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    N-Phenethylnormorphine

    Topic: Chemistry

     From Handwiki - Reading time: 4 min
    N-Phenethylnormorphine
    N-Phenethylnormorphine.svg
    Identifiers
    PubChem CID
    ChemSpider
    ChEMBL
    Chemical and physical data
    FormulaC24H25NO3
    Molar mass375.468 g·mol−1
    3D model (JSmol)
      (verify)

    N-Phenethylnormorphine is an opioid analgesic drug derived from morphine by replacing the N-methyl group with β-phenethyl.[1] It is around eight to fourteen times more potent than morphine as a result of this modification,[2] in contrast to most other N-substituted derivatives of morphine, which are substantially less active, or act as antagonists.[3] 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.[4][5]

    See also

    References

    1. ↑ "Notes: An Improved Synthesis of N-Phenethylnormorphine and Analogs". Journal of Organic Chemistry 23 (9): 1387–1388. 1958. doi:10.1021/jo01103a615. 
    2. ↑ "The search for new analgesics". Journal of Chronic Diseases 4 (1): 59–71. July 1956. doi:10.1016/0021-9681(56)90007-8. PMID 13332043. 
    3. ↑ "Analgesics. 1. Synthesis and analgesic properties of N-sec-alkyl- and N-tert-alkylnormorphines". Journal of Medicinal Chemistry 21 (5): 415–22. May 1978. doi:10.1021/jm00203a002. PMID 207868. 
    4. ↑ "Molecular docking reveals a novel binding site model for fentanyl at the mu-opioid receptor". Journal of Medicinal Chemistry 43 (3): 381–91. February 2000. doi:10.1021/jm9903702. PMID 10669565. 
    5. ↑ Molecular modeling of opioid receptor-ligand complexes. Progress in Medicinal Chemistry. 40. 2002. pp. 107–35. doi:10.1016/S0079-6468(08)70083-3. ISBN 9780444510549. 



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