3-[(2S)-1-nitroso-1,2,3,6-tetrahydropyridin-2-yl]pyridine

• ChemBase ID: 175428
• Molecular Formular: C10H11N3O
• Molecular Mass: 189.21384
• Monoisotopic Mass: 189.09021199
• SMILES: C1=CC[C@H](N(C1)N=O)c1cccnc1
• Canonical SMILES: O=NN1CC=CC[C@H]1c1cccnc1
• InChI: InChI=1S/C10H11N3O/c14-12-13-7-2-1-5-10(13)9-4-3-6-11-8-9/h1-4,6,8,10H,5,7H2/t10-/m0/s1
• InChIKey: ZJOFAFWTOKDIFH-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(2S)-1-nitroso-1,2,3,6-tetrahydropyridin-2-yl]pyridine
• IUPAC Traditional name: 3-[(2S)-1-nitroso-3,6-dihydro-2H-pyridin-2-yl]pyridine
• Synonyms: (2S)-1,2,3,6-Tetrahydro-1-nitroso-2,3'-bipyridine; N-Nitrosoanatabine; NAT; N'-Nitrosoanatabine; (S)-N-Nitroso Anatabine

Database IDs

• CAS Number: 71267-22-6
• PubChem SID: 164231338
• PubChem CID: 51291

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.1825304
• LogD (pH = 7.4): 1.2486048
• Log P: 1.2495335
• Molar Refractivity: 55.281 cm^3
• Polarizability: 20.131771 Å^3
• Polar Surface Area: 45.56 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Oil

Safety Information

• Storage Condition: Amber Vial, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - N524745

The S-enantiomer metabolite of tobacco, a specific N-nitrosamines with carcinogenic activity.

REFERENCES

• Hoffmann, D., et al.: Cancer Res., 39, 2505 (1979)
• Hecht, S., et al.: Chem. Res. Toxicol., 11, 559 (1979)
• Hecht, S., et al.: Mutation. Res., 424, 127 (1979)
• Wang, M., et al.: Chem. Res. Toxicol., 16, 616 (1979)