7919. Pseudomorphine

Nomenclature

CAS number: 125-24-6
(5′α,6'α)-7,7′,8,8′-Tetradehydro-4,5:4′,5′-diepoxy-17,17′-dimethyl-[2,2′-bimorphinan]-3,3′,6,6′-tetrol; 2,2′-bimorphine; pseudomorphine (C34 alkaloid).
C34H36N2O6; mol wt 568.66.
C 71.81%, H 6.38%, N 4.93%, O 16.88%.

Description and references

A dimolecular base formed by the gentle oxidation of morphine in alkaline soln. Refs: Broockmann, Polstorff, Ber. 13, 88 (1880); Bentley, Dyke, J. Chem. Soc. 1959, 2574. Review and bibliography: K. W. Bentley, The Chemistry of the Morphine Alkaloids (Oxford, 1954) p 54.

Derivative

Trihydrate.

Properties

Crystalline powder; levorotatory in acid soln. Becomes anhydr at 150° and dec at about 327°. Insol in cold water, alcohol, ether, dil H2SO4. Slightly sol in cold, more sol in hot ammonia; sol in fixed alkali hydroxide solns, in pyridine, aniline, benzyl alcohol, guaiacol.

Note

Name pseudomorphine is also used for the C17 alkaloid base.