(E)-Capsaicin

Pricing Availability   Qty
Cat.No. 0462 - (E)-Capsaicin | C18H27NO3 | CAS No. 404-86-4
Description: Prototypic vanilloid receptor agonist
Chemical Name: (E)-N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methyl-6-nonenamide
Purity: ≥98% (HPLC)
Datasheet
Citations (38)
Reviews
Literature (2)

Biological Activity

Prototypic vanilloid receptor agonist (pEC50 values are 7.97 and 7.10 at rat and human VR1 receptors respectively). Excites a subset of primary afferent sensory neurons, with subsequent antinociceptive and anti-inflammatory effects. Reversibly inhibits aggregation of platelets. Also available as part of the Vanilloid TRPV1 Receptor Tocriset™.

Technical Data

M. Wt 305.42
Formula C18H27NO3
Storage Store at RT
Purity ≥98% (HPLC)
CAS Number 404-86-4
PubChem ID 1548943
InChI Key YKPUWZUDDOIDPM-SOFGYWHQSA-N
Smiles COC1=C(O)C=CC(CNC(=O)CCCC\C=C\C(C)C)=C1

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

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 15.27 50
ethanol 15.27 50

Preparing Stock Solutions

The following data is based on the product molecular weight 305.42. 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.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
0.5 mM 6.55 mL 32.74 mL 65.48 mL
2.5 mM 1.31 mL 6.55 mL 13.1 mL
5 mM 0.65 mL 3.27 mL 6.55 mL
25 mM 0.13 mL 0.65 mL 1.31 mL

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

Product Datasheets

Certificate of Analysis / Product Datasheet
Select another batch:

References

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

Bevan and Szolcsani (1990) Sensory neuron-specific actions of capsaicin: mechanisms and application. TiPS 11 330 PMID: 2203194

Hogaboam and Wallace (1991) Inhibition of platelet aggregation by capsaicin. An effect unrelated to actions on sensory afferent neurons. Eur.J.Pharmacol. 202 129 PMID: 1786800

Holzer (1991) Capsaicin-cellular targets, mechanism of actions, and selectivity for thin sensory neurons. Pharmacol.Rev. 43 143 PMID: 1852779

Ralevic et al (2001) Cannabinoid activation of recombinant and endogenous vanilloid receptors. Eur.J.Pharmacol. 424 211 PMID: 11672565


If you know of a relevant reference for (E)-Capsaicin, please let us know.

View Related Products by Target

View Related Products by Product Action

View all TRPV Agonists

Keywords: (E)-Capsaicin, (E)-Capsaicin supplier, Prototypic, vanilloid, receptor, agonists, Vanillioid, Receptors, VR1, TRPV, TRP, Channels, Transient, Receptor, Potential, 0462, Tocris Bioscience

38 Citations for (E)-Capsaicin

Citations are publications that use Tocris products. Selected citations for (E)-Capsaicin include:

Shi et al (2015) Alterations in serotonin, transient receptor potential channels and protease-activated receptors in rats with irritable bowel syndrome attenuated by Shugan decoction. Front Cell Neurosci 21 4852 PMID: 25944998

Zakharov et al (2015) Hunting for origins of migraine pain: cluster analysis of spontaneous and capsaicin-induced firing in meningeal trigeminal nerve fibers. J Transl Med 9 287 PMID: 26283923

Wang et al (2015) Mother root of Aconitum carmichaelii Debeaux exerts antinociceptive effect in Complet Freund's Adjuvant-induced mice: roles of dynorpin/κ-opioid system and transient receptor potential vanilloid type-1 ion channel. PLoS One 13 284 PMID: 26320055

Chen et al (2015) Berberine Improves Intestinal Motility and Visceral Pain in the Mouse Models Mimicking Diarrhea-Predominant Irritable Bowel Syndrome (IBS-D) Symptoms in an Opioid-Receptor Dependent Manner. Nature 10 e0145556 PMID: 26700862

