| Identification | Back Directory | [Name]
VASICINONE | [CAS]
486-64-6 | [Synonyms]
VASICINONE
l-Vasicinone
2,3-Dihydro-3-hydroxypyrrolo[2,1-b]quinazolin-9(1H)-one
(3R)-2,3-Dihydro-3-hydroxypyrrolo[2,1-b]quinazolin-9(1H)-one
(3R)-2,3-Dihydro-3β-hydroxypyrrolo[2,1-b]quinazoline-9(1H)-one
Pyrrolo[2,1-b]quinazolin-9(1H)-one,2,3-dihydro-3-hydroxy-, (3S)- | [Molecular Formula]
C11H10N2O2 | [MDL Number]
MFCD11519457 | [MOL File]
486-64-6.mol | [Molecular Weight]
202.21 |
| Chemical Properties | Back Directory | [Melting point ]
200-202℃ | [Boiling point ]
320.7°C (rough estimate) | [density ]
1.50 | [refractive index ]
1.5300 (estimate) | [storage temp. ]
2-8°C | [solubility ]
Soluble in chloroform and ethanol; | [form ]
powder | [pka]
12.76±0.20(Predicted) | [color ]
White | [Water Solubility ]
1.597g/L(25 ºC) | [InChI]
InChI=1S/C11H10N2O2/c14-9-5-6-13-10(9)12-8-4-2-1-3-7(8)11(13)15/h1-4,9,14H,5-6H2/t9-/m0/s1 | [InChIKey]
SDIVYZXRQHWCKF-VIFPVBQESA-N | [SMILES]
N1C2=C(C=CC=C2)C(=O)N2CC[C@H](O)C=12 |
| Hazard Information | Back Directory | [Description]
A further alkaloid present in Adhatoda vasica and Peganum harmala, this base
forms colourless crystals from 95 per cent EtOH. It has [α]22D - 100° (c 0.5,
CHCL3) and the ultraviolet spectrum has absorption maxima at 227, 272, 302
and 315 mfJ.. The alkaloid yields a series of crystalline salts with mineral acids,
e.g. the hydrochloride, m.p. 232-4°C; hydro bromide, m.p. 254-5°C (dec.);
hydriodide, m.p. 222-6°C (dec.); nitrate, m.p. 138-9° C (dec.) and the sulphate,
m.p. l82-5°C (dec.). The optically inactive form of the base has been prepared
synthetically, m.p. 211- 2°C. The alkaloid is an active bronchodilator. | [Uses]
Vasicinone is a quinazoline alkaloid isolated from the Adhatoda vasica. Vasicinone is a potential agent for Parkinson's disease and possibly other oxidative stress-related neurodegenerative disorders[1]. | [Definition]
ChEBI: Vasicinone is a member of quinazolines. | [target]
P450 (e.g. CYP17) | [References]
Ghose et al., J. Chem. Soc., 2740 (1932)
Morris, Horford, Adams., J. Amer. Chem. Soc., 57,951 (1935)
Mehta, Naravane, Desai., J. Org. Chem., 28, 445 (1963) |
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