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
Clinical data
Legal status
?
Identifiers
CAS number 751-01-9 YesY
ATC code ?
PubChem CID 6438241
ChemSpider 4942728 YesY
Chemical data
Formula C27H25NO5 
Mol. mass 443.490 g/mol
 YesY (what is this?)  (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[edit]

References[edit]

  1. ^ Lien, E. J.; Tong, G. L.; Srulevitch, D. B.; Dias, C. (1978). "QSAR of Narcotic Analgetic Agents" (pdf). NIDA Research Monograph 1978 (22): 186–196. PMID 30907. 
  2. ^ Buckett, W. R. (1965). "Some Pharmacological Studies With 14-Cinnamoyloxycodeinone". The Journal of Pharmacy and Pharmacology 17 (11): 759–760. PMID 4379812. 
  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