3-[(2S)-1-nitrosopyrrolidin-2-yl]pyridine

• ChemBase ID: 128522
• Molecular Formular: C9H11N3O
• Molecular Mass: 177.20314
• Monoisotopic Mass: 177.09021199
• SMILES: O=NN1CCC[C@H]1c1cnccc1
• Canonical SMILES: O=NN1CCC[C@H]1c1cccnc1
• InChI: InChI=1S/C9H11N3O/c13-11-12-6-2-4-9(12)8-3-1-5-10-7-8/h1,3,5,7,9H,2,4,6H2/t9-/m0/s1
• InChIKey: XKABJYQDMJTNGQ-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(2S)-1-nitrosopyrrolidin-2-yl]pyridine
• IUPAC Traditional name: N-nitrosonornicotine
• Synonyms: N’-Nitrosonornicotine; (S)-3-(1-Nitroso-2-pyrrolidinyl)pyridine; 1’-Demethyl-1’-nitroso-nicotine; (2S)-N'-Nitrosonornicotine; N-Nitrosonornicotine

Database IDs

• CAS Number: 16543-55-8
• PubChem SID: 162222829
• PubChem CID: 12613538; 27919
• Chemspider ID: 19957766
• KEGG ID: C16452
• Wikipedia Title: N-Nitrosonornicotine

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.94362146
• LogD (pH = 7.4): 1.0100449
• Log P: 1.010979
• Molar Refractivity: 49.7174 cm^3
• Polarizability: 18.538322 Å^3
• Polar Surface Area: 45.56 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol; Soluble in water
• Apperance: Oily yellow liquid; Yellow Oil
• Melting Point: 47°C
• Boiling Point: 154°C
• Flash Point: 177°C (350.6°F)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - N535001

A tobacco alkaloid as risk factor of human cancer.

REFERENCES

• Stepanov, I., et al.: Cancer Res., 69, 8236 (2009)
• Maertens, R., et al.: Chem. Res. Toxicol., 22, 1406 (2009)
• Gaworski, C., et al.: Toxicol., 269, 54 (2009)