14-Cinnamoyloxycodeinone

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.

14-Cinnamoyloxycodeinone
Identifiers
IUPAC name
  • 7,8-didehydro-4,5α-epoxy-14-cinnamoyl-3-methoxy-17-methylmorphinan-6-one
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC27H25NO5
Molar mass443.499 g·mol−1
3D model (JSmol)
SMILES
  • 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
  • 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 Y
  • Key:BWZTYCFJIMYOHI-JKGZCERPSA-N Y
  (verify)

See also

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.
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