| Identification | Back Directory | [Name]
[2R,(-)]-3,9-Dihydro-8-methoxy-9-methyl-2-isopropylfuro[2,3-b]quinoline-4(2H)-one | [CAS]
82-40-6 | [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)- | [Molecular Formula]
C16H19NO3 | [MOL File]
82-40-6.mol | [Molecular Weight]
273.33 |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [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) |
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