1736. Canadine

Nomenclature

CAS number: 522-97-4
5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine; 9,10-dimethoxy-2,3-(methylenedioxy)berbine; 5,6,13,13a-tetrahydro-9,10-dimethoxy-2,3-(methylenedioxy)-8H-dibenzo[a,g]quinolizine; tetrahydroberberine; xanthopuccine.
C20H21NO4; mol wt 339.39.
C 70.78%, H 6.24%, N 4.13%, O 18.86%.

Description and references

A protoberberine alkaloid from Corydalis cava (L.), Schweigg & Korte (C. tuberosa DC.), Fumariaceae: Sp"ath, Julian, Ber. 64, 1131 (1931). Prepn by reduction of berberine: Bersch, Seufert, ibid. 70, 1121 (1937); Awe, Hertel, Arch. Pharm. 288, 516 (1955); Russell, J. Am. Chem. Soc. 78, 3115 (1956). Configuration: Corrodi, Hardegger, Helv. Chim. Acta 39, 889 (1956). Other syntheses: Kametani et al., J. Chem. Soc. C 1969, 2036; 1971, 2709; M. Cushman, F. W. Dekon, J. Org. Chem. 44, 407 (1979); K. Iwasa et al., ibid. 46, 4744 (1981); N. S. Narasimhan et al., Tetrahedron Lett. 22, 2797 (1981). Pharmacology: F. Sadritdinov, M. B. Sultanov, C.A. 66, 74714v (1967). Review: R. H. F. Manske, H. L. Holmes, The Alkaloids vol. 4 (Academic Press, New York, 1954) pp 91-92.

Chemical structure

Properties

LD50 in mice (mg/kg): 940 orally; 790 s.c.; 100 i.v. (Sadritdinov, Sultanov).

Derivative

d-Form.

Nomenclature

CAS number: 2086-96-6

Properties

mp 132°. [α]D15 +299° (chloroform). Sol in aq methanol.

Derivative

l-Form.

Nomenclature

CAS number: 5096-57-1

Properties

Crystals from methanol, mp 135°. [α]D22 -308°; -317° (c = 0.28; 0.4, both in methanol). Sol in aq methanol.

Derivative

dl-Form.

Nomenclature

CAS number: 29074-38-2

Properties

mp 172° (Sp"ath, Julian), also reported as 163-165° (Cushman, Dekon). uv max (95% ethanol): 209, 284 nm (ε 28,300; 5200). Sol in aq methanol.