N-Phenethylnormorphine

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]

N-Phenethylnormorphine
Identifiers
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC24H25NO3
Molar mass375.459 g/mol g·mol−1
3D model (JSmol)
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See also

References
  1. Small, L.; Eddy, N.; Ager, J.; May, E. (1958). "Notes: An Improved Synthesis of N-Phenethylnormorphine and Analogs". Journal of Organic Chemistry. 23 (9): 1387. doi:10.1021/jo01103a615.
  2. Eddy, N. (1956). "The Search for New Analgesics". Journal of Chronic Diseases. 4 (1): 59–71. doi:10.1016/0021-9681(56)90007-8. PMID 13332043.
  3. DeGraw, J. I.; Lawson, J. A.; Crase, J. L.; Johnson, H. L.; Ellis, M.; Uyeno, E. T.; Loew, G. H.; Berkowitz, D. S. (1978). "Analgesics. 1. Synthesis and Analgesic Properties of N-sec-Alkyl and N-tert-Alkylnormorphines". Journal of Medicinal Chemistry. 21 (5): 415–422. doi:10.1021/jm00203a002. PMID 207868.
  4. Subramanian, G.; Paterlini, M. G.; Portoghese, P. S.; Ferguson, D. M. (February 2000). "Molecular Docking Reveals a Novel Binding Site Model for Fentanyl at the mu-Opioid Receptor". Journal of Medicinal Chemistry. 43 (3): 381–391. doi:10.1021/jm9903702. PMID 10669565.
  5. McFadyen, I.; Metzger, T.; Subramanian, G.; Poda, G.; Jorvig, E.; Ferguson, D. M. (2002). "Molecular Modeling of Opioid Receptor-Ligand Complexes". Progress in Medicinal Chemistry. Progress in Medicinal Chemistry. 40: 107–135. doi:10.1016/S0079-6468(08)70083-3. ISBN 9780444510549. PMID 12516524.
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