Chemistry:14-Cinnamoyloxycodeinone

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Short description: Opioid analgesic drug
14-Cinnamoyloxycodeinone
14-cinnamoyloxycodeinone2DCSD.svg
1,4-cinnamoyloxycodeinone 3D BS.png
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC27H25NO5
Molar mass443.499 g·mol−1
3D model (JSmol)
  (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

References

  1. "QSAR of narcotic analgetic agents". NIDA Research Monograph 1978 (22): 186–96. 1978. PMID 30907. http://archives.drugabuse.gov/pdf/monographs/22.pdf. Retrieved 2011-06-01. 
  2. "Some pharmacological studies with 14-cinnamoyloxycodeinone". The Journal of Pharmacy and Pharmacology 17 (11): 759–60. November 1965. doi:10.1111/j.2042-7158.1965.tb07602.x. PMID 4379812. 
  3. "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. December 1964. doi:10.1111/j.2042-7158.1964.tb07539.x. PMID 14265944.