2,3-dihydroxybutanedioic acid; 3-(pyrrolidin-2-yl)pyridine

• ChemBase ID: 16257
• Molecular Formular: C13H18N2O6
• Molecular Mass: 298.29182
• Monoisotopic Mass: 298.11648631
• SMILES: c1c(cccn1)C1NCCC1.C(=O)(C(O)C(O)C(=O)O)O
• Canonical SMILES: C1CNC(C1)c1cccnc1.OC(=O)C(C(C(=O)O)O)O
• InChI: InChI=1S/C9H12N2.C4H6O6/c1-3-8(7-10-5-1)9-4-2-6-11-9;5-1(3(7)8)2(6)4(9)10/h1,3,5,7,9,11H,2,4,6H2;1-2,5-6H,(H,7,8)(H,9,10)
• InChIKey: QLCHSFANIMPXON-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3-dihydroxybutanedioic acid; 3-(pyrrolidin-2-yl)pyridine
• IUPAC Traditional name: (+-)-nornicotine; (.+-.)-tartaric acid; (.+-.)-tartaric acid; pyridine, 3-(2-pyrrolin-2-yl); (.+-.)-tartaric acid; 2-(3-pyridyl)pyrrolidine
• Synonyms: 2-[3-Pyridyl]pyrrolidine Bitartrate; (±)-1'-Demethylnicotine Bitartrate; (±)-3-(2-Pyrrolidinyl)pyridine Bitartrate; (RS)-Nornicotine Bitartrate; (±)-Nornicotine Bitartrate; 2-(3-Pyridinyl)pyrrolidine Bitartrate; 3-(Pyrrolidin-2-yl)pyridine Bitartrate; rac-Nornicotine Bitartrate; 3-Pyrrolidin-2-yl-pyridine tartrate (1:1); (±) Nornicotine tartrate (1:1); 3-Pyrrolidin-2-yl-pyridine tartrate(1:1)

Database IDs

• MDL Number: MFCD06801280
• PubChem SID: 160979564
• PubChem CID: 44118549

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -2.4496567
• LogD (pH = 7.4): -1.8956487
• Log P: 0.7794868
• Molar Refractivity: 44.3603 cm^3
• Polarizability: 17.60328 Å^3
• Polar Surface Area: 24.92 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: White Solid
• Melting Point: 65-70°C

Safety Information

• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Purity: 95%

DETAILS

Toronto Research Chemicals - N757020

rac-Nornicotine is a metabolite of rac-Nicotine (N412420).

REFERENCES

• Hecht, S., et al.: Carcinogenesis, 9, 875 (1988)
• Rivenson, A., et al.: Cancer Res., 48, 6912 (1988)
• Hoffmann, D., et al.: Chem. Res. Toxicol., 14, 767 (1988)
• Kool, J., et al.: J. Med. Chem., 49, 3287 (1988)
• Kool, J., et al.: Drug Metab. Dispos., 35, 6