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Codeinone

Names
IUPAC name 3-Methoxy-17-methyl-7,8-didehydro-4,5α-epoxymorphinan-6-one
Preferred IUPAC name (4R,4aR,7aR,12bS)-9-Methoxy-3-methyl-2,3,4,4a,7,7a-hexahydro-1H-4,12-methanobenzofuroisoquinolin-7-one
Identifiers
CAS Number	467-13-0
3D model (JSmol)	Interactive image
ChEBI	CHEBI:18399
ChEMBL	ChEMBL257627
ChemSpider	4573639
ECHA InfoCard	100.006.716
KEGG	C06171
PubChem CID	5459910
UNII	22B5AW0ANN
CompTox Dashboard (EPA)	DTXSID70196909
InChI InChI=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/s1Key: XYYVYLMBEZUESM-CMKMFDCUSA-N 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/s1Key: XYYVYLMBEZUESM-CMKMFDCUBF
SMILES O=C1\C=C/54N(CC52c3c(O12)c(OC)ccc3C4)C
Properties
Chemical formula	C18H19NO3
Molar mass	297.35 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is  ?) Infobox references

Codeinone is an isoquinolone alkaloid found in the opium poppy. 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–as well as of oxycodone, though the latter can also be synthesized from thebaine.

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.

References

1. "codeinone (CHEBI:18399)". www.ebi.ac.uk. Retrieved 28 October 2023.
2. Lenz, Rainer; Zenk, Meinhart H. (April 1995). "Stereoselective reduction of codeinone, the penultimate enzymic step during morphine biosynthesis in Papaver somniferum". Tetrahedron Letters. 36 (14): 2449–2452. doi:10.1016/0040-4039(95)00278-K.
3. Synthesis of Oxycodone from Codeine. Aug 2004 static snapshot of Rhodium site archive hosted by Erowid, May 2005
4. Oxycodone / 14-hydroxydihydrocodeinone Synthesis; with alternative synthesis of 14-hydroxycodeinone intermediate. J. Med. Chem., 1974, 17, 1117
5. Hitosugi N, Nagasaka H, Sakagami H, Matsumoto I, Kawase M (2003). Anticancer Res. 23(3B):2569-76. PMID 12894543

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