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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H22O6
Molecular Weight 394.4172
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ROTENONE

SMILES

[H][C@@]12COC3=CC(OC)=C(OC)C=C3[C@]1([H])C(=O)C4=C(O2)C5=C(O[C@H](C5)C(C)=C)C=C4

InChI

InChIKey=JUVIOZPCNVVQFO-HBGVWJBISA-N
InChI=1S/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

HIDE SMILES / InChI

Molecular Formula C23H22O6
Molecular Weight 394.4172
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Rotenone is a selective, non-specific botanical insecticide with some acaricidal properties. Rotenone is used in home gardens for insect control, for lice and tick control on pets, and for fish eradications as part of water body management. Rotenone is a rotenoid plant extract obtained from such species as barbasco, cub, haiari, nekoe, and timbo. These plants are members of the pea (Leguminosae) family. Rotenone-containing extracts are taken from the roots, seeds, and leaves of the various plants. This chemical has been used in one form or another as a crop insecticide since 1848 and has been recognized as a registered pesticide in the United States under the Federal Insecticide Fungicide Rodenticide Act (FIFRA) since 1947. Rotenone has also been found to also have properties of a pescicide where it is generally used to rid environments of non-native predatory fish species. Rotenone is a commonly used neurotoxin to produce in vivo and in vitro Parkinson's disease models. Rotenone is the classical inhibitor of NADH: ubiquinone oxidoreductase.

CNS Activity

Curator's Comment: Rotenone is lipophilic and can cross the blood–brain barrier. Rotenone is a commonly used neurotoxin to produce in vivo and in vitro Parkinson's disease models.

Originator

Curator's Comment: Emmanuel Geoffroy first isolated rotenone from a specimen of Rotenone, now called Lonchocarpus nicou, while traveling in French Guiana.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
PESTENE

Approved Use

For poultry, pigeons and pigs. For the treatment of Round Worms (Ascaridia Galli) in Poultry (Ascaridia columbae) in Pigeons; Round Worms (Ascaris suum) and Nodule Worms (Oesophagostomum spp) in Pigs.
PubMed

