Codeinone

Codeinone
Names
	IUPAC name (5α)-7,8-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-one
Identifiers
CAS Number	467-13-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:18399 ;
ChEMBL	ChEMBL257627 ;
ChemSpider	4573639 ;
ECHA InfoCard	100.006.716
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/s1 Key: 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/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).

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.^[1] The latter can also be synthesized from thebaine, however.^[2]

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.^[3]

References

^ Synthesis of Oxycodone from Codeine. Aug 2004 static snapshot of Rhodium site archive hosted by Erowid, May 2005
^ Oxycodone / 14-hydroxydihydrocodeinone Synthesis; with alternative synthesis of 14-hydroxycodeinone intermediate. J. Med. Chem., 1974, 17, 1117
^ Hitosugi N, Nagasaka H, Sakagami H, Matsumoto I, Kawase M (2003). Anticancer Res. 23(3B):2569-76. PMID 12894543

[1] Synthesis of Oxycodone from Codeine. Aug 2004 static snapshot of Rhodium site archive hosted by Erowid, May 2005

[2] Oxycodone / 14-hydroxydihydrocodeinone Synthesis; with alternative synthesis of 14-hydroxycodeinone intermediate. J. Med. Chem., 1974, 17, 1117

[3] Hitosugi N, Nagasaka H, Sakagami H, Matsumoto I, Kawase M (2003). Anticancer Res. 23(3B):2569-76. PMID 12894543

[1]

[2]

[3]

Names

IUPAC name (5α)-7,8-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-one
Identifiers
CAS Number	467-13-0
3D model (JSmol)	Interactive image
ChEBI	CHEBI:18399
ChEMBL	ChEMBL257627
ChemSpider	4573639
ECHA InfoCard	100.006.716
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/s1 Key: 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/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).