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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A Marriage of Convenience: Combining the Power of Isocyanide‐Based Multicomponent Reactions with the Versatility of (Hetero)norbornene Chemistry
TL;DR: The bicyclo[2.2.1]heptene (norbornene) moiety has been demonstrated to be a very versatile scaffold when employed to broaden the scope of the multicomponent approach, making it perfectly suited for diversity-oriented synthesis.
Journal ArticleDOI
Epibatidine: A Promising Natural Alkaloid in Health
Bahare Salehi,Simona Sestito,Simona Rapposelli,Gregorio Peron,Daniela Calina,Mehdi Sharifi-Rad,Farukh Sharopov,Natália Martins,Javad Sharifi-Rad +8 more
TL;DR: The affinity of epibatidine and its synthetic derivatives, analogues to nAChRs for α4β2 subtype, pharmacokinetic parameters, and its role in health are discussed.
Journal ArticleDOI
The promise and pitfalls of a nicotinic cholinergic approach to pain management.
TL;DR: The collective studies performed to date indicate that a multitude of nicotinic receptor agonists, constituting disparate pharmacological pro®les, are antinociceptive in several species, including man (Table 1).
Journal ArticleDOI
Desymmetrization of cyclic olefins via asymmetric Heck reaction and hydroarylation
Sijia Liu,Jianrong Zhou +1 more
TL;DR: An asymmetric Heck reaction allows desymmetrization of substituted cyclic olefins in high dr and ee through bisphosphine oxide, which is uniquely stereoselective for this purpose.
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Synthesis and evaluation of N-[11C]methylated analogues of epibatidine as tracers for positron emission tomographic studies of nicotinic acetylcholine receptors.
Andrew G. Horti,Ursula Scheffel,Alane S. Kimes,John L. Musachio,Hayden T. Ravert,William B. Mathews,Yougen Zhan,Paige Finley,Edythe D. London,Robert F. Dannals +9 more
TL;DR: Four halogen-substituted analogues of N-methylepibatidine, a nicotinic acetylcholine receptor (nAChR) ligand, and the acute toxicity of the corresponding authentic nonlabeled compounds appeared to be related to their lipophilicity.