2550. Corytuberine

Nomenclature

CAS number: 517-56-6
(6aS)-5,6,6a,7-Tetrahydro-2,10-dimethoxy-6-methyl-4H-dibenzo[de,g]quinoline-1,11-diol; 2,10-dimethoxy-6aα-aporphine-1,11-diol; 1,11-dihydroxy-2,10-dimethoxyaporphine.
C19H21NO4; mol wt 327.37.
C 69.71%, H 6.47%, N 4.28%, O 19.55%.

Description and references

In Corydalis cava (L.) Schweigg & K"orte (C. tuberosa DC), in Dicentra formosa (Andr.) Walp., Fumariaceae. Isoln: Sp"ath, Berger, Ber. 64, 2038 (1931); Manske, Can. J. Res. 10, 521 (1934). Synthesis of (±)-form: Tomita, Kikkawa, JP 58 6466 (1958 to Shionogi), C.A. 54, 1584i (1960); T. Kametani, M. Ihara, J. Chem. Soc. Perkin Trans. 1 1980, 629. Biosynthesis studies: Blaschke, Biochem. Physiol. Alkaloide, Int. Symp., 4th, K. Mothes, Ed. (Akad.-Verlag, Berlin, 1972) pp 283-286. Biomimetric total synthesis: T. Kametani et al., Heterocycles 5, 175 (1976).

Chemical structure

Derivative

Pentahydrate.

Properties

Leaflets, plates, turning gray on exposure to light. mp 240° dec (dry). uv max (methanol): 227, 272, 311.5 nm. Sol in alc, hot water; slightly sol in ether, chloroform, ethyl acetate. [α]D20 +283° (alc). The dried crystals are hygroscopic and quickly attract 1 mol H2O from the air.

Derivative

Hydrochloride.
C19H21NO4.HCl; mol wt 363.84.
C 62.72%, H 6.09%, N 3.85%, O 17.59%, Cl 9.74%.

Properties

Crystals from alcohol-ether, dec above 250°; [α]D20 +168°; sparingly sol in water.

Derivative

Methyl ether see Corydine.