| 词条 | Codeinone |
| 释义 |
| Verifiedfields = changed | verifiedrevid = 460106136 | ImageFile = Codeinone.svg | ImageSize = | IUPACName =(5α)-7,8-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-one | OtherNames = |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 4573639 | 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 | InChIKey = XYYVYLMBEZUESM-CMKMFDCUBF | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = XYYVYLMBEZUESM-CMKMFDCUSA-N | CASNo_Ref = {{cascite|changed|??}} | CASNo = 467-13-0 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 257627 | PubChem = 5459910 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 18399 | SMILES = O=C1\\C=C/[C@H]5[C@@H]4N(CC[C@@]52c3c(O[C@@H]12)c(OC)ccc3C4)C }} |Section2={{Chembox Properties | Formula = | C=18 | H=19 | N=1 | O=3 | MolarMass = 297.35 g/mol | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}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;{{Citation needed|date=September 2008}} as well as of oxycodone.[1] The latter can also be synthesized from thebaine, however.[2] Chemical structureCodeinone 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 activityThrough 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] References1. ^[https://www.erowid.org/archive/rhodium/chemistry/oxycodone.html Synthesis of Oxycodone from Codeine.] Aug 2004 static snapshot of Rhodium site archive hosted by Erowid, May 2005 {{Analgesics}}{{Opioidergics}}{{analgesic-stub}}2. ^[https://www.scribd.com/doc/77193676/Oxycodone-Synthesis 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}} 6 : Morphinans|Phenol ethers|Ethers|Ketones|Mu-opioid agonists|Semisynthetic opioids |
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