Resiniferatoxin | 57444-62-9

MedKoo Cat#: 330117 | Name: Resiniferatoxin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Resiniferatoxin is a natural analog of capsaicin isolated from some plants of the genus Euphorbia, including E. resinifera. Resiniferatoxin modulates the Th1 immune response and protects the host during intestinal nematode infection. Intraluminal Administration of Resiniferatoxin Protects against <i>Clostridium difficile</i> Toxin A-Induced Colitis.

Chemical Structure

Resiniferatoxin

CAS#57444-62-9

Theoretical Analysis

MedKoo Cat#: 330117

Name: Resiniferatoxin

CAS#: 57444-62-9

Chemical Formula: C37H40O9

Exact Mass: 628.2672

Molecular Weight: 628.72

Elemental Analysis: C, 70.68; H, 6.41; O, 22.90

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 850.00	2 Weeks

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Related CAS #

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Synonym

Resiniferatoxin; RTX

IUPAC/Chemical Name

4-hydroxy-3-methoxy-benzeneacetic acid, [(2S,3aR,3bS,6aR,9aR,9bR,10R,11aR)-3a,3b,6,6a,9a,10,11,11a-octahydro-6a-hydroxy-8,10-dimethyl-11a-(1-methylethenyl)-7-oxo-2-(phenylmethyl)-7H-2,9b-epoxyazuleno[5,4-e]-1,3-benzodioxol-5-yl]methyl ester

InChi Key

DSDNAKHZNJAGHN-MXTYGGKSSA-N

InChi Code

InChI=1S/C37H40O9/c1-21(2)35-17-23(4)37-27(33(35)44-36(45-35,46-37)19-24-9-7-6-8-10-24)14-26(18-34(41)30(37)13-22(3)32(34)40)20-43-31(39)16-25-11-12-28(38)29(15-25)42-5/h6-15,23,27,30,33,38,41H,1,16-20H2,2-5H3/t23-,27+,30-,33-,34-,35-,36-,37-/m1/s1

SMILES Code

O=C(OCC(C[C@]12O)=C[C@]3([H])[C@@]4([C@]2([H])C=C(C)C1=O)[C@H](C)C[C@@]5(C(C)=C)[C@]3([H])O[C@](O4)(CC6=CC=CC=C6)O5)CC7=CC=C(O)C(OC)=C7

