2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane

• ChemBase ID: 105363
• Molecular Formular: C11H13ClN2
• Molecular Mass: 208.68732
• Monoisotopic Mass: 208.07672611
• SMILES: Clc1ncc(cc1)C1CC2CCC1N2
• Canonical SMILES: Clc1ccc(cn1)C1CC2NC1CC2
• InChI: InChI=1S/C11H13ClN2/c12-11-4-1-7(6-13-11)9-5-8-2-3-10(9)14-8/h1,4,6,8-10,14H,2-3,5H2
• InChIKey: NLPRAJRHRHZCQQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane
• IUPAC Traditional name: epibatidine
• Synonyms: Epibatidine; (±)-EPIBATIDINE

Database IDs

• CAS Number: 140111-52-0
• PubChem SID: 162092382
• PubChem CID: 1204; 11031065
• CHEMBL: 298826
• Chemspider ID: 10399316
• DrugBank ID: DB07720
• KEGG ID: C11690
• Wikipedia Title: Epibatidine

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -1.3915857
• LogD (pH = 7.4): -1.0436354
• Log P: 1.8435768
• Molar Refractivity: 57.3916 cm^3
• Polarizability: 22.39249 Å^3
• Polar Surface Area: 24.92 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: 0°C, Store Under Nitrogen, Protect from light
• European Hazard Symbols: Toxic (T)
• Risk Statements: R:23/24/25
• Safety Statements: S:22-35-45-36/37/39

Product Information

• Purity: 99%

DETAILS

MP Biomedicals - 02159918

Synthetic Purity: 99% Most potent agonist to the nicotinic acetylcholine receptor known. The natural (+) isomer is 2 fold more potent than the (-) anantiomer with respect to analgesic activity in mice. Both enantiomers bind with high affinity (Ki=0.045 and 0.3058 nM respectively) to rat brain membrane nicotinic receptors.

REFERENCES

• Spande, T.F., et al., J. Am. Chem. Soc., 114: 3475 (1992).
• Qian, C., et al., Eur. J. Pharmacol., 250: R13 (1993).
• Badio, B. and Daly, J.W., Mol. Pharmacol., 45: 563 (1994).