(E)-Capsaicin

Cat. No. 0462

(E)-Capsaicin C18H27NO3 [404-86-4]

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Chemical Name: (E)-N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methyl-6-nonenamide

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
Solubility:
Soluble to 50 mM in DMSO and to 50 mM in ethanol
Purity:
>98 %
Storage:
Store at RT
CAS No:
404-86-4

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
All Tocris products are intended for laboratory research use only.

Certificate of Analysis / Product Datasheet / Safety Data Sheet

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

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.

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

If you know of a relevant reference for this product please let us know.

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

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.

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

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.

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

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.

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.

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

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

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.

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

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.

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

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.

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.

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

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.

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.

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

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.

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.

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.

Do you know of a great paper that uses (E)-Capsaicin from Tocris? If so please let us know.show all ▼show less ▲

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

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