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Epibatidine: a novel (chloropyridyl)azabicycloheptane with potent analgesic activity from an ecuadoran poison frog

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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 alkaloids

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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

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.
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