Isocodeine

Chemical compound From Wikipedia, the free encyclopedia

Isocodeine

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.[1]

Quick Facts Names, Identifiers ...
Isocodeine
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Names
IUPAC name
3-Methoxy-17-methyl-7,8-didehydro-4,5α-epoxymorphinan-6β-ol
Systematic IUPAC name
(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
Other names
6-Isocodeine; α-Isocodeine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.366
EC Number
  • 208-101-3
UNII
  • 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
  • O[C@@H]2\C=C/[C@H]5[C@@H]4N(CC[C@@]51c3c(O[C@H]12)c(OC)ccc3C4)C
Properties
C18H21NO3
Molar mass 299.370 g·mol−1
Melting point 173 to 174 °C (343 to 345 °F; 446 to 447 K)[1]
Hazards
GHS labelling:
GHS06: ToxicGHS07: Exclamation mark
Danger
H301, H302, H331
P261, P264, P270, P271, P301+P310, P301+P312, P304+P340, P311, P321, P330, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dozens of derivatives and analogs of isocodeine and the related compound isomorphine have been produced.[2] 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.[3]

References

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