(6α)-2,8β-Dimethoxy-10,11-[methylenebis(oxy)]rheadan-3-ol

This history of this alkaloid from opium is somewhat confused. Merck and Hesse both isolated compounds of this name which were subsequently shown to be mixtures of alkaloids, in particular meconidine (q.v.) and rhoeadine (q.v.). The base obtained by Rakshit from the Et20 extract of Indian opium was assigned the formula C19H2304N and may be identical with the present alkaloid although only one methoxyl group was stated to be present. The alkaloid crystallized from light petroleum as pale yellow or colourless prisms, m.p. 133-5°C; [α]²⁹_Dl? - 139.9° (CHC13). The salts that have been described are the hydrochloride, m.p. 155°C; [α]²⁹_Di? - 118.8° (H20); the nitrate, m.p. 122°C; [α]³²_D - 115.4° (H20); platinich1oride, m.p. 204°C (dec.) and the picrate, m.p. 198°C (dec.).The identity of the alkaloid has now been firmly established and the structure determined. It contains two methoxyl groups, an imino group and a phenolic hydroxyl group.

Merck., Annalen, 21,201 (1837)
Hesse., ibid, 153,49 (1870) Rakshit., J. Chern. Soc., 115,455 (1919)
Rakshit., Ber., 59,2473 (1926)
Machiguchi., J. Pharrn. Soc., Japan, No 529, 19 (1926)
Rajagopalan.,J. Org. Chern., 10,175 (1945)
Structure: Brochmann-Hanssen, Hirai., J. Pharrn. Sci., 56, 1658 (1967)