Resiniferatoxin

Resiniferatoxin
File:Resiniferatoxin.svg
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number	57444-62-9
PubChem	104826
MeSH	resiniferatoxin
style="background: #F8EABA; text-align: center;" colspan="2" | Properties
Molecular formula	C37H40O9
Molar mass	628.71 g/mol
Density	1.35 ± 0.1 g/cm³
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Resiniferatoxin (RTX) is a naturally occurring, ultrapotent capsaicin analog that activates the vanilloid receptor in a subpopulation of primary afferent sensory neurons involved in nociception (the transmission of physiological pain). RTX causes a novel 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.

Research is being conducted at the National Institutes of Health and the University of Pennsylvania to design a novel class of analgesics from the latex of resin spurge (Euphorbia resinifera), a cactus-like plant commonly found in Morocco that contains high concentrations of RTX.

Total synthesis

A total synthesis of (+)-resiniferatoxin was completed by the Wender group at Stanford University in 1997. As of 2007 this represented the only complete total synthesis of any member of the daphnane family of molecules.

Toxicity

Resiniferatoxin is toxic and can produce chemical burns. Animal experiments indicate that ingestion of less than 40 g may be fatal or cause serious damage to health.

See also

• Capsaicin
• Discovery and development of TRPV1 antagonists
• Iodoresiniferatoxin
• Transient receptor potential
• Tinyatoxin

External links

• Fiery pepper may hold key to easing painfr:Résiniferatoxine

*Christopher S. J. Walpole; et al. (1996). "Similarities and Differences in the Structure-Activity Relationships of Capsaicin and Resiniferatoxin Analogues". J. Med. Chem. 39 (15): 2939–2952. doi:10.1021/jm960139d. PMID 8709128. CS1 maint: Explicit use of et al. (link)

Szallasi A, Blumberg PM (1989). "Resiniferatoxin, a phorbol-related diterpene, acts as an ultrapotent analog of capsaicin, the irritant constituent in red pepper". Neuroscience. 30 (2): 515–20. doi:10.1016/0306-4522(89)90269-8. 

Szallasi A, Blumberg PM (1990). "Resiniferatoxin and its analogs provide novel insights into the pharmacology of the vanilloid (capsaicin) receptor". Life Sci. 47 (16): 1399–408. doi:10.1016/0024-3205(90)90518-V. 

Szallasi A, Blumberg PM (1992). "Vanilloid receptor loss in rat sensory ganglia associated with long term desensitization to resiniferatoxin". Neurosci Lett. 140 (1): 51–4. doi:10.1016/0304-3940(92)90679-2. 

Olah Z; et al. (2001). "Ligand-induced dynamic membrane changes and cell deletion conferred by vanilloid receptor 1". J. Biol. Chem. 276 (14): 11021–30. doi:10.1074/jbc.M008392200. PMID 11124944. CS1 maint: Explicit use of et al. (link)

Neubert JK; et al. (2003). "Peripherally induced resiniferatoxin analgesia". Pain. 104 (1-2): 219–28. doi:10.1016/S0304-3959(03)00009-5. CS1 maint: Explicit use of et al. (link)

Karai L; et al. (2004). "Deletion of vanilloid receptor 1-expressing primary afferent neurons for pain control". J Clin Invest. 113 (9): 1344–52. doi:10.1172/JCI20449. PMC 398431 Freely accessible. PMID 15124026. CS1 maint: Explicit use of et al. (link)

Brown DC; et al. (2005). "Physiologic and antinociceptive effects of intrathecal resiniferatoxin in a canine bone cancer model". Anesthesiology. 103 (5): 1052–9. doi:10.1097/00000542-200511000-00020. CS1 maint: Explicit use of et al. (link)

Wender, P.A.; Jesudason, Cynthia D.; Nakahira, Hiroyuki; Tamura, Norikazu; Tebbe, Anne Louise; Ueno, Yoshihide (1997). "The First Synthesis of a Daphnane Diterpene: The Enantiocontrolled Total Synthesis of (+)-Resiniferatoxin". J. Am. Chem. Soc. 119: 12976–12977. doi:10.1021/ja972279y. 

http://www.scripps.edu/chem/baran/images/grpmtgpdf/Seiple_Mar_07.pdf

Material Safety Data Sheet for resiniferatoxin, 2009