123464-89-1

Basic information

• Product Name: N-(3R)-1-AZABICYCLO[2.2.2]OCT-3-YL-4-CHLOROBENZAMIDE
• Synonyms: N-(3R)-1-AZABICYCLO[2.2.2]OCT-3-YL-4-CHLOROBENZAMIDE;PNU 282987;N-(3R)-1-Azabicyclo[2.2.2]oct-3-yl-4-chlorobenzamide hydrochloride;N-(3R)-1-Azabicyclo[2.2.2]oct-3-yl-4-chlorobenzamide hydrochloride PNU 282987;PNU282987 HCl;PNU 282987(PNU 282987 hydrochloride)
• CAS NO: 123464-89-1
• Molecular Formula: C14H17ClN2O
• Molecular Weight: 264.75058
• Product Categories: Acetylcholine receptor;Inhibitors
• Mol File: 123464-89-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 240-242℃
• Boiling Point: 431.5°Cat760mmHg
• Flash Point: 214.8°C
• Appearance: /
• Density: 1.27g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.612
• Storage Temp.: Store at RT
• Solubility: Soluble in DMSO (up to 25 mg/ml)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months.
• CAS DataBase Reference: N-(3R)-1-AZABICYCLO[2.2.2]OCT-3-YL-4-CHLOROBENZAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3R)-1-AZABICYCLO[2.2.2]OCT-3-YL-4-CHLOROBENZAMIDE(123464-89-1)
• EPA Substance Registry System: N-(3R)-1-AZABICYCLO[2.2.2]OCT-3-YL-4-CHLOROBENZAMIDE(123464-89-1)

Safety Data

• Hazardous Substances Data: 123464-89-1(Hazardous Substances Data)

Usage

Description

N-(3R)-1-AZABICYCLO[2.2.2]OCT-3-YL-4-CHLOROBENZAMIDE is a complex organic compound with a unique molecular structure. It is characterized by its bicyclic arrangement and the presence of a chlorobenzamide group. N-(3R)-1-AZABICYCLO[2.2.2]OCT-3-YL-4-CHLOROBENZAMIDE has potential applications in various fields due to its specific chemical properties and interactions.

Uses

Used in Pharmaceutical Industry:
N-(3R)-1-AZABICYCLO[2.2.2]OCT-3-YL-4-CHLOROBENZAMIDE is used as a therapeutic agent for targeting specific receptors or enzymes in the treatment of various diseases. Its unique molecular structure allows it to interact with biological targets, potentially leading to the development of new drugs for treating conditions such as neurological disorders, cancer, or other medical conditions.
Used in Chemical Research:
In the field of chemical research, N-(3R)-1-AZABICYCLO[2.2.2]OCT-3-YL-4-CHLOROBENZAMIDE can be used as a starting material or a building block for the synthesis of more complex molecules. Its unique structure and functional groups make it a valuable compound for exploring new chemical reactions and developing novel synthetic pathways.
Used in Material Science:
The compound may also find applications in material science, where its specific properties can be utilized to create new materials with unique characteristics. For example, it could be used in the development of advanced polymers, coatings, or other materials with specific mechanical, electrical, or optical properties.

Biological Activity

Highly selective α 7 nAChR agonist (K i = 26 nM) displaying negligible blockade of α 1 β 1 γ δ and α 3 β 4 nAChRs (IC 50 ≥ 60 μ M). Found to be inactive against a panel of 32 receptors at 1 μ M, except 5-HT 3 receptors (K i = 930 nM).

Biochem/physiol Actions

Primary Targetα7 nAChRs

References

1) Bodnar?et al.?(2005),?Discovery and structure-activity relationship of quinuclidine benzamides as agonists of α7 nicotinic acetylcholine receptors; J. Med. Chem.?48?905 2) Stuckenholz?et al.?(2013),?The α7 nAChR agonist PNU-282987 reduces inflammation and MPTP-induced nigral dopaminergic cell loss in mice; J. Parkinsons Dis.?3?161 3) Vicens?et al. (2013),?Motor and anxiety effects of PNU-282987, an alpha7 nicotinic receptor agonist, and stress in an animal model of Alzheimer’s disease; Curr. Alzheimer Res.?10?516 4) Navarro?et al.?(2015),?Alpha7 nicotinic receptor activation protects against oxidative stress via heme-oxygenase I induction; Biochem. Pharmacol.?97?473 5) McLean?et al.?(2016),?Nicotinic α7 and α4β2 agonists enhance the formation and retrieval of recognition memory: Potential mechanisms for cognitive performance enhancement in neurological and psychiatric disorders; Behav. Brain Res.?302?73

InChI:InChI=1/C14H17ClN2O/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)/t13-/m0/s1

Upstream product

• 6530-09-2