MoA Working Group}}</ref> It inhibits the transfer of electrons from iron-sulfur centers in ] to ]. This interferes with ] during the creation of usable cellular energy (]).<ref name="Hayes" /> Complex I is unable to pass off its electron to ], creating a back-up of electrons within the mitochondrial matrix. Cellular oxygen is reduced to the radical, creating ], which can damage ] and other components of the mitochondria.<ref name=Nature>{{cite journal |last=Mehta |first=Suresh |title=Neuroprotective role of mitochondrial uncoupling protein 2 in cerebral stroke |journal=Journal of Cerebral Blood Flow and Metabolism |pmid=19240738 |volume=29 |doi=10.1038/jcbfm.2009.4 |year=2009 |issue=6 |pages=1069–78 |doi-access=free}}</ref>
			Rotenone is used in biomedical research to study the oxygen consumption rate of cells, usually in combination with ] (an ] inhibitor), ] (an ATP synthase inhibitor) and ] (a mitochondrial ]).<ref>{{cite journal |vauthors=Divakaruni AS, Rogers GW, Murphy AN |year=2014 |title=Measuring Mitochondrial Function in Permeabilized Cells Using the Seahorse XF Analyzer or a Clark-Type Oxygen Electrode |journal=Curr Protoc Toxicol |volume=60 |pages=25.2.1–16 |doi=10.1002/0471140856.tx2502s60 |pmid=24865646 |s2cid=21195854}}</ref>
	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.<ref>{{cite journal | doi = 10.1371/journal.pone.0008762 | pmc = 2808242 | url = http://precedings.nature.com/documents/3352/version/3 | pmid = 20098733 | title = Progression of Parkinson's Disease Pathology Is Reproduced by Intragastric Administration of Rotenone in Mice | year = 2010 | last1 = Pan-Montojo | first1 = Francisco | last2 = Anichtchik | first2 = Oleg | last3 = Dening | first3 = Yanina | last4 = Knels | first4 = Lilla | last5 = Pursche | first5 = Stefan | last6 = Jung | first6 = Roland | last7 = Jackson | first7 = Sandra | last8 = Gille | first8 = Gabriele | last9 = Spillantini | first9 = Maria Grazia | journal = PLoS ONE | volume = 5 | issue = 1 | pages = e8762 | editor1-last = Kleinschnitz | editor1-first = Christoph}}</ref>
			Rotenone also inhibits ] assembly.<ref>{{cite journal| vauthors=Heinz S, Freyberger A, Lawrenz B, Schladt L, Schmuck G, Ellinger-Ziegelbauer H| title=Mechanistic Investigations of the Mitochondrial Complex I Inhibitor Rotenone in the Context of Pharmacological and Safety Evaluation| journal=Scientific Reports| volume=7| pages=45465| doi=10.1038/srep45465| pmid=28374803| pmc=5379642| year=2017| bibcode=2017NatSR...745465H}}</ref>
	In 2011, a US National Institutes of Health study showed a link between rotenone use and Parkinson's disease in farm workers.<ref name="Tanner 2011"/>
			== Presence in plants ==
	==See also==
			Rotenone is produced by extraction from the roots and stems of several tropical and subtropical plant species, especially those belonging to the genera '']'' and '']''.