Stanley et al (2015) Cannabidiol causes endothelium-dependent vasorelaxation of human mesenteric arteries via CB1 activation. Neuropsychopharmacology 107 568 PMID: 26092099

Bhaskaran and Smith (2010) Effects of TRPV1 activation on synaptic excitation in the dentate gyrus of a mouse model of temporal lobe epilepsy. World J Gastroenterol 223 529 PMID: 20144892

Cobellis et al (2010) A gradient of 2-arachidonoylglycerol regulates mouse epididymal sperm cell start-up. Biol Reprod 82 451 PMID: 19812302

Bautista et al (2005) Pungent products from garlic activate the sensory ion channel TRPA1. Br J Pharmacol 102 12248 PMID: 16103371

Bang et al (2004) Neurokinin-1 receptor antagonists protect mice from CD95- and tumor necrosis factor-α-mediated apoptotic liver damage. J Neurosci 308 1174 PMID: 14617692

Chen et al (2014) Antinociceptive effects of novel melatonin receptor agonists in mouse models of abdominal pain. Mol Pain 20 1298 PMID: 24574803

Nash et al (2012) 7-tert-Butyl-6-(4-chloro-phenyl)-2-thioxo-2,3-dihydro-1H-pyrido[2,3-d]pyrimidin-4-one, a classic polymodal inhibitor of transient receptor potential vanilloid type 1 with a reduced liability for hyperthermia, is analgesic and ameliorates visceral hypersen J Pharmacol Exp Ther 342 389 PMID: 22566669

Melis et al (2004) Endocannabinoids mediate presynaptic inhibition of glutamatergic transmission in rat ventral tegmental area DA neurons through activation of CB1 receptors. J Neurosci 24 53 PMID: 14715937

Smart et al (2002) 'Entourage' effects of N-acyl ethanolamines at human vanilloid receptors. Comparison of effects upon anandamide-induced vanilloid receptor activation and upon anandamide metabolism. Headache 136 452 PMID: 12023948

Izzo et al (2001) Effect of vanilloid drugs on gastrointestinal transit in mice. Br J Pharmacol 132 1411 PMID: 11264233

Yissachar et al (2017) An Intestinal Organ Culture System Uncovers a Role for the Nervous System in Microbe-Immune Crosstalk. Cell 168 1135 PMID: 28262351

Craib et al (2001) A possible role of lipoxygenase in the activation of vanilloid receptors by anandamide in the guinea-pig bronchus. Neurochem Int 134 42581 PMID: 11522594

Diniz et al (2019) Dual mechanism of TRKB activation by anandamide through CB1 and TRPV1 receptors. PeerJ 7 e6493 PMID: 30809460

Ma et al (2015) Experimental evidence for alleviating nociceptive hypersensitivity by single application of capsaicin. Mol Pain 11 22 PMID: 25896608

Rossi et al (2014) Interleukin-1β causes excitotoxic neurodegeneration and multiple sclerosis disease progression by activating the apoptotic protein p53. Mol Neurodegener 9 56 PMID: 25495224

Wang et al (2014) Innervation of enteric mast cells by primary spinal afferents in guinea pig and human small intestine. Am J Physiol Gastrointest Liver Physiol 307 G719 PMID: 25147231

Nguyen et al (2014) Transient receptor potential vanilloid type 1 channel may modulate opioid reward. Neuropsychopharmacology 39 2414 PMID: 24732880

Hartley et al (2013) Development and experimental application of an HPLC procedure for the determination of capsaicin and dihydrocapsaicin in serum samples from human subjects. Indian J Clin Biochem 28 329 PMID: 24426233

Nesuashvili et al (2013) Sensory nerve terminal mitochondrial dysfunction activates airway sensory nerves via transient receptor potential (TRP) channels. Mol Pharmacol 83 1007 PMID: 23444014

Benninger et al (2008) Control of excitatory synaptic transmission by capsaicin is unaltered in TRPV1 vanilloid receptor knockout mice. Br J Pharmacol 52 89 PMID: 17651868

