Catalog Number: 0462
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.
Background References
  1. Cannabinoid activation of recombinant and endogenous vanilloid receptors.
    Ralevic et al.
    Eur.J.Pharmacol., 2001;424:211
  2. Sensory neuron-specific actions of capsaicin: mechanisms and application.
    Bevan and Szolcsani
    TiPS, 1990;11:330
  3. Inhibition of platelet aggregation by capsaicin. An effect unrelated to actions on sensory afferent neurons.
    Hogaboam and Wallace
    Eur.J.Pharmacol., 1991;202:129
  4. Capsaicin-cellular targets, mechanism of actions, and selectivity for thin sensory neurons.
    Holzer
    Pharmacol.Rev., 1991;43:143
Citations:

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

28 Citations: Showing 1 - 10
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  1. Hunting for origins of migraine pain: cluster analysis of spontaneous and capsaicin-induced firing in meningeal trigeminal nerve fibers.
    Authors: Zakharov Et al.
    J Transl Med 2015;9:287
  2. Alterations in serotonin, transient receptor potential channels and protease-activated receptors in rats with irritable bowel syndrome attenuated by Shugan decoction.
    Authors: Shi Et al.
    Front Cell Neurosci 2015;21:4852
  3. 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.
    Authors: Wang Et al.
    PLoS One 2015;13:284
  4. Experimental evidence for alleviating nociceptive hypersensitivity by single application of capsaicin.
    Authors: Ma Et al.
    Mol Pain 2015;11:22
  5. 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.
    Authors: Chen Et al.
    Nature 2015;10:e0145556
  6. Cannabidiol causes endothelium-dependent vasorelaxation of human mesenteric arteries via CB1 activation.
    Authors: Stanley Et al.
    Neuropsychopharmacology 2015;107:568
  7. Interleukin-1β causes excitotoxic neurodegeneration and multiple sclerosis disease progression by activating the apoptotic protein p53.
    Authors: Rossi Et al.
    Mol Neurodegener 2014;9:56
  8. Transient receptor potential vanilloid type 1 channel may modulate opioid reward.
    Authors: Nguyen Et al.
    Neuropsychopharmacology 2014;39:2414
  9. Innervation of enteric mast cells by primary spinal afferents in guinea pig and human small intestine.
    Authors: Wang Et al.
    Am J Physiol Gastrointest Liver Physiol 2014;307:G719
  10. Antinociceptive effects of novel melatonin receptor agonists in mouse models of abdominal pain.
    Authors: Chen Et al.
    Mol Pain 2014;20:1298
  11. Sensory nerve terminal mitochondrial dysfunction activates airway sensory nerves via transient receptor potential (TRP) channels.
    Authors: Nesuashvili Et al.
    Mol Pharmacol 2013;83:1007
  12. Bacteria activate sensory neurons that modulate pain and inflammation.
    Authors: Chiu Et al.
    World J Gastroenterol 2013;501:52
  13. Functional expression of purinergic P2 receptors and transient receptor potential channels by the human urothelium.
    Authors: Shabir Et al.
    Diabetes 2013;305:F396
  14. Development and experimental application of an HPLC procedure for the determination of capsaicin and dihydrocapsaicin in serum samples from human subjects.
    Authors: Hartley Et al.
    Indian J Clin Biochem 2013;28:329
  15. 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.
    Authors: Gao Et al.
    Acta Neurochir Suppl 2012;61:1381
  16. Increase of capsaicin-induced trigeminal Fos-like immunoreactivity by 5-HT(7) receptors.
    Authors: Martínez-García Et al.
    Cardiovasc Res 2011;51:1511
  17. Functional plasticity of central TRPV1 receptors in brainstem dorsal vagal complex circuits of streptozotocin-treated hyperglycemic mice.
    Authors: Zsombok Et al.
    Exp Neurol 2011;31:14024
  18. Capsaicin pre-treatment provides neurovascular protection against neonatal hypoxic-ischemic brain injury in rats.
    Authors: Khatibi Et al.
    Mol Pain 2011;111:225
  19. Impact of central and peripheral TRPV1 and ROS levels on proinflammatory mediators and nociceptive behavior.
    Authors: Westlund Et al.
    Proc Natl Acad Sci U S A 2010;6:46
  20. A putative 'pre-nervous' endocannabinoid system in early echinoderm development.
    Authors: Buznikov Et al.
    Dev Neurosci 2010;32:1
  21. Effects of TRPV1 activation on synaptic excitation in the dentate gyrus of a mouse model of temporal lobe epilepsy.
    Authors: Bhaskaran and Smith
    World J Gastroenterol 2010;223:529
  22. TRPV1 channels mediate long-term depression at synapses on hippocampal interneurons.
    Authors: Gibson Et al.
    Neuron 2008;57:746
  23. Control of excitatory synaptic transmission by capsaicin is unaltered in TRPV1 vanilloid receptor knockout mice.
    Authors: Benninger Et al.
    Br J Pharmacol 2008;52:89
  24. Spinal NKCC1 blockade inhibits TRPV1-dependent referred allodynia.
    Authors: Pitcher Et al.
    J Pharmacol Exp Ther 2007;3:17
  25. Pungent products from garlic activate the sensory ion channel TRPA1.
    Authors: Bautista Et al.
    Br J Pharmacol 2005;102:12248
  26. Neurokinin-1 receptor antagonists protect mice from CD95- and tumor necrosis factor-α-mediated apoptotic liver damage.
    Authors: Bang Et al.
    J Neurosci 2004;308:1174
  27. 'Entourage' effects of N-acyl ethanolamines at human vanilloid receptors. Comparison of effects upon anandamide-induced vanilloid receptor activation and upon anandamide metabolism.
    Authors: Smart Et al.
    Headache 2002;136:452
  28. A possible role of lipoxygenase in the activation of vanilloid receptors by anandamide in the guinea-pig bronchus.
    Authors: Craib Et al.
    Neurochem Int 2001;134:42581
Expand to show all 28 Citations

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