| Revision as of 09:56, 11 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,081 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CASNo').← Previous edit |
Latest revision as of 23:47, 28 October 2023 edit undoKimen8 (talk | contribs)Extended confirmed users5,112 edits Try to clean up messy article with lacking lead; still needs work |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 443539469 |
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| verifiedrevid = 460106136 |
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| ImageFile = Codeinone.svg |
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| ImageFile = Codeinone.svg |
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| ImageSize = |
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| ImageSize = |
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| IUPACName =(5α)-7,8-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-one |
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| IUPACName = 3-Methoxy-17-methyl-7,8-didehydro-4,5α-epoxymorphinan-6-one |
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| PIN = (4''R'',4a''R'',7a''R'',12b''S'')-9-Methoxy-3-methyl-2,3,4,4a,7,7a-hexahydro-1''H''-4,12-methanobenzofuroisoquinolin-7-one |
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| OtherNames = |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4573639 |
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| ChemSpiderID = 4573639 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = XYYVYLMBEZUESM-CMKMFDCUSA-N |
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| StdInChIKey = XYYVYLMBEZUESM-CMKMFDCUSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 467-13-0 --> |
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| CASNo = 467-13-0 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 22B5AW0ANN |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 257627 |
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| ChEMBL = 257627 |
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| PubChem = 5459910 |
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| PubChem = 5459910 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 18399 |
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| ChEBI = 18399 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C06171 |
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| SMILES = O=C1\C=C/54N(CC52c3c(O12)c(OC)ccc3C4)C |
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| SMILES = O=C1\C=C/54N(CC52c3c(O12)c(OC)ccc3C4)C |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = |
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| Formula = | C=18 | H=19 | N=1 | O=3 |
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| C=18 | H=19 | N=1 | O=3 |
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| MolarMass = 297.35 g/mol |
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| MolarMass = 297.35 g/mol |
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| Appearance = |
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| Appearance = |
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| BoilingPt = |
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| BoilingPt = |
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| Solubility = }} |
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| Solubility = }} |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| MainHazards = |
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| FlashPt = |
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| FlashPt = |
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| Autoignition = }} |
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| AutoignitionPt = }} |
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}} |
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}} |
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'''Codeinone''' is an isoquinolone alkaloid<ref name="CHEBI">{{cite web |title=codeinone (CHEBI:18399) |url=https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:18399 |website=www.ebi.ac.uk |access-date=28 October 2023}}</ref> found in the ].<ref name="Lenz1995">{{cite journal |last1=Lenz |first1=Rainer |last2=Zenk |first2=Meinhart H. |title=Stereoselective reduction of codeinone, the penultimate enzymic step during morphine biosynthesis in Papaver somniferum |journal=Tetrahedron Letters |date=April 1995 |volume=36 |issue=14 |pages=2449–2452 |doi=10.1016/0040-4039(95)00278-K}}</ref> As an analgesic, it is one-third the potency of ]. It is an important intermediate in the production of ]–a painkiller about three-quarters the potency of morphine{{Citation needed|date=September 2008}}–as well as of ],<ref> Aug 2004 static snapshot of Rhodium site archive hosted by Erowid, May 2005</ref> though the latter can also be synthesized from ].<ref> J. Med. Chem., 1974, 17, 1117</ref> |
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'''Codeinone''' is 1/3 as active as ] as an ] but it is an important intermediate in the production of ], a painkiller about 3/4 the potency of morphine.{{Fact|date=September 2008}} |
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==Chemical structure== |
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==Chemical structure== |
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Codeinone can described as the methylether of ]: 3-methyl-morphinone. |
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Codeinone can be described as the methylether of ]: 3-methyl-morphinone. |
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Codeinone can be also described as the ] of ]: codein-6-on. |
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Codeinone can be also described as the ] of ]: codeine-6-one. |
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==Apoptotic activity == |
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Through renewed interest into possible anti-tumor activities of some of the ] ]s and derivatives, unrelated to their antinociceptive properties and habit-forming effects, the oxidation product of codeine has been found to induce cell death in three different human cancer cell lines ''in vitro''.<ref>Hitosugi N, Nagasaka H, Sakagami H, Matsumoto I, Kawase M (2003). ''Anticancer Res.'' 23(3B):2569-76. {{PMID|12894543}}</ref> |
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==References== |
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==References== |
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{{Reflist|2}} |
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{{Unreferenced|date=September 2008}} |
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{{reflist}} |
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{{Analgesics}} |
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{{Analgesics}} |
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{{Opioidergics}} |
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{{analgesic-stub}} |
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{{analgesic-stub}} |
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