(6r,7r,7As)-n-methylhexahydro-1h-1,6-epoxypyrrolizin-7-amine

BeschreibungThis oily alkaloid has been obtained from a species of grass, Lotium cuneatum Nevski. It has a density of D 20 1.1343 and a refractive index of n20D 1.5505. It behaves as a diacidic base yielding a series of well crystalline salts and derivatives, e.g. the dihydrochloride, m.p. 256-7°C; [α]15D + 6.2° (H20); dihydrobromide, m.p. 254-5°C (dec.); [α]20D + 3.5° (c 4.29, H20); dihydriodide, m.p. 233-5°C (dec.); [α]34D + 5.0° (c 13.2 H20); perchlorate, m.p. 282°C with almost explosive decomposition; sulphate, yellow needles, m.p. 250-2°C (dec.); mononitrate,m.p. 208-2l0°C; dinitrate, m.p. l48-9°C; [α]38D + 6.18° (c 6.94, H20); dipicrate, m.p. 258-260°C (dec.); methiodide, m.p. 2l0-loC and the N-nitroso derivative, m.p. 64°C. The N-acetyl derivative yields a crystalline hydrochloride, m.p. 197-8°C; [α]20D + 36.9° (H20) and the N-methyl compound is obtained as a colourless oil, b.p. 90-l oC/2 mm; [α]31D+ 9.31° (c 9.5, MeOH). The alkaloid possesses an ether oxygen bridging the pyrrolizidine moiety.