PubMed

TitleDatePubMed
Rotenone and pyruvate prevent the tert-butylhydroperoxide-induced necrosis of U937 cells and allow them to proliferate.
1999 Aug 20
Chronic systemic pesticide exposure reproduces features of Parkinson's disease.
2000 Dec
Role of oxidants in NF-kappa B activation and TNF-alpha gene transcription induced by hypoxia and endotoxin.
2000 Jul 15
GLUT-1 reduces hypoxia-induced apoptosis and JNK pathway activation.
2000 May
Mitochondrial dysfunction increases expression of endothelin-1 and induces apoptosis through caspase-3 activation in rat cardiomyocytes in vitro.
2000 Nov
Mitochondrial dysfunction of cardiomyocytes causing impairment of cellular energy metabolism induces apoptosis, and concomitant increase in cardiac endothelin-1 expression.
2000 Nov
Rac1 inhibits TNF-alpha-induced endothelial cell apoptosis: dual regulation by reactive oxygen species.
2000 Sep
Mitochondrial-derived oxidants and quartz activation of chemokine gene expression.
2001
Interleukin 1-induced cyclooxygenase and nitric oxide synthase gene expression in the rat dorsal root ganglia is modulated by antioxidants.
2001
Dependence of excitotoxic neurodegeneration on mitochondrial aconitase inactivation.
2001 Aug
Endothelin-1 production is enhanced by rotenone, a mitochondrial complex I inhibitor, in cultured rat cardiomyocytes.
2001 Dec
Dopaminergic cell death induced by MPP(+), oxidant and specific neurotoxicants shares the common molecular mechanism.
2001 Feb
Hypoxia-induced upregulation of eNOS gene expression is redox-sensitive: a comparison between hypoxia and inhibitors of cell metabolism.
2001 Jul
Pesticides directly accelerate the rate of alpha-synuclein fibril formation: a possible factor in Parkinson's disease.
2001 Jul 6
Leptin induces mitochondrial superoxide production and monocyte chemoattractant protein-1 expression in aortic endothelial cells by increasing fatty acid oxidation via protein kinase A.
2001 Jul 6
Parkinson disease: etiology, pathogenesis and future of gene therapy.
2001 Sep
Role of mitochondrial oxidant generation in endothelial cell responses to hypoxia.
2002 Apr 1
Proteasome inhibitors stimulate activator protein-1 pathway via reactive oxygen species production.
2002 Aug 28
Distinct role for microglia in rotenone-induced degeneration of dopaminergic neurons.
2002 Feb 1
Activation of matrix metalloproteinase-2 by overexpression of manganese superoxide dismutase in human breast cancer MCF-7 cells involves reactive oxygen species.
2002 Jun 7
Chronic systemic complex I inhibition induces a hypokinetic multisystem degeneration in rats.
2003 Feb
Subcutaneous rotenone exposure causes highly selective dopaminergic degeneration and alpha-synuclein aggregation.
2003 Jan
Metallothionein attenuates 3-morpholinosydnonimine (SIN-1)-induced oxidative stress in dopaminergic neurons.
2003 Jun
Hypoxia and stretch regulate intercellular communication in vascular smooth muscle cells through reactive oxygen species formation.
2003 Oct 1
NF-E2-related factor-2 mediates neuroprotection against mitochondrial complex I inhibitors and increased concentrations of intracellular calcium in primary cortical neurons.
2003 Sep 26
Rotenone induces non-specific central nervous system and systemic toxicity.
2004 Apr
Rotenone induces apoptosis via activation of bad in human dopaminergic SH-SY5Y cells.
2004 Dec
Chronic exposure to rotenone models sporadic Parkinson's disease in Drosophila melanogaster.
2004 Dec 1
Lipopolysaccharide induces matrix metalloproteinase-9 expression via a mitochondrial reactive oxygen species-p38 kinase-activator protein-1 pathway in Raw 264.7 cells.
2004 Dec 1
Trichomonas hydrogenosomes contain the NADH dehydrogenase module of mitochondrial complex I.
2004 Dec 2
Source of early reactive oxygen species in the apoptosis induced by transforming growth factor-beta in fetal rat hepatocytes.
2004 Jan 1
Induction and inhibition of aromatase (CYP19) activity by natural and synthetic flavonoid compounds in H295R human adrenocortical carcinoma cells.
2004 Nov
Sensitivity of zebrafish to environmental toxins implicated in Parkinson's disease.
2004 Nov-Dec
Effect of fraxetin on antioxidant defense and stress proteins in human neuroblastoma cell model of rotenone neurotoxicity. Comparative study with myricetin and N-acetylcysteine.
2005 Dec 15
Similar patterns of mitochondrial vulnerability and rescue induced by genetic modification of alpha-synuclein, parkin, and DJ-1 in Caenorhabditis elegans.
2005 Dec 30
Effect of sesamin in Acanthopanax senticosus HARMS on behavioral dysfunction in rotenone-induced parkinsonian rats.
2005 Jan
Redox regulation of p38 MAPK activation and expression of ICAM-1 and heme oxygenase-1 in human alveolar epithelial (A549) cells.
2005 Jan-Feb
Role of mitochondria in the regulation of hypoxia-inducible factor-1alpha in the rat carotid body glomus cells.
2005 Jul
PACAP protects neuronal differentiated PC12 cells against the neurotoxicity induced by a mitochondrial complex I inhibitor, rotenone.
2005 Jul 18
Sleep disturbances in the rotenone animal model of Parkinson disease.
2005 May 3
The mitochondrial complex I inhibitor rotenone triggers a cerebral tauopathy.
2005 Nov
Hypertonic induction of COX-2 in collecting duct cells by reactive oxygen species of mitochondrial origin.
2005 Oct 14
Activation of group III metabotropic glutamate receptors attenuates rotenone toxicity on dopaminergic neurons through a microtubule-dependent mechanism.
2006 Apr 19
Albumin-bound fatty acids induce mitochondrial oxidant stress and impair antioxidant responses in proximal tubular cells.
2006 Aug
Mitochondrial disease activates transcripts of the unfolded protein response and cell cycle and inhibits vesicular secretion and oligodendrocyte-specific transcripts.
2006 Aug
The regulation of rotenone-induced inflammatory factor production by ATP-sensitive potassium channel expressed in BV-2 cells.
2006 Feb 13
Enhanced sensitivity of DJ-1-deficient dopaminergic neurons to energy metabolism impairment: role of Na+/K+ ATPase.
2006 Jul
Patents

