Codeinone

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 ;
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/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). verify (what is ?) Infobox references

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]

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]

References

↑ "codeinone (CHEBI:18399)". www.ebi.ac.uk. Retrieved 28 October 2023.
↑ 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.
↑ 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). "Analysis of apoptosis signaling pathway in human cancer cells by codeinone, a synthetic derivative of codeine". Anticancer Res. 23 (3B): 2569–76. PMID 12894543.

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[CHEBI-1] "codeinone (CHEBI:18399)". www.ebi.ac.uk. Retrieved 28 October 2023.

[Lenz1995-2] 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). "Analysis of apoptosis signaling pathway in human cancer cells by codeinone, a synthetic derivative of codeine". Anticancer Res. 23 (3B): 2569–76. PMID 12894543.

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Chemical structure

Apoptotic activity

References