My watch list
my.bionity.com  
Login  

Epibatidine



Epibatidine
IUPAC name (4S,6R)-6-(6-chloro-3-pyridyl)-7-azabicyclo[2.2.1]heptane
Identifiers
CAS number 140111-52-0
PubChem 105084
MeSH Epibatidine
SMILES C1CC2C(CC1N2)C3=CN=C(C=C3)Cl
Properties
Molecular formula C11H13ClN2
Molar mass 208.687
Melting point

59-66 °C

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Epibatidine is an alkaloid that originally is found in the skin of a neotropical poisonous frog, Epipedobates tricolor, found in modern Ecuador. It was initially isolated by John Daly at the National Institutes of Health, and was found to be a powerful analgesic, about 200 times more potent than morphine.[1] Because the natural source of epibatidine can only supply a small quantity, several laboratory syntheses have been developed.[2]

Additional recommended knowledge

Interestingly, the compound is not an opioid; instead, it is similar to nicotine and appears to act by binding and activating nicotinic acetylcholine receptors. While epibatidine may be too toxic to use in clinical practice, the compound represents a new lead in the drug design of new analgesics.[3]

References

  1. ^ *Epibatidine - A review by Matthew J. Dowd
  2. ^ Olivo, Horacio F.; Hemenway, Michael S. Recent syntheses of epibatidine. A review. Organic Preparations and Procedures International (2002), 34(1), 1-26.
  3. ^ Carroll, F. Ivy. Epibatidine structure-activity relationships. Bioorganic & Medicinal Chemistry Letters (2004), 14(8), 1889-1896.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Epibatidine". A list of authors is available in Wikipedia.
Your browser is not current. Microsoft Internet Explorer 6.0 does not support some functions on Chemie.DE