Codeinone (original) (raw)

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Codeinone
Names
IUPAC name 3-Methoxy-17-methyl-7,8-didehydro-4,5α-epoxymorphinan-6-one
Preferred IUPAC name (4_R_,4a_R_,7a_R_,12b_S_)-9-Methoxy-3-methyl-2,3,4,4a,7,7a-hexahydro-1_H_-4,12-methano[1]benzofuro[3,2-_e_]isoquinolin-7-one
Identifiers
CAS Number 467-13-0 checkY
3D model (JSmol) Interactive image
ChEBI CHEBI:18399 checkY
ChEMBL ChEMBL257627 checkY
ChemSpider 4573639 checkY
ECHA InfoCard 100.006.716 Edit this at Wikidata
KEGG C06171 checkY
PubChem CID 5459910
UNII 22B5AW0ANN checkY
CompTox Dashboard (EPA) DTXSID70196909 Edit this at Wikidata
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 checkYKey: XYYVYLMBEZUESM-CMKMFDCUSA-N checkYInChI=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/[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 checkY☒N ?) Infobox references

Chemical compound

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 can be described as the methylether of morphinone: 3-methyl-morphinone.

Codeinone can be also described as the ketone of codeine: codeine-6-one.

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]

  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