N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-4-chlorobenzamide hydrate hydrochloride

• ChemBase ID: 153987
• Molecular Formular: C14H20Cl2N2O2
• Molecular Mass: 319.2268
• Monoisotopic Mass: 318.09018325
• SMILES: c1cc(ccc1C(=O)N[C@H]1CN2CCC1CC2)Cl.O.Cl
• Canonical SMILES: O=C(c1ccc(cc1)Cl)N[C@H]1CN2CCC1CC2.O.Cl
• InChI: InChI=1S/C14H17ClN2O.ClH.H2O/c15-12-3-1-11(2-4-12)14(18)16-13-9-17-7-5-10(13)6-8-17;;/h1-4,10,13H,5-9H2,(H,16,18);1H;1H2/t13-;;/m0../s1
• InChIKey: OCWLMMBVXIESNP-GXKRWWSZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-4-chlorobenzamide hydrate hydrochloride
• IUPAC Traditional name: N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-4-chlorobenzamide hydrate hydrochloride
• Synonyms: N-(3R)-1-Azabicyclo[2.2.2]oct-3-yl-4-chloro-benzamide monohydrochloride hydrate; PNU-282987 hydrate

Database IDs

• PubChem SID: 162248126; 24898770
• PubChem CID: 16219883

CALCULATED PROPERTIES

• Acid pKa: 14.822551
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.30775958
• LogD (pH = 7.4): 1.4356446
• Log P: 2.0272558
• Molar Refractivity: 72.8082 cm^3
• Polarizability: 27.991882 Å^3
• Polar Surface Area: 32.34 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: solid

Safety Information

• Storage Condition: desiccated
• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C14H17ClN2O · HCl · xH2O

DETAILS

Sigma Aldrich - P6499

Caution
Air sensitive
Biochem/physiol Actions
Decreased expression of a homomeric alpha7 nicotinic acetylcholine receptor (nAChR) is connected with inability to process sensory information in schizophrenia. PNU-282987 is a novel selective agonist of the alpha7 nAChR that evoked whole-cell currents from cultured rat hippocampal neurons that were sensitive to the selective alpha7 nAChR antagonist methyllycaconitine (MLA) and enhanced GABAergic synaptic activity. The alpha7 nAChR agonist PNU-282987 improves auditory gating and enhances hippocampal oscillatory activity. These results provide further support for the concept that drugs that selectively activate alpha7 nAChRs may offer a novel, potential pharmacotherapy in treatment of schizophrenia.