Gibson et al (2008) TRPV1 channels mediate long-term depression at synapses on hippocampal interneurons. Neuron 57 746 PMID: 18341994

Chiu et al (2013) Bacteria activate sensory neurons that modulate pain and inflammation. World J Gastroenterol 501 52 PMID: 23965627

Shabir et al (2013) Functional expression of purinergic P2 receptors and transient receptor potential channels by the human urothelium. Diabetes 305 F396 PMID: 23720349

Chen et al (2016) Spatial Distribution of the Cannabinoid Type 1 and Capsaicin Receptors May Contribute to the Complexity of Their Crosstalk. Sci Rep 6 33307 PMID: 27653550

Gao et al (2012) Transient receptor potential vanilloid type 1-dependent regulation of liver-related neurons in the paraventricular nucleus of the hypothalamus diminished in the type 1 diabetic mouse. Acta Neurochir Suppl 61 1381 PMID: 22492526

Khatibi et al (2011) Capsaicin pre-treatment provides neurovascular protection against neonatal hypoxic-ischemic brain injury in rats. Mol Pain 111 225 PMID: 21725760

Martínez-García et al (2011) Increase of capsaicin-induced trigeminal Fos-like immunoreactivity by 5-HT(7) receptors. Cardiovasc Res 51 1511 PMID: 22082421

Zsombok et al (2011) Functional plasticity of central TRPV1 receptors in brainstem dorsal vagal complex circuits of streptozotocin-treated hyperglycemic mice. Exp Neurol 31 14024 PMID: 21957263

Westlund et al (2010) Impact of central and peripheral TRPV1 and ROS levels on proinflammatory mediators and nociceptive behavior. Proc Natl Acad Sci U S A 6 46 PMID: 20691059

Balleza-Tapia et al (2018) TrpV1 receptor activation rescues neuronal function and network gamma oscillations from Aβ-induced impairment in mouse hippocampus in vitro. Elife 7 PMID: 30417826

Buznikov et al (2010) A putative 'pre-nervous' endocannabinoid system in early echinoderm development. Dev Neurosci 32 1 PMID: 19907129

Pitcher et al (2007) Spinal NKCC1 blockade inhibits TRPV1-dependent referred allodynia. J Pharmacol Exp Ther 3 17 PMID: 17603899

Fairless et al (2013) Membrane potential measurements of isolated neurons using a voltage-sensitive dye. PLoS One 8 e58260 PMID: 23516458

Ahern et al (2005) Extracellular cations sensitize and gate capsaicin receptor TRPV1 modulating pain signaling. J Neurosci 25 5109 PMID: 15917451


Do you know of a great paper that uses (E)-Capsaicin from Tocris? Please let us know.

Reviews for (E)-Capsaicin

There are currently no reviews for this product. Be the first to review (E)-Capsaicin and earn rewards!

Have you used (E)-Capsaicin?

Submit a review and receive an Amazon gift card.

$50/€35/£30/$50CAN/¥300 Yuan/¥5000 Yen for first to review with an image

$25/€18/£15/$25CAN/¥75 Yuan/¥1250 Yen for a review with an image

$10/€7/£6/$10 CAD/¥70 Yuan/¥1110 Yen for a review without an image

Submit a Review

Literature in this Area

Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* or download your copy today!

*Please note that Tocris will only send literature to established scientific business / institute addresses.


Pain

Pain Research Product Guide

A collection of over 280 products for pain research, the guide includes research tools for the study of:

  • Nociception
  • Ion Channels
  • G-Protein-Coupled Receptors
  • Intracellular Signaling
Pain

Pain Poster

Peripheral sensitization is the reduction in the threshold of excitability of sensory neurons that results in an augmented response to a given external stimulus. This poster outlines the excitatory and inhibitory signaling pathways involved in modulation of peripheral sensitization. The role of ion channels, GPCRs, neurotrophins, and cytokines in sensory neurons are also described.