2492. Columbamine

Nomenclature

CAS number: 3621-36-1
5,6-Dihydro-2-hydroxy-3,9,10-trimethoxydibenzo[a,g]quinolizinium; 7,8,13,13α-tetradehydro-2-hydroxy-3,9,10-trimethoxyberbinium.
[C20H20NO4]+.

Description and references

Found in Jatrorrhiza palmata (DC.) Miers (J. columba Miers), Menispermaceae: Breslau, Arch. Pharm. 245, 586 (1908); Sp"ath, Burger, Ber. 59, 1486 (1926); Reed, Diss. Abstr. 23, 3638 (1963); from Berberis lambertii R. N. Parker, Berberidaceae: Chatterjee, Banerjee, J. Indian Chem. Soc. 30, 705 (1953). Synthesis from berberine: Cava, Reed, J. Org. Chem. 32, 1640 (1967).

Chemical structure

Properties

The free base has not been described, but its quaternary salts are known.

Derivative

Chloride hemipentahydrate.
C20H20ClNO4.2 1/2 H2O; mol wt 418.87.
C 57.35%, H 6.02%, Cl 8.46%, N 3.34%, O 24.83%.

Properties

Orange-yellow needles, mp 194°. Sol in water, alcohol.

Derivative

Chloride tetrahydrate.
C20H20ClNO4.4H2O; mol wt 445.89.
C 53.87%, H 6.33%, Cl 7.95%, N 3.14%, O 28.71%.

Properties

Orange-yellow prisms, mp 184°.

Derivative

Iodide.

Properties

Orange-yellow needles, mp 224°. Sol in water, alcohol.