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Merck
CN

R8756

Resiniferatoxin

from Euphorbia poisonii, ~95%

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About This Item

Empirical Formula (Hill Notation):
C37H40O9
CAS Number:
57444-62-9
Molecular Weight:
628.71
PubChem Substance ID:
24899411
UNSPSC Code:
12352200
Beilstein/REAXYS Number:
5371150
MDL number:
MFCD00135927

Key Documents

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SMILES string

[H][C@@]12C=C(C)C(=O)[C@@]1(O)CC(COC(=O)Cc3cc(O)cc(OC)c3)=CC4[C@H]5O[C@]7(Cc6ccccc6)O[C@]5(C[C@@H](C)[C@]24O7)C(C)=C

InChI

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

InChI key

IKYCZSUNGFRBJS-PMIKMUNESA-N

biological source

Euphorbia poisonii

assay

~95%

storage temp.

−20°C

Quality Level

100

Gene Information

rat ... Trpv1(83810)

Application

Resiniferatoxin has been used as an agonist to transient receptor potential vanilloid 2 (TRPV2):
  • for complex preparation for cryo-electron microscopy structural studies
  • to test its effect towards immune responses to P. aeruginosa in sensory neurons associated with the cornea
  • to study its effects in the denervation of the peripheral sensory nerves in psoriatic mice

Biochem/physiol Actions

Resiniferatoxin (RTX) is an analog of capsaicin. It effectively ablates corneal sensory neurons by activating transient receptor potential vanilloid 1 (TRPV1) channels. RTX facilitates corneal bacterial clearance. It also elicits protective functionality towards cardiac function in a rat model with congestive heart failure (CHF).
Potent VR1 vanilloid receptor agonist that has been used to label the vanilloid receptor in sensory ganglia; activates protein kinase C. Diterpene ester that is related to phorbol, but is not tumorigenic.
Potent VR1 vanilloid receptor agonist.

pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

hcodes

H301,H314

Hazard Classifications

Acute Tox. 3 Oral - Skin Corr. 1A

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKBW9486V
MKCC8692
MKBS9744V
MKBQ8345V
SLBD1649V

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J Szolcsanyi et al.
The Journal of pharmacology and experimental therapeutics, 255(2), 923-928 (1990-11-01)
Resiniferatoxin (RTX) has been shown to function as an ultrapotent analog of capsaicin. It is reported here that RTX, like capsaicin, acts selectively on primary sensory neurons in rats to produce ultrastructural alterations and calcitonin gene-related peptide depletion. To evaluate
P K Matsuoka et al.
International urogynecology journal, 23(9), 1147-1153 (2012-05-10)
The objective of the study was to assess the effectiveness of intravesical treatment for painful bladder syndrome (PBS). A systematic review was performed until December 31, 2010. The selection criteria included only randomized controlled trials of PBS patients who received
Yu-Lin Hsieh et al.
Experimental neurology, 235(1), 316-325 (2012-03-07)
Patients suffering from sensory neuropathy due to skin denervation frequently have paradoxical manifestations of reduced nociception and neuropathic pain. However, there is a lack of satisfactory animal models to investigate these phenomena and underlying mechanisms. We developed a mouse system
M B Chancellor et al.
The Journal of urology, 162(1), 3-11 (1999-06-24)
Pharmacological treatment of the overactive bladder relies on partially blocking the efferent parasympathetic innervation to the detrusor with anticholinergic drugs. However, often these drugs have troublesome side effects and doses are insufficient to restore continence in patients with detrusor instability.
M Van Lookeren Campagne et al.
Neuroscience letters, 137(1), 129-132 (1992-03-16)
We conducted an electron microscopic immunocytochemical study to locate B-50/GAP43 in various cellular elements of hippocampal neurons grown in dissociated cell culture. B-50 was detected with pre- and post-embedding immunoincubation, using affinity-purified B-50 antibodies and secondary antibodies coated on gold
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