3-[(2S)-1-methylpyrrolidin-2-yl]pyridin-1-ium-1-olate

• ChemBase ID: 82187
• Molecular Formular: C10H14N2O
• Molecular Mass: 178.23096
• Monoisotopic Mass: 178.11061308
• SMILES: [n+]1(cc(ccc1)[C@H]1N(CCC1)C)[O-]
• Canonical SMILES: CN1CCC[C@H]1c1ccc[n+](c1)[O-]
• InChI: InChI=1S/C10H14N2O/c1-11-6-3-5-10(11)9-4-2-7-12(13)8-9/h2,4,7-8,10H,3,5-6H2,1H3/t10-/m0/s1
• InChIKey: YHXKVHQFWVYXIC-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(2S)-1-methylpyrrolidin-2-yl]pyridin-1-ium-1-olate
• IUPAC Traditional name: 3-[(2S)-1-methylpyrrolidin-2-yl]pyridin-1-ium-1-olate
• Synonyms: 3-(1-methyl-2-pyrrolidinyl)pyridinium-1-olate; 3-[(2S)-1-Methyl-2-pyrrolidinyl]pyridine 1-Oxide; Nicotine N-Oxide; Nicotine 1-Oxide; (S)-3-(1-Methyl-2-pyrrolidinyl)pyridine 1-Oxide; Nicotine 1-N-Oxide; (2'S)-Nicotine 1-Oxide

Database IDs

• CAS Number: 2820-55-5
• MDL Number: MFCD01570271
• PubChem SID: 162069306
• PubChem CID: 211457

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -2.772414
• LogD (pH = 7.4): -0.9987772
• Log P: -0.09762224
• Molar Refractivity: 53.3445 cm^3
• Polarizability: 19.887423 Å^3
• Polar Surface Area: 28.7 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Benzene; Chloroform; Dichloromethane; Ethanol
• Apperance: Light Yellow Low Melting Solid

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• Storage Warning: Very Hygroscopic

DETAILS

Toronto Research Chemicals - N428000

Nicotine-1’-N-oxide is a derivative of Nicotine (N412420) found in the leaves, stems, and roots of N. tabacum, N. affinis and N. sylvestris. Nicotine-1’-N-oxide has also been identified as metabolites of nicotine in animals and in man. The metabolism of

REFERENCES

• Phillipson, J.D., et al.: Phytochemistry, 14, 2683 (1975)
• Sindelar, R.D., et al.: Appl. Environ. Microbiol., 38, 836 (1975)