OCOTINE

Description

A bisbenzylisoquinoline alkaloid, this base occurs in Ocotea Rodiaei (greenheart)and forms long, colourless needles from MeOH. It has [α] ²⁴ _D+ 40° (c 1.0, CHCI3) and the ultraviolet spectrum exhibits two absorption maxima at 224 and 284 mil. One hydroxyl group and four methoxyl groups are present. The alkaloid furnishes a crystalline hydrochloride as colourless needles when crystallized from dilute HC1, m.p. 250-260°C (dec.); [α] ²⁹ _D+ 84° (c 2.9, MeOH). The O-methyl ether forms crystals from MeOH, m.p. 156-8°C while the N-methyl derivative has m.p. 198-200°C; [α] _D+ 74.6° (c 2.0, CHCI3) and gives a dimethiodide as colourless prisms, m.p. about 250°C (dec.). Treatment with AC20 in pyridine furnishes the O,N-diacetyl derivative as a microcrystalline powder, m.p. 159- 161°C. The dipicrate has also been prepared with m.p. 184-6°C.

References

Grundon, McGarvey., J. Chern. Soc., 2739 (1960)
Structure: Chan et al., J. Chern. Soc., C, 2479 (1967)