8858. Stylopine

Nomenclature

CAS number: 7461-02-1
6,7,12b,13-Tetrahydro-4H-bis[1,3]benzodioxolo[5,6-a:4′,5′-g]quinolizine; 2,3:9,10-bis(methylenedioxy)-13a-berbine; tetrahydrocoptisine.
C19H17NO4; mol wt 323.34.
C 70.58%, H 5.30%, N 4.33%, O 19.79%.

Description and references

From root of Stylophorum diphyllum (Michx.) Nutt, Corydalis cava Schwg. and Chelidonium majus L., Papaveraceae: Schlotterbeck, Watkins, Ber. 35, 7 (1902); Spth, Julian, Ber. 64, 1131 (1931); Manske, Can. J. Res. B20, 53 (1942); Slavik, Collect. Czech. Chem. Commun. 20, 198 (1955); Bandelin, Malesh, J. Am. Pharm. Assoc. 45, 702 (1956); Slavik, Collect. Czech. Chem. Commun. 26, 2933 (1961).

Chemical structure

Derivative

dl-Form.

Properties

Crystals from chloroform + methanol, mp 222-224°.

Derivative

Hydrochloride.
C19H18ClNO4; mol wt 359.80.
C 63.43%, H 5.04%, Cl 9.85%, N 3.89%, O 17.79%.

Properties

Needles from methanol + HCl, mp 266-269°.

Derivative

l-Form.

Properties

Needles from chloroform + ethanol, mp 203°. [α]D25 300° (c = 0.53 in chloroform). Practically insol in water; sol in alc, glacial acetic acid; slightly sol in dil acids.

Derivative

d-Form.

Properties

Crystals from alcohol, mp 203-204°. [α]D25 +310° (c = 0.88 in chloroform). Sol in chloroform; slightly sol in ether, ethanol, methanol.