Synthesis and nicotinic receptor activity of a hydroxylated tropane

Bioorg Med Chem Lett. 2004 Jan 5;14(1):271-3. doi: 10.1016/j.bmcl.2003.09.081.

Abstract

(+/-)-3alpha-hydroxy homoepibatidine 4 has been synthesized from the alkaloid scopolamine 5 and its properties as a nicotinic agonist assessed. While still binding strongly, the compound showed reduced agonist potency for the alpha(4)beta(2) nAChR compared with the parent compound epibatidine 1. Compound 4 also displayed generally similar binding and selectivity profiles at alpha(4)beta(2), alpha(2)beta(4), alpha(3)beta(4), and alpha(4)beta(4) nAChR subtypes to those for nicotine.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Humans
  • Hydroxylation / drug effects
  • Nicotinic Agonists / chemistry*
  • Nicotinic Agonists / metabolism*
  • Nicotinic Agonists / pharmacology
  • Protein Binding / drug effects
  • Protein Binding / physiology
  • Rats
  • Receptors, Nicotinic / metabolism*
  • Tropanes / chemistry*
  • Tropanes / metabolism*
  • Tropanes / pharmacology

Substances

  • Nicotinic Agonists
  • Receptors, Nicotinic
  • Tropanes