(5R)-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one

• ChemBase ID: 91506
• Molecular Formular: C10H12N2O
• Molecular Mass: 176.21508
• Monoisotopic Mass: 176.09496301
• SMILES: n1cccc(c1)[C@@H]1N(C(=O)CC1)C
• Canonical SMILES: O=C1CC[C@@H](N1C)c1cccnc1
• InChI: InChI=1S/C10H12N2O/c1-12-9(4-5-10(12)13)8-3-2-6-11-7-8/h2-3,6-7,9H,4-5H2,1H3/t9-/m1/s1
• InChIKey: UIKROCXWUNQSPJ-SECBINFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R)-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one
• IUPAC Traditional name: (5R)-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one
• Synonyms: (5S)-(-)-1-Methyl-5-(pyridin-3-yl)pyrrolidin-2-one; S-(-)-Cotinine; (5R)-(+)-1-Methyl-5-(3-pyridiyl)-2-pyrrolidinone; (+)-Cotinine; (R)-Cotinine; Ba 2701; R-(+)-Cotinine

Database IDs

• CAS Number: 32162-64-4; 486-56-6
• MDL Number: MFCD00077696
• PubChem SID: 162078205
• PubChem CID: 21907

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.14203912
• LogD (pH = 7.4): 0.20968148
• Log P: 0.21063453
• Molar Refractivity: 49.2805 cm^3
• Polarizability: 19.111326 Å^3
• Polar Surface Area: 33.2 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethanol; Water
• Apperance: Colourless to Light Brown Solid
• Melting Point: 48-50°C; 48-51°C
• Boiling Point: 145-150°C/3mm; 145-150°C/3 mm
• Flash Point: >110°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Harmful/Irritant

DETAILS

Apollo Scientific Ltd - OR7251T

A major metabolite of nicotine in humans.

Toronto Research Chemicals - C724990

The R metabolite of Nicotine. This is the unnatural isomer of Cotinine. Carcinogen.

REFERENCES

• Frankenburg, V.: J. Am. Chem. Soc., 79, 149 (1957)
• Thompson, J.A., et al.: J. Chromatog., 231, 53 (1957)
• Seeman, J.I., et al.: J. Org. Chem., 51, 1548 (1986)