(1S,2S)-1-methyl-2-(pyridin-3-yl)pyrrolidin-1-ium-1-olate

• ChemBase ID: 175124
• Molecular Formular: C10H14N2O
• Molecular Mass: 178.23096
• Monoisotopic Mass: 178.11061308
• SMILES: c1cncc(c1)[C@H]1[N@+](CCC1)([O-])C
• Canonical SMILES: [O-][N@@+]1(C)CCC[C@H]1c1cccnc1
• InChI: InChI=1S/C10H14N2O/c1-12(13)7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3/t10-,12-/m0/s1
• InChIKey: RWFBQHICRCUQJJ-JQWIXIFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S)-1-methyl-2-(pyridin-3-yl)pyrrolidin-1-ium-1-olate
• IUPAC Traditional name: (1S,2S)-1-methyl-2-(pyridin-3-yl)pyrrolidin-1-ium-1-olate
• Synonyms: (1’S,2’S)-trans-Nicotine 1’-Oxide; 3-[(1S,2S)-1-Methyl-1-oxido-2-pyrrolidinyl]pyridine; (1S-cis)-3-(1-Methyl-2-pyrrolidinyl)pyridine N-Oxide; (1S,2S)-syn-Nicotine N'-oxide; (1'S,2'S)-trans-Nicotine-1'-N-oxide; Nicotine-cis-N-oxide; (1S-cis)-3-(1-Methyl-1-oxido-2-pyrrolidinyl)pyridine; (1'S,2'S)-Nicotine 1'-Oxide

Database IDs

• CAS Number: 51095-86-4
• PubChem SID: 164231034
• PubChem CID: 12313859

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -0.024156854
• LogD (pH = 7.4): 0.037301652
• Log P: 0.03815951
• Molar Refractivity: 51.6999 cm^3
• Polarizability: 19.558786 Å^3
• Polar Surface Area: 39.77 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Water
• Apperance: Yellow to Pale Orange Solid
• Melting Point: 168-170°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - N427500

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 a metabolite 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)