Title: Dicentrine
CAS Registry Number: 517-66-8
CAS Name: 6,7,7a,8-Tetrahydro-10,11-dimethoxy-7-methyl-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline
Additional Names: 9,10-dimethoxy-1,2-(methylenedioxy)aporphine; 1,2-methylenedioxy-9,10-dimethoxyaporphine
Molecular Formula: C20H21NO4
Molecular Weight: 339.39
Percent Composition: C 70.78%, H 6.24%, N 4.13%, O 18.86%
Literature References: d-Form prevalent in nature. Found in Dicentra pusilla Sieb. & Zucc., Fumariaceae and several other Dicentra species. Related to actinodaphnine, and laurotetanine, q.q.v. Isoln: Y. Asahina, Arch. Pharm. 247, 201 (1909). Isoln of l-form from Duguetia A. St. Hil., Annonaceae: Casagrande, Ferrari, Farmaco Ed. Sci. 25, 442 (1970). Synthesis of dl-form: Haworth et al., J. Chem. Soc. 127, 2018 (1925); Cava et al., Tetrahedron 29, 2245 (1973). Resolution of isomers: Haworth et al., J. Chem. Soc. 129, 29 (1926).
Derivative Type: dl-Form
Properties: Prisms from methanol, mp 178-179°. Freely sol in chloroform, ethyl acetate, acetone, benzene, hot alcohol. Moderately sol in ether, cold alcohol. Absorption max: Girardet, J. Chem. Soc. 1931, 2630.
Melting point: mp 178-179°
Derivative Type: d-Form
Properties: Long prisms from ether. mp 169°. [a]D17 +64.1° (c = 1.433 in chloroform). Freely sol in alcohol, ethyl acetate, benzene.
Melting point: mp 169°
Optical Rotation: [a]D17 +64.1° (c = 1.433 in chloroform)
Derivative Type: l-Form
Properties: Long prisms from ether. mp 169°. [a]D17 -63.5° (c = 1.70 in chloroform).
Melting point: mp 169°
Optical Rotation: [a]D17 -63.5° (c = 1.70 in chloroform)
Derivative Type: dl-Hydrochloride
Molecular Formula: C20H21NO4.HCl
Molecular Weight: 375.85
Percent Composition: C 63.91%, H 5.90%, N 3.73%, O 17.03%, Cl 9.43%
Properties: Small needles from water, dec 263-265°.
Derivative Type: dl-Methiodide monohydrate
Molecular Formula: C20H21NO4.CH3I.H2O
Molecular Weight: 499.34
Percent Composition: C 50.51%, H 5.25%, N 2.81%, O 16.02%, I 25.41%
Properties: Plates, mp 228-229°.
Melting point: mp 228-229°

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