Resiniferatoxin

For other uses, see RTX.

Resiniferatoxin
Names
IUPAC name
[(1R,2R,6R,10S,11R,13R,15R,17R)-13-Benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl 2-(4-hydroxy-3-methoxyphenyl)acetate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
MeSH resiniferatoxin
UNII
  • 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 ☒N
    Key: DSDNAKHZNJAGHN-MXTYGGKSSA-N checkY
  • C[C@@H]1C[C@]2([C@H]3[C@H]4[C@]1([C@@H]5C=C(C(=O)[C@]5(CC(=C4)COC(=O)Cc6ccc(c(c6)OC)O)O)C)O[C@](O3)(O2)Cc7ccccc7)C(=C)C
Properties
C37H40O9
Molar mass 628.718 g·mol−1
Density 1.35 ± 0.1 g/cm3
insoluble in water and hexane, soluble in ethyl acetate, ethanol, methanol, acetone, chloroform, and dichloromethane.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Resiniferatoxin
HeatAbove peak (highly toxic from pungency as defined by TRPV1 activation)
Scoville scale16,000,000,000 SHU

Resiniferatoxin (RTX) is a naturally occurring chemical found in resin spurge (Euphorbia resinifera), a cactus-like plant commonly found in Morocco, and in Euphorbia poissonii found in northern Nigeria.[1] It is a potent functional analog of capsaicin, the active ingredient in chili peppers.[2]

  1. ^ Euphorbia poissonii in BoDD – Botanical Dermatology Database
  2. ^ Walpole CS, Bevan S, Bloomfield G, Breckenridge R, James IF, Ritchie T, et al. (July 1996). "Similarities and differences in the structure-activity relationships of capsaicin and resiniferatoxin analogues". Journal of Medicinal Chemistry. 39 (15): 2939–2952. doi:10.1021/jm960139d. PMID 8709128.