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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Application of the aza-Diels-Alder reaction in the synthesis of natural products.
TL;DR: The development of asymmetric, in particular catalytic enantioselective intramolecular aza-Diels-Alder reaction in the total synthesis of natural products remains highly challenging, and will no doubt see enormous advances in the future.
Journal ArticleDOI
Nicotine differentially activates inhibitory and excitatory neurons in the dorsal spinal cord
TL;DR: Two neuronal populations in the dorsal horn of the spinal cord are distinguished: GABAergic/glycinergic inhibitory interneurons, and calbindin (CA) or NK1 receptor (NK1‐R) expressing, excitatory interneerons and projection neurons.
Journal ArticleDOI
A rhodium IBiox[(-)-menthyl] complex as a highly selective catalyst for the asymmetric hydroarylation of azabicyles: an alternative route to epibatidine
Jason Bexrud,Mark Lautens +1 more
TL;DR: The synthesis and characterization of a new chiral rhodium N-heterocyclic carbene complex, Rh(IBiox[(-)-menthyl](CO)(2)Cl, is reported and the very high enantioselectivity exhibited by this complex, as a catalyst for the asymmetric hydroarylation of azabicycles, is demonstrated and applied to the synthesis of epibatidine.
Journal ArticleDOI
Synthesis of (+/-)-Epibatidine and Its Analogues.
TL;DR: A nonopiate analgesic, epibatidine, isolated from the skin of the Ecuadoran poison frog was synthesized in racemic form starting from tropinone, featuring the novel synthesis of the 7-azabicyclo-heptane ring system by contraction of the Tropinone skeleton via Favorskii rearrangement.
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ABT-594 [(R)-5-(2-azetidinylmethoxy)-2-chloropyridine]: a novel, orally effective antinociceptive agent acting via neuronal nicotinic acetylcholine receptors: II. In vivo characterization.
Anthony W. Bannon,Michael W. Decker,Peter Curzon,Michael J. Buckley,David J.B. Kim,Richard J. Radek,Lynch John K,James T. Wasicak,Nan-Horng Lin,William H. Arnold,Mark W. Holladay,Michael Williams,Stephen P. Arneric +12 more
TL;DR: It is demonstrated that ABT-594 is a potent antinociceptive agent with full efficacy in models of acute and persistent pain and that these effects are mediated predominately by an action at central neuronal nAChRs.