3,7-Diazabicyclane: a new narcotic analgesic

J Med Chem. 1986 Oct;29(10):2111-3. doi: 10.1021/jm00160a054.

Abstract

The synthesis of a series of 9-phenyl-3,7-diazabicyclanes and 9-(m-hydroxyphenyl)-3,7-diazabicyclanes is described. Members of both series were tested for antinociception in rat tail withdrawal and mouse acetic acid writhing assays. Their affinities for opiate receptors in rat brain homogenate were also determined. The 9-phenyl compounds, 1a-c, were inactive. However, the 9-(m-hydroxyphenyl) analogues, 2a-c, were found to possess significant activity in the writhing assay, comparable to that of morphine. All activity was reversed by naloxone.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Analgesics, Opioid / chemical synthesis*
  • Analgesics, Opioid / pharmacology
  • Animals
  • Bridged Bicyclo Compounds / chemical synthesis*
  • Bridged Bicyclo Compounds / pharmacology
  • Bridged-Ring Compounds / chemical synthesis*
  • Mice
  • Rats
  • Receptors, Opioid / drug effects
  • Structure-Activity Relationship

Substances

  • Analgesics, Opioid
  • Bridged Bicyclo Compounds
  • Bridged-Ring Compounds
  • Receptors, Opioid