Resiniferatoxin

Chembox new
Name = Resiniferatoxin
ImageFile = Resiniferatoxin.svg
ImageName =
IUPACName =
Section1 = Chembox Identifiers
CASNo = 57444-62-9
PubChem = 104826
MeSHName = resiniferatoxin
Section2 = Chembox Properties
Formula = C₃₇H₄₀O₉
MolarMass = 628.71 g/mol
Density = 1.35 ± 0.1 g/cm³

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). [cite journal | author = Szallasi A, Blumberg PM | year = 1989 | title = Resiniferatoxin, a phorbol-related diterpene, acts as an ultrapotent analog of capsaicin, the irritant constituent in red pepper | journal = Neuroscience | volume = 30 | issue = 2 | pages = 515–20 | doi = 10.1016/0306-4522(89)90269-8] [cite journal | author = Szallasi A, Blumberg PM | year = 1990 | title = Resiniferatoxin and its analogs provide novel insights into the pharmacology of the vanilloid (capsaicin) receptor | journal = Life Sci. | volume = 47 | issue = 16 | pages = 1399–408 | doi = 10.1016/0024-3205(90)90518-V] 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. [cite journal | author = Szallasi A, Blumberg PM | year = 1992 | title = Vanilloid receptor loss in rat sensory ganglia associated with long term desensitization to resiniferatoxin | journal = Neurosci Lett. | volume = 140 | issue = 1 | pages = 51–4 | doi = 10.1016/0304-3940(92)90679-2] [cite journal | author = Olah Z "et al." | year = 2001 | title = Ligand-induced dynamic membrane changes and cell deletion conferred by vanilloid receptor 1 | journal = J. Biol. Chem. | volume = 276 | issue = 14 | pages = 11021–30 | doi = 10.1074/jbc.M008392200 | pmid = 11124944]

Research is being conducted at the National Institutes of Health [cite journal | author = Neubert JK "et al." | year = 2003 | title = Peripherally induced resiniferatoxin analgesia | journal = Pain | volume = 104 | issue = 1-2 | pages = 219–28 | doi = 10.1016/S0304-3959(03)00009-5] [cite journal | author = Karai L "et al." | year = 2004 | title = Deletion of vanilloid receptor 1-expressing primary afferent neurons for pain control | journal = J Clin Invest. | volume = 113 | issue = 9 | pages = 1344–52] and the University of Pennsylvania [cite journal | author = Brown DC "et al." | year = 2005 | title = Physiologic and antinociceptive effects of intrathecal resiniferatoxin in a canine bone cancer model | journal = Anesthesiology | volume = 103 | issue =5 | pages = 1052–9 | doi = 10.1097/00000542-200511000-00020] 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.

A total synthesis of (+)-resiniferatoxin was completed by the Wender group at Stanford University in 1997. [cite journal | journal = J. Am. Chem. Soc. | year = 1997 | volume = 119 | pages = 12976–12977 | doi = 10.1021/ja972279y | title = The First Synthesis of a Daphnane Diterpene: The Enantiocontrolled Total Synthesis of (+)-Resiniferatoxin | author = Wender, P.A.] As of 2007, this represents the only complete total synthesis of any member of the daphnane family of molecules. [http://www.scripps.edu/chem/baran/images/grpmtgpdf/Seiple_Mar_07.pdf]

ee also

* Capsaicin
* Transient receptor potential

References

*cite journal | author=Christopher S. J. Walpole, et al | title=Similarities and Differences in the Structure-Activity Relationships of Capsaicin and Resiniferatoxin Analogues | journal=J. Med. Chem. | year=1996 | volume=39 | pages=2939–2952 | doi=10.1021/jm960139d

External links

* [http://seattlepi.nwsource.com/health/255908_pain17.html Fiery pepper may hold key to easing pain]