Appearance

Solid powder

Purity

>80% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 628.72 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	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Parisi JR, Martins de Andrade AL, Torres Silva JR, Silva ML. Antiallodynic effect of intrathecal resiniferatoxin on neuropathic pain model of chronic constriction injury. Acta Neurobiol Exp (Wars). 2017;77(4):317-322. PubMed PMID: 29369297. 2: Hockman TM, Cisternas AF, Jones B, Butt MT, Osborn KG, Steinauer JJ, Malkmus SA, Yaksh TL. Target engagement and histopathology of neuraxial resiniferatoxin in dog. Vet Anaesth Analg. 2018 Mar;45(2):212-226. doi: 10.1016/j.vaa.2017.10.005. Epub 2017 Dec 5. PubMed PMID: 29361418. 3: Muñoz-Carrillo JL, Muñoz-López JL, Muñoz-Escobedo JJ, Maldonado-Tapia C, Gutiérrez-Coronado O, Contreras-Cordero JF, Moreno-García MA. Therapeutic Effects of Resiniferatoxin Related with Immunological Responses for Intestinal Inflammation in Trichinellosis. Korean J Parasitol. 2017 Dec;55(6):587-599. doi: 10.3347/kjp.2017.55.6.587. Epub 2017 Dec 31. Review. PubMed PMID: 29320813; PubMed Central PMCID: PMC5776891. 4: Raithel SJ, Sapio MR, LaPaglia DM, Iadarola MJ, Mannes AJ. Transcriptional Changes in Dorsal Spinal Cord Persist after Surgical Incision Despite Preemptive Analgesia with Peripheral Resiniferatoxin. Anesthesiology. 2018 Mar;128(3):620-635. doi: 10.1097/ALN.0000000000002006. PubMed PMID: 29271803. 5: Hsieh YL, Kan HW, Chiang H, Lee YC, Hsieh ST. Distinct TrkA and Ret modulated negative and positive neuropathic behaviors in a mouse model of resiniferatoxin-induced small fiber neuropathy. Exp Neurol. 2018 Feb;300:87-99. doi: 10.1016/j.expneurol.2017.10.026. Epub 2017 Oct 26. PubMed PMID: 29106982. 6: Hashimoto S, Katoh SI, Kato T, Urabe D, Inoue M. Total Synthesis of Resiniferatoxin Enabled by Radical-Mediated Three-Component Coupling and 7-endo Cyclization. J Am Chem Soc. 2017 Nov 15;139(45):16420-16429. doi: 10.1021/jacs.7b10177. Epub 2017 Oct 31. PubMed PMID: 29041773. 7: Lepiarczyk E, Bossowska A, Kaleczyc J, Skowrońska A, Majewska M, Majewski M, Majewski M. The Influence of Resiniferatoxin (RTX) and Tetrodotoxin (TTX) on the Distribution, Relative Frequency, and Chemical Coding of Noradrenergic and Cholinergic Nerve Fibers Supplying the Porcine Urinary Bladder Wall. Toxins (Basel). 2017 Oct 3;9(10). pii: E310. doi: 10.3390/toxins9100310. PubMed PMID: 28972567; PubMed Central PMCID: PMC5666357. 8: Fukushima A, Mamada K, Iimura A, Ono H. Supraspinal-selective TRPV1 desensitization induced by intracerebroventricular treatment with resiniferatoxin. Sci Rep. 2017 Sep 29;7(1):12452. doi: 10.1038/s41598-017-12717-5. PubMed PMID: 28963471; PubMed Central PMCID: PMC5622082. 9: Bessaguet F, Danigo A, Magy L, Sturtz F, Desmoulière A, Demiot C. Candesartan prevents resiniferatoxin-induced sensory small-fiber neuropathy in mice by promoting angiotensin II-mediated AT2 receptor stimulation. Neuropharmacology. 2017 Nov;126:142-150. doi: 10.1016/j.neuropharm.2017.08.039. Epub 2017 Sep 5. PubMed PMID: 28882562. 10: Leo M, Schulte M, Schmitt LI, Schäfers M, Kleinschnitz C, Hagenacker T. Intrathecal Resiniferatoxin Modulates TRPV1 in DRG Neurons and Reduces TNF-Induced Pain-Related Behavior. Mediators Inflamm. 2017;2017:2786427. doi: 10.1155/2017/2786427. Epub 2017 Aug 2. PubMed PMID: 28831207; PubMed Central PMCID: PMC5558708. 11: Muñoz-Carrillo JL, Contreras-Cordero JF, Muñoz-López JL, Maldonado-Tapia CH, Muñoz-Escobedo JJ, Moreno-García MA. Resiniferatoxin modulates the Th1 immune response and protects the host during intestinal nematode infection. Parasite Immunol. 2017 Sep;39(9). doi: 10.1111/pim.12448. Epub 2017 Jun 27. PubMed PMID: 28580764. 12: Vigna SR. Intraluminal Administration of Resiniferatoxin Protects against Clostridium difficile Toxin A-Induced Colitis. Gastroenterol Res Pract. 2017;2017:8438172. doi: 10.1155/2017/8438172. Epub 2017 Apr 17. PubMed PMID: 28484490; PubMed Central PMCID: PMC5412210. 13: Zhu Y, Zeng Q. Re: Resiniferatoxin for treatment of lifelong premature ejaculation: A preliminary study. Int J Urol. 2017 Mar;24(3):243-244. doi: 10.1111/iju.13283. Epub 2017 Feb 16. PubMed PMID: 28208208. 14: Shi B. Response to Re: Resiniferatoxin for treatment of lifelong premature ejaculation: A preliminary study. Int J Urol. 2017 Mar;24(3):244. doi: 10.1111/iju.13288. Epub 2017 Feb 1. PubMed PMID: 28147446. 15: Salas MM, Clifford JL, Hayden JR, Iadarola MJ, Averitt DL. Local Resiniferatoxin Induces Long-Lasting Analgesia in a Rat Model of Full Thickness Thermal Injury. Pain Med. 2017 Dec 1;18(12):2453-2465. doi: 10.1093/pm/pnw260. PubMed PMID: 27794548. 16: Aizawa N, Fukuhara H, Fujimura T, Homma Y, Igawa Y. Direct influence of systemic desensitization by resiniferatoxin on the activities of Aδ- and C-fibers in the rat primary bladder mechanosensitive afferent nerves. Int J Urol. 2016 Nov;23(11):952-956. doi: 10.1111/iju.13181. Epub 2016 Aug 10. PubMed PMID: 27509829. 17: Lepiarczyk E, Dudek A, Kaleczyc J, Majewski M, Markiewicz W, Radziszewski P, Bossowska A. The influence of resiniferatoxin on the chemical coding of caudal mesenteric ganglion neurons supplying the urinary bladder in the pig. J Physiol Pharmacol. 2016 Aug;67(4):625-632. PubMed PMID: 27779483. 18: Bert J, Mahowald ML, Frizelle S, Dorman CW, Funkenbusch SC, Krug HE. The Effect of Treatment with Resiniferatoxin and Capsaicin on Dynamic Weight Bearing Measures and Evoked Pain Responses in a Chronic Inflammatory Arthritis Murine Model. Intern Med Rev (Wash D C). 2016;2016(6). pii: 89. PubMed PMID: 27774522; PubMed Central PMCID: PMC5070479. 19: Lei Y, Sun Y, Lu C, Ma Z, Gu X. Activated Glia Increased the Level of Proinflammatory Cytokines in a Resiniferatoxin-Induced Neuropathic Pain Rat Model. Reg Anesth Pain Med. 2016 Nov/Dec;41(6):744-749. PubMed PMID: 27429048. 20: Laverdet B, Girard D, Bayout A, Bordeau N, Demiot C, Desmoulière A. Effects of small-fiber neuropathy induced by resiniferatoxin on skin healing and axonal regrowth after burn. Burns. 2017 May;43(3):562-572. doi: 10.1016/j.burns.2016.09.016. Epub 2016 Oct 12. PubMed PMID: 27743736.