N-Phenethylnormorphine: Difference between revisions

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+{{Short description|Chemical compound}}
 {{DISPLAYTITLE:''N''-Phenethylnormorphine}}
 {{Drugbox
-| verifiedrevid = 444655361
+| verifiedrevid = 451559953
 | IUPAC_name = 3,6-dihydroxy-7,8-didehydro-4,5α-epoxy-17-(2-phenylethyl)morphinan
 | image = N-Phenethylnormorphine.svg
-| width = 220
 | drug_name = ''N''-Phenethylnormorphine
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 | legal_US =
 | legal_status =
 | routes_of_administration =
 <!--Pharmacokinetic data-->
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 | metabolism =
 | elimination_half-life =
 | excretion =
 <!--Identifiers-->
+| CAS_number_Ref = {{cascite|correct|??}}
 | CAS_number =
 | ATC_prefix =
@@ Line 34: / Line 35: @@
 | DrugBank =
 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
-| ChemSpiderID =
+| ChemSpiderID      = 34254115
 | synonyms =
+| ChEMBL = 3275472
 <!--Chemical data-->
 | C=24 | H=25 | N=1 | O=3
+| smiles            = c1ccc(cc1)CCN2CC[C@]34c5c6ccc(c5O[C@H]3[C@H](C=C[C@H]4[C@H]2C6)O)O
-| molecular_weight = 375.459 g/mol
+| StdInChI          = 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
-| smiles = c6ccccc6CCN4CCC25C1Oc3c2c(ccc3O)CC4C5C=CC1O
+| StdInChIKey       = BXKJGGVENHTVBF-JFDOVZFRSA-N
-| InChI =
-| InChIKey =
 }}
-'''''N''-Phenethylnormorphine''' is an [[opiate]] [[analgesic]] drug derived from [[morphine]] by replacing the ''N''-methyl group with β-phenethyl.<ref>{{Cite doi|10.1021/jo01103a615}}</ref> It is around eight to fourteen times more potent than morphine as a result of this modification,<ref>{{Cite doi|10.1016/0021-9681(56)90007-8}}</ref> in contrast to most other N-substituted derivatives of morphine which are substantially less active, or act as [[Receptor antagonist|antagonists]].<ref>{{Cite doi|10.1021/jm00203a002}}</ref> 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]].<ref name="pmid10669565">{{cite journal |author=Subramanian G, Paterlini MG, Portoghese PS, Ferguson DM |title=Molecular docking reveals a novel binding site model for fentanyl at the mu-opioid receptor |journal=Journal of Medicinal Chemistry |volume=43 |issue=3 |pages=381–91 |year=2000 |month=February |pmid=10669565 |doi= 10.1021/jm9903702|url=}}</ref><ref>{{Cite doi|10.1016/S0079-6468(08)70083-3}}</ref>
+'''''N''-Phenethylnormorphine''' is an [[opioid]] [[analgesic]] drug derived from [[morphine]] by replacing the ''N''-methyl group with β-phenethyl.<ref>{{cite journal | vauthors = Small L, Eddy N, Ager J, May E | year = 1958 | title = Notes: An Improved Synthesis of N-Phenethylnormorphine and Analogs | journal = Journal of Organic Chemistry | volume = 23 | issue = 9 | pages = 1387–1388 | doi = 10.1021/jo01103a615 }}</ref> It is around eight to fourteen times more potent than morphine as a result of this modification,<ref>{{cite journal | vauthors = Eddy NB | title = The search for new analgesics | journal = Journal of Chronic Diseases | volume = 4 | issue = 1 | pages = 59–71 | date = July 1956 | pmid = 13332043 | doi = 10.1016/0021-9681(56)90007-8 }}</ref> in contrast to most other N-substituted derivatives of morphine, which are substantially less active, or act as [[Receptor antagonist|antagonists]].<ref>{{cite journal | vauthors = DeGraw JI, Lawson JA, Crase JL, Johnson HL, Ellis M, Uyeno ET, Loew GH, Berkowitz DS | display-authors = 6 | title = Analgesics. 1. Synthesis and analgesic properties of N-sec-alkyl- and N-tert-alkylnormorphines | journal = Journal of Medicinal Chemistry | volume = 21 | issue = 5 | pages = 415–22 | date = May 1978 | pmid = 207868 | doi = 10.1021/jm00203a002 }}</ref> 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]].<ref name="pmid10669565">{{cite journal | vauthors = Subramanian G, Paterlini MG, Portoghese PS, Ferguson DM | title = Molecular docking reveals a novel binding site model for fentanyl at the mu-opioid receptor | journal = Journal of Medicinal Chemistry | volume = 43 | issue = 3 | pages = 381–91 | date = February 2000 | pmid = 10669565 | doi = 10.1021/jm9903702 }}</ref><ref>{{cite book | vauthors = McFadyen I, Metzger T, Subramanian G, Poda G, Jorvig E, Ferguson DM | title = Molecular modeling of opioid receptor-ligand complexes | volume = 40 | pages = 107–35 | year = 2002 | pmid = 12516524 | doi = 10.1016/S0079-6468(08)70083-3 | isbn = 9780444510549 | series = Progress in Medicinal Chemistry }}</ref>
-==See also==
+== See also ==
 * [[14-Cinnamoyloxycodeinone]]
 * [[14-Phenylpropoxymetopon]]
 * [[7-PET]]
+* [[MR-2096]]
 * [[N-Phenethyl-14-ethoxymetopon|''N''-Phenethyl-14-ethoxymetopon]]
 * [[N-Phenethylnordesomorphine|''N''-Phenethylnordesomorphine]]
@@ Line 57: / Line 59: @@
 * [[Ro4-1539]]
-==References==
+== References ==
-{{Reflist}}
+{{Reflist|2}}
+{{Opioidergics}}
 {{DEFAULTSORT:Phenethylnormorphine, N-}}
-[[Category:Morphinans]]
+[[Category:4,5-Epoxymorphinans]]
 [[Category:Semisynthetic opioids]]
-[[Category:Mu-opioid agonists]]
+[[Category:Mu-opioid receptor agonists]]