N-Phenethylnormorphine

N-Phenethylnormorphine
Identifiers
	IUPAC name 3,6-dihydroxy-7,8-didehydro-4,5α-epoxy-17-(2-phenylethyl)morphinan;
PubChem CID	46908217;
CompTox Dashboard (EPA)	DTXSID101018229 ;
Chemical and physical data
Formula	C24H25NO3
Molar mass	375.459 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c6ccccc6CCN4CCC25C1Oc3c2c(ccc3O)CC4C5C=CC1O;
	(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]

References

^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi: 10.1021/jo01103a615 , please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi= 10.1021/jo01103a615 instead.
^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi: 10.1016/0021-9681(56)90007-8 , please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi= 10.1016/0021-9681(56)90007-8 instead.
^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi: 10.1021/jm00203a002 , please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi= 10.1021/jm00203a002 instead.
^ Subramanian, G.; Paterlini, M. G.; Portoghese, P. S.; Ferguson, D. M. (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 12516524 , please use {{cite journal}} with |pmid= 12516524 instead.

[1] Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi: 10.1021/jo01103a615 , please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi= 10.1021/jo01103a615 instead.

[2] Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi: 10.1016/0021-9681(56)90007-8 , please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi= 10.1016/0021-9681(56)90007-8 instead.

[3] Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi: 10.1021/jm00203a002 , please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi= 10.1021/jm00203a002 instead.

[pmid10669565-4] Subramanian, G.; Paterlini, M. G.; Portoghese, P. S.; Ferguson, D. M. (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

[5] Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 12516524 , please use {{cite journal}} with |pmid= 12516524 instead.

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See also

References