(1R,12S)-5,8,14-triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2,4,6,8,10-pentaene; (2R,3R)-2,3-dihydroxybutanedioic acid

• ChemBase ID: 154658
• Molecular Formular: C17H19N3O6
• Molecular Mass: 361.34926
• Monoisotopic Mass: 361.12738534
• SMILES: c1cnc2cc3c(cc2n1)[C@@H]1C[C@H]3CNC1.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O
• Canonical SMILES: N1C[C@@H]2C[C@H](C1)c1c2cc2c(c1)nccn2.O[C@H]([C@H](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)/t8-,9+;1-,2-/m.1/s1
• InChIKey: TWYFGYXQSYOKLK-CYUSMAIQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,12S)-5,8,14-triazatetracyclo[10.3.1.0^2,^1^1.0^4,^9]hexadeca-2,4,6,8,10-pentaene; (2R,3R)-2,3-dihydroxybutanedioic acid
• IUPAC Traditional name: L(+)-tartaric acid; chantix
• Synonyms: 7,8,9,10-Tetrahydro-6,10-methano-6H-pyrazino[2,3-h][3]benzazepine tartrate; Champix; Varenicline tartrate

Database IDs

• CAS Number: 375815-87-5
• MDL Number: MFCD08460603
• PubChem SID: 162248796
• PubChem CID: 6918678

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: >5 mg/mL
• Apperance: white to off-white powder

Safety Information

• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 22-50
• Safety Statements: 22-57
• GHS Pictograms: GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H400
• GHS Precautionary statements: P273
• RID/ADR: UN 2811 6.1/PG 1
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C13H13N3 · C4H6O6

DETAILS

Sigma Aldrich - PZ0004

Legal Information
Sold for research purposes under agreement from Pfizer Inc.
Biochem/physiol Actions
Varenicline tartrate is a partial α4β2 nicotinic receptor agonist and α7 full agonist. Varenicline competitively binds to α4β2 receptors and partially stimulates without creating a full nicotine effect, while simultaneoudly blocking the ability of nicotine to bind to the receptors. Varenicline thus blocks the ability of nicotine to activate α4β2 receptors and stimulate the central nervous mesolimbic dopamine system, believed to be the neuronal mechanism underlying reinforcement and reward experienced upon smoking.