The synthesis and preliminary pharmacological evaluation of 4-methyl fentanyl

Bioorg Med Chem Lett. 2000 Sep 4;10(17):2011-4. doi: 10.1016/s0960-894x(00)00394-2.

Abstract

The synthesis of 4-methyl fentanyl, a prototype of a novel class of fentanyl analogues has been effected in 5 steps, starting from N-ethoxycarbonyl-4-piperidone (approximately 20% overall yield). In the key step, N-phenylation of secondary aliphatic amide intermediare was achieved by a novel reaction, using diphenyliodonium chloride for the phenyl group transfer. Preliminary pharmacological results indicate that 4-methyl fentanyl is a super potent narcotic analgesic, about four times more potent than fentanyl.

MeSH terms

  • Analgesics, Opioid / chemical synthesis*
  • Analgesics, Opioid / pharmacology
  • Animals
  • Fentanyl / analogs & derivatives*
  • Fentanyl / chemical synthesis
  • Fentanyl / pharmacology
  • Rats
  • Structure-Activity Relationship

Substances

  • Analgesics, Opioid
  • Fentanyl