12-02607. Corycavamine [Archived]

Nomenclature

CAS number: 521-85-7
(14R)-4,6,7,14-Tetrahydro-5,14-dimethylbis[1,3]benzodioxolo[4,5-c:5′,6′-g]azecin-13(5H)-one; 7,13-dimethyl-2,3:9,10-bis(methylenedioxy)-7,13a-secoberbin-13a-one.
C21H21NO5; mol wt 367.40.
C 68.65%, H 5.76%, N 3.81%, O 21.77%.

Description and references

In Corydalis cava (L.) Schweigg & Korte (C. tuberosa DC.), Fumariaceae: Gadamer et al., Arch. Pharm. 240, 81 (1902). Structure: von Bruchhausen, ibid. 263, 570 (1925). Corycavamine and corycavine originally depicted as the keto and enol tautomers, resp.

Chemical structure

Properties

Rhombic columns from ether and alcohol, mp 149°. Is converted to corycavine at the mp. [α]D20 +167° (chloroform). Sol in alcohol and chloroform.

Derivative

dl-Form.

Nomenclature

Corycavine.

Properties

Orthorhombic plates from alc, mp 218°, mp 222° in vac. Very slightly sol in water; sol in abs alcohol and chloroform; unstable to light.

Status

This monograph has been retired and is no longer subject to revision or update.