Rotenone

Rotenone is a classical inhibitor of complex I of the mitochondrial electron transport chain, inhibiting NADH/DB oxidoreductase and NADH oxidase with IC50 values of 28.8 and 5.1 nM, respectively. In substantia nigra pars compacta neurons, it activates ATP-sensitive potassium channels and increases the production of reactive oxygen species (ROS) in the mitochondria, effects that are decreased by the antioxidant trolox (Cay-10011659). In rodents, rotenone induces dopaminergic cell death in the substantia nigra, formation of cytoplasmic inclusions similar to Lewy bodies, oxidative damage to proteins, and parkinsonian symptoms of bradykinesia and rigidity. In a rat model of Parkinson's disease, chronic rotenone administration of 1.5 and 2.5 mg/kg per day for two months reduces tyrosine hydroxylase levels in the posterior striatum and prefrontal cortex, induces catalepsy, and decreases spontaneous locomotion and exploration in the open field test. Formulations containing rotenone have been used as insecticides and piscicides.Formal Name: (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. CAS Number: 83-79-4. Synonyms: Nicouline, NSC 8505, NSC 26258, Tubatoxin. Molecular Formula: C23H22O6. Formula Weight: 394.4. Purity: >95%. Formulation: (Request formulation change), A crystalline solid. Solubility: Chloroform: 50 mg/ml, DMSO: 50 mg/ml, Ethanol: 5 mg/ml. lambdamax: 236, 294 nm. SMILES: COC(C(OC)=C1)=CC2=C1[C@@](C(C(C=CC3=C4C[C@H](C(C)=C)O3)=C4O5)=O)([H])[C@@]5([H])CO2. InChi Code: 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. InChi Key: JUVIOZPCNVVQFO-HBGVWJBISA-N.