Codeinone

{{chembox

| Verifiedfields = changed

| verifiedrevid = 460106136

| ImageFile = Codeinone.svg

| ImageSize =

| IUPACName = 3-Methoxy-17-methyl-7,8-didehydro-4,5α-epoxymorphinan-6-one

| PIN = (4R,4aR,7aR,12bS)-9-Methoxy-3-methyl-2,3,4,4a,7,7a-hexahydro-1H-4,12-methano[1]benzofuro[3,2-e]isoquinolin-7-one

| OtherNames =

|Section1={{Chembox Identifiers

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

| ChemSpiderID = 4573639

| InChI = 1/C18H19NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-12,17H,7-9H2,1-2H3/t11-,12+,17-,18-/m0/s1

| InChIKey = XYYVYLMBEZUESM-CMKMFDCUBF

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

| StdInChI = 1S/C18H19NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-12,17H,7-9H2,1-2H3/t11-,12+,17-,18-/m0/s1

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

| StdInChIKey = XYYVYLMBEZUESM-CMKMFDCUSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 467-13-0

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

| UNII = 22B5AW0ANN

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 257627

| PubChem = 5459910

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 18399

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C06171

| SMILES = O=C1\C=C/[C@H]5[C@@H]4N(CC[C@@]52c3c(O[C@@H]12)c(OC)ccc3C4)C

}}

|Section2={{Chembox Properties

| Formula = | C=18 | H=19 | N=1 | O=3

| MolarMass = 297.35 g/mol

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility = }}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt = }}

}}

Codeinone is an isoquinolone alkaloid{{cite web |title=codeinone (CHEBI:18399) |url=https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:18399 |website=www.ebi.ac.uk |access-date=28 October 2023}} found in the opium poppy.{{cite journal |last1=Lenz |first1=Rainer |last2=Zenk |first2=Meinhart H. |title=Stereoselective reduction of codeinone, the penultimate enzymic step during morphine biosynthesis in Papaver somniferum |journal=Tetrahedron Letters |date=April 1995 |volume=36 |issue=14 |pages=2449–2452 |doi=10.1016/0040-4039(95)00278-K}} As an analgesic, it is one-third the potency of codeine. It is an important intermediate in the production of hydrocodone–a painkiller about three-quarters the potency of morphine{{Citation needed|date=September 2008}}–as well as of oxycodone,[https://www.erowid.org/archive/rhodium/chemistry/oxycodone.html Synthesis of Oxycodone from Codeine.] Aug 2004 static snapshot of Rhodium site archive hosted by Erowid, May 2005 though the latter can also be synthesized from thebaine.[https://www.scribd.com/doc/77193676/Oxycodone-Synthesis Oxycodone / 14-hydroxydihydrocodeinone Synthesis; with alternative synthesis of 14-hydroxycodeinone intermediate.] J. Med. Chem., 1974, 17, 1117