5'-Iodoresiniferatoxin

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Cat.No. 1362 - 5'-Iodoresiniferatoxin | C37H39IO9 | CAS No. 535974-91-5
Description: Potent, silent TRPV1 antagonist
Alternative Names: Iodoresiniferatoxin, 5'-IRTX
Chemical Name: 6,7-Deepoxy-6,7-didehydro-5-deoxy-21-dephenyl-21-(phenylmethyl)-daphnetoxin,20-(4-hydroxy-5-iodo-3-methoxybenzeneacetate)
Purity: ≥98% (HPLC)
Datasheet
Citations (15)
Reviews
Literature

Biological Activity

Potent and silent vanilloid receptor antagonist, 40-fold more potent than capsazepine (Cat. No. 0464). Binds to TRPV1 (VR1) receptors expressed in HEK293 cells with a Ki of 5.8 nM.

Technical Data

M. Wt 754.6
Formula C37H39IO9
Storage Desiccate at -20°C
Purity ≥98% (HPLC)
CAS Number 535974-91-5
PubChem ID 16219535
InChI Key TZUJORCXGLGWDV-RYACRXIZSA-N
Smiles O=C1C(C)=C[C@]2([H])[C@@](O)1CC(COC(CC5=CC(I)=C(O)C(OC)=C5)=O)=C[C@]3([H])[C@@](O6)2[C@H](C)C[C@@]4(C(C)=C)[C@@H]3OC6(CC7=CC=CC=C7)O4

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

Solubility Soluble in DMSO and to 100 mM in ethanol

Preparing Stock Solutions

The following data is based on the product molecular weight 754.6. 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.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.33 mL 6.63 mL 13.25 mL
5 mM 0.27 mL 1.33 mL 2.65 mL
10 mM 0.13 mL 0.66 mL 1.33 mL
50 mM 0.03 mL 0.13 mL 0.27 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 biological activity of the product.

Marinelli et al (2002) Capsaicin activation of glutamatergic synaptic transmission in the rat locus coeruleus in vitro. J.Physiol. 543 531 PMID: 12205187

Wahl et al (2001) Iodo-resiniferatoxin, a new potent vanilloid receptor antagonist. Mol.Pharmacol. 59 9 PMID: 11125018

Seabrook et al (2001) Properties of iodo-resiniferatoxin - a high affinity VR1 vanilloid receptor antagonist. Soc.Neurosci.Abstr. 925.9


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Keywords: 5'-Iodoresiniferatoxin, 5'-Iodoresiniferatoxin supplier, Potent, silent, TRPV1, antagonists, Vanillioid, Receptors, VR1, Channels, Transient, Receptor, Potential, 5-Iodoresiniferatoxin, 5-IRTX, Iodoresiniferatoxin, 5'-IRTX, TRPV, 1362, Tocris Bioscience

15 Citations for 5'-Iodoresiniferatoxin

Citations are publications that use Tocris products. Selected citations for 5'-Iodoresiniferatoxin include:

Zsombok et al (2011) Functional plasticity of central TRPV1 receptors in brainstem dorsal vagal complex circuits of streptozotocin-treated hyperglycemic mice. PLoS One 31 14024 PMID: 21957263

Marinelli et al (2007) N-arachidonoyl-dopamine tunes synaptic transmission onto dopaminergic neurons by activating both cannabinoid and vanilloid receptors. Neuropsychopharmacology 32 298 PMID: 16760924

Gao et al (2012) 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. Pain 61 1381 PMID: 22492526

Ruparel et al (2012) Plasticity of cytochrome P450 isozyme expression in rat trigeminal ganglia neurons during inflammation. J Neurosci 153 2031 PMID: 22633978

Musella (2017) A novel crosstalk within the endocannabinoid system controls GABA transmission in the striatum. Sci Rep 7 7363 PMID: 28779174

Derbenev et al (2006) Vanilloid-mediated heterosynaptic facilitation of inhibitory synaptic input to neurons of the rat dorsal motor nucleus of the vagus. J Neurosci 26 9666 PMID: 16988037

Vigna (2014) 5-Aminosalicylic Acid Inhibits Acute Clostridium difficile Toxin A-Induced Colitis in Rats. PLoS One 2014 389621 PMID: 25045574

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

Woolcott et al (2015) High-fat diet-induced insulin resistance does not increase plasma anandamide levels or potentiate anandamide insulinotropic effect in isolated canine islets. J Neurosci Res 10 e0123558 PMID: 25855974

Raboune et al (2014) Novel endogenous N-acyl amides activate TRPV1-4 receptors, BV-2 microglia, and are regulated in brain in an acute model of inflammation. Front Cell Neurosci 8 195 PMID: 25136293

Capasso et al (2014) Palmitoylethanolamide normalizes intestinal motility in a model of post-inflammatory accelerated transit: involvement of CB? receptors and TRPV1 channels. Br J Pharmacol 171 4026 PMID: 24818658

Barbonetti et al (2010) Energetic metabolism and human sperm motility: impact of CB1 receptor activation. Endocrinology 151 5882 PMID: 20962050

El-Hashim and Jaffal (2009) Nerve growth factor enhances cough and airway obstruction via TrkA receptor- and TRPV1-dependent mechanisms. Thorax 64 791 PMID: 19497920

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

Xu et al (2009) Increases in transient receptor potential vanilloid-1 mRNA and protein in primary afferent neurons stimulated by protein kinase C and their possible role in neurogenic inflammation. Int J Inflam 87 482 PMID: 18752301


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