Nomenclature
CAS number: 795-38-0
(5α,6β)-4,5-Epoxy-3-methoxy-17-methylmorphinan-6-ol; DHIC.
C
18H
23NO
3; mol wt 301.38.
C 71.73%, H 7.69%, N 4.65%, O 15.93%.
Description and references
Differs from dihydrocodeine only by the spatial
arrangement of the ‐CHOH‐ group. Prepn by catalytic reduction
of isocodeine: Speyer, Krauss, Ann. 432, 233 (1923); Lutz, Small, J. Am. Chem. Soc. 54, 4724 (1932); Rapoport,
Payne, J. Org. Chem. 15, 1097 (1950); by epimerization of dihydrocodeine: Baizer, US 2774762 (1956 to N.Y. Quinine
and Chem. Works).
Properties
Prisms from ethanol, mp 199-200°.Derivative
Acid tartrate.
C
18H
23NO
3.C
4H
6O
6; mol wt 451.47.
C 58.53%, H 6.47%, N 3.10%, O 31.89%.
Properties
Crystals, mp 192°, [α]D29 -65.3°.Derivative
Acid tartrate trihydrate.
C
18H
23NO
3.C
4H
6O
6.3H
2O; mol wt 505.51.
C 52.27%, H 6.98%, N 2.77%, O 37.98%.
Properties
Crystals from water, mp about 180°. [α]D26 -62.4° (c = 1.94). Soly
at 24° = 4.5 g/100 ml H2O.Derivative
Methiodide.
C
18H
23NO
3.CH
3I; mol wt 443.32.
C 51.48%, H 5.91%, N 3.16%, O 10.83%, I 28.63%.
Properties
Crystals from ethanol, dec 269-272°.