4-methoxy-1-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

• ChemBase ID: 177533
• Molecular Formular: C8H8N2O2
• Molecular Mass: 164.16132
• Monoisotopic Mass: 164.05857751
• SMILES: c1cc(c(c(=O)n1C)C#N)OC
• Canonical SMILES: N#Cc1c(OC)ccn(c1=O)C
• InChI: InChI=1S/C8H8N2O2/c1-10-4-3-7(12-2)6(5-9)8(10)11/h3-4H,1-2H3
• InChIKey: PETSAYFQSGAEQY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-methoxy-1-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
• IUPAC Traditional name: ricinine; 4-methoxy-1-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
• Synonyms: 1,2-Dihydro-4-methoxy-1-methyl-2-oxo-3-pyridinecarbonitrile; 1,2-Dihydro-4-methoxy-1-methyl-2-oxonicotinonitrile; Recinine; NSC 409913; NSC 642604; Ricinin; Ricinine; 1,2-Dihydro-4-methoxy-1-methyl-2-oxo-3-pyridinecarbonitrile; 4-Methoxy-2-oxo-1-methyl-1,2-dihydronicotinonitrile; 3-Cyano-4-methoxy-1-methyl-2-pyridone; Ricinine

Database IDs

• CAS Number: 524-40-3
• PubChem SID: 164233443
• PubChem CID: 10666

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -0.2337896
• LogD (pH = 7.4): -0.2337896
• Log P: -0.2337896
• Molar Refractivity: 44.6391 cm^3
• Polarizability: 16.039297 Å^3
• Polar Surface Area: 53.33 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Blocker of the GABA(A) receptor

Product Information

• Biological Source: Alkaloid from Ricinus communis (castor-oil) seed (Euphorbiaceae)
• Application(s): Nootropic

DETAILS

Toronto Research Chemicals - R495550

Ricinine is an alkaloid extract from the seeds of the castor-oil plant (Ricinus communalis). Ricinine is a central nervous system stimulant that could potentially be a cognition-enhancing agent used for the treatment of human amnesias. Ricinine also has b

REFERENCES

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• Zhao, Z. et al.: Zhong. Niang., 6, 13 (1999)
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• Robinson, T., Phytochemistry, 1978, 17, 1903, (biosynth)
• Soriano-Garcia, M., Acta Cryst. C, 1989, 45, 957, (cryst struct)
• Sax, N.I., Dangerous Properties of Industrial Materials, 5th edn., Van Nostrand Reinhold, 1979