(-)-Vasicinone
Basic information
- CAS
486-64-6- Standard SMILES
O=c1c2ccccc2nc2n1CC[C@@H]2O- InChIKey
SDIVYZXRQHWCKF-VIFPVBQESA-N- Molecular formula
- C11H10N2O2
- Average molar mass
- 202.21 g/mol
- Monoisotopic mass
- 202.07422757
Overview
Vasicinone is a member of quinazolines.
Names & identifiers
- Preferred name
- (-)-Vasicinone
- IUPAC
- (3S)-3-hydroxy-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one
- English name
- VASICINONE
- Molecular formula
- C11H10N2O2
- Molecular weight
- 202.21
Names & synonyms
VASICINONE486-64-6(-)-Vasicinonel-VasicinoneG6T5819NXM(3S)-3-hydroxy-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one(3S)-3-hydroxy-2,3-dihydro-1H-pyrrolo(2,1-b)quinazolin-9-oneRefChem:193788(3S)-3-hydroxy-1H,2H,3H,9H-pyrrolo[2,1-b]quinazolin-9-one(S)-3-Hydroxy-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-oneC10744AC1L9DON
Show more names
Vasicinone-RMVasicinone, 10 mM in DMSO2,3-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)-onePyrrolo[2,1-b]quinazolin-9(1H)-one,2,3-dihydro-3-hydroxy-, (3S)-
UNII-G6T5819NXMVasicinone (Standard)3-hydroxy-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-oneVasicinone, analytical standardCHEBI:9936orb1217986orb1297732orb3140787
Database identifiers
- CAS
486-64-6- PubChem CID
- 442935
- DTXSID
DTXSID80964090- ChEMBL
CHEMBL3120244- ChEBI
CHEBI:9936- UNII
- G6T5819NXM
- EC Number
- 683-100-2
- Nikkaji
- J783.610D
Properties
Computed structural properties
- XLogP
- 0.4
- Topological polar surface area
- 52.9 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 327
Physicochemical properties
- Melting point
- 200 · 200-202℃
- Boiling point
- 320.7 °C · 320.7°C (rough estimate)
- Density
- 1.5 · 1.50
- refractive index
- 1.53 · 1.5300 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- Soluble in chloroform and ethanol;
- form
- powder
- pka
- 12.76 · 12.76±0.20(Predicted)
- color
- White
- Water Solubility
- 1.597 g/L · 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
- FDA UNII
- 6 T5819NXM · G6T5819NXM
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- WGK 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P501-P270-P264-P301+P312+P330
Chemistry & industry
Applications
DescriptionA 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.
UsesVasicinone 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].
Additional notes
DefinitionChEBI: Vasicinone is a member of quinazolines.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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