Dialkylaminoalkylnaphthalenes as novel opioid-like analgesics

Bioorg Med Chem. 2000 Apr;8(4):769-75. doi: 10.1016/s0968-0896(00)00011-0.

Abstract

The study of dialkylaminoalkylnaphthalenes as novel opioid-like analgesics is reported. In particular, the synthesis of (1R,2R/1S,2S)-1-ethyl-1-[2-(6-hydroxynaphthyl)]-1-hydrox-2-m ethyl-2-dimethylaminoethane and its structural analogue (1R,2R/1S,2S)-1-ethyl-1-[2-(6-fluoronaphthyl)]-1-hydroxy-2-methyl- 2-dimethylaminoethane and the configurational analysis by X-ray and 1H NMR spectroscopy are described. Pharmacological profiles are discussed on the basis of the experimental results of analgesia tests (hot plate and writhing test) and rota-rod test, which was performed to distinguish analgesia from drug-induced motor changes. The compounds showed dose-dependent antinociception, with less potency than morphine. Motor coordination appeared to be less involved.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Analgesics, Opioid / chemistry
  • Analgesics, Opioid / metabolism
  • Analgesics, Opioid / pharmacology*
  • Animals
  • Cell Line
  • Crystallography, X-Ray
  • Humans
  • Magnetic Resonance Spectroscopy
  • Male
  • Mice
  • Molecular Structure
  • Naphthalenes / chemistry
  • Naphthalenes / metabolism
  • Naphthalenes / pharmacology*
  • Radioligand Assay
  • Receptors, Opioid / metabolism
  • Spectrophotometry, Infrared

Substances

  • Analgesics, Opioid
  • Naphthalenes
  • Receptors, Opioid