| Identification | Back Directory | [Name]
RHOEADINE | [CAS]
2718-25-4 | [Synonyms]
rheadine
rhoeadin
RHOEADINE
Brn 0098745
(+)-Rheadine
Rheadine (8ci)
RHODIZONIC ACID Dihydrate(RG)
8β-Methoxy-16-methyl-2,3:10,11-bis[methylenebis(oxy)]rheadan
8-beta-methoxy-16-methyl-2,3:10,11-bis(methylenebis(oxy))rheadan
3:10,11-bis(methylenebis(oxy))-8-methoxy-16-methyl-(8-beta)-rheada
Rheadan, 8-methoxy-16-methyl-2,3:10,11-bis(methylenebis(oxy))-, (8-beta)-
(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
[1,3]Dioxolo[4,5-h]-1,3-dioxolo[7,8][2]benzopyrano[3,4-a][3]benzazepine, 5b,6,7,8,13b,15-hexahydro-15-methoxy-6-methyl-, (5bR,13bR,15S)- | [Molecular Formula]
C21H21NO6 | [MDL Number]
MFCD00075892 | [MOL File]
2718-25-4.mol | [Molecular Weight]
383.4 |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [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) |
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