4-[methyl(nitroso)amino]-1-[(2H4)pyridin-3-yl]butan-1-one

• ChemBase ID: 174136
• Molecular Formular: C10H13N3O2
• Molecular Mass: 207.22912
• Monoisotopic Mass: 207.10077667
• SMILES: c1ccncc1C(=O)CCCN(C)N=O
• Canonical SMILES: O=NN(CCCC(=O)c1cccnc1)C
• InChI: InChI=1S/C10H13N3O2/c1-13(12-15)7-3-5-10(14)9-4-2-6-11-8-9/h2,4,6,8H,3,5,7H2,1H3
• InChIKey: FLAQQSHRLBFIEZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[methyl(nitroso)amino]-1-[(^2H₄)pyridin-3-yl]butan-1-one
• IUPAC Traditional name: 4-[methyl(nitroso)amino]-1-[(^2H₄)pyridin-3-yl]butan-1-one
• Synonyms: 4-(N-Methyl-N-nitrosamino)-1-(3-pyridyl-d4)-1-butanone; NNK-d4; 4-(Methylnitrosamino)-1-(3-pyridyl-d4)-1-butanone

Database IDs

• CAS Number: 764661-24-7
• PubChem SID: 164230046
• PubChem CID: 12147167

CALCULATED PROPERTIES

• Acid pKa: 15.470998
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 0.5703659
• LogD (pH = 7.4): 0.57872987
• Log P: 0.5788377
• Molar Refractivity: 57.2497 cm^3
• Polarizability: 21.209179 Å^3
• Polar Surface Area: 62.63 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 58-60°C

Safety Information

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

DETAILS

Toronto Research Chemicals - M325751

Labelled NNK (M325750). This compound was present in the highest concentrations in smokeless tobacco out of the nitrosamines identified. It is likely to be important in the etiology of cancers of the lung, oral cavity, and pancreas in people who use taba

REFERENCES

• Koenigs, L., et al.: Drug Metab. Dispos., 25, 1407 (1997)
• Gu, J., et al.: Toxicol. Appl. Pharmacol., 165, 158 (1997)
• Jalas, J., et al.: Chem. Res. Toxicol., 18, 95 (1997)
• Zhu, L., et al.: Drug Metab. Dispos., 34, 1672 (1997)