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Codeinone

This article will address the topic of Codeinone, which has become increasingly relevant in today's society. From different perspectives and contexts, Codeinone has become a point of interest for leaders, researchers, academics and the general public. Throughout history, Codeinone has been the subject of discussion and debate, fueling conversations and questions that have led to significant advances in various areas. In this sense, it is essential to delve deeper into the analysis of Codeinone, considering its current impact and the possible future implications that it allows us to glimpse. Thus, this article will seek to offer a comprehensive and updated vision of Codeinone, with the purpose of promoting greater understanding and reflection on this topic that is so relevant in contemporary society.

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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-methanobenzofuroisoquinolin-7-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.716 Edit this at Wikidata
KEGG
UNII
  • 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 checkY
    Key: XYYVYLMBEZUESM-CMKMFDCUSA-N checkY
  • 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
  • O=C1\C=C/54N(CC52c3c(O12)c(OC)ccc3C4)C
Properties
C18H19NO3
Molar mass 297.35 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
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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

  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). "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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