Lunacridine
Title: Lunacridine
CAS Registry Number: 83-58-9
CAS Name: 3-[(2R)-2-Hydroxy-3-methylbutyl]-4,8-dimethoxy-1-methyl-2(1H)-quinolinone
Molecular Formula: C17H23NO4
Molecular Weight: 305.37
Percent Composition: C 66.86%, H 7.59%, N 4.59%, O 20.96%
Literature References: From bark of Lunasia costulata Miq., and L. quercifolia K. Schum. et Lauterb., Rutaceae. (+)-Form is naturally occurring. Isoln: Boorsma, Bull. Inst. Bot. Buitenzorg 21, 8 (1904). Structure: Goodwin, Horning, J. Am. Chem. Soc. 81, 1908 (1959). Synthesis: Clarke, Grundon, J. Chem. Soc. 1964, 438. Synthesis and stereochemistry: R. M. Bowman et al., J. Chem. Soc. Perkin Trans. 1 1973, 1051. Short synthesis of racemate: M. Ramesh, P. Shanmugam, Indian J. Chem. 24B, 767 (1985).
Properties: Crystals from methanol/water, mp 86-87°. [a]25589 +28.1°; [a]25436 +76.5° (c = 0.935 in ethanol). uv spectra: Goodwin, Horning, loc. cit. Very slightly sol in water; freely sol in alcohol, benzene, chloroform, ether, ethyl acetate, carbon disulfide, petr ether.
Melting point: mp 86-87°
Optical Rotation: [a]25589 +28.1°; [a]25436 +76.5° (c = 0.935 in ethanol)
 
Derivative Type: Hydroperchlorate
Molecular Formula: C17H24ClNO8
Molecular Weight: 405.83
Percent Composition: C 50.31%, H 5.96%, Cl 8.74%, N 3.45%, O 31.54%
Properties: Shiny flakes from methanol/ether, mp 146-148°; remelts at 193-195°. [a]25589 +22.3°; [a]25436 +60.7° (c = 0.750 in ethanol).
Melting point: mp 146-148°; remelts at 193-195°
Optical Rotation: [a]25589 +22.3°; [a]25436 +60.7° (c = 0.750 in ethanol)
 
Derivative Type: (±)-Form
CAS Registry Number: 52306-35-1
Properties: Prisms from petr ether, mp 72-74°. uv max (methanol): 239, 258, 285, 292, 333 nm (e 24000, 26300, 8300, 7800, 3100).
Melting point: mp 72-74°
Absorption maximum: uv max (methanol): 239, 258, 285, 292, 333 nm (e 24000, 26300, 8300, 7800, 3100)

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