Neopine
Title: Neopine
CAS Registry Number: 467-14-1
CAS Name: (5a,6a)-8,14-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol
Additional Names: b-codeine
Molecular Formula: C18H21NO3
Molecular Weight: 299.36
Percent Composition: C 72.22%, H 7.07%, N 4.68%, O 16.03%
Literature 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).
Properties: Long needles from petr ether, mp 127.5°. [a]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.
Melting point: mp 127.5°
Optical Rotation: [a]D23 -28° (c = 7.5 in chloroform)
 
Derivative Type: Hydrobromide
Molecular Formula: C18H21NO3.HBr
Molecular Weight: 380.28
Percent Composition: 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°. [a]D23 +17° (c = 3.7). Relatively insol in water, making possible a separation from other more sol hydrobromides of various opium alkaloids.
Optical Rotation: [a]D23 +17° (c = 3.7)
 
NOTE: Incorrectly called hydroxycodeine, cf. L. J. Sargent, U. Weiss, J. Org. Chem. 25, 987 (1960).

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