14-Cinnamoyloxycodeinone

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14-Cinnamoyloxycodeinone
14-cinnamoyloxycodeinone2DCSD.svg
Systematic (IUPAC) name
7,8-didehydro-4,5α-epoxy-14-cinnamoyl-3-methoxy-17-methylmorphinan-6-one
Identifiers
CAS Number 751-01-9 YesY
PubChem CID: 6438241
ChemSpider 4942728 YesY
Chemical data
Formula C27H25NO5
Molecular mass 443.490 g/mol
  • CN1CC[C@]23[C@@H]4C(=O)C=C[C@]2([C@H]1CC5=C3C(=C(C=C5)OC)O4)OC(=O)/C=C/C6=CC=CC=C6
  • InChI=1S/C27H25NO5/c1-28-15-14-26-23-18-9-10-20(31-2)24(23)32-25(26)19(29)12-13-27(26,21(28)16-18)33-22(30)11-8-17-6-4-3-5-7-17/h3-13,21,25H,14-16H2,1-2H3/b11-8+/t21-,25+,26+,27-/m1/s1 YesY
  • Key:BWZTYCFJIMYOHI-JKGZCERPSA-N YesY
  (verify)

14-Cinnamoyloxycodeinone is the most potent example in a series of opiate analgesic drugs discovered in the 1960s, with > ×100 times the potency of morphine.[1] It is a derivative of hydroxycodeinone, being the 14-cinnamate ester.[2] In another paper, Buckett assigns the potency as 177 with a range (depending on animal and test) of ×101 - ×310.[3] It may be of interest to researchers that the allyl group in this compound and in allylprodine overlay very closely.

See also

References

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  2. Lua error in package.lua at line 80: module 'strict' not found.
  3. 'The relationship between analgesic activity, acute toxicity and chemical structure in esters of 14-hydroxycodeinone' W.R.Buckett J. Pharm. Pharmacol., 1964, 16, Suppl., 68T-71T



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