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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

COC1=CC2=C(C=C1OC)[C@H]3[C@@H](CO2)OC4=C5C[C@@H](OC5=CC=C4C3=O)C(C)=C

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

Description

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
4.4 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
PESTENE

PubMed

Sample Use Guides

In Vivo Use Guide
Rats: Intraperitoneal injection of rotenone (2 mg/kg/day) to Wistar rats produced typical PD symptoms.
Route of Administration: Intraperitoneal
In Vitro Use Guide
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.