Rotenone

Pricing Availability   Qty
Description: Inhibits complex I of the mitochondrial electron transport chain
Chemical 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
Purity: ≥95% (HPLC)
Datasheet
Citations (14)
Reviews (2)
Literature (1)

Biological Activity for Rotenone

Rotenone is a mitochondrial electron transport chain inhibitor (IC50 = 1.7 - 2.2 μM at complex I). Inhibits NADH oxidation by cardiac sarcoplasmic reticulum (IC50 = 3.4 nM). Commonly used pesticide and induces Parkinsonism in animal models. May also inhibit autophagy induction; blocks lysosomal degradation of autophagic vacuoles. Cell-permeable and brain penetrant.

Technical Data for Rotenone

M. Wt 394.42
Formula C23H22O6
Storage Store at RT
Purity ≥95% (HPLC)
CAS Number 83-79-4
PubChem ID 6758
InChI Key JUVIOZPCNVVQFO-HBGVWJBISA-N
Smiles C=[C@](C)[C@@H](C5)OC4=C5C(O3)=C(C=C4)C([C@@]([C@@]3([H])CO2)([H])C1=C2C=C(OC)C(OC)=C1)=O

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data for Rotenone

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 39.44 100

Preparing Stock Solutions for Rotenone

The following data is based on the product molecular weight 394.42. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.54 mL 12.68 mL 25.35 mL
5 mM 0.51 mL 2.54 mL 5.07 mL
10 mM 0.25 mL 1.27 mL 2.54 mL
50 mM 0.05 mL 0.25 mL 0.51 mL

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Product Datasheets for Rotenone

Certificate of Analysis / Product Datasheet
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References for Rotenone

References are publications that support the biological activity of the product.

Cherednichenko et al (2004) NADH oxidase activity of rat cardiac sarcoplasmic reticulum regulates calcium-induced calcium release. Circ.Res. 94 478 PMID: 14699012

Uversky (2004) Neurotoxicant-induced animal models of Parkinson's disease: understanding the role of rotenone, maneb and paraquat in neurodegeneration. Cell Tissue Res. 318 225 PMID: 15258850

Gomez et al (2007) Pesticides and impairment of mitochondrial function in relation with the parkinsonian syndrome. Front.Biosci. 12 1079 PMID: 17127363

Mader et al (2012) Rotenone inhibits autophagic flux prior to inducing cell death. ACS Chem.Neurosci. 3 1063 PMID: 23259041


If you know of a relevant reference for Rotenone, please let us know.

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Keywords: Rotenone, Rotenone supplier, inhibitors, inhibits, complex, I, mitochondrial, electron, transport, chain, Oxidative, phosphorylation, parkinson's, parkinsons, parkinsonism, Phosphorylation, 3616, Tocris Bioscience

14 Citations for Rotenone

Citations are publications that use Tocris products. Selected citations for Rotenone include:

Heng et al (2022) SOX2 mediates metabolic reprogramming of prostate cancer cells. Oncogene 41 1190-1202 PMID: 35067686

Kurt I et al (2021) Single-cell resolved imaging reveals intra-tumor heterogeneity in glycolysis, transitions between metabolic states, and their regulatory mechanisms. Cell Rep 34 108750 PMID: 33596424

Battefeld et al (2019) High-Frequency Microdomain Ca2+ Transients and Waves during Early Myelin Internode Remodeling. Cell Rep 26 182 PMID: 30605675

Toby et al (2020) The influence of hypoxia and energy depletion on the response of endothelial cells to the vascular disrupting agent combretastatin A-4-phosphate. Sci Rep 10 9926 PMID: 32555222

Luke et al (2020) Automated Quantification of Mitochondrial Fragmentation in an In Vitro Parkinson's Disease Model. Curr Protoc Neurosci 94 e105 PMID: 33147381

Hui et al (2019) Loss of PINK1 causes age-dependent decrease of dopamine release and mitochondrial dysfunction. Neurobiol Aging 75 1-10 PMID: 30504091

Beyer et al (2014) An acute rise in intraluminal pressure shifts the mediator of flow-mediated dilation from nitric oxide to hydrogen peroxide in human arterioles. Am J Physiol Heart Circ Physiol 307 H1587 PMID: 25260615

Shai et al (2016) Maintenance and propagation of a deleterious mitochondrial genome by the mitochondrial unfolded protein response. Nature 533 416-9 PMID: 27135930

Sandra L et al (2023) Transcriptome, proteome, and protein synthesis within the intracellular cytomatrix. iScience 26 105965 PMID: 36824274

Juliana et al (2012) Non-transcriptional priming and deubiquitination regulate NLRP3 inflammasome activation. Leukemia 287 36617 PMID: 22948162

Banh et al (2016) PTP1B controls non-mitochondrial oxygen consumption by regulating RNF213 to promote tumour survival during hypoxia. Nat Cell Biol 18 803 PMID: 27323329

Martin et al (2017) A Role for Mitochondrial Translation in Promotion of Viability in K-Ras Mutant Cells. Cell Rep 20 427 PMID: 28700943

Moloney et al (2017) Subcellular localization of the FLT3-ITD oncogene plays a significant role in the production of NOX- and p22(phox)-derived reactive oxygen species in acute myeloid leukemia. Leuk Res 52 34 PMID: 27870947

Agarwal et al (2017) Transient Opening of the Mitochondrial Permeability Transition Pore Induces Microdomain Calcium Transients in Astrocyte Processes. Neuron 93 587 PMID: 28132831


Do you know of a great paper that uses Rotenone from Tocris? Please let us know.

Reviews for Rotenone

Average Rating: 4.5 (Based on 2 Reviews.)

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Strong inhibitor of the mitochondrial complex I..
By Anonymous on 11/12/2021
Assay Type: In Vitro
Species: Rat
Cell Line/Tissue: motor neurons

Effect of rotenone (10 micromolar) on AMPA induced ROS formation in motor neurons.

review image

Good choice!.
By Anton Mukhamedshin on 02/22/2019
Assay Type: Ex Vivo
Species: Human
Cell Line/Tissue: Platelets

I use it to inhibit mitochondrial electron transport chain in platelets. It helps to understand the role of mitochondria in thrombosis.

Nice delivery time and all works well!


Literature in this Area

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