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Submit Review(E)-Capsaicin
Description: TRPV agonist
Chemical Name: (E)-N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methyl-6-nonenamide
Purity: ≥98% (HPLC)
Biological Activity for (E)-Capsaicin
(E)-Capsaicin is a 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.
Technical Data for (E)-Capsaicin
| 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 for (E)-Capsaicin
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 15.27 | 50 | |
| ethanol | 15.27 | 50 |
Preparing Stock Solutions for (E)-Capsaicin
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 |
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Product Datasheets for (E)-Capsaicin
References for (E)-Capsaicin
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.
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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
Diniz et al (2019) Dual mechanism of TRKB activation by anandamide through CB1 and TRPV1 receptors. PeerJ 7 e6493 PMID: 30809460
Fairless et al (2013) Membrane potential measurements of isolated neurons using a voltage-sensitive dye. PLoS One 8 e58260 PMID: 23516458
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
Buznikov et al (2010) A putative 'pre-nervous' endocannabinoid system in early echinoderm development. Dev Neurosci 32 1 PMID: 19907129
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
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
Ma et al (2015) Experimental evidence for alleviating nociceptive hypersensitivity by single application of capsaicin. Mol Pain 11 22 PMID: 25896608
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
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
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
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
Ahern et al (2005) Extracellular cations sensitize and gate capsaicin receptor TRPV1 modulating pain signaling. J Neurosci 25 5109 PMID: 15917451
Pitcher et al (2007) Spinal NKCC1 blockade inhibits TRPV1-dependent referred allodynia. J Pharmacol Exp Ther 3 17 PMID: 17603899
Izzo et al (2001) Effect of vanilloid drugs on gastrointestinal transit in mice. Br J Pharmacol 132 1411 PMID: 11264233
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
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
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
Do you know of a great paper that uses (E)-Capsaicin from Tocris? Please let us know.
Reviews for (E)-Capsaicin
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Capsaicin mEPSCs in spinal dorsal horn neuron.
By
Allen Dickie on 03/24/2023
Assay Type: Ex Vivo
Species: Mouse
Whole cell patch clamp recording of mEPSCs in spinal dorsal horn interneuron, in ex vivo slice preparation, in response to bath application of capsaicin (2 µM).
