publication . Article . 1997

Synthesis and nicotinic activity of epiboxidine: an isoxazole analogue of epibatidine

John W. Daly; Barbara Badio; H. Martin Garraffo; Carlton V Plummer; William L. Padgett;
Open Access
  • Published: 01 Feb 1997
Abstract Synthetic (±)-epiboxidine (exo-2-(3-methyl-5-isoxazolyl)-7-azabicyclo[2.2.1]heptane) is a methylisoxazole analog of the alkaloid epibatidine, itself a potent nicotinic receptor agonist with antinociceptive activity. Epiboxidine contains a methylisoxazolyl ring replacing the chloropyridinyl ring of epibatidine. Thus, it is also an analog of another nicotinic receptor agonist, ABT 418 (( S )-3-methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole), in which the pyridinyl ring of nicotine has been replaced by the methylisoxazolyl ring. Epiboxidine was about 10-fold less potent than epibatidine and about 17-fold more potent than ABT 418 in inhibiting [ 3 H]nicotine b...
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free text keywords: Pharmacology, Stereochemistry, Nicotinic agonist, Nicotine, medicine.drug, medicine, Chemistry, Acetylcholine receptor, Epiboxidine, chemistry.chemical_compound, Isoxazole, Alkaloid, ABT-418, Epibatidine
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