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

Melting point:

86-87°

alpha 

25589 +28.1°; 25436 +76.5° (c = 0.935 in ethanol)

Hazard and Precautionary Statements (GHS)

3-[(2R)-2-hydroxy-3-methyl-butyl]-4,8-dimethoxy-1-methyl-quinolin-2-on e Chemical Properties,Usage,Production

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]²⁴_D + 30.1 ° and [α]²⁴₄₃₆ + 81.8°. Boorsma gives a specific rotation of [α]²⁸_D + 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]²⁵_{58925436+ 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)