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(E)-Capsaicin

Catalog #: 0462
38 Citations 1 Review Datasheet / COA / SDS
Catalog # Availability Size / Price Qty
0462/100
(E)-Capsaicin | CAS No. 404-86-4 | TRPV Agonists
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Description: TRPV agonist

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

Purity: ≥98%

Product Details
Citations (38)
Supplemental Products
Reviews (1)
Biological Activity Technical Data Background Product Datasheets Calculators

Biological Activity

(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

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

Background References

  1. TRPA1 is a polyunsaturated fatty acid sensor in mammals.
    Motter AL, Ahern GP,
    PLoS ONE, 2012;7(6):e38439.
  2. N-Arachidonoyl Dopamine Modulates Acute Systemic Inflammation via Nonhematopoietic TRPV1
    SK Lawton, F Xu, A Tran, E Wong, A Prakash, M Schumacher, J Hellman, K Wilhelmsen
    J. Immunol., 2017;0(0):.
  3. The endocannabinoid/endovanilloid N-arachidonoyl dopamine (NADA) and synthetic cannabinoid WIN55,212-2 abate the inflammatory activation of human endothelial cells.
    Wilhelmsen K, Khakpour S, Tran A, Sheehan K, Schumacher M, Xu F, Hellman J
    J Biol Chem, 2014;289(19):13079-100.
  4. High-throughput genotoxicity assay identifies antioxidants as inducers of DNA damage response and cell death.
    Fox JT, Sakamuru S, Huang R
    Proc. Natl. Acad. Sci. U.S.A., 2012;109(14):5423-8.
  5. Interleukin-1beta causes excitotoxic neurodegeneration and multiple sclerosis disease progression by activating the apoptotic protein p53.
    Rossi S, Motta C, Studer V, Macchiarulo G, Volpe E, Barbieri F, Ruocco G, Buttari F, Finardi A, Mancino R, Weiss S, Battistini L, Martino G, Furlan R, Drulovic J, Centonze D
    Mol Neurodegener, 2014;9(0):56.
  6. Sensory neuron-specific actions of capsaicin: mechanisms and application.
    Bevan and Szolcsani
    TiPS, 1990;11:330
  7. Inhibition of platelet aggregation by capsaicin. An effect unrelated to actions on sensory afferent neurons.
    Hogaboam and Wallace
    Eur.J.Pharmacol., 1991;202:129
  8. Capsaicin-cellular targets, mechanism of actions, and selectivity for thin sensory neurons.
    Holzer
    Pharmacol.Rev., 1991;43:143
  9. Cannabinoid activation of recombinant and endogenous vanilloid receptors.
    Ralevic et al.
    Eur.J.Pharmacol., 2001;424:211

Product Datasheets

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Citations for (E)-Capsaicin

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

38 Citations: Showing 1 - 10

  1. Dual mechanism of TRKB activation by anandamide through CB1 and TRPV1 receptors.
    Authors: Diniz Et al.
    PeerJ  2019;7:e6493
  2. TrpV1 receptor activation rescues neuronal function and network gamma oscillations from Aβ-induced impairment in mouse hippocampus in vitro.
    Authors: Balleza-Tapia Et al.
    Elife  2018;7
  3. An Intestinal Organ Culture System Uncovers a Role for the Nervous System in Microbe-Immune Crosstalk.
    Authors: Yissachar Et al.
    Cell  2017;168:1135
  4. Spatial Distribution of the Cannabinoid Type 1 and Capsaicin Receptors May Contribute to the Complexity of Their Crosstalk.
    Authors: Chen Et al.
    Sci Rep  2016;6:33307
  5. 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
  6. 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
  7. 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
  8. Experimental evidence for alleviating nociceptive hypersensitivity by single application of capsaicin.
    Authors: Ma Et al.
    Mol Pain  2015;11:22
  9. 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
  10. Cannabidiol causes endothelium-dependent vasorelaxation of human mesenteric arteries via CB1 activation.
    Authors: Stanley Et al.
    Neuropsychopharmacology  2015;107:568
  11. 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
  12. Transient receptor potential vanilloid type 1 channel may modulate opioid reward.
    Authors: Nguyen Et al.
    Neuropsychopharmacology  2014;39:2414
  13. 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
  14. Antinociceptive effects of novel melatonin receptor agonists in mouse models of abdominal pain.
    Authors: Chen Et al.
    Mol Pain  2014;20:1298
  15. Membrane potential measurements of isolated neurons using a voltage-sensitive dye.
    Authors: Fairless Et al.
    PLoS One  2013;8:e58260
  16. Sensory nerve terminal mitochondrial dysfunction activates airway sensory nerves via transient receptor potential (TRP) channels.
    Authors: Nesuashvili Et al.
    Mol Pharmacol  2013;83:1007
  17. Bacteria activate sensory neurons that modulate pain and inflammation.
    Authors: Chiu Et al.
    World J Gastroenterol  2013;501:52
  18. Functional expression of purinergic P2 receptors and transient receptor potential channels by the human urothelium.
    Authors: Shabir Et al.
    Diabetes  2013;305:F396
  19. 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
  20. 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
  21. 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
    Authors: Nash Et al.
    J Pharmacol Exp Ther  2012;342:389
  22. Increase of capsaicin-induced trigeminal Fos-like immunoreactivity by 5-HT(7) receptors.
    Authors: Martínez-García Et al.
    Cardiovasc Res  2011;51:1511
  23. 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
  24. Capsaicin pre-treatment provides neurovascular protection against neonatal hypoxic-ischemic brain injury in rats.
    Authors: Khatibi Et al.
    Mol Pain  2011;111:225
  25. A gradient of 2-arachidonoylglycerol regulates mouse epididymal sperm cell start-up.
    Authors: Cobellis Et al.
    Biol Reprod  2010;82:451
  26. 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
  27. A putative 'pre-nervous' endocannabinoid system in early echinoderm development.
    Authors: Buznikov Et al.
    Dev Neurosci  2010;32:1
  28. 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
  29. TRPV1 channels mediate long-term depression at synapses on hippocampal interneurons.
    Authors: Gibson Et al.
    Neuron  2008;57:746
  30. 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
  31. Spinal NKCC1 blockade inhibits TRPV1-dependent referred allodynia.
    Authors: Pitcher Et al.
    J Pharmacol Exp Ther  2007;3:17
  32. Extracellular cations sensitize and gate capsaicin receptor TRPV1 modulating pain signaling.
    Authors: Ahern Et al.
    J Neurosci  2005;25:5109
  33. Pungent products from garlic activate the sensory ion channel TRPA1.
    Authors: Bautista Et al.
    Br J Pharmacol  2005;102:12248
  34. 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
  35. Endocannabinoids mediate presynaptic inhibition of glutamatergic transmission in rat ventral tegmental area DA neurons through activation of CB1 receptors.
    Authors: Melis Et al.
    J Neurosci  2004;24:53
  36. '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
  37. 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
  38. Effect of vanilloid drugs on gastrointestinal transit in mice.
    Authors: Izzo Et al.
    Br J Pharmacol  2001;132:1411

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enteric nerve study
By Anonymous on 04/26/2023
Species: Mouse

Using for trpv1 neuron activation

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