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Revision as of 13:13, 4 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'StdInChI', 'StdInChIKey', 'CAS_number').← Previous edit Latest revision as of 10:43, 21 October 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,126 edits removed Category:Phenols; added Category:Hydroxyarenes using HotCat 
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{{Short description|Chemical compound}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
⚫ | IUPAC_name = 6-β-azido- 4,5-α-epoxy- 17-methyl- morphinan- 3-ol
| Watchedfields = changed
⚫ | image = Azidomorphine.png
| verifiedrevid = 458966745
⚫ | width = 220
⚫ | IUPAC_name = (6β)-Azido-4,5-α-epoxy-17-methyl morphinan-3-ol
| image = Azidomorphine2DCSD2.svg
| alt = Skeletal formula of azidomorphine
⚫ | width = 200
⚫ | image2 = Azidomorphine-3D-spacefill.png
| alt2 = Space-filling model of the azidomorphine molecule
| width2 = 180


<!--Clinical data--> <!--Clinical data-->
Line 13: Line 21:
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US = | legal_US =
| legal_status = | legal_status =
| routes_of_administration = | routes_of_administration =


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
Line 21: Line 29:
| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|CAS}}
| CAS_number = <!-- blanked - oldvalue: 22952-87-0 --> | CAS_number = 22952-87-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = U973VU74ER
| ATC_prefix = none | ATC_prefix = none
| ATC_suffix = | ATC_suffix =
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C17H20N4O2/c1-21-7-6-17-10-3-4-11(19-20-18)16(17)23-15-13(22)5-2-9(14(15)17)8-12(10)21/h2,5,10-12,16,22H,3-4,6-8H2,1H3/t10-,11+,12+,16-,17-/m0/s1 | StdInChI = 1S/C17H20N4O2/c1-21-7-6-17-10-3-4-11(19-20-18)16(17)23-15-13(22)5-2-9(14(15)17)8-12(10)21/h2,5,10-12,16,22H,3-4,6-8H2,1H3/t10-,11+,12+,16-,17-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KZOKOEQTKWBKOK-XHQKLZHNSA-N | StdInChIKey = KZOKOEQTKWBKOK-XHQKLZHNSA-N
| PubChem = 5488848 | PubChem = 5488848
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = | DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4590009 | ChemSpiderID = 4590009


<!--Chemical data--> <!--Chemical data-->
| C=17 | H=20 | N=4 | O=2 | C=17 | H=20 | N=4 | O=2
| molecular_weight = 312.366 g/mol
| smiles = ==N\45Oc1c2c(ccc1O)C3N(CC253CC4)C | smiles = ==N\45Oc1c2c(ccc1O)C3N(CC253CC4)C
| InChI = 1/C17H20N4O2/c1-21-7-6-17-10-3-4-11(19-20-18)16(17)23-15-13(22)5-2-9(14(15)17)8-12(10)21/h2,5,10-12,16,22H,3-4,6-8H2,1H3/t10-,11+,12+,16-,17-/m0/s1
| InChIKey = KZOKOEQTKWBKOK-XHQKLZHNBX
| synonyms = Azidomorphine | synonyms = Azidomorphine
}} }}


'''Azidomorphine'''<ref>US Patent 3880862</ref> is an ] analogue that is a derivative of ], where the 7,8 double bond has been saturated and the 6-hydroxy group has been replaced by an ] group.<ref>Knoll J, Furst S, Kelemen K. The pharmacology of azidomorphine and azidocodeine. ''Journal of Pharmacy and Pharmacology''. 1973;25(12):929-939. PMID 4150295</ref> '''Azidomorphine'''<ref>{{cite patent | country = GB | number = 1396663 | title = Analgesic Compositions }}</ref> is an ] analogue that is a derivative of ], where the 7,8 double bond has been saturated and the 6-hydroxy group has been replaced by an ] group.<ref>{{cite journal | vauthors = Knoll J, Fürst S, Kelemen K | title = The pharmacology of azidomorphine and azidocodeine | journal = The Journal of Pharmacy and Pharmacology | volume = 25 | issue = 12 | pages = 929–39 | date = December 1973 | pmid = 4150295 | doi = 10.1111/j.2042-7158.1973.tb09982.x | s2cid = 41506653 }}</ref>


Azidomorphine binds with high affinity to the ],<ref>Horváth K, Wollemann M. Azidomorphine is an agonist of high-affinity opioid receptor binding sites. ''Neurochemical Research''. 1986 Nov;11(11):1565-9. PMID 2825053</ref> and is around 40x more potent than morphine ''in vivo''. It has similar effects to morphine including ], ] and ]. However its addiction liability has been found to be slightly lower than that of morphine in animal studies.<ref>Knoll J. Azidomorphines: a new family of potent analgesics with low dependence capacity. ''Progress in Neuropsychopharmacology''. 1979;3(1-3):95-108. PMID 45567</ref><ref>Hill RC, Roemer D, Buescher H. Investigations of the analgesic and morphine-like properties of azidomorphine. ''Journal of Pharmacology and Experimental Therapeutics''. 1977 Jun;201(3):580-6. PMID 405472</ref> Azidomorphine binds with high affinity to the ],<ref>{{cite journal | vauthors = Horváth K, Wollemann M | title = Azidomorphine is an agonist of high-affinity opioid receptor binding sites | journal = Neurochemical Research | volume = 11 | issue = 11 | pages = 1565–9 | date = November 1986 | pmid = 2825053 | doi = 10.1007/bf00965775 | s2cid = 29580383 }}</ref> and is around 40× more potent than morphine ''in vivo''. It has similar effects to morphine, including ], ], and ]. However, its addiction liability has been found to be slightly lower than that of morphine in animal studies.<ref>{{cite journal | vauthors = Knoll J | title = Azidomorphines: a new family of potent analgesics with low dependence capacity | journal = Progress in Neuro-Psychopharmacology | volume = 3 | issue = 1–3 | pages = 95–108 | year = 1979 | pmid = 45567 | doi = 10.1016/0364-7722(79)90074-2 }}</ref><ref>{{cite journal | vauthors = Hill RC, Roemer D, Buescher H | title = Investigations of the analgesic and morphine-like properties of azidomorphine | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 201 | issue = 3 | pages = 580–6 | date = June 1977 | pmid = 405472 }}</ref>


== References == == References ==
{{reflist}} {{Reflist|2}}


{{Opioidergics}}
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