14-Cinnamoyloxycodeinone

14-Cinnamoyloxycodeinone
	File:14-cinnamoyloxycodeinone2DCSD.svg
	File:1,4-cinnamoyloxycodeinone 3D BS.png
Identifiers
	IUPAC name 7,8-didehydro-4,5α-epoxy-14-cinnamoyl-3-methoxy-17-methylmorphinan-6-one;
CAS Number	751-01-9 ;
PubChem CID	6438241;
ChemSpider	4942728 ;
UNII	M9VES83RLJ;
E number	{{#property:P628}}
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Chemical and physical data
Formula	C27H25NO5
Molar mass	443.499 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:BWZTYCFJIMYOHI-JKGZCERPSA-N ;
	(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.

References

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[1]

[2]

[3]

14-Cinnamoyloxycodeinone

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Identifiers
File:14-cinnamoyloxycodeinone2DCSD.svg
File:1,4-cinnamoyloxycodeinone 3D BS.png
IUPAC name 7,8-didehydro-4,5α-epoxy-14-cinnamoyl-3-methoxy-17-methylmorphinan-6-one
CAS Number	751-01-9^Y
PubChem CID	6438241
ChemSpider	4942728^Y
UNII	M9VES83RLJ
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C₂₇H₂₅NO₅
Molar mass	443.499 g·mol⁻¹
3D model (JSmol)	Interactive image
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)

14-Cinnamoyloxycodeinone

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References

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