Title: Isocorydine
CAS Registry Number: 475-67-2
CAS Name: (6aS)-5,6,6a,7-Tetrahydro-1,2,10-trimethoxy-6-methyl-4H-dibenzo[de,g]quinolin-11-ol
Additional Names: 1,2,10-trimethoxy-6aa-aporphin-11-ol; 11-hydroxy-1,2,10-trimethoxyaporphine; artabotrine; luteanine
Molecular Formula: C20H23NO4
Molecular Weight: 341.40
Percent Composition: C 70.36%, H 6.79%, N 4.10%, O 18.75%
Literature References: From tubers of Corydalis cava (L.) Schweigg. & Korte (C. tuberosa DC., Fumariaceae); Artabotrys suaveolens Blume, Anonaceae; Papaver oreophilum Rupr.; Phoebe clemensii Allen (Lauraceae) and others. Isoln: Gadamer, Arch. Pharm. 249, 669 (1911); Johns, Lamberton, Aust. J. Chem. 20, 1277 (1967); Pfeifer, Mann, Pharmazie 23, 82 (1968). Structure: Späth, Berger, Ber. 64, 2038 (1931); Gulland et al., J. Chem. Soc. 1931, 2885; Barger, Sargent, ibid. 1939, 991. Identity with artabotrine: Schlittler, Huber, Helv. Chim. Acta 35, 111 (1952); with luteanine: Manske, Can. J. Res. 21B, 13 (1943). Total synthesis: Kametani et al., Tetrahedron 27, 5367 (1971). Pharmacology: Berezhinskaya et al., Farmakol. Toksikol. (Moscow) 31, 44 (1968), C.A. 68, 94521z (1968).
Properties: Plates from ethanol or acetone, mp 185°. [a]D20 +195° (chloroform). Sol in ether, chloroform, alcohol, acetone, alkali hydroxide. Practically insol in water, alkali carbonates.
Melting point: mp 185°
Optical Rotation: [a]D20 +195° (chloroform) |