3181. Dihydrothebaine

Nomenclature

CAS number: 561-25-1
(5α)-6,7-Didehydro-4,5-epoxy-3,6-dimethoxy-17-methylmorphinan.
C19H23NO3; mol wt 313.39.
C 72.82%, H 7.40%, N 4.47%, O 15.32%.

Description and references

Prepd by reduction of thebaine: Small et al., J. Am. Chem. Soc. 58, 1457 (1936); K. W. Bentley, The Chemistry of the Morphine Alkaloids (Oxford, 1954) p 204.

Chemical structure

Properties

Prisms from ethyl acetate, mp 162-163°. [α]D20 -267° (c = 1.02 in benzene). Sol in alcohol, benzene, ethyl acetate. Insol in water, alkalies.

Derivative

Methyl iodide.
C20H23NO4.CH3I; mol wt 483.34.
C 52.18%, H 5.42%, N 2.90%, O 13.24%, I 26.26%.

Properties

Rods from alc, mp 257°.