ChemicalBook > CAS DataBase List > [2R,(-)]-3,9-Dihydro-8-methoxy-9-methyl-2-isopropylfuro[2,3-b]quinoline-4(2H)-one

[2R,(-)]-3,9-Dihydro-8-methoxy-9-methyl-2-isopropylfuro[2,3-b]quinoline-4(2H)-one

Product Name
[2R,(-)]-3,9-Dihydro-8-methoxy-9-methyl-2-isopropylfuro[2,3-b]quinoline-4(2H)-one
CAS No.
82-40-6
Chemical Name
[2R,(-)]-3,9-Dihydro-8-methoxy-9-methyl-2-isopropylfuro[2,3-b]quinoline-4(2H)-one
Synonyms
C10711;Lunacrine;[2R,(-)]-3,9-Dihydro-8-methoxy-9-methyl-2-isopropylfuro[2,3-b]quinolin-4(2H)-one;[2R,(-)]-3,9-Dihydro-8-methoxy-9-methyl-2-isopropylfuro[2,3-b]quinoline-4(2H)-one;Furo[2,3-b]quinolin-4(2H)-one, 3,9-dihydro-8-methoxy-9-methyl-2-(1-methylethyl)-, (2R)-
CBNumber
CB62179717
Molecular Formula
C16H19NO3
Formula Weight
273.33
MOL File
82-40-6.mol
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[2R,(-)]-3,9-Dihydro-8-methoxy-9-methyl-2-isopropylfuro[2,3-b]quinoline-4(2H)-one Property

Melting point:
117-119°
alpha 
25589 -50.4°; 25436 -116° (c = 0.806 in ethanol)
Boiling point:
416.35°C (rough estimate)
Density 
1.0888 (rough estimate)
refractive index 
1.5500 (estimate)
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Hazard and Precautionary Statements (GHS)

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[2R,(-)]-3,9-Dihydro-8-methoxy-9-methyl-2-isopropylfuro[2,3-b]quinoline-4(2H)-one Chemical Properties,Usage,Production

Description

A further alkaloid obtained from the bark of Lunasia costulata Miq., this base belongs to the furoquinolone group of alkaloids. It crystallizes as the monohydrate in colourless needles from AcOET, m.p. 95.5°C, losing H20 at lOOoC to give the anhydrous form with the above melting point. The alkaloid has [α]28D - 58° (EtOH). The following salts have been prepared: the hydrochloride, m.p. l64-5°C; [α]28D - 23° (H20); hydro bromide, m.p. 170-1 DC; hydriodide, m.p. 196-7°C; aurichloride, m.p. l76-7°C; picrate, m.p. 2l3-4°C and the methiodide, m.p. l30-loC (dec.). The last of these, on treatment with moist silver oxide produces an isomer of lunacrine, m.p. 85-6°C, this behaviour resembling that of certain other Rutaceous alkaloids, e.g. Skimmianine (q.v.). The (+)-form oflunacrine has m.p. 119-1200 C; [α]25589 + 66° and [α]25436+ 100°. This form also yields a crystalline perchlorate, m.p. 178-1800 C. The optically inactive form has been prepared as colourless crystals from AcOEt-pentane, m.p. l46-8°C.The alkaloid inhibits peristaltic movement of the isolated intestine. The median lethal dose of the hydrochloride is approximately 78.7 mgm per kilo when injected intravenously in mice. It is also stated to reduce arterial blood pressure in cats.

Definition

ChEBI: Lunacrine is an organic heterotricyclic compound, an organonitrogen heterocyclic compound and an oxacycle.

References

Boorsma.,Meded. Lands. Plant., 31, 13, 126 (1899)
Boorsma.,Bull. Inst. Bot. Buit., No. 31, 8, 25 (1904)
Steldt, Chen., J. Amer. Pharm. Assoc., 32, 107 (1942)
Goodwin, Horning.,J. Amer. Chem. Soc., 81, 1908 (1959)
Clarke, Grundon., Chem. & Ind., 556 (1962)
Clarke, Grundon., J. Chem. Soc., 438 (1964)

[2R,(-)]-3,9-Dihydro-8-methoxy-9-methyl-2-isopropylfuro[2,3-b]quinoline-4(2H)-one Preparation Products And Raw materials

Raw materials

Preparation Products

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[2R,(-)]-3,9-Dihydro-8-methoxy-9-methyl-2-isopropylfuro[2,3-b]quinoline-4(2H)-one Suppliers

82-40-6, [2R,(-)]-3,9-Dihydro-8-methoxy-9-methyl-2-isopropylfuro[2,3-b]quinoline-4(2H)-oneRelated Search:


  • [2R,(-)]-3,9-Dihydro-8-methoxy-9-methyl-2-isopropylfuro[2,3-b]quinolin-4(2H)-one
  • [2R,(-)]-3,9-Dihydro-8-methoxy-9-methyl-2-isopropylfuro[2,3-b]quinoline-4(2H)-one
  • Lunacrine
  • C10711
  • Furo[2,3-b]quinolin-4(2H)-one, 3,9-dihydro-8-methoxy-9-methyl-2-(1-methylethyl)-, (2R)-
  • 82-40-6