N-Phenethylnormorphine

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N-Phenethylnormorphine
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Systematic (IUPAC) name
3,6-dihydroxy-7,8-didehydro-4,5α-epoxy-17-(2-phenylethyl)morphinan
Chemical data
Formula C24H25NO3
Molar mass 375.459 g/mol[[Script error: No such module "String".]]
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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

References

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  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. 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. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  5. ↑ McFadyen, I.; Metzger, T.; Subramanian, G.; Poda, G.; Jorvig, E.; Ferguson, D. (2002). "4 Molecular Modeling of Opioid Receptor-Ligand Complexes". 40: 107. doi:10.1016/S0079-6468(08)70083-3.  edit
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