2527. Coptisine

Nomenclature

CAS number: 3486-66-6
6,7-Dihydrobis[1,3]benzodioxolo[5,6-a:4′,5′-g]quinolizinium; 7,8,13,13a-tetradehydro-2,3:9,10-bismethylenedioxyberbinium; bis[methylenedioxy]protoberberine.
[C19H14NO4]+.

Description and references

From root of Coptis japonica Makino, Ranunculaceae. Extraction procedure: Kitasato, C.A. 21, 2700 (1927). Structure: Sp"ath, Posega, Ber. 62, 1029 (1929); cf. Huang-Minlon, Ber. 69, 1744 (1936). Prepn from rhoeageninediol: Klásek et al., Tetrahedron Lett. 1968, 4549.

Chemical structure

Derivative

Hydroxide.
C19H15NO5; mol wt 337.33.
C 67.65%, H 4.48%, N 4.15%, O 23.71%.

Properties

Yellowish needles from alc, mp 218°. Absorption spectrum: Kitasato, Acta Phytochim. 3, 175 (1927). Very slightly sol in water; sparingly in alcohol; sol in alkalies.

Derivative

Chloride.

Properties

Orange prisms, not melted at 300°.

Derivative

Iodide.

Properties

Yellow needles, dec above 280°.

Derivative

Sulfate.

Properties

Yellow crystals, insol in water and alcohol (enables separation from berberine and worenine).