14-Cinnamoyloxycodeinone

{{Short description|Opioid analgesic drug}}

{{Drugbox

| verifiedrevid = 451560435

| IUPAC_name = 7,8-didehydro-4,5α-epoxy-14-cinnamoyl-3-methoxy-17-methylmorphinan-6-one

| image = 14-cinnamoyloxycodeinone2DCSD.svg

| image_class = skin-invert-image

| width = 220px

| image2 = 1,4-cinnamoyloxycodeinone 3D BS.png

| image_class2 = bg-transparent

| width2 = 220px

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| protein_bound =

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| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 751-01-9

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = M9VES83RLJ

| ATC_prefix =

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| PubChem = 6438241

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4942728

| synonyms =

| C=27 | H=25 | N=1 | O=5

| 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

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = 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.{{cite journal | vauthors = Lien EJ, Tong GL, Srulevitch DB, Dias C | title = QSAR of narcotic analgetic agents | journal = NIDA Research Monograph | volume = 1978 | issue = 22 | pages = 186–96 | year = 1978 | pmid = 30907 | url = http://archives.drugabuse.gov/pdf/monographs/22.pdf | access-date = 2011-06-01 | url-status = dead | archive-url = https://web.archive.org/web/20111015120524/http://archives.drugabuse.gov/pdf/monographs/22.pdf | archive-date = 2011-10-15 }} It is a derivative of {{Not a typo|hydroxycodeinone}}, being the 14-cinnamate ester.{{cite journal | vauthors = Buckett WR | title = Some pharmacological studies with 14-cinnamoyloxycodeinone | journal = The Journal of Pharmacy and Pharmacology | volume = 17 | issue = 11 | pages = 759–60 | date = November 1965 | pmid = 4379812 | doi = 10.1111/j.2042-7158.1965.tb07602.x | s2cid = 40424914 }} In another paper, Buckett assigns the potency as 177 with a range (depending on animal and test) of 101–310×.{{cite journal | vauthors = Buckett WR | title = The relationship between analgesic activity, acute toxicity and chemical structure in esters of 14-hydroxycodeinone | journal = The Journal of Pharmacy and Pharmacology | volume = 16 | pages = SUPPL:68–71T | date = December 1964 | pmid = 14265944 | doi = 10.1111/j.2042-7158.1964.tb07539.x | s2cid = 23049905 }} It may be of interest to researchers that the allyl group in this compound and in allylprodine overlay very closely.