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N-Phenethylnormorphine

Chemical compound

Chemical compound

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N-Phenethylnormorphine is an opioid analgesic drug derived from morphine by replacing the N-methyl group with β-phenethyl. It is around eight to fourteen times more potent than morphine as a result of this modification, in contrast to most other N-substituted derivatives of morphine, which are substantially less active, or act as antagonists. Binding studies have helped to explain the increased potency of N-phenethylnormorphine, showing that the phenethyl group extends out to reach an additional binding point deeper inside the μ-opioid receptor cleft, analogous to the binding of the phenethyl group on fentanyl.

References

References

  1. (1958). "Notes: An Improved Synthesis of N-Phenethylnormorphine and Analogs". Journal of Organic Chemistry.
  2. (July 1956). "The search for new analgesics". Journal of Chronic Diseases.
  3. (May 1978). "Analgesics. 1. Synthesis and analgesic properties of N-sec-alkyl- and N-tert-alkylnormorphines". Journal of Medicinal Chemistry.
  4. (February 2000). "Molecular docking reveals a novel binding site model for fentanyl at the mu-opioid receptor". Journal of Medicinal Chemistry.
  5. (2002). "Molecular modeling of opioid receptor-ligand complexes".
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4,5-epoxymorphinans semisynthetic-opioids mu-opioid-receptor-agonists
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