Structure via PubChem · Public domain (PubChem)
resiniferatoxin
Sign in to saveAlso known as RTX, (+)-resiniferatoxin
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. It is a potent functional analog of capsaicin, the active ingredient in chili peppers.
Key facts
- Pepper.heat
- Highly toxic and caustic non-capsaicinoid TRPV1 agonist - considered " above peak"
- Pepper.scoville
- 16,000,000,000
via Wikipedia infobox
Chemical data
- Formula
- C37H40O9
- Molecular weight
- 628.7 g/mol
- IUPAC name
- [(1R,2R,6R,10S,11R,13S,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
- SMILES
- 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)CC6=CC(=C(C=C6)O)OC)O)C)O[C@](O3)(O2)CC7=CC=CC=C7)C(=C)C
- InChIKey
- DSDNAKHZNJAGHN-MXTYGGKSSA-N
- XLogP
- 4.5
- Polar surface area
- 121 Ų
- H-bond donors
- 2
- H-bond acceptors
- 9
- Formal charge
- 0
via PubChem
Wikidata facts
- Has part
- hydrogen
- Mass
- 628.2672328599998
Show 9 more facts
- found in taxon
- Euphorbia poissonii
- chemical formula
- C₃₇H₄₀O₉
- Scoville grade
- 15000000000
- Commons category
- Resiniferatoxin
- isomeric SMILES
- 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
- density
- 1.35
- flash point
- 240.3
- refractive index
- 1.643
- canonical SMILES
- O=C(OCC1=CC2C3OC4(OC3(C(=C)C)CC(C)C2(O4)C5C=C(C(=O)C5(O)C1)C)CC=6C=CC=CC6)CC7=CC=C(O)C(OC)=C7
Sources (7)
via Wikidata · CC0
~5 min read
Encyclopedic overview
7 sectionsContents
- Biological activity
- Total synthesis
- Toxicity
- Research
- See also
- References
- External links
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. It is a potent functional analog of capsaicin, the active ingredient in chili peppers.
==Biological activity== Resiniferatoxin has a score of 16 billion Scoville heat units, making pure resiniferatoxin about 500 to 1000 times hotter than pure capsaicin. Resiniferatoxin activates transient vanilloid receptor 1 (TRPV1) in a subpopulation of primary afferent sensory neurons involved in nociception, the transmission of physiological pain. TRPV1 is an ion channel in the plasma membrane of sensory neurons and stimulation by resiniferatoxin causes this ion channel to become permeable to cations, especially calcium. The influx of cations causes the neuron to depolarize, transmitting signals similar to those that would be transmitted if the innervated tissue were being burned or damaged. This stimulation is followed by desensitization and analgesia, in part because the nerve endings die from calcium overload.
Excerpted from Wikipedia’s “resiniferatoxin” article, available under the CC BY-SA 4.0 licence.