Synthesis and analgesic activities of 2,5-dimethyl-2'-hydroxy-9alpha- and -beta-propyl-6,7-benzomorphans

J Med Chem. 1975 Aug;18(8):854-7. doi: 10.1021/jm00242a022.

Abstract

The 2,5-dimethyl-2'-hydroxy-9alpha- and-beta-propyl-6,7-benzomorphans were synthesized from 4-methyl-3-propylpyridine in five steps, in an overall yield of 14 and 5%, respectively. The required 4-methyl-3-propylpyridine was prepared in an overally yield of 34% by a four-step sequence. The benzomorphans were about as potent as, or more potent than, morphine in vivo.

MeSH terms

  • Analgesics / chemical synthesis*
  • Animals
  • Benzomorphans / analogs & derivatives
  • Benzomorphans / chemical synthesis*
  • Benzomorphans / pharmacology
  • Hot Temperature
  • Mice
  • Morphinans / chemical synthesis*
  • Reaction Time / drug effects

Substances

  • Analgesics
  • Benzomorphans
  • Morphinans