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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α9-nicotinic acetylcholine receptors contribute to the maintenance of chronic mechanical hyperalgesia, but not thermal or mechanical allodynia
TL;DR: The α9-nAChR appears to be a valid target for pharmacological compounds that alleviate long-term mechanical hyperalgesia and may be of use as a prophylactic drug to prevent the development of some symptoms of chronic pain.
Pathophysiology and Clinical Implications
TL;DR: This review will cover the relevant pharmacology of nicotine and other ligands at the nicotinic acetylcholine receptor as related to pain, explore the association of cigarette smoking with chronic painful conditions and potential mechanisms to explain this association, and examine clinical implications for the care of smokers with pain.
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A Simplified Method for the Preparation of Ethynyl P-Tolyl Sulfone and Ethynyl Phenyl Sulfone
Zhengming Chen,Mark L. Trudell +1 more
TL;DR: Silica gel mediated desilylation of aryl 2-(trimethylsilyl)ethynyl sulfones was found to greatly simplify the synthesis of the acetylenic sulfones.
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A unified asymmetric approach to substituted hexahydroazepine and 7-azabicyclo[2.2.1]heptane ring systems from D(−)-quinic acid: Application to the formal synthesis of (−)-balanol and (−)-epibatidine
E. Albertini,Achille Barco,Simonetta Benetti,Carmela De Risi,Gian Piero Pollini,Vinicio Zanirato +5 more
TL;DR: In this paper, a chiron was used as the starting building block for enantioselective syntheses of (3R,4S)-N-p-toluenesulfonyl-3,4-epoxy-hexahydroazepine 17 and (1R, 4S)-n-tert-butoxycarbonyl 7-azabicyclo[2.2.1]heptane nucleus of 43.
Journal ArticleDOI
Synthesis of epibatidine isomers: Reductive Heck coupling of 2-azabicyclo[2.2.1]hept-5-ene derivatives
Caroline D. Cox,John R. Malpass +1 more
TL;DR: The coupling of N -protected 2-azabicyclo[2.2.1]heptanes and 2-chloro-5-iodopyridine under reductive Heck conditions gives approximately equal amounts of exo -5- and exo-6- (6′-loro-3′-pyridyl)-2-aza-cyclo[1.2]-heptane isomers.