82-40-6

Basic information

• Product Name: [2R,(-)]-3,9-Dihydro-8-methoxy-9-methyl-2-isopropylfuro[2,3-b]quinoline-4(2H)-one
• Synonyms: [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
• CAS NO: 82-40-6
• Molecular Formula: C16H19NO3
• Molecular Weight: 273.33
• Mol File: 82-40-6.mol
• Article Data: 0

Chemical Properties

• Melting Point: 117-119°
• Boiling Point: 416.35°C (rough estimate)
• Flash Point: 194.1°C
• Appearance: /
• Density: 1.0888 (rough estimate)
• Vapor Pressure: 1.6E-06mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• CAS DataBase Reference: [2R,(-)]-3,9-Dihydro-8-methoxy-9-methyl-2-isopropylfuro[2,3-b]quinoline-4(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: [2R,(-)]-3,9-Dihydro-8-methoxy-9-methyl-2-isopropylfuro[2,3-b]quinoline-4(2H)-one(82-40-6)
• EPA Substance Registry System: [2R,(-)]-3,9-Dihydro-8-methoxy-9-methyl-2-isopropylfuro[2,3-b]quinoline-4(2H)-one(82-40-6)

Safety Data

• Hazardous Substances Data: 82-40-6(Hazardous Substances Data)

Usage

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.

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)

InChI:InChI=1/C16H19NO3/c1-9(2)13-8-11-15(18)10-6-5-7-12(19-4)14(10)17(3)16(11)20-13/h5-7,9,13H,8H2,1-4H3/t13-/m1/s1