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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Total synthesis of (-)-epibatidine using an asymmetric diels-alder reaction with a chiral n-acylnitroso dienophile
TL;DR: An asymmetric total synthesis of (−)-epibatidine (1), isolated from the skin of the Ecuadorian poison frog, Epipedobates tricolor, of the family Dendrobatidae, has been achieved by virtue of the development of asymmetric hetero Diels−Alder (D−A) cycloaddition with an N-acylnitroso dienophile bearing the optically active 8-arylmenthol as a chiral source.
Journal ArticleDOI
Epibatidine binding sites and activity in the spinal cord.
TL;DR: The NMDA receptor antagonist, AP-5, inhibited the pressor, tachycardic and irritation responses elicited by intrathecal (-)-epibatidine, confirming a role for spinal excitatory amino acids released by the nicotinic agonist.
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Positive and negative effects of alcohol and nicotine and their interactions: a mechanistic review
TL;DR: The negative impact of drinking–smoking co-morbidity followed by factors that appear to contribute to the high rate of co-use of alcohol and nicotine are reviewed.
Journal ArticleDOI
Synthesis and nicotinic acetylcholine receptor binding properties of exo-2-(2'-fluoro-5'-pyridinyl)-7-azabicyclo-[2.2.1]heptane: a new positron emission tomography ligand for nicotinic receptors.
F. Liang,Hernán A. Navarro,Philip Abraham,Pravin Kotian,Y.‐S. Ding,J. Fowler,N. Volkow,Michael J. Kuhar,Frank I. Carroll +8 more
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Bioassay-guided isolation of epiquinamide, a novel quinolizidine alkaloid and nicotinic agonist from an Ecuadoran poison frog, Epipedobates tricolor.
TL;DR: Analytical HPLC fractionation, combined with an off-line 96-well fluorescent bioassay screen, has been developed and used for the separation and screening of a natural product extract and was found to be very sensitive for the detection of compounds active at nicotinic receptors.