Codeinone

Codeinone is an isoquinolone alkaloid^[1] found in the opium poppy.^[2] 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]}–as well as of oxycodone,^[3] though the latter can also be synthesized from thebaine.^[4]

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-methano[1]benzofuro[3,2-e]isoquinolin-7-one
Identifiers
CAS Number	467-13-0 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:18399 Y
ChEMBL	ChEMBL257627 Y
ChemSpider	4573639 Y
ECHA InfoCard	100.006.716
KEGG	C06171 Y
PubChem CID	5459910
UNII	22B5AW0ANN Y
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/s1 Y Key: XYYVYLMBEZUESM-CMKMFDCUSA-N Y 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 Key: XYYVYLMBEZUESM-CMKMFDCUBF
SMILES O=C1\C=C/[C@H]5[C@@H]4N(CC[C@@]52c3c(O[C@@H]12)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 [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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.^[5]