Capsazepine

Pricing Availability Delivery Time Qty
Cat.No. 0464 - Capsazepine | C19H21ClN2O2S | CAS No. 138977-28-3
Description: Vanilloid receptor antagonist; also activator of ENaCδ
Chemical Name: N-[2-(4-Chlorophenyl)ethyl]-1,3,4,5-tetrahydro-7,8-dihydroxy-2H-2-benzazepine-2-carbothioamide
Purity: ≥99% (HPLC)
Datasheet
Citations (37)
Literature

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™.

Compound Libraries

Capsazepine is also offered as part of the Tocriscreen Plus. Find out more about compound libraries available from Tocris.

Technical Data

M. Wt 376.9
Formula C19H21ClN2O2S
Storage Store at RT
Purity ≥99% (HPLC)
CAS Number 138977-28-3
PubChem ID 2733484
InChI Key DRCMAZOSEIMCHM-UHFFFAOYSA-N
Smiles OC1=C(O)C=C2CN(CCCC2=C1)C(=S)NCCC1=CC=C(Cl)C=C1

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.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 37.69 100
ethanol 9.42 25

Preparing Stock Solutions

The following data is based on the product molecular weight 376.9. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.65 mL 13.27 mL 26.53 mL
5 mM 0.53 mL 2.65 mL 5.31 mL
10 mM 0.27 mL 1.33 mL 2.65 mL
50 mM 0.05 mL 0.27 mL 0.53 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

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

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

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


If you know of a relevant reference for Capsazepine, please let us know.

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View all TRPV Antagonists

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

37 Citations for Capsazepine

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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


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Pain Research Product Guide

A collection of over 250 products for pain research, the guide includes research tools for the study of:

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Peripheral sensitization is the reduction in the threshold of excitability of sensory neurons that results in an augmented response to a given external stimulus. This poster outlines the excitatory and inhibitory signaling pathways involved in modulation of peripheral sensitization. The role of ion channels, GPCRs, neurotrophins, and cytokines in sensory neurons are also described.

Pathways for Capsazepine

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