6460. Neopine

Nomenclature

CAS number: 467-14-1
(5α,6α)-8,14-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol; β-codeine.
C18H21NO3; mol wt 299.36.
C 72.22%, H 7.07%, N 4.68%, O 16.03%.

Description and references

An alkaloid from opium, isomeric with codeine. Prepn from 14-bromocodeinone: Conroy, US 2797222 (1957 to Merck & Co.); from thebaine: S. Makleit et al., Acta Chim. Acad. Sci. Hung. 94, 161 (1977).

Chemical structure

Properties

Long needles from petr ether, mp 127.5°. [α]D23 -28° (c = 7.5 in chloroform). The absorption spectrum seems identical with that of codeine: Dobbie, Lauder, J. Chem. Soc. 99, 34 (1911). Solubilities about the same as those of codeine, q.v.

Derivative

Hydrobromide.
C18H21NO3.HBr; mol wt 380.28.
C 56.85%, H 5.83%, N 3.68%, O 12.62%, Br 21.01%.

Properties

Prismatic crystals from water, darkens about 240°, dec 283°. [α]D23 +17° (c = 3.7). Relatively insol in water, making possible a separation from other more sol hydrobromides of various opium alkaloids.

Note

Incorrectly called hydroxycodeine, cf. L. J. Sargent, U. Weiss, J. Org. Chem. 25, 987 (1960).