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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LC-MS Supported Studies on the in Vitro Metabolism of both Enantiomers of Flubatine and the in Vivo Metabolism of (+)-[18F]Flubatine—A Positron Emission Tomography Radioligand for Imaging α4β2 Nicotinic Acetylcholine Receptors
Friedrich-Alexander Ludwig,René Smits,Steffen Fischer,Cornelius K. Donat,Alexander Hoepping,Peter Brust,Jörg Steinbach +6 more
TL;DR: Both enantiomers of [18F]flubatine are promising radioligands for neuroimaging of α4β2 nicotinic acetylcholine receptors by positron emission tomography by PET and a detailed examination of the metabolism in vitro and in vivo has been performed.
Journal ArticleDOI
Metal‐Catalyzed Reactions between 2‐Azabicyclo[2.2.1]hept‐5‐en‐3‐ones and Arylboronic Acids
TL;DR: In this paper, the coupling reactions of 2-azabicyclo[221]hept-5-en-3-ones with arylboronic acids were successful carried out under microwave irradiation conditions and yielded N-aryl and C-aryl derivatives of 1, respectively.
Journal ArticleDOI
Determination of the in vitro metabolism of (+)- and (−)-epibatidine
TL;DR: Comparison of the metabolism of the (+)- and (-)-enantiomers revealed species differences in the extent of metabolism, and chiral analysis from a metabolic time course of racemic material revealed enantiomers to be metabolised to approximately the same extent.
Journal ArticleDOI
Transcriptomic Signatures of Experimental Alkaloid Consumption in a Poison Frog.
Eugenia Sanchez,Eugenia Sanchez,Ariel Rodríguez,José Horacio Grau,Stefan Lötters,Sven Künzel,Ralph A. Saporito,Eva Ringler,Eva Ringler,Stefan Schulz,Katharina C. Wollenberg Valero,Miguel Vences +11 more
TL;DR: An exploratory skin gene expression experiment in which captive-bred dendrobatids were fed alkaloids and found a consistent pattern of up-regulation of genes related to muscle and mitochondrial processes, probably due to the lack of mutations related to alkaloid resistance in these species.
Journal ArticleDOI
Comparison of N-[11C]methyl-norchloroepibatidine and N-[11C]methyl-2-(2-pyridyl)-7-azabicyclo[2.2.1]heptane with N-[11C]methyl-epibatidine in small animal PET studies
TL;DR: Structural variations of the nicotinic acetylcholine receptor radioligand N-[(11)C]methyl-epibatidine were made to form N-methyl-norchloroepib atidine and N- methyl-NorchloroEPB and the modified pyridine ring had a significantly lower uptake.