			Some of the plants containing rotenone:
			* Hoary pea or goat's rue ('']'') – North America
			* Jícama ('']'') – North America
			* Cubé plant or lancepod ('']'') – South America<ref name="Fang">{{cite journal |vauthors=Fang N, Casida J |title=Cubé resin insecticide: identification and biological activity of 29 rotenoid constituents |journal=J Agric Food Chem |volume=47 |issue=5 |pages=2130–6 |year=1999 |pmid=10552508 |doi=10.1021/jf981188x}}</ref>
			** The root extract is referred to as cubé resin
			* Barbasco ('']'') – South America<ref name="Fang" />
			** The root extract is referred to as cubé resin
			* Tuba plant ('']'') – southeast Asia and southwest Pacific islands
			** The root extract is referred to as derris or derris root
			* Jewel vine ('']'') – southeast Asia and southwest Pacific islands
			** The root extract is referred to as derris or derris root
			* Common Mullein (''] L.)''<ref>{{cite book |title= Peterson Field Guides to Medicinal Plants and Herbs of Eastern and Central North America |edition= 2nd |pages= 130–131 }}</ref>
			* Cork-bush ('']'') – southern Africa<ref name="Palgrave">{{cite book |last=Coates Palgrave |first=Keith |title=Trees of Southern Africa |publisher=] |year=2002 |isbn=978-0-86977-081-8}}</ref>
			* Florida fishpoison tree ('']'') – southern Florida, Caribbean<ref name=Nellis>Nellis, David N. (1994). Seashore plants of South Florida and the Caribbean. Pineapple Press. 160 p.</ref>
			* Several species of '']'' and '']'' in ]<ref name="Barton">{{cite book |title=Comprehensive Natural Products Chemistry |publisher=] |isbn=978-0-08-091283-7 |year=1999 |url=https://books.google.com/books?id=AqdTiNIaA74C&q=rotenone+millettia&pg=PT10698 |vauthors=Barton D, Meth-Cohn O}}</ref>
			== Mammalian toxicity ==
			Rotenone is classified by the ] as moderately hazardous.<ref name="who">{{cite book |author1=International Programme on Chemical Safety |author2=] (UNEP)|author3=International Labour Organization |author4=World Health Organization |title=The WHO Recommended Classification of Pesticides by Hazard |publisher=] |isbn=978-92-4-154663-8 |year=2007 |url=https://www.who.int/ipcs/publications/pesticides_hazard/en/ |archive-url= https://web.archive.org/web/20040708001948/http://www.who.int/ipcs/publications/pesticides_hazard/en/ |url-status=dead |archive-date=July 8, 2004 |access-date=2007-12-02}}</ref> It is mildly toxic to ]s and other ]s, but extremely toxic to insects and aquatic life, including fish. This higher toxicity in fish and insects is because the ] rotenone is easily taken up through the ]s or ], but not as easily through the skin or the ]. Rotenone is toxic to ] '']''.<ref>{{cite journal |pmid=22727881 |doi=10.1016/j.tox.2012.06.007 |volume=300 |issue=3 |title=Induction of apoptotic erythrocyte death by rotenone |date=October 2012 |pages=132–7 |last1=Lupescu |first1=Adrian |last2=Jilani |first2=Kashif |last3=Zbidah |first3=Mohanad |last4=Lang |first4=Florian |journal=Toxicology|bibcode=2012Toxgy.300..132L }}</ref>
			The lowest lethal dose for a child is not known, but death occurred in a 3.5-year-old child who had ingested 40&nbsp;mg/kg rotenone solution.<ref name="wood" /> Human deaths from rotenone poisoning are rare because its irritating action causes vomiting.<ref>{{cite journal|journal=Pesticides News |volume=54 |year=2001 |pages=20–21 |title=Rotenone |url=http://www.pan-uk.org/pestnews/Actives/rotenone.htm}}</ref> Deliberate ingestion of rotenone can be fatal.<ref name="wood">{{cite journal |vauthors=Wood DM, Alsahaf H, Streete P, Dargan PI, Jones AL |title=Fatality after deliberate ingestion of the pesticide rotenone: a case report |journal=Critical Care |volume=9 |issue=3 |pages=R280–4 |date=June 2005 |pmid=15987402 |pmc=1175899 |doi=10.1186/cc3528 |doi-access=free }}</ref>
			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 ]; 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 ], consistent with prior findings.<ref>{{Cite journal |last1=Pamies |first1=David |last2=Block |first2=Katharina |last3=Lau |first3=Pierre |last4=Gribaldo |first4=Laura |last5=Pardo |first5=Carlos A. |last6=Barreras |first6=Paula |last7=Smirnova |first7=Lena |last8=Wiersma |first8=Daphne |last9=Zhao |first9=Liang |last10=Harris |first10=Georgina |last11=Hartung |first11=Thomas |last12=Hogberg |first12=Helena T. |date=2018-09-01 |title=Rotenone exerts developmental neurotoxicity in a human brain spheroid model |journal=Toxicology and Applied Pharmacology |series=Alternative Approaches to Developmental Neurotoxicity Evaluation |language=en |volume=354 |pages=101–114 |doi=10.1016/j.taap.2018.02.003 |issn=0041-008X |pmc=6082736 |pmid=29428530|bibcode=2018ToxAP.354..101P }}</ref>
			=== Parkinson's disease ===
			In 2000, injecting rotenone into rats was reported to cause the development of symptoms similar to those of ] (PD). Rotenone was continuously applied over a period of five weeks, mixed with ] and ] to enhance tissue penetration, and injected into the ].<ref>{{cite journal |vauthors=Caboni P, Sherer T, Zhang N, Taylor G, Na H, Greenamyre J, Casida J |title=Rotenone, deguelin, their metabolites, and the rat model of Parkinson's disease |journal=Chem Res Toxicol |volume=17 |issue=11 |pages=1540–8 |year=2004 |pmid=15540952 |doi= 10.1021/tx049867r }}</ref> The study does not directly suggest rotenone exposure is responsible for PD in humans, but is consistent with the belief that ] to ] increases the likelihood of the disease.<ref></ref> In 2011, a US ] 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 ].<ref name="Tanner 2011">{{cite journal |vauthors=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 |year=2011 |title=Rotenone, Paraquat and Parkinson's Disease |journal=Environmental Health Perspectives |volume=119 |issue=6 |pages=866–72 |doi=10.1289/ehp.1002839 |issn=0091-6765 |pmc=3114824 |pmid=21269927}}</ref> Exposure to the chemical in the field can be avoided by wearing a gas mask with filter, which is standard ] procedure in modern application of the chemical.
