Journal ArticleDOI
Epibatidine: a novel (chloropyridyl)azabicycloheptane with potent analgesic activity from an ecuadoran poison frog
Thomas F. Spande,H. M. Garraffo,M. W. Edwards,Herman J. C. Yeh,Lewis K. Pannell,John W. Daly +5 more
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TLDR
A potent non-opioid analgesic, epibatidine, has been isolated from skins of the Ecuadoran poison frog, Epipedobates tricolor, and its structure determined by MS, IR, and 1 H NMR analyses as exo-2-(6-chloro-3-pyridyl)-7-azabicyclo[2.2.1]heptane represents a unique new class of alkaloids.Abstract:
A potent non-opioid analgesic, epibatidine, has been isolated from skins of the Ecuadoran poison frog, Epipedobates tricolor, and its structure determined by MS, IR, and 1 H NMR analyses as exo-2-(6-chloro-3-pyridyl)-7-azabicyclo[2.2.1]heptane. It represents a unique new class of alkaloidsread more
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Journal ArticleDOI
Medicinal Chemical Studies of Anti-Inflammatory and Analgesic Natural Products
TL;DR: The highly potent analgesic alkaloid epibatidine from the frog skin has been synthesized and recharacterized as a very strong acetylcholine nicotinic receptor agonist.
Journal ArticleDOI
The 7-azanorbornane nucleus of epibatidine: 7-azabicyclo[2.2.1]heptan-7-ium chloride
TL;DR: 7-Azabicyclo[2.2.1]heptane (7-azanorbornane) is a bridged heterocyclic nucleus found in epibatidine and the structural characterization of the parent ring as its hydrochloride salt has been carried out.
DissertationDOI
Structure-Function Studies of Nicotinic Acetylcholine Receptors Using Unnatural Amino Acids and Synthetic Agonist Analogs
TL;DR: This thesis describes structure-function studies of the prototypical Cys-loop ligand-gated ion channel, the nicotinic acetylcholine receptors (nAChRs), and identifies a speculative role for the vicinal disulfide that involves the formation of a functionally important network of hydrogen bonds.