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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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Spontaneous cardiac tamponade in a premature infant.
S Menahem
Journal of paediatrics and child health, 28(6), 467-467 (1992-12-01)
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
Arpad Szallasi et al.
Expert opinion on investigational drugs, 21(9), 1351-1369 (2012-07-12)
With 336 reviews, the capsaicin receptor TRPV1 arguably represent today's most extensively reviewed analgesic target. TRPV1 is strategically located at the peripheral terminals of primary sensory neurons where pain is generated. TRPV1 as a target for analgesic drugs has been
G Appendino et al.
Life sciences, 60(10), 681-696 (1997-01-01)
Resiniferatoxin, an ultrapotent capsaicin analog present in the latex of Euphorbia resinifera, interacts at a specific membrane recognition site (referred to as the vanilloid receptor), expressed by primary sensory neurons mediating pain perception as well as neurogenic inflammation. Desensitization to
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