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| | RHOEADINE Basic information |
| Product Name: | RHOEADINE | | Synonyms: | 3:10,11-bis(methylenebis(oxy))-8-methoxy-16-methyl-(8-beta)-rheada;8-beta-methoxy-16-methyl-2,3:10,11-bis(methylenebis(oxy))rheadan;rheadine;rhoeadin;RHOEADINE;(5bR,13bR,15S)-5b,6,7,8,13b,15-Hexahydro-15-Methoxy-6-Methyl-[1,3]dioxolo[4,5-h]-1,3-dioxolo[7,8][2]benzopyrano[3,4-a][3]benzazepine;8β-Methoxy-16-methyl-2,3:10,11-bis[methylenebis(oxy)]rheadan;Brn 0098745 | | CAS: | 2718-25-4 | | MF: | C21H21NO6 | | MW: | 383.4 | | EINECS: | | | Product Categories: | Amines;Chiral Reagents;Alkaloids;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals | | Mol File: | 2718-25-4.mol |  |
| | RHOEADINE Chemical Properties |
| Melting point | 222°C | | alpha | D23 +235° (c = 1.01 in chloroform); D22 +174° (c = 0.69 in pyridine) | | Boiling point | 510.32°C (rough estimate) | | density | 1.3202 (rough estimate) | | refractive index | 1.5614 (estimate) | | pka | 6.40±0.40(Predicted) | | Water Solubility | 832.6mg/L(25 ºC) | | LogP | 3.920 (est) |
| | RHOEADINE Usage And Synthesis |
| Description | This alkaloid was found by Hesse in Papaver rhoeas Linn (red poppy) and its
reputed existence in opium now appears doubtful. The base crystallizes from a
mixture of CHCl3 and Et20 and sublimes at 21 5-225°C/0.02 mm. It has
[α]17.5D + 232° (CHCI 3) or [α]19D + 243° (CHCl3). It behaves as a weak base and
is sparingly soluble in H20, alkaline solutions and most organic solvents. It
dissolves in mineral acids giving an intensely red solution but investigation shows that only a small proportion of the alkaloid is used to produce the colour, the
major part being converted into a colourless, crystalline substance, Rhoeagenine,
a much stronger base, non-volatile, and stable to acids. This base is not isomeric
with the alkaloid as first thought but has the formula C2oH1906N, m.p. 236-8°C; [α]19D + l68° (AcOH).).
Rhoeadine itself contains two methylenedioxy groups, one methoxy group
and an N-methyl group. The salts are not easy to prepare but a crystalline
hydriodide dihydrate is formed by addition of KI to a solution of the alkaloid in
AcOH. The ultraviolet spectrum of the alkaloid shows absorption maxima at 205,
240 and 292 mμ. | | Uses | An isoquinoline alkaloid used in the therapeutic field particularly for the prevention and the treatment of pathologies implying a central and/or peripheral disorder. | | Uses | As an isoquinoline alkaloid, Rhoeadine can be used in the therapeutic field particularly for the prevention and the treatment of pathologies implying a central and/or peripheral disorder.
| | Definition | ChEBI: Rhoeadine is an alkaloid. | | References | Hesse., Annalen, Suppl., 4, 50 (1S65)
Hesse., ibid, 140, 145 (1S66)
Spath., Monatsh., 68,33 (1936)
Awe., Arch. Pharm., 279,116 (1941)
Santavy etat., Collect. Czech. Chem. Commun., 30,335,3479 (1965)
Mass spectrum:
Dolejs, Hanus., Tetrahedron, 23, 2997 (1967)
Stereochemistry:
Shamma et at., Chem. Commun., 212 (1968) |
| | RHOEADINE Preparation Products And Raw materials |
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