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Stereoisomers of N-[1-hydroxy-(2-phenylethyl)-3-methyl-4-piperidyl]- N-phenylpropanamide: synthesis, stereochemistry, analgesic activity, and opioid receptor binding characteristics.
  • Z. Wang, Y. Zhu, +4 authors Z. Chi
  • Chemistry, Medicine
  • Journal of medicinal chemistry
  • 1 September 1995
TLDR
The results suggested that the analgesic effects of ohmefentanyl are mediated by interaction between the agents and opioid mu receptors in the central nervous system and the 3R,4S configuration at the piperidine 3- and 4-carbon atoms and the S configuration atThe phenylethyl 2-carbon atom are beneficial for analgesic potency and inhibitory effects in GPI and MVD. Expand
[Analgesic activity and toxicity of potent analgesics, ohmefentanyl and mefentanyl].
The analgesic potency and the duration of ohmefentanyl {N-[1-(2-hydroxy-2-phenylethyl)-3-methyl-4-piperidyl]-N-phenylpropanamide, OMF}, mefentanylExpand
[3H]Ohmefentanyl preferentially binds to μ-opioid receptors but also labels σ-sites in rat brain sections
Ohmefentanyl has been shown to be 6300 times more potent than morphine for analgesia. The receptor binding characteristics and distribution of [3H]ohmefentanyl in rat brain sections are presented.Expand
Theoretical studies on opioid receptors and ligands. I. Molecular modeling and QSAR studies on the interaction mechanism of fentanyl analogs binding to ?-opioid receptor
Based on our previous result of the three-dimensional model of the μ-opioid receptor, binding conformations of 13 fentanyl analogs and three-dimensional structures for the complexs of these analogsExpand
[3H]ohmefentanyl preferentially binds to mu-opioid receptors but also labels sigma-sites in rat brain sections.
Ohmefentanyl has been shown to be 6300 times more potent than morphine for analgesia. The receptor binding characteristics and distribution of [3H]ohmefentanyl in rat brain sections are presented.Expand
Opioid peptide receptor studies, 11: Involvement of Tyr148, Trp318 and His319 of the rat μ‐opioid receptor in binding of μ‐selective ligands
TLDR
The role of weak electrostatic and hydrogen‐bonding “π‐π” interactions of the O atom of the carbonyl group and the phenyl ring structures of RTI‐4614–4 and its four enantiomers with residues Tyr148, Trp318, and His319 were explored via site‐directed mutagenesis and indicate the importance of Tyr148 and His 319 for the binding of fentanyl derivatives to the μ receptor. Expand
Studies on synthesis and relationship between analgesic activity and receptor affinity for 3-methyl fentanyl derivatives.
TLDR
The result shows that the analgesic potency of the derivatives of this series is mainly dependent on binding affinity for opiate receptor. Expand
Molecular modeling of mu opioid receptor and its interaction with ohmefentanyl.
TLDR
The ligand-receptor interaction model should be helpful for rational design of novel analgesic and investigate the action mechanism of ohmefentanyl on the receptor. Expand
Building 3D-structural model of kappa opioid receptor and studying its interaction mechanism with dynorphin A(1-8).
TLDR
Some amino acid residues positioned in EL2, TM3, TM4, and TM5 form the binding site and therefore determine the selectivity of kappa peptide agonist. Expand
OHMEFENTANYL——A NEW AGONIST FOR μ-OPIATE RECEPTOR
Ohmefentanyl (F 7302, N[1-(β-hydroxy-β-phenylethyt)-3-methyl-4-piperidyl]-N-phenylpropionamide) is a potent synthetic analgesic agent. The analgesic activity of ohmefentanyl in mice is 6300 timesExpand
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