			Studies with primary cultures of rat ]s and ] have shown low doses of rotenone (below 10 nM) induce oxidative damage and death of ] ],<ref>{{cite journal |vauthors=Gao HM, Liu B, Hong JS |title=Critical role for microglial NADPH oxidase in rotenone-induced degeneration of dopaminergic neurons |journal=The Journal of Neuroscience |volume=23 |issue=15 |pages=6181–7 |date=July 2003 |pmid=12867501 |pmc=6740554 |doi=10.1523/JNEUROSCI.23-15-06181.2003 }}</ref> and it is these neurons in the ] 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.<ref>{{cite journal |vauthors=Freestone PS, Chung KK, Guatteo E, Mercuri NB, Nicholson LF, Lipski J |title=Acute action of rotenone on nigral dopaminergic neurons--involvement of reactive oxygen species and disruption of Ca2+ homeostasis |journal=The European Journal of Neuroscience |volume=30 |issue=10 |pages=1849–59 |date=November 2009 |pmid=19912331 |doi=10.1111/j.1460-9568.2009.06990.x |s2cid=205515222}}</ref> 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 ] ] 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 ]. Further studies involving MPTP have failed to show development of ], a key component to PD pathology. However at least one study recently has found evidence of ] of the same chemical makeup as that which makes up Lewy bodies with similar pathology to Parkinson's disease in aged ]s from MPTP.<ref>{{Cite journal |vauthors=Huang B, Wu S, Wang Z, Ge L, Rizak JD, Wu J, Li J, Xu L, Lv L, Yin Y, Hu X |date=2018-05-21 |title=Phosphorylated α-Synuclein Accumulations and Lewy Body-like Pathology Distributed in Parkinson's Disease-Related Brain Areas of Aged Rhesus Monkeys Treated with MPTP |journal=Neuroscience |language=en |volume=379 |pages=302–315 |doi=10.1016/j.neuroscience.2018.03.026 |pmid=29592843 |s2cid=4969894 |issn=0306-4522}}</ref> Therefore, the mechanism behind MPTP as it relates to Parkinson's disease is not fully understood.<ref> -- Basic Neurochemistry -- NCBI Bookshelf, American Society for Neurochemistry</ref> Because of these developments, rotenone was investigated as a possible Parkinson-causing agent. Both MPTP and rotenone are ] and can cross the ].
			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.<ref>{{cite journal |vauthors=Pan-Montojo F, Anichtchik O, Dening Y, Knels L, Pursche S, Jung R, Jackson S, Gille G, Spillantini MG |date=2010 |title=Progression of Parkinson's Disease Pathology Is Reproduced by Intragastric Administration of Rotenone in Mice |journal=PLOS ONE |volume=5 |issue=1 |pages=e8762 |editor1-last=Kleinschnitz |editor1-first=Christoph |doi=10.1371/journal.pone.0008762 |pmc=2808242 |pmid=20098733 |bibcode=2010PLoSO...5.8762P |doi-access=free }}</ref>
			== See also ==
			* ]
	* ]		* ]
	==References==		== References ==
	{{reflist}}		{{reflist}}
	==External links==		== External links ==
	* ,		* ,
			* {{Webarchive|url=https://web.archive.org/web/20070609164832/http://www.nysaes.cornell.edu/pp/resourceguide/mfs/11rotenone.php |date=2007-06-09 }}
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			{{Monoamine neurotoxins}}
	{{Neurotoxins}}
			{{Androgen receptor modulators}}
	{{Dopaminergics}}
			{{Estrogen receptor modulators}}
	{{Rotenoid}}		{{Rotenoid}}
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