5161. Isocorybulbine

Nomenclature

CAS number: 22672-74-8
(13S-trans)-5,8,13,13a-Tetrahydro-3,9,10-trimethoxy-13-methyl-6H-dibenzo[a,g]quinolizin-2-ol; 3,9,10-trimethoxy-13α-methyl-13aβ-berbin-2-ol; 2-hydroxy-13-methyl-3,9,10-trimethoxyberbine.
C21H25NO4; mol wt 355.43.
C 70.96%, H 7.09%, N 3.94%, O 18.01%.

Description and references

From tubers of Corydalis cava (L.) Schweigg. & Korte (C. tuberosa DC., Fumariaceae): Gadamer, Arch. Pharm. 240, 19 (1902). Structure: Spth, Dobrowsky, Ber. 58, 1274 (1925). Synthesis: Spth, Holter, ibid. 59, 2800 (1926). Abs configuration: P. W. Jeffs, Experientia 21, 690 (1965); K. Iwasa et al., J. Org. Chem. 46, 4744 (1981).

Chemical structure

Properties

Leaflets, mp 179-180°; also given as 187-188°. [α]D15 +301° in chloroform. Sol in alcohol, dil acids.

Derivative

Methiodide.
C21H25NO4.CH3I; mol wt 497.37.
C 53.13%, H 5.67%, N 2.82%, O 12.87%, I 25.52%.

Properties

Crystals, mp 218-221°.