6867. Oripavine
Nomenclature
CAS number: 467-04-9
(5α)-6,7,8,14-Tetrahydro-4,5-epoxy-6-methoxy-17-methylmorphinan-3-ol; O3-demethylthebaine. C18H19NO3; mol wt 297.35.
C 72.71%, H 6.44%, N 4.71%, O 16.14%.
Description and 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°. [α]D20 -211.8°.Derivative
Hydrochloride.C18H19NO3.HCl; mol wt 333.81.
C 64.77%, H 6.04%, N 4.20%, O 14.38%, Cl 10.62%.
Properties
Crystals, dec 244-245°.Derivative
Methiodide.C18H19NO3.CH3I; mol wt 439.29.
C 51.95%, H 5.05%, N 3.19%, O 10.93%, I 28.89%.