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N-Phenethylnormorphine

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Chemical compound

Pharmaceutical compound

N-Phenethylnormorphine
Identifiers

IUPAC name 3,6-dihydroxy-7,8-didehydro-4,5α-epoxy-17-(2-phenylethyl)morphinan
PubChemCID	46908217
ChemSpider	34254115^Y
ChEMBL	ChEMBL3275472
CompTox Dashboard(EPA)	DTXSID101018229
Chemical and physical data
Formula	C₂₄H₂₅NO₃
Molar mass	375.468 g·mol⁻¹
3D model (JSmol)	Interactive image
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
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N-Phenethylnormorphine is anopioid analgesic drug derived frommorphine by replacing theN-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 asantagonists.^[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 theμ-opioid receptor cleft, analogous to the binding of the phenethyl group onfentanyl.^[4]^[5]

References

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^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.
^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.
^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.
^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.
^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.