| Identification | Back Directory | [Name]
(6α)-2,8β-Dimethoxy-10,11-[methylenebis(oxy)]rheadan-3-ol | [CAS]
18104-24-0 | [Synonyms]
Porphyroxine
Papaverrubine D
(6α)-2,8β-Dimethoxy-10,11-[methylenebis(oxy)]rheadan-3-ol
1,3-Dioxolo[7,8][2]benzopyrano[3,4-a][3]benzazepin-11-ol, 5b,6,7,8,12b,14-hexahydro-10,14-dimethoxy-, (5bR,12bS,14S)- | [Molecular Formula]
C20H21NO6 | [MOL File]
18104-24-0.mol | [Molecular Weight]
371.384 |
| Hazard Information | Back Directory | [Description]
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]29Dl? - 139.9° (CHC13). The salts that have been described are the hydrochloride, m.p.
155°C; [α]29Di? - 118.8° (H20); the nitrate, m.p. 122°C; [α]32D
- 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. | [References]
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)
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