6391-64-6

This bisbenzylisoquinoline alkaloid from Ocotea rodiaei was originally considered to have the formulae C36H4006N2 or C36H4406N2. When crystallized from EtOH it yields cubic crystals but from MeOH it forms slender needles. It has [α]¹⁸_D + 134° (c 0.63, CHCI3) or + 157° (c 1.0, CHCI3). The ultraviolet spectrum in EtOH has absorption maxima at 233 and 285 ITlJ.1 with a shoulder at 292 mJ.1. The monohydrochloride forms cubic crystals from EtOH, m.p. 255-9°C (dec.); [α]_D + 74° (c 1.0, H20); the dimethiodide, m.p. 321°C (dec.); [α]²⁰_D+ 68° (c 0.147, H20); the dimethochloride, m.p. 286°C (dec.); [α]_D + 81.5° (c 0.98, H20) and the dimethopicrate, existing in two crystal forms, m.p. 180°C and 253°C respectively. Four methoxyl groups and one phenolic hydroxyl group are present, the alkaloid furnishing the O-methyl derivative, m.p. 172-3°C; [α]_D + 85° (c 0.57, CHCI 3) which also yields crystalline salts, e.g. the hydrochloride, m.p. 232-6°C (dec.) and the dimethiodide, m.p. 294-8°C (dec.); [α]_D + 47° (H20).

ChEBI: Rodiasine is an isoquinoline alkaloid fundamental parent and a bisbenzylisoquinoline alkaloid.

McKennis et aI., 1. Arner. Chern. Soc., 78,245 (1956)
Grundon, McGarvey.,1. Chern. Soc., 27 39 (1960)
Hearst.,1. Org. Chern., 29,466 (1964)
Structure:
Grundon, McGarvey.,J. Chern. Soc., C, 1082 (1966)
Chan et ai., ibid, 2479 (1967)