N-Phenethylnormorphine

N-Phenethylnormorphine

Systematic (IUPAC) name
3,6-dihydroxy-7,8-didehydro-4,5α-epoxy-17-(2-phenylethyl)morphinan
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
ATC code	?
PubChem	CID 46908217
Chemical data
Formula	C24H25NO3
Mol. mass	375.459 g/mol
SMILES	eMolecules & PubChem
Y(what is this?)  (verify)

N-Phenethylnormorphine is an opiate 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 mu opioid receptor cleft, analogous to the binding of the phenethyl group on fentanyl.^[4][5]

See also

• 14-Cinnamoyloxycodeinone
• 14-Phenylpropoxymetopon
• 7-PET
• N-Phenethyl-14-ethoxymetopon
• N-Phenethylnordesomorphine
• Phenomorphan
• RAM-378
• Ro4-1539

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.  edit
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.  edit
3. ^ DeGraw JI, L. J.; 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.  edit
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, D. (2002). "4 Molecular Modeling of Opioid Receptor-Ligand Complexes". Progress in Medicinal Chemistry Volume 40. Progress in Medicinal Chemistry. 40. pp. 107. doi:10.1016/S0079-6468(08)70083-3. ISBN 9780444510549.  edit