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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Unique spirocyclopiperazinium salt III: further investigation of monospirocyclopiperazinium (MSPZ) salts as potential analgesics.
TL;DR: Two novel classes of monospirocyclopiperazinium salts were designed, synthesized, and evaluated for their in vivo analgesic activities and 3d exhibited the most potent activity with low toxicity.
Journal ArticleDOI
6′-Methylpyrido[3,4- b ]norhomotropane: synthesis and outstanding potency in relation to the α4β2 nicotinic receptor pharmacophore model
TL;DR: In this pharmacophore model, the 6-methyl substituent may be equivalent to the acetyl methyl of acetylcholine as discussed by the authors, which is the equivalent of the (1R)-pyridonorhomotropane with natural (1 R)-epibatidine.
Journal ArticleDOI
Does batrachotoxin autoresistance coevolve with toxicity in Phyllobates poison-dart frogs?
TL;DR: Reconstructions suggest that BTX resistance arose at the root of Phyllobates, coinciding with the evolution of BTX secretion, but little or no further evolution of autoresistance seems to have occurred, despite large increases in toxicity throughout the history of these frogs.
Journal ArticleDOI
The regioselectivity of the addition of benzeneselenyl chloride to 7-azanorborn-5-ene-2-yl derivatives is controlled by the 2-substituent: new entry into 3-and 4-hydroxy-5-substituted prolines
Agostina A. Ruggiu,Robert Łysek,Elena Moreno-Clavijo,Antonio J. Moreno-Vargas,Inmaculada Robina,Pierre Vogel +5 more
TL;DR: The electrophilic addition of benzeneselenyl chloride to the alkene moiety of 7-azabicyclo[2.2.1]hept-5en-2-yl derivatives has been studied in this paper.