An inhibitor of mitochondrial complex I
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Rotenone

Item No. 13995

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
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
A crystalline solid
Solubility(Learn about Variance in Solubility)
Chloroform: 50 mg/mlDMSO: 50 mg/mlEthanol: 5 mg/ml
λmax
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

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    50 mg

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    100 mg

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    Cayman Chemical
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    Product Description

    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.1 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 (Item No. 10011659).2 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.3 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.4 Formulations containing rotenone have been used as insecticides and piscicides.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tormo, J.R., Gallardo, T., Peris, E., et al. Inhibitory effects on mitochondrial complex I of semisynthetic mono-tetrahydrofuran acetogenin derivatives. Bioorg. Med. Chem. Lett. 13(22), 4101-4105 (2003).

    2. Freestone, P.S., Chung, K.K., Guatteo, E., et al. Acute action of rotenone on nigral dopaminergic neurons--involvement of reactive oxygen species and disruption of Ca2+ homeostasis. Eur. J. Neurosci. 30(10), 1849-1859 (2009).

    3. Uversky, V.N. Neurotoxicant-induced animal models of Parkinson’s disease: Understanding the role of rotenone, maneb and paraquat in neurodegeneration. Cell Tissue Res. 318(1), 225-241 (2004).

    4. Alam, M., and Schmidt, W.J. Rotenone destroys dopaminergic neurons and induces parkinsonian symptoms in rats. Behav. Brain Res. 136(1), 317-324 (2002).

    5. Soloway, S.B. Naturally occurring insecticides. Environ. Health Perspect. 14, 109-117 (1976).

    Product Citations

    Alavi, M.V. Tau phosphorylation and OPA1 proteolysis are unrelated events: Implications for Alzheimer’s Disease. Biochim. Biophys. Acta Mol. Cell Res. 1868(12), 119116 (2021).

    Izreig, S., Gariepy, A., Kaymak, I., et al. Repression of LKB1 by miR-17~92 sensitizes MYC-dependent lymphoma to biguanide treatment. Cell Rep. Med. 1(2), 100014 (2020).