14-Cinnamoyloxycodeinone

Opioid analgesic drug 451560435 7,8-didehydro-4,5α-epoxy-14-cinnamoyl-3-methoxy-17-methylmorphinan-6-one 14-cinnamoyloxycodeinone2DCSD.svg skin-invert-image 220px 1,4-cinnamoyloxycodeinone 3D BS.png bg-transparent 220px correct CAS 751-01-9 correct FDA M9VES83RLJ 6438241 correct drugbank correct chemspider 4942728 27 25 1 5 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 correct chemspider 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 correct chemspider BWZTYCFJIMYOHI-JKGZCERPSA-N 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. Lien EJ, Tong GL, Srulevitch DB, Dias C QSAR of narcotic analgetic agents NIDA Research Monograph 1978 22 186–96 1978 30907 http://archives.drugabuse.gov/pdf/monographs/22.pdf 2011-06-01 dead https://web.archive.org/web/20111015120524/http://archives.drugabuse.gov/pdf/monographs/22.pdf 2011-10-15 It is a derivative of hydroxycodeinone, being the 14-cinnamate ester. Buckett WR Some pharmacological studies with 14-cinnamoyloxycodeinone The Journal of Pharmacy and Pharmacology 17 11 759–60 November 1965 4379812 10.1111/j.2042-7158.1965.tb07602.x 40424914 In another paper, Buckett assigns the potency as 177 with a range (depending on animal and test) of 101–310×. Buckett WR 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 14265944 10.1111/j.2042-7158.1964.tb07539.x 23049905 It may be of interest to researchers that the allyl group in this compound and in allylprodine overlay very closely. See also 14-Phenylpropoxymetopon 7-PET Methocinnamox N-Phenethylnormorphine N-Phenethyl-14-ethoxymetopon Phenomorphan RAM-378 Ro4-1539 References Category:4,5-Epoxymorphinans Category:Semisynthetic opioids Category:Mu-opioid receptor agonists