Capsazepine

Cat. No. 0464

Capsazepine C19H21ClN2O2S [138977-28-3]

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Chemical Name: N-[2-(4-Chlorophenyl)ethyl]-1,3,4,5-tetrahydro-7,8-dihydroxy-2H-2-benzazepine-2-carbothioamide

Biological Activity

Selective vanilloid receptor antagonist (Ki = 3.2 μM). Inhibits carrageenan inflammation-induced hyperalgesic responses in the rat. Also activates amiloride-sensitive epithelial Na+ channel ENaCδ. Also available as part of the Vanilloid TRPV1 Receptor Tocriset™.

Technical Data

M.Wt:
376.9
Formula:
C19H21ClN2O2S
Solubility:
Soluble to 25 mM in ethanol and to 100 mM in DMSO
Purity:
>99 %
Storage:
Store at RT
CAS No:
138977-28-3

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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Yamamura et al (2004) Capsazepine is a novel activator of the δ subunit of the human epithelial Na+ channel. J.Biol.Chem. 279 44483. PMID: 15308635.

Kwak et al (1998) A capsaicin-receptor antagonist, capsazepine, reduces inflammation-induced hyperalgesic responses in the rat: evidence for an endogenous capsaicin-like substance. Neuroscience 86 619. PMID: 9881874.

Dickenson and Dray (1991) Selective antagonism of capsaicin by capsazepine: evidence for a spinal receptor site in capsaicin-induced antinociception. Br.J.Pharmacol. 104 1045. PMID: 1810591.

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

Citations are publications that use Tocris products. Selected citations for Capsazepine include:

Borrelli et al (2015) Palmitoylethanolamide, a naturally occurring lipid, is an orally effective intestinal anti-inflammatory agent. PLoS One 172 142. PMID: 25205418.

Eskander et al (2015) Persistent Nociception Triggered by Nerve Growth Factor (NGF) Is Mediated by TRPV1 and Oxidative Mechanisms. Br J Pharmacol 35 8593. PMID: 26041925.

Lin et al (2015) Palmitoylethanolamide inhibits glutamate release in rat cerebrocortical nerve terminals. J Neurosci 16 5555. PMID: 25768340.

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

Smith et al (2015) The Effects of the Endocannabinoids Anandamide and 2-Arachidonoylglycerol on Human Osteoblast Proliferation and Differentiation. PLoS One 10 e0136546. PMID: 26414859.

Vijayvergiya et al (2015) Measurement of Ensemble TRPV1 Ion Channel Currents Using Droplet Bilayers. PLoS One 10 e0141366. PMID: 26513481.

Wang et al (2015) Hydrogen sulfide-induced itch requires activation of Cav3.2 T-type calcium channel in mice. Int J Mol Sci 5 16768. PMID: 26602811.

Lu et al (2014) H2 S modulates duodenal motility in male rats via activating TRPV1 and K(ATP) channels. Proc Natl Acad Sci U S A 171 1534. PMID: 24345161.

Morelli et al (2014) Cross-talk between alpha1D-adrenoceptors and transient receptor potential vanilloid type 1 triggers prostate cancer cell proliferation. BMC Cancer 14 921. PMID: 25481381.

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.

Graham et al (2013) Epidermal keratinocyte polarity and motility require Ca2+ influx through TRPV1. J Cell Sci 126 4602. PMID: 23943873.

Malenczyk et al (2013) CB1 cannabinoid receptors couple to focal adhesion kinase to control insulin release. J Biol Chem 288 32685. PMID: 24089517.

Albert et al (2012) TRPV4 channels mediate the infrared laser-evoked response in sensory neurons. J Neurophysiol 107 3227. PMID: 22442563.

Casarotto et al (2012) Opposing roles for cannabinoid receptor type-1 (CB1) and transient receptor potential vanilloid type-1 channel (TRPV1) on the modulation of panic-like responses in rats. Br J Pharmacol 37 478. PMID: 21937980.

