Article · Wikipedia archive · Last revised Jun 29, 2026

14-Cinnamoyloxycodeinone

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

Last revised
Jun 29, 2026
Read time
≈ 1 min
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Wikipedia ↗
14-Cinnamoyloxycodeinone
Identifiers
  • 7,8-didehydro-4,5α-epoxy-14-cinnamoyl-3-methoxy-17-methylmorphinan-6-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC27H25NO5
Molar mass443.499 g·mol−1
3D model (JSmol)
  • 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 checkY
  • Key:BWZTYCFJIMYOHI-JKGZCERPSA-N checkY
  (verify)

14-Cinnamoyloxycodeinone is the most potent example in a series of opiate analgesic drugs discovered in the 1960s, with over 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

See also

References

References

  1. Lien EJ, Tong GL, Srulevitch DB, Dias C (1978). "QSAR of narcotic analgetic agents" (PDF). NIDA Research Monograph. 1978 (22): 186–96. PMID 30907. Archived from the original (PDF) on 2011-10-15. Retrieved 2011-06-01.
  2. Buckett WR (November 1965). "Some pharmacological studies with 14-cinnamoyloxycodeinone". The Journal of Pharmacy and Pharmacology. 17 (11): 759–60. doi:10.1111/j.2042-7158.1965.tb07602.x. PMID 4379812. S2CID 40424914.
  3. Buckett WR (December 1964). "The relationship between analgesic activity, acute toxicity and chemical structure in esters of 14-hydroxycodeinone". The Journal of Pharmacy and Pharmacology. 16: SUPPL:68–71T. doi:10.1111/j.2042-7158.1964.tb07539.x. PMID 14265944. S2CID 23049905.