Synthesis and analgesic activity of stereoisomers of cis-fluoro-ohmefentanyl

Pharmazie. 2003 May;58(5):300-2.

Abstract

Four stereoisomers 1a-d of cis-fluoro-ohmefentanyl have been synthesized. Their absolute configurations were determined by X-ray analysis of (3S,4R,2'S)-(-)-cis-I d. The analgesic activity (mice, sc, hot plate) revealed extreme stereodifferences. The ED50 value of (3R,4S,2'S)-(+)-cis-I (1a) was 0.000774 mg/kg (17958 times more potent than that of morphine), while the corresponding antipode 1c was almost inactive.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Analgesics, Opioid / chemical synthesis*
  • Analgesics, Opioid / pharmacology*
  • Animals
  • Chemical Phenomena
  • Chemistry, Physical
  • Crystallography, X-Ray
  • Fentanyl / analogs & derivatives
  • Fentanyl / chemical synthesis*
  • Fentanyl / pharmacology
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Mice
  • Molecular Conformation
  • Morphine / pharmacology
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Analgesics, Opioid
  • Indicators and Reagents
  • cis-fluoro-ohmefentanyl
  • Morphine
  • Fentanyl