Sample Use Guides

Rats: Intraperitoneal injection of rotenone (2 mg/kg/day) to Wistar rats produced typical PD symptoms.
Route of Administration: Intraperitoneal
In human induced pluripotent stem cells Rotenone was found to induce the activation of Nrf2 signaling particularly at the highest tested concentration (100 nM), as shown by Nrf2 nuclear translocation and the up-regulation of the Nrf2-downstream antioxidant enzymes, NQO1 and SRXN1.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:05:51 GMT 2023
Edited
by admin
on Fri Dec 15 15:05:51 GMT 2023
Record UNII
03L9OT429T
Record Status Validated (UNII)
Record Version
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Name Type Language
ROTENONE
GREEN BOOK   HSDB   ISO   MART.   MI  
Common Name English
ROTENONE [ISO]
Common Name English
ROTENONE [MI]
Common Name English
TUBATOXIN
Common Name English
ROTENONE [GREEN BOOK]
Common Name English
NSC-26258
Code English
ROTENONE [MART.]
Common Name English
ROTENONE [HSDB]
Common Name English
1,2,12,12A-TETRAHYDRO-8,9-DIMETHOXY-2-(1-METHYLETHENYL)-(1)BENZOPYRANO(3,4-B)FURO(2,3-H)(1)BENZOPYRAN-6(6AH)-ONE
Common Name English
DACTINOL
Common Name English
(2R,6AS,12AS)-1,2,6,6A,12,12A-HEXAHYDRO-2-ISOPROPENYL-8,9-DIMETHOXYCHROMENO(3,4-B)FURO(2,3-H)CHROMEN-6-ONE
Common Name English
(2R,6AS,12AS)-1,2,12,12A-TETRAHYDRO-8,9-DIMETHOXY-2-(1-METHYLETHENYL)(1)BENZOPYRANO(3,4-B)FURO(2,3-H)(1)BENZOPYRAN-6(6AH)-ONE
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 71003
Created by admin on Fri Dec 15 15:05:51 GMT 2023 , Edited by admin on Fri Dec 15 15:05:51 GMT 2023
NCI_THESAURUS C737
Created by admin on Fri Dec 15 15:05:51 GMT 2023 , Edited by admin on Fri Dec 15 15:05:51 GMT 2023
Code System Code Type Description
FDA UNII
03L9OT429T
Created by admin on Fri Dec 15 15:05:51 GMT 2023 , Edited by admin on Fri Dec 15 15:05:51 GMT 2023
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PUBCHEM
6758
Created by admin on Fri Dec 15 15:05:51 GMT 2023 , Edited by admin on Fri Dec 15 15:05:51 GMT 2023
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EPA CompTox
DTXSID6021248
Created by admin on Fri Dec 15 15:05:51 GMT 2023 , Edited by admin on Fri Dec 15 15:05:51 GMT 2023
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ECHA (EC/EINECS)
201-501-9
Created by admin on Fri Dec 15 15:05:51 GMT 2023 , Edited by admin on Fri Dec 15 15:05:51 GMT 2023
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RXCUI
1366666
Created by admin on Fri Dec 15 15:05:51 GMT 2023 , Edited by admin on Fri Dec 15 15:05:51 GMT 2023
PRIMARY RxNorm
HSDB
1762
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MESH
D012402
Created by admin on Fri Dec 15 15:05:51 GMT 2023 , Edited by admin on Fri Dec 15 15:05:51 GMT 2023
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NCI_THESAURUS
C76087
Created by admin on Fri Dec 15 15:05:51 GMT 2023 , Edited by admin on Fri Dec 15 15:05:51 GMT 2023
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NSC
26258
Created by admin on Fri Dec 15 15:05:51 GMT 2023 , Edited by admin on Fri Dec 15 15:05:51 GMT 2023
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DRUG BANK
DB11457
Created by admin on Fri Dec 15 15:05:51 GMT 2023 , Edited by admin on Fri Dec 15 15:05:51 GMT 2023
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DAILYMED
03L9OT429T
Created by admin on Fri Dec 15 15:05:51 GMT 2023 , Edited by admin on Fri Dec 15 15:05:51 GMT 2023
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EVMPD
SUB130991
Created by admin on Fri Dec 15 15:05:51 GMT 2023 , Edited by admin on Fri Dec 15 15:05:51 GMT 2023
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MERCK INDEX
m9673
Created by admin on Fri Dec 15 15:05:51 GMT 2023 , Edited by admin on Fri Dec 15 15:05:51 GMT 2023
PRIMARY Merck Index
CHEBI
28201
Created by admin on Fri Dec 15 15:05:51 GMT 2023 , Edited by admin on Fri Dec 15 15:05:51 GMT 2023
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CAS
83-79-4
Created by admin on Fri Dec 15 15:05:51 GMT 2023 , Edited by admin on Fri Dec 15 15:05:51 GMT 2023
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SMS_ID
100000156877
Created by admin on Fri Dec 15 15:05:51 GMT 2023 , Edited by admin on Fri Dec 15 15:05:51 GMT 2023
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WIKIPEDIA
ROTENONE
Created by admin on Fri Dec 15 15:05:51 GMT 2023 , Edited by admin on Fri Dec 15 15:05:51 GMT 2023
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ALANWOOD
rotenone
Created by admin on Fri Dec 15 15:05:51 GMT 2023 , Edited by admin on Fri Dec 15 15:05:51 GMT 2023
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