1-nitroso-5-(pyridin-3-yl)pyrrolidin-2-yl acetate

• ChemBase ID: 175493
• Molecular Formular: C11H13N3O3
• Molecular Mass: 235.23922
• Monoisotopic Mass: 235.09569129
• SMILES: C1CC(N(C1c1cccnc1)N=O)OC(=O)C
• Canonical SMILES: O=NN1C(CCC1c1cccnc1)OC(=O)C
• InChI: InChI=1S/C11H13N3O3/c1-8(15)17-11-5-4-10(14(11)13-16)9-3-2-6-12-7-9/h2-3,6-7,10-11H,4-5H2,1H3
• InChIKey: CPPDSVYFZZCUAX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-nitroso-5-(pyridin-3-yl)pyrrolidin-2-yl acetate
• IUPAC Traditional name: 1-nitroso-5-(pyridin-3-yl)pyrrolidin-2-yl acetate
• Synonyms: 1-Nitroso-5-(3-pyridinyl)-2-pyrrolidinol 2-Acetate; 5'-Acetoxy-N'-nitrosonornicotine; rac N'-Nitrosonornicotine 5'-Acetate(Mixture of Diastereomers)

Database IDs

• CAS Number: 68743-65-7
• PubChem SID: 164231403
• PubChem CID: 149448

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 0.7921165
• LogD (pH = 7.4): 0.8582494
• Log P: 0.8591791
• Molar Refractivity: 60.0092 cm^3
• Polarizability: 23.045116 Å^3
• Polar Surface Area: 71.86 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Pale Brown Oil

Safety Information

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

DETAILS

Toronto Research Chemicals - N534995

A stable precursor of the active metabolite 5'-hydroxy(+/-)-N'-nitrosonornicotine (NNN-5'-OH).

REFERENCES

• Hecht, S., et al.: Chem. Res. Toxicol., 11, 559 (1998)
• Jalas, J., et al.: Chem. Res. Toxicol., 18, 95 (1998)
• Lao, Y., et al.: Chem. Res. Toxicol., 20, 246 (1998)