Hydroxycodeinone

Title: Hydroxycodeinone
CAS Registry Number: 508-54-3
CAS Name: 5a-7,8-Didehydro-4,5a-epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one
Additional Names: 14-hydroxycodeinone
Molecular Formula: C18H19NO4
Molecular Weight: 313.35
Percent Composition: C 68.99%, H 6.11%, N 4.47%, O 20.42%
Literature References: Preparation from thebaine: Freund, Speyer, J. Prakt. Chem. 94, 135 (1916). From codeine: Merck, DE 411530; Frdl. 15, 1516; K. W. Bentley, The Chemistry of the Morphine Alkaloids (Oxford, 1954). Improved synthesis: F. M. Hauser et al., J. Med. Chem. 17, 1117 (1974). Isoln from Papaver bracteatum Lindl.: H. G. Theuns et al., Phytochemistry 16, 753 (1977).
Properties: Plates from 96% alcohol + few drops chloroform, dec 275°. Freely sol in CHCl3, methyl Cellosolve, petr ether, ethyl acetate; slightly sol in alcohol. Practically insol in water, ether; also insol in aq alkaline solns.
Derivative Type: Hydrochloride monohydrate
Molecular Formula: C18H19NO4.HCl.H2O
Molecular Weight: 367.82
Percent Composition: C 58.78%, H 6.03%, N 3.81%, O 21.75%, Cl 9.64%
Properties: Rods from water, dec 285-286°. [a]D20 -150° (c = 2.5).
Optical Rotation: [a]D20 -150° (c = 2.5)
NOTE: This is a controlled substance (opiate): 21 CFR, 1308.12.
Hydroxydione Sodium Hydroxyglutamic Acid Hydroxylamine Hydroxylupanine Hydroxymercurichlorophenols