3-(1-nitrosopyrrolidin-2-yl)pyridine

• ChemBase ID: 157162
• Molecular Formular: C9H11N3O
• Molecular Mass: 177.20314
• Monoisotopic Mass: 177.09021199
• SMILES: c1cc(cnc1)C1CCCN1N=O
• Canonical SMILES: O=NN1CCCC1c1cccnc1
• 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
• InChIKey: XKABJYQDMJTNGQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(1-nitrosopyrrolidin-2-yl)pyridine
• IUPAC Traditional name: nitrosonornicotine
• Synonyms: NNN; 1-Nitroso-2-(3-pyridyl)pyrrolidine; 3-(1-Nitroso-2-pyrrolidinyl)pyridine; N′-Nitrosonornicotine; 3-[(2R,S)-1-Nitroso-2-pyrrolidinyl]pyridine; anti-N’-Nitrosonornicotine; syn-N’-Nitrosonornicotine; rac-N'-Nitroso Nornicotine; 1-亚硝基-2-(3-吡啶基)吡咯烷; 3-(1-亚硝基-2-吡咯烷基)吡啶; N′-亚硝基降烟碱

Database IDs

• CAS Number: 80508-23-2
• MDL Number: MFCD00274581
• PubChem SID: 162251299
• PubChem CID: 27919

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: Acetone; Chloroform; Methanol
• Apperance: Light Yellow Low Melting Solid

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 25-40
• Safety Statements: 36/37-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H351
• GHS Precautionary statements: P281-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Product Information

• Purity: ≥99.0% (HPLC)
• Grade: analytical standard
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C9H11N3O

DETAILS

Sigma Aldrich - 75285

General description
Standard for Supelco MIP SPE cartridges. For more information request Supelco Literature T407075, T706031

Toronto Research Chemicals - N535000

N'-Nitrosonornicotine (NNN) is a tobacco alkaloid known as esophageal carcinogen. NNN is the cause of esophageal and oral cavity cancer in smokers and snuff dippers. The studies showed that the carcinogenicity of (S)-NNN, the predominant enantiomer in to

REFERENCES

• Anto, R., et al.: Carcinogenesis, 23, 1511 (2002)
• Pfeifer, G., et al.: Oncogene, 21, 7435 (2002)
• Shishodia, S., et al.: Cancer Res., 64, 5004 (2002)
• Jin, Z., et al.: J. Biol. Chem., 279, 23837 (2002)