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{{chembox| Verifiedfields = changed| verifiedrevid = 460106136| ImageFile = Codeinone.svg| ImageSize = | IUPACName = 3-Methoxy-17-methyl-7,8-didehydro-4,5α-epoxymorphinan-6-one| PIN = (4R,4aR,7aR,12bS)-9-Methoxy-3-methyl-2,3,4,4a,7,7a-hexahydro-1H-4,12-methano[1]benzofuro[3,2-e]isoquinolin-7-one| OtherNames = |Section1={{Chembox Identifiers

correct|chemspider}}| ChemSpiderID = 4573639| InChI = 1/C18H19NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-12,17H,7-9H2,1-2H3/t11-,12+,17-,18-/m0/s1| InChIKey = XYYVYLMBEZUESM-CMKMFDCUBF

correct|chemspider}}| StdInChI = 1S/C18H19NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-12,17H,7-9H2,1-2H3/t11-,12+,17-,18-/m0/s1

correct|chemspider}}| StdInChIKey = XYYVYLMBEZUESM-CMKMFDCUSA-N

correct|CAS}}| CASNo = 467-13-0

correct|FDA}}| UNII = 22B5AW0ANN

correct|EBI}}| ChEMBL = 257627| PubChem = 5459910

correct|EBI}}| ChEBI = 18399

correct|kegg}}| KEGG = C06171| SMILES = O=C1C=C/[C@H]5[C@@H]4N(CC[C@@]52c3c(O[C@@H]12)c(OC)ccc3C4)C}}|Section2={{Chembox Properties

C=18

N=1 | O=3| MolarMass = 297.35 g/mol| Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }}|Section3={{Chembox Hazards| MainHazards = | FlashPt = | AutoignitionPt = }}}} Codeinone is an isoquinolone alkaloidWEB, codeinone (CHEBI:18399),weblink www.ebi.ac.uk, 28 October 2023, found in the opium poppy.JOURNAL, Lenz, Rainer, Zenk, Meinhart H., Stereoselective reduction of codeinone, the penultimate enzymic step during morphine biosynthesis in Papaver somniferum, Tetrahedron Letters, April 1995, 36, 14, 2449–2452, 10.1016/0040-4039(95)00278-K, As an analgesic, it is one-third the potency of codeine. It is an important intermediate in the production of hydrocodone–a painkiller about three-quarters the potency of morphine{{Citation needed|date=September 2008}}–as well as of oxycodone,Synthesis of Oxycodone from Codeine. Aug 2004 static snapshot of Rhodium site archive hosted by Erowid, May 2005 though the latter can also be synthesized from thebaine.Oxycodone / 14-hydroxydihydrocodeinone Synthesis; with alternative synthesis of 14-hydroxycodeinone intermediate. J. Med. Chem., 1974, 17, 1117 Chemical structure Codeinone can be described as the methylether of morphinone: 3-methyl-morphinone.Codeinone can be also described as the ketone of codeine: codeine-6-one. Apoptotic activity Through renewed interest into possible anti-tumor activities of some of the opium alkaloids 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.Hitosugi N, Nagasaka H, Sakagami H, Matsumoto I, Kawase M (2003). Anticancer Res. 23(3B):2569-76. {{PMID|12894543}} References {{Reflist|2}}{{Analgesics}}{{Opioidergics}}{{analgesic-stub}}