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| '''Codeinone''' is |
'''Codeinone''' is an isoquinolone alkaloid<ref name="CHEBI">{{cite web |title=codeinone (CHEBI:18399) |url=https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:18399 |website=www.ebi.ac.uk |access-date=28 October 2023}}</ref> found in the ].<ref name="Lenz1995">{{cite journal |last1=Lenz |first1=Rainer |last2=Zenk |first2=Meinhart H. |title=Stereoselective reduction of codeinone, the penultimate enzymic step during morphine biosynthesis in Papaver somniferum |journal=Tetrahedron Letters |date=April 1995 |volume=36 |issue=14 |pages=2449–2452 |doi=10.1016/0040-4039(95)00278-K}}</ref> As an analgesic, it is one-third the potency of ]. It is an important intermediate in the production of ]–a painkiller about three-quarters the potency of morphine{{Citation needed|date=September 2008}}–as well as of ],<ref> Aug 2004 static snapshot of Rhodium site archive hosted by Erowid, May 2005</ref> though the latter can also be synthesized from ].<ref> J. Med. Chem., 1974, 17, 1117</ref> | ||
| ==Chemical structure== | ==Chemical structure== | ||
Latest revision as of 23:47, 28 October 2023
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| Names | |
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| 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 | |
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| 3D model (JSmol) | |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.006.716 
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| KEGG | |
| PubChem CID | |
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| CompTox Dashboard (EPA) | |
InChI
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SMILES
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| 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 , 100 kPa).
 N verify (what is ?)
Infobox references
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Codeinone is an isoquinolone alkaloid found in the opium poppy. 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–as well as of oxycodone, though the latter can also be synthesized from thebaine.
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.
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). Anticancer Res. 23(3B):2569-76. PMID 12894543
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| δ-opioid (DOR) |
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