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
IUPAC name
  • 3,6-dihydroxy-7,8-didehydro-4,5α-epoxy-17-(2-phenylethyl)morphinan
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC24H25NO3
Molar mass375.468 g·mol−1
3D model (JSmol)
SMILES
  • c1ccc(cc1)CCN2CC[C@]34c5c6ccc(c5O[C@H]3[C@H](C=C[C@H]4[C@H]2C6)O)O
InChI
  • InChI=1S/C24H25NO3/c26-19-8-6-16-14-18-17-7-9-20(27)23-24(17,21(16)22(19)28-23)11-13-25(18)12-10-15-4-2-1-3-5-15/h1-9,17-18,20,23,26-27H,10-14H2/t17-,18+,20-,23-,24-/m0/s1
  • Key:BXKJGGVENHTVBF-JFDOVZFRSA-N
  (verify)

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): 1387–1388. doi:10.1021/jo01103a615.
  2. Eddy NB (July 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 JI, Lawson JA, Crase JL, Johnson HL, Ellis M, Uyeno ET, et al. (May 1978). "Analgesics. 1. Synthesis and analgesic properties of N-sec-alkyl- and N-tert-alkylnormorphines". Journal of Medicinal Chemistry. 21 (5): 415–22. doi:10.1021/jm00203a002. PMID 207868.
  4. Subramanian G, Paterlini MG, Portoghese PS, Ferguson DM (February 2000). "Molecular docking reveals a novel binding site model for fentanyl at the mu-opioid receptor". Journal of Medicinal Chemistry. 43 (3): 381–91. doi:10.1021/jm9903702. PMID 10669565.
  5. McFadyen I, Metzger T, Subramanian G, Poda G, Jorvig E, Ferguson DM (2002). Molecular modeling of opioid receptor-ligand complexes. Progress in Medicinal Chemistry. Vol. 40. pp. 107–35. doi:10.1016/S0079-6468(08)70083-3. ISBN 9780444510549. PMID 12516524.
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