Kaszás et al (2012) Small molecule positive allosteric modulation of TRPV1 activation by vanilloids and acidic pH. Dev Neurosci 340 152. PMID: 22005042.

Liu et al (2012) Betulinic acid targets YY1 and ErbB2 through cannabinoid receptor-dependent disruption of microRNA-27a:ZBTB10 in breast cancer. Mol Cancer Ther 11 1421. PMID: 22553354.

Muzzi et al (2012) Ischemic neuroprotection by TRPV1 receptor-induced hypothermia. Br J Pharmacol 32 978. PMID: 22434066.

Canetta et al (2011) Type III Nrg1 back signaling enhances functional TRPV1 along sensory axons contributing to basal and inflammatory thermal pain sensation. J Cereb Blood Flow Metab 6 e25108. PMID: 21949864.

Li and Burrell (2011) Associative, bidirectional changes in neural signaling utilizing NMDA receptor- and endocannabinoid-dependent mechanisms. Learn Mem 18 545. PMID: 21844187.

Ruparel et al (2011) Desensitization of transient receptor potential ankyrin 1 (TRPA1) by the TRP vanilloid 1-selective cannabinoid arachidonoyl-2 chloroethanolamine. Neurochem Int 80 117. PMID: 21441412.

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

Buznikov et al (2010) A putative 'pre-nervous' endocannabinoid system in early echinoderm development. Exp Neurol 32 43101. PMID: 19907129.

Kim and Alger (2010) Reduction in endocannabinoid tone is a homeostatic mechanism for specific inhibitory synapses. Nat Neurosci 13 592. PMID: 20348918.

Yuan and Burrell (2010) Endocannabinoid-dependent LTD in a nociceptive synapse requires activation of a presynaptic TRPV-like receptor. J Neurophysiol 104 2766. PMID: 20884761.

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

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

Melis et al (2008) Endogenous fatty acid ethanolamides suppress nicotine-induced activation of mesolimbic dopamine neurons through nuclear receptors. J Neurosci 28 13985. PMID: 19091987.

Moezi et al (2006) Anandamide mediates hyperdynamic circulation in cirrhotic rats via CB(1) and VR(1) receptors. J Pharmacol Exp Ther 149 898. PMID: 17043671.

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

Gavva et al (2005) AMG 9810 [(E)-3-(4-t-butylphenyl)-N-(2,3-dihydrobenzo[b][1,4] dioxin-6-yl)acrylamide], a novel vanilloid receptor 1 (TRPV1) antagonist with antihyperalgesic properties. J Pharmacol Exp Ther 313 474. PMID: 15615864.

Kwolek et al (2005) Central and peripheral components of the pressor effect of anandamide in urethane-anaesthetized rats. Br J Pharmacol 145 567. PMID: 15834445.

Akerman et al (2004) Anandamide acts as a vasodilator of dural blood vessels in vivo by activating TRPV1 receptors. Br J Pharmacol 142 1354. PMID: 15277315.

Price et al (2004) Cannabinoid receptor-independent actions of the aminoalkylindole WIN 55,212-2 on trigeminal sensory neurons. Br J Pharmacol 142 257. PMID: 15155534.

Akerman et al (2003) Vanilloid type 1 receptors (VR1) on trigeminal sensory nerve fibres play a minor role in neurogenic dural vasodilatation, and are involved in capsaicin-induced dural dilation. Sci Rep 140 718. PMID: 14534154.

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

Do you know of a great paper that uses Capsazepine from Tocris? If so please let us know.show all ▼show less ▲

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Keywords: Capsazepine, supplier, Vanilloid, receptor, antagonists, activators, ENaCdelta, vanilloid, Vanillioid, Receptors, VR1, TRPV, TRP, Channels, Transient, Receptor, Potential, Sodium, Epithelial, ENaC, Na+, Tocris Bioscience, TRPV Antagonist products

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