N-(2-Cyanoethyl) derivatives of meperidine, ketobemidone, and a potent 6,7-benzomorphan

J Med Chem. 1979 Jul;22(7):889-90. doi: 10.1021/jm00193a028.

Abstract

The N-(2-cyanoethyl)-9alpha-ethyl-5-methyl-6,7-benzomorphan (1c) is a more potent antinociceptive and has stronger receptor binding affinity than its N-methyl analogue 1b. The N-(2-cyanoethyl)-4-phenylpiperidine compounds 2b and 3b were almost inactive compared to their N-methyl congeners 2a and 3a, respectively. It appears that the pharmacological effect of the N-(2-cyanoethyl) moiety is dependent on the opioid on which it is substituted.

Publication types

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

MeSH terms

  • Analgesics / chemical synthesis*
  • Analgesics / metabolism
  • Animals
  • Benzomorphans / analogs & derivatives
  • Benzomorphans / chemical synthesis*
  • Benzomorphans / metabolism
  • Benzomorphans / pharmacology
  • Binding, Competitive
  • Brain / metabolism
  • Dihydromorphine / metabolism
  • Haplorhini
  • Humans
  • In Vitro Techniques
  • Macaca mulatta
  • Meperidine / analogs & derivatives*
  • Meperidine / chemical synthesis
  • Meperidine / metabolism
  • Meperidine / pharmacology
  • Mice
  • Morphinans / chemical synthesis*
  • Morphine Dependence / physiopathology
  • Nitriles / chemical synthesis*
  • Piperidines / chemical synthesis*
  • Rats
  • Structure-Activity Relationship

Substances

  • Analgesics
  • Benzomorphans
  • Morphinans
  • Nitriles
  • Piperidines
  • Meperidine
  • Dihydromorphine