(1,2-Diphenylethyl) piperazines as potent opiate-like analgesics; the unusual relationships between stereoselectivity and affinity to opioid receptor

Life Sci. 1983:33 Suppl 1:431-4. doi: 10.1016/0024-3205(83)90534-9.

Abstract

A series of novel diphenylethylpiperazines were synthesized, and analgesic activities and opioid receptor interactions were evaluated. Analgesic activity of S(+) enantiomer of 1-cyclohexyl analogues (I-C6) was as potent as morphine. This compound showed narcotic properties. Racemate of I-C6 demonstrated the most potent analgesic activities among the enantiomorphic pairs. The R(-) isomer and (-) spa, NN-dimethyl-1, 2-diphenylethylamine, had mu-agonist like character. The S(+) isomer possessed high affinity for all types of the receptor, especially favorable for delta and kappa, in the different manner from opiate-like analgesics. It is conceivable that opioid receptor has various subsites, and this S(+) enantiomer alter the conformation of the receptor.

MeSH terms

  • Analgesia
  • Animals
  • Brain / metabolism
  • Mice
  • Piperazines / pharmacology*
  • Rats
  • Receptors, Opioid / drug effects
  • Receptors, Opioid / metabolism*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Piperazines
  • Receptors, Opioid