2,3-dihydroxybutanedioic acid; 5,8,14-triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2,4,6,8,10-pentaene

• ChemBase ID: 179467
• Molecular Formular: C17H19N3O6
• Molecular Mass: 361.34926
• Monoisotopic Mass: 361.12738534
• SMILES: C(C(O)C(=O)O)(O)C(=O)O.c12c(nccn1)cc1c(c2)C2CNCC1C2
• Canonical SMILES: N1CC2CC(C1)c1c2cc2c(c1)nccn2.OC(C(C(=O)O)O)C(=O)O
• InChI: InChI=1S/C13H13N3.C4H6O6/c1-2-16-13-5-11-9-3-8(6-14-7-9)10(11)4-12(13)15-1;5-1(3(7)8)2(6)4(9)10/h1-2,4-5,8-9,14H,3,6-7H2;1-2,5-6H,(H,7,8)(H,9,10)
• InChIKey: TWYFGYXQSYOKLK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3-dihydroxybutanedioic acid; 5,8,14-triazatetracyclo[10.3.1.0^2,^1^1.0^4,^9]hexadeca-2,4,6,8,10-pentaene
• IUPAC Traditional name: (.+-.)-tartaric acid; varenicline
• Synonyms: 7,8,9,10-Tetrahydro-6,10-methano-6H-pyrazino[2,3-h][3]benzazepine (2R,3R)-2,3- dihydroxybutanedioate; Champix; CP 526555-18; Varenicline Tartrate

Database IDs

• CAS Number: 375815-87-5
• PubChem SID: 164235377
• PubChem CID: 46783232

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -2.1916635
• LogD (pH = 7.4): -1.2709792
• Log P: 1.007628
• Molar Refractivity: 61.303 cm^3
• Polarizability: 25.210518 Å^3
• Polar Surface Area: 37.81 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Tan Solid
• Melting Point: 206-208°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - V098490

Nicotinic α4β2 acetylcholine receptor partial agonist. Aid in smoking cessation.

REFERENCES

• Benowitz, N., et al.: Clin. Pharmacol. Ther., 44, 23 (1988)
• Cohen, C., et al.: J. Pharmacol. Exp. Ther., 306, 407 (1988)
• Tapper, A., et al.: Science, 306, 1029 (1988)
• Coe, J., et al.: J. Med. Chem., 48, 3474 (1988)
• Obach, R., et al.: Drug Metab. Disp