Codeinone

{{chembox | Verifiedfields = changed | verifiedrevid = 460106136 | ImageFile = Codeinone.svg | ImageClass = skin-invert-image | ImageSize = | IUPACName = 3-Methoxy-17-methyl-7,8-didehydro-4,5α-epoxymorphinan-6-one | PIN = (4''R'',4a''R'',7a''R'',12b''S'')-9-Methoxy-3-methyl-2,3,4,4a,7,7a-hexahydro-1''H''-4,12-methano[1]benzofuro[3,2-''e'']isoquinolin-7-one | OtherNames = |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|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 | StdInChI_Ref = {{stdinchicite|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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = XYYVYLMBEZUESM-CMKMFDCUSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 467-13-0 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 22B5AW0ANN | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 257627 | PubChem = 5459910 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 18399 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C06171 | SMILES = O=C1\C=C/[C@H]5[C@@H]4N(CC[C@@]52c3c(O[C@@H]12)c(OC)ccc3C4)C }} |Section2={{Chembox Properties | Formula = | C=18 | H=19 | N=1 | O=3 | MolarMass = 297.35 g/mol | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }} '''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 opium poppy.<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 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,<ref>[https://www.erowid.org/archive/rhodium/chemistry/oxycodone.html Synthesis of Oxycodone from Codeine.] Aug 2004 static snapshot of Rhodium site archive hosted by Erowid, May 2005</ref> though the latter can also be synthesized from thebaine.<ref>[https://www.scribd.com/doc/77193676/Oxycodone-Synthesis Oxycodone / 14-hydroxydihydrocodeinone Synthesis; with alternative synthesis of 14-hydroxycodeinone intermediate.] J. Med. Chem., 1974, 17, 1117</ref>

==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''.<ref>{{cite journal | last1 = Hitosugi | first1 = N | last2 = Nagasaka | first2 = H | last3 = Sakagami | first3 = H | last4 = Matsumoto | first4 = I | last5 = Kawase | first5 = M | year = 2003 | title = Analysis of apoptosis signaling pathway in human cancer cells by codeinone, a synthetic derivative of codeine| url = | journal = Anticancer Res. | volume = 23 | issue = 3B| pages = 2569–76 | pmid = 12894543 }}</ref>

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

Category:Catechol ethers Category:Enones Category:4,5-Epoxymorphinans Category:Mu-opioid receptor agonists Category:Semisynthetic opioids