Oripavine
Title: Oripavine
CAS Registry Number: 467-04-9
CAS Name: (5a)-6,7,8,14-Tetrahydro-4,5-epoxy-6-methoxy-17-methylmorphinan-3-ol
Additional Names: O3-demethylthebaine
Molecular Formula: C18H19NO3
Molecular Weight: 297.35
Percent Composition: C 72.71%, H 6.44%, N 4.71%, O 16.14%
Literature References: From Papaver orientale L., and P. bracteatum Lindl., Papaveraceae: Junusov et al., Ber. 68, 2158 (1935); Kiselev, Konovalova, J. Gen. Chem. USSR 18, 142 (1948). Identity of O-methyl derivative with thebaine: eidem, Zh. Obshch. Khim. 18, 855 (1948). Biosynthesis: Gross, Dawson, Biochemistry 2, 186 (1963). Reviews: H. L. Holmes in The Alkaloids vol. II, Manske, Holmes, Eds. (Academic Press, New York, 1952) p 167; K. W. Bentley, The Chemistry of the Morphine Alkaloids (Oxford, 1954) pp 192-196. Synthesis from morphine: Barber, Rapoport, J. Med. Chem. 18, 1074 (1975).
Properties: Crystals, mp 200-201°. [a]D20 -211.8°.
Melting point: mp 200-201°
Optical Rotation: [a]D20 -211.8°
 
Derivative Type: Hydrochloride
Molecular Formula: C18H19NO3.HCl
Molecular Weight: 333.81
Percent Composition: C 64.77%, H 6.04%, N 4.20%, O 14.38%, Cl 10.62%
Properties: Crystals, dec 244-245°.
 
Derivative Type: Methiodide
Molecular Formula: C18H19NO3.CH3I
Molecular Weight: 439.29
Percent Composition: C 51.95%, H 5.05%, N 3.19%, O 10.93%, I 28.89%
Properties: Crystals, dec 207-208°.

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