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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Identification and initial structure-activity relationships of (R)-5-(2-azetidinylmethoxy)-2-chloropyridine (ABT-594), a potent, orally active, non-opiate analgesic agent acting via neuronal nicotinic acetylcholine receptors.
Mark W. Holladay,James T. Wasicak,Nan-Horng Lin,Yun He,Keith B. Ryther,Anthony W. Bannon,Michael J. Buckley,David J.B. Kim,Michael W. Decker,David J. Anderson,Jeffrey E. Campbell,Theresa A. Kuntzweiler,Diana L. Donnelly-Roberts,Marietta Piattoni-Kaplan,Clark A. Briggs,Michael Williams,Stephen P. Arneric +16 more
TL;DR: Structural-activity studies of analogues related to 3-pyridyl ether compounds suggest that the N-unsubstituted azetidine moiety and the 2-chloro substituent on the pyridine ring are important contributors to potent analgesic activity.
Journal ArticleDOI
A total synthesis of (±)-epibatidine
Simon C. Clayton,Andrew C. Regan +1 more
TL;DR: In this paper, a total synthesis of the potent non-opiate analgesic alkaloid epibatidine is described, in which the key step is a reductive palladium-catalysed Heck-type coupling.
Journal ArticleDOI
Synthesis and nicotinic acetylcholine receptor in vivo binding properties of 2-fluoro-3-[2(S)-2-azetidinylmethoxy]pyridine: a new positron emission tomography ligand for nicotinic receptors.
Doll F,Dolci L,H. Valette,Hinnen F,Vaufrey F,Ilonka Guenther,C. Fuseau,Christine Coulon,Michel Bottlaender,C. Crouzel +9 more
TL;DR: The lead compound of a new series of 3-pyridyl ethers, the azetidine derivative A-85380, is a potent and selective ligand for the human alpha4beta2 nicotinic acetylcholine receptor (nAChR) subtype and appears to be a suitable radioligand for brain imaging nAChRs with PET.
Journal ArticleDOI
Using Physical Chemistry To Differentiate Nicotinic from Cholinergic Agonists at the Nicotinic Acetylcholine Receptor
TL;DR: The binding of three distinct agonists-ACh, nicotine, and epibatidine-to the nicotinic acetylcholine receptor has been probed using unnatural amino acid mutagenesis to illustrate the subtleties and complexities of the interactions between drugs and membrane receptors and establish a paradigm for obtaining detailed structural information.