Bulbocapnine
Title: Bulbocapnine
CAS Registry Number: 298-45-3
CAS Name: (7aS)-6,7,7a,8-Tetrahydro-11-methoxy-7-methyl-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinolin-12-ol
Additional Names: 10-methoxy-1,2-(methylenedioxy)-6aa-aporphin-11-ol
Molecular Formula: C19H19NO4
Molecular Weight: 325.36
Percent Composition: C 70.14%, H 5.89%, N 4.30%, O 19.67%
Literature References: From root of Corydalis cava (L.) Schweigg. & Körte (C. tuberosa DC), Fumariaceae and Dicentra canadensis Walp., Papaveraceae. Isoln: Freund, Josephi, Ber. 25, 2411 (1892); Manske, Can. J. Res. 7, 258 (1932). Pharmacology and toxicity study: H. Molitar, J. Pharmacol. Exp. Ther. 56, 85 (1936). Structure: Gadamer, Chem. Ztg. 34, 1004 (1910). Configuration: Ayer, Taylor, J. Chem. Soc. 1956, 472; Corrodi, Hardegger, Helv. Chim. Acta 39, 889 (1956). Synthesis: Kikkawa, C.A. 54, 4649b (1960). Peripheral-dopamine-receptor blocking activity: R. G. Pendleton et al., Arch. Pharmacol. 289, 171 (1975).
 
Derivative Type: dl-Form
Properties: Columns, mp 213-214°. Absorption max: Brustier, C.A. 49, 12127b (1955).
Melting point: mp 213-214°
 
Derivative Type: l-Form
Properties: Columns, mp 202-203°. [a]D22 -239°.
Melting point: mp 202-203°
Optical Rotation: [a]D22 -239°
 
Derivative Type: d-Form
Properties: Columns, mp 201-203°. [a]D22 +231°. Practically insol in water, sol in alcohol, chloroform. LD50 s.c. in mice: 195 mg/kg (Molitar).
Melting point: mp 201-203°
Optical Rotation: [a]D22 +231°
Toxicity data: LD50 s.c. in mice: 195 mg/kg
 
Derivative Type: Methyl ether
Molecular Formula: C20H21NO4
Molecular Weight: 339.39
Percent Composition: C 70.78%, H 6.24%, N 4.13%, O 18.86%
Properties: Crystals from petr ether, mp 129°. [a]D20+260°. Absorption max: Girardet, J. Chem. Soc. 1931, 2630.
Melting point: mp 129°
Optical Rotation: [a]D20+260°

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