Codeinone

Codeinone

Names
IUPAC name (5α)-7,8-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-one
Identifiers
CAS Number	467-13-0 N
ChEBI	CHEBI:18399 Y
ChEMBL	ChEMBL257627 Y
ChemSpider	4573639 Y
Jmol 3D model	Interactive image
PubChem	5459910
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
Vapor pressure	{{{value}}}
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

Codeinone is 1/3 as active as codeine as an analgesic but it is an important intermediate in the production of hydrocodone, a painkiller about 3/4 the potency of morphine; as well as of oxycodone, a painkiller roughly half again more or up to 1.7× the strength of morphine. The latter can also be synthesized from thebaine, however.

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.