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83-58-9

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83-58-9 Structure

83-58-9 Structure
IdentificationBack Directory
[Name]

3-[(2R)-2-hydroxy-3-methyl-butyl]-4,8-dimethoxy-1-methyl-quinolin-2-on e
[CAS]

83-58-9
[Synonyms]

C10710
Lunacridine
3-[(2R)-2-hydroxy-3-methyl-butyl]-4,8-dimethoxy-1-methyl-quinolin-2-on e
[Molecular Formula]

C17H23NO4
[MOL File]

83-58-9.mol
Chemical PropertiesBack Directory
[Melting point ]

86-87°
[alpha ]

25589 +28.1°; 25436 +76.5° (c = 0.935 in ethanol)
Hazard InformationBack Directory
[Description]

This alkaloid was first described by Boorsma who obtained it from the bark of Lunasia costulata Miq (Syn. L. amara Blanco). The base is a quinolone derivative and crystallizes as colourless needles from AcOEt. It is dextrorotatory having [α]24D + 30.1 ° and [α]24436 + 81.8°. Boorsma gives a specific rotation of [α]28D + 31.6°. The solutions of the alkaloid show a weak blue fluorescence in artificial light. A crystalline perchlorate is known, m.p. 146-8°C and 193-5°C after intermediate solidification. This salt is also dextrorotatory with [α]2558925436+ 60.7°. The structure has been demonstrated to be 3-(2-hydroxy-3- methylbutyl)-4: 8-dimethoxy-l-methyl-2-quinolone. The alkaloid described under this name by Dieterle and Beyl appears to be identical with lunamarine (q.v.).
[Definition]

ChEBI:Lunacridine is a member of quinolines.
[References]

Boorsma., Meded. Lands. Plant., 31, 13, 126 (1899)
Boorsma.,Bull. Inst. Bot. Buit., No. 31, 8, 25 (1904)
Dieterle, Beyl., Arch. Pharm., 275, 174 (1937)
Steldt, Chen.,J. Amer. Pharm. Assoc., 32, 107 (1943)
Goodwin, Horning.,J. Amer. Chem. Soc., 81, 1908 (1959)
Clarke, Grundon., Chem. & Ind., 556 (1962)
Clarke, Grundon.,J. Chem. Soc., 438 (1964)
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