1-[(2R)-1-methylpyrrolidin-2-yl]propan-2-one

• ChemBase ID: 127765
• Molecular Formular: C8H15NO
• Molecular Mass: 141.2108
• Monoisotopic Mass: 141.11536411
• SMILES: CC(=O)C[C@H]1CCCN1C
• Canonical SMILES: CC(=O)C[C@H]1CCCN1C
• InChI: InChI=1S/C8H15NO/c1-7(10)6-8-4-3-5-9(8)2/h8H,3-6H2,1-2H3/t8-/m1/s1
• InChIKey: ADKXZIOQKHHDNQ-MRVPVSSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R)-1-methylpyrrolidin-2-yl]propan-2-one
• IUPAC Traditional name: (+)-hygrine
• Synonyms: Hygrine; 1-[(2R)-1-Methyl-2-pyrrolidinyl]-2-propanone; (+)-Hygrine; (+)-N-Methyl-2-acetonylpyrrolidine; (R)-(+)-Hygrine; D-(+)-Hygrine

Database IDs

• CAS Number: 496-49-1
• PubChem SID: 162222083
• PubChem CID: 440933
• CHEBI ID: 46750
• Chemspider ID: 389762
• KEGG ID: C06179
• Wikipedia Title: Hygrine

CALCULATED PROPERTIES

• Acid pKa: 18.5427
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -2.613609
• LogD (pH = 7.4): -1.1645176
• Log P: 0.7003556
• Molar Refractivity: 41.5344 cm^3
• Polarizability: 16.334124 Å^3
• Polar Surface Area: 20.31 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 193–195 °C

DETAILS

Toronto Research Chemicals - H997500

A pyrrolidine alkaloid derivative having antispasmodic activity. Occurs in leaves of Erythroxylon coca Lam., and is the immediate precursor of Cuscohygrine in Scopolia lurida and also of Hyoscyamine in Datura stramonium.

REFERENCES

• Gambaro, V., et al.: Phytochemistry, 22, 1838 (1983)
• Hashimoto, T., et al.: J. Biol. Chem., 266, 4648 (1983)
• Zarate, R., et al.: J. Chem. Ecol., 23, 2059 (1983)