6690. Norcodeine

Nomenclature

CAS number: 467-15-2
(5α,6α)-7,8-Didehydro-4,5-epoxy-3-methoxymorphinan-6-ol; N-desmethylcodeine; normorphine 3-methyl ether.
C17H19NO3; mol wt 285.34.
C 71.56%, H 6.71%, N 4.91%, O 16.82%.

Description and references

Prepn from acetylcodeine: von Braun, Ber. 47, 2312 (1914); DE 286743 (1914); Chem. Zentralbl. 1915, II, 862; Frdl. 12, 741; Houben 4, 588; cf. DE 289273 (1914); from codeine N-oxide: Diels, Fischer, Ber. 49, 1723 (1916); from codeine: Speyer, Walther, Ber. 63, 822 (1930).

Chemical structure

Properties

Plates or needles from acetone or ethyl acetate, mp 185°. Sparingly sol in water, ether. Moderately sol in acetone. Freely sol in hot methanol, ethanol.

Derivative

Hydrochloride trihydrate.
C17H19NO3.HCl.3H2O; mol wt 375.84.
C 54.33%, H 6.97%, N 3.73%, O 25.54%, Cl 9.43%.

Properties

Needles from water. When anhydr, dec 309°. Sparingly sol in cold water, more sol in hot water. Freely sol in methanol, ethanol. Almost insol in acetone.

Derivative

Sulfate.
2C17H19NO3.H2SO4; mol wt 668.75.
C 61.06%, H 6.03%, N 4.19%, O 23.92%, S 4.79%.

Properties

Crystals, freely sol in water.

Derivative

Acetate (salt).
C17H19NO3.C2H4O2; mol wt 345.39.
C 66.07%, H 6.71%, N 4.06%, O 23.16%.

Properties

Crystals, freely sol in water.