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Submit ReviewCapsazepine
Description: TRPV 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)
Biological Activity for Capsazepine
Capsazepine is a 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.
Technical Data for Capsazepine
| 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.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for Capsazepine
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| ethanol | 9.42 | 25 | |
| DMSO | 37.69 | 100 |
Preparing Stock Solutions for Capsazepine
The following data is based on the product molecular weight 376.9. 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 |
|---|---|---|---|
| 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 for Capsazepine
References for Capsazepine
References are publications that support the biological activity of the product.
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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Keywords: Capsazepine, Capsazepine supplier, Vanilloid, receptor, antagonists, activators, ENaCdelta, vanilloid, Vanillioid, Receptors, VR1, TRPV, TRP, Channels, Transient, Receptor, Potential, Sodium, Epithelial, ENaC, Na+, 0464, Tocris Bioscience
55 Citations for Capsazepine
Citations are publications that use Tocris products. Selected citations for Capsazepine include:
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
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
Cheng et al (2019) The role of Nav1.7 and methylglyoxal-mediated activation of TRPA1 in itch and hypoalgesia in a murine model of type 1 diabetes. Theranostics 9 4287 PMID: 31285762
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
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
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
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
Buznikov et al (2010) A putative 'pre-nervous' endocannabinoid system in early echinoderm development. Exp Neurol 32 43101 PMID: 19907129
Ma et al (2015) Experimental evidence for alleviating nociceptive hypersensitivity by single application of capsaicin. Mol Pain 11 22 PMID: 25896608
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
Akerman et al (2007) Cannabinoid (CB1) receptor activation inhibits trigeminovascular neurons. J Pharmacol Exp Ther 320 64 PMID: 17018694
Bambico et al (2007) Cannabinoids elicit antidepressant-like behavior and activate serotonergic neurons through the medial prefrontal cortex. J Neurosci 27 11700 PMID: 17959812
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
Melis et al (2008) Endogenous fatty acid ethanolamides suppress nicotine-induced activation of mesolimbic DA 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
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
Kamiya et al (2018) Electrophysiological measurement of ion channels on plasma/organelle membranes using an on-chip lipid bilayer system. Sci Rep 8 17498 PMID: 30504856
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 Ins release. J Biol Chem 288 32685 PMID: 24089517
Samineni et al (2011) Post-ictal analgesia in genetically epilepsy-prone rats is induced by audiogenic seizures and involves cannabinoid receptors in the periaqueductal gray. Brain Res 1389 177 PMID: 21439272
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
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
Hamtiaux et al (2012) The association of N-palmitoylethanolamine with the FAAH inhibitor URB597 impairs melanoma growth through a supra-additive action. BMC Cancer 12 92 PMID: 22429826
Hamtiaux et al (2011) Increasing antiproliferative properties of endocannabinoids in N1E-115 neuroblastoma cells through inhibition of their metabolism. PLoS One 6 e26823 PMID: 22046372
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
Kagaya et al (2002) Characterization of the anandamide induced depolarization of guinea-pig isolated vagus nerve. Br J Pharmacol 137 39 PMID: 12183329
Mazzone and Canning (2002) Synergistic interactions between airway afferent nerve subtypes mediating reflex bronchospasm in guinea pigs. Am J Physiol Regul Integr Comp Physiol 283 R86 PMID: 12069934
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. Mol Pharmacol 134 42581 PMID: 11522594
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
Derbenev and Smith (2013) Dexamethasone rapidly increases GABA release in the dorsal motor nucleus of the vagus via retrograde messenger-mediated enhancement of TRPV1 activity. PLoS One 8 e70505 PMID: 23936221
Ruparel et al (2012) The cytochrome P450 inhibitor, ketoconazole, inhibits oxidized linoleic acid metabolite-mediated peripheral inflammatory pain. Mol Pain 8 73 PMID: 23006841
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
Baker (2004) The cannabinomimetic arachidonyl-2-chloroethylamide (ACEA) acts on capsaicin-sensitive TRPV1 receptors but not cannabinoid receptors in rat joints. Br J Pharmacol 142 1361 PMID: 15277316
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
Diniz et al (2019) Dual mechanism of TRKB activation by anandamide through CB1 and TRPV1 receptors. PeerJ 7 e6493 PMID: 30809460
Wu and Tasker (2017) Nongenomic Glucocorticoid Suppression of a Postsynaptic Potassium Current via Emergent Autocrine Endocannabinoid Signaling in Hypothalamic Neuroendocrine Cells following Chronic Dehydration. Eneuro 4 PMID: 28966975
Saliba (2017) AM404, paracetamol metabolite, prevents prostaglandin synthesis in activated microglia by inhibiting COX activity. J Neuroinflammation 14 246 PMID: 29237478
Do you know of a great paper that uses Capsazepine from Tocris? Please let us know.
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