A morphine type alkaloid isolated from Sinomenium acutum Rehd. and Wils, the base is laevorotatory with[α]16D - 112° (EtOH) or - 81.60 (CHCI3). It yields a series of crystalline salts and derivatives including the perchlorate, m.p. 117°C;
tartrate, m.p. 203-4°C; picrate, m.p. 222°C (dec.); oxime, m.p. 223°C and the
methiodide, m.p. 216°C. The alkaloid also forms the O-acetate, m.p. 175°C;
[α]D - 125° (EtOH) with AC20 in pyridine, indicative of a phenolic hydroxyl
group. On hydrogenation it forms tetrahydrosinoacutinol, C19H2704N, m.p.
216°C. The O-methyl ether yields a crystalline methiodide which contains
Me2CO when obtained from this solvent, m.p. 163-6°C. According to Johns and
his co-workers, the alkaloid is also present in Cassytha pubescens R. Br.
Chu, Lo, Chou., Acta Chirn. Sinica., 30,265 (1964)
Barton, Korby, Kirby., Chern. Cornrnun., 52 (1965)
Chambers, Haynes, Stuart., ibid, 449 (1966)
Johns, Lamberton, Sioumis., Austral. J. Chern., 19,2331 (1966)
Circular dichroism:
Snatzke, Wollenberg.,l. Chern. Soc., C, 1681 (1966)
