Resiniferatoxin
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| Names | |
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| IUPAC name
[(1R,6R,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
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| Identifiers | |
57444-62-9  |
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| ChEMBL | ChEMBL448382 |
| ChemSpider | 21106474  |
| 2491 | |
| Jmol 3D model | Interactive image |
| MeSH | resiniferatoxin |
| PubChem | 104826 |
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| Properties | |
| C37H40O9 | |
| Molar mass | 628.71 g/mol |
| Density | 1.35 ± 0.1 g/cm³ |
| insoluble | |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| Infobox references | |
| Resiniferatoxin | |
|---|---|
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| Heat | Above peak |
| Scoville scale | 16,000,000,000 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 an ultrapotent analog of capsaicin, the active ingredient in chili pepper.[2]
Overview
It activates the vanilloid receptor in a subpopulation of primary afferent sensory neurons involved in nociception (the transmission of physiological pain).[3][4] RTX causes an ion channel in the plasma membrane of sensory neurons — the transient receptor potential vanilloid 1 — to become permeable to cations, most particularly the calcium cation; this evokes a powerful irritant effect followed by desensitization and analgesia.[5][6]
Total synthesis
A total synthesis of (+)-resiniferatoxin was completed by the Wender group at Stanford University in 1997.[7] As of 2007[update], this represented the only complete total synthesis of any member of the daphnane family of molecules.[8]
Toxicity
Resiniferatoxin is toxic and can inflict chemical burns. Animal experiments suggest that, in humans, ingestion of as little as 10 g may be fatal or cause serious damage to health.[9] Using the Scoville scale, resiniferatoxin is estimated to have a rating of 16 billion,[10] one thousand times higher than the rating for pure capsaicin.
See also
- Discovery and development of TRPV1 antagonists
- Iodoresiniferatoxin
- Transient receptor potential
- Tinyatoxin
References
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- ↑ Euphorbia poissonii in BoDD – Botanical Dermatology Database
- ↑ *Lua error in package.lua at line 80: module 'strict' not found.
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- ↑ http://www.scripps.edu/chem/baran/images/grpmtgpdf/Seiple_Mar_07.pdf
- ↑ Material Safety Data Sheet for resiniferatoxin, 2009
- ↑ 100 Questions & Answers About Overactive Bladder and Urinary Incontinence, Pamela Ellsworth and David A. Gordon, Jones and Bartlett Publishers via Google Books
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- Neurotoxins
- Plant toxins
- Analgesics
- Total synthesis
- Terpenes and terpenoids
- Carboxylate esters
- Orthoesters
