2927. Desomorphine

Nomenclature

CAS number: 427-00-9
4,5a-Epoxy-17-methylmorphinan-3-ol; dihydrodesoxymorphine-D; Permonid.
C17H21NO2; mol wt 271.35.
C 75.25%, H 7.80%, N 5.16%, O 11.79%.

Description and references

Synthesis, physical data: L. F. Small et al., J. Am. Chem. Soc. 55, 3863 (1933).

Chemical structure

Properties

Rectangular plates from acetone-water. Sublimes in high vacuum between 140° and 170°. Anhydr base, mp 189°. [α]D28 -77° (c = 1.6 in methanol). Sol in acetone, ethyl acetate. Alcoholic solns darken and acquire a reddish color.

Derivative

Hemihydrate.

Properties

Crystals from ethyl acetate, mp 162-164°. [α]D28 -79° (c = 1.08 in ethyl acetate).

Derivative

Hydrochloride.
C17H21NO2.HCl; mol wt 307.82.
C 66.33%, H 7.20%, N 4.55%, O 10.40%, Cl 11.52%.

Properties

Crystals from alcohol, [α]D27 -67° (c = 0.90). Very sol in water.

Derivative

Hydrogen sulfate dihydrate.
(C17H21NO2)2.H2SO4.2H2O; mol wt 676.82.
C 60.34%, H 7.15%, N 4.14%, O 23.64%, S 4.74%.

Properties

Scales, plates from water, brown at 210°, unmelted at 230°. Sol in 40 parts water; freely sol in hot water. Soln is stable to boiling. [α]D29 -60° (c = 1.43).

Note

This is a controlled substance (opium derivative): 21 CFR, 1308.11.

Therapeutic Category

Analgesic.

Keywords

Analgesic; Opioids; Phenanthrenes