isocodeine

{{Chembox

| ImageFile = Isocodeine structure.svg

| ImageSize = 180px

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

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

| OtherNames = 6-Isocodeine; α-Isocodeine

|Section1={{Chembox Identifiers

| CASNo = 509-64-8

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

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

| UNII = XWN5Y2Y8ZQ

| PubChem = 5324288

| EC_number = 208-101-3

| ChemSpiderID = 4481821

| SMILES = O[C@@H]2\C=C/[C@H]5[C@@H]4N(CC[C@@]51c3c(O[C@H]12)c(OC)ccc3C4)C

| StdInChI = 1S/C18H21NO3/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/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13+,17-,18-/m0/s1

| StdInChIKey = OROGSEYTTFOCAN-KEMUOJQUSA-N

}}

|Section2={{Chembox Properties

| C=18 | H=21 | N=1 | O=3

| Appearance =

| Density =

| MeltingPtC = 173 to 174

| MeltingPt_ref = {{Cite journal | author = Simon, Csaba | journal = Synthetic Communications | year = 1991 | volume = 21 | issue = 3 | pages = 407–412 | doi = 10.1080/00397919108016763 | title = Application of the Mitsunobu Reaction for the Preparation of Isomorphine and Isocodeine Derivatives | last2 = Hosztafi | first2 = Sándor | last3 = Makleit | first3 = Sándor}}

| BoilingPt =

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

| GHSPictograms = {{GHS06}}{{GHS07}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|301|302|331}}

| PPhrases = {{P-phrases|261|264|270|271|301+310|301+312|304+340|311|321|330|403+233|405|501}}

}}

}}

Isocodeine is an opioid research chemical related to codeine. It is an epimer of codeine that can be prepared from codeine via a Mitsunobu reaction.

Dozens of derivatives and analogs of isocodeine and the related compound isomorphine have been produced.{{cite report | publisher = National Research Council (US) | title = Report of Committee on drug addiction, 1929-1941}} One of these, dihydroisocodeine is a pharmaceutical four times stronger than dihydrocodeine and thus six times stronger than codeine which was used more extensively in the past in Continental Europe and other locales. Other isomers of codeine include allocodeine, pseudocodeine, heterocodeine and substances with intermediate qualities such as pseudoallocodeine and formylallocodeine can be prepared in the laboratory.Report of the Committee On Drug Addiction 1929-1941 with Monographs, 1941, National Research Council (US) Washington DC, 1116 pages (Chapter 7)