2546. Corydine

Nomenclature

CAS number: 476-69-7
(6aS)-5,6,6a,7-Tetrahydro-2,10,11-trimethoxy-6-methyl-4H-dibenzo[de,g]quinolin-1-ol; 2,10,11-trimethoxy-6aα-aporphin-1-ol; 1-hydroxy-2,10,11-trimethoxyaporphine.
C20H23NO4; mol wt 341.40.
C 70.36%, H 6.79%, N 4.10%, O 18.75%.

Description and references

The methyl ether of corytuberine. Occurs in Corydalis cava (L.) Schweigg & K"orte (C. tuberosa DC), Fumariaceae, in the dextrorotatory form. Isoln: Gadamer, Ziegenbein, Arch. Pharm. 240, 94 (1902). Structure: Sp"ath, Berger, Ber. 64, 2038 (1931). Synthesis: Hey, Palluel, J. Chem. Soc. 1957, 2926; Arumugam et al., Ber. 91, 40 (1958); Jackson, Martin, Chem. Commun. 1965, 142, 420; eidem, J. Chem. Soc. C 1966, 2222. uv spectrum: Shamma, Yao, J. Org. Chem. 36, 3253 (1971).

Chemical structure

Properties

Tetragonal prisms from ether, mp 149°. [α]D20 +204° (c = 1.6 in chloroform). Freely sol in chloroform, alcohol, ethyl acetate; moderately sol in ether.

Derivative

dl-Hydrochloride monohydrate.
C20H23NO4.HCl.H2O; mol wt 395.88.
C 60.68%, H 6.62%, N 3.54%, O 20.21%, Cl 8.96%.

Properties

Crystals from ethanol + ether, sinters at 205°, dec 228°. Sparingly sol in water.