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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Synthesis of epibatidine
TL;DR: In this paper, a total synthesis of racemic epibatidine, a natural product with analgesic activity, was described, which starts from simple, known precursors, to provide the alkaloid in six steps.
Journal ArticleDOI
Synthesis of optically pure epibatidine analogs: (1R, 2R, 5S)-2β-(2-chloro-5-pyridinyl)-8-azabicyclo[3.2.1]octane and (1R, 2S, 5S)-2α-(2-chloro-5-pyridinyl)-8-azabicyclo[3.2.1]octane from (−)-cocaine
TL;DR: Two optically pure epibatidine analogs, 4 and 5, which contain the 8-azabicyclo[3.2.1] octane ring system were synthesized from (−)-cocaine as discussed by the authors.
Journal ArticleDOI
Conformationally Constrained Nicotines. 1-Pyridinyl-7-azabicyclo[2.2.1]heptane and 1-Pyridinyl-8-azabicyclo[3.2.1]octane Analogues
TL;DR: In this article, 3-lithiopyridine was added to the γ-carbonyl of a protected glutamate, followed by intramolecular imine formation and stereospecific catalytic hydrogenation of the resultant pyrroline to give cis-5-pyridinylproline.
Journal ArticleDOI
Discovery of (-)-7-methyl-2-exo-[3'-(6-[18F]fluoropyridin-2-yl)-5'-pyridinyl]-7-azabicyclo[2.2.1]heptane, a radiolabeled antagonist for cerebral nicotinic acetylcholine receptor (alpha4beta2-nAChR) with optimal positron emission tomography imaging properties.
Yongjun Gao,Hiroto Kuwabara,Charles E. Spivak,Yingxian Xiao,Kenneth J. Kellar,Hayden T. Ravert,Anil Kumar,Mohab Alexander,John Hilton,Dean F. Wong,Robert F. Dannals,Andrew G. Horti +11 more
TL;DR: The combination of imaging properties suggests that [(18)F]-(-)- 6c is a potentially superior replacement for 2-[(18]F]fluoro-A-85380 and 6-[( 18)F?]fluoro -A- 85380, the only available nAChR PET radioligands for humans.
Journal ArticleDOI
Neurochemical pathways involved in the protective effects of nicotine and ethanol in preventing the development of Parkinson's disease: potential targets for the development of new therapeutic agents.
TL;DR: In this short review, neurochemical targets are identified where nicotine, and possibly ethanol, may interact to prevent the occurrence of Parkinson's disease.