3-[(2S)-1-methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olate

• ChemBase ID: 164992
• Molecular Formular: C10H12N2O2
• Molecular Mass: 192.21448
• Monoisotopic Mass: 192.08987763
• SMILES: c1ccc(c[n+]1[O-])[C@@H]1CCC(=O)N1C
• Canonical SMILES: [O-][n+]1cccc(c1)[C@@H]1CCC(=O)N1C
• InChI: InChI=1S/C10H12N2O2/c1-11-9(4-5-10(11)13)8-3-2-6-12(14)7-8/h2-3,6-7,9H,4-5H2,1H3/t9-/m0/s1
• InChIKey: CIPULDKLIIVIER-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(2S)-1-methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olate
• IUPAC Traditional name: 3-[(2S)-1-methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olate
• Synonyms: (5S)-1-Methyl-5-(1-oxido-3-pyridinyl)-2-pyrrolidinone; (-)-Cotinine N-oxide; 1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone N-Oxide; (S)-Cotinine N-Oxide

Database IDs

• CAS Number: 36508-80-2
• PubChem SID: 162259125
• PubChem CID: 9815514

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -1.0495306
• LogD (pH = 7.4): -1.0495225
• Log P: -1.0495224
• Molar Refractivity: 52.97 cm^3
• Polarizability: 19.596342 Å^3
• Polar Surface Area: 45.77 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane
• Apperance: White to Off-White Solid
• Melting Point: 116-117°C

Safety Information

• Storage Condition: -20°C Freezer, Under inert atmosphere

DETAILS

Toronto Research Chemicals - C725200

A major metabolite of Nicotine (N412450) in humans. Carcinogen.

REFERENCES

• Oscarson, M., et al.: Drug Metab. Dispos., 29, 91 (2001)
• Ezzati, M., et al.: Lancet, 362, 271 (2001)
• Damaj, M., et al.: J. Pharmacol. Exp. Ther., 320, 250 (2001)