Epibatidine

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Template:Chembox E number
Epibatidine
IUPAC name (4S,6R)-6-(6-chloro-3-pyridyl)-7-azabicyclo[2.2.1]heptane
Identifiers
3D model (JSmol)
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MeSH Epibatidine
Properties
C11H13ClN2
Molar mass 208.687
Melting point
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]

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.

External links


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