Isocodeine

Isocodeine

Names
IUPAC name (5α,6β)-3-Methoxy-17-methyl-7,8-didehydro-4,5-epoxymorphinan-6-ol
Other names 6-Isocodeine; α-Isocodeine
Identifiers
CAS Number	509-64-8
ChemSpider	4481821
Jmol interactive 3D	Image
InChI InChI=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 Key: OROGSEYTTFOCAN-KEMUOJQUSA-N InChI=1/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 Key: OROGSEYTTFOCAN-KEMUOJQUBO
SMILES O[C@@H]2\C=C/[C@H]5[C@@H]4N(CC[C@@]51c3c(O[C@H]12)c(OC)ccc3C4)C
Properties
Chemical formula	C18H21NO3
Molar mass	299.37 g·mol^−1
Melting point	173 to 174 °C (343 to 345 °F; 446 to 447 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Isocodeine is an opioid research chemical related to codeine. It is an epimer of codeine that can be prepared from it by a Mitsunobu reaction.^[1]

Dozens of derivatives and analogs of isocodeine and the related compound isomorphine have been produced.^[2]

References

1. Simon, Csaba; Hosztafi, Sándor; Makleit, Sándor (1991). "Application of the Mitsunobu Reaction for the Preparation of Isomorphine and Isocodeine Derivatives". Synthetic Communications 21 (3): 407–412. doi:10.1080/00397919108016763.
2. "Report of Committee on drug addiction, 1929-1941". National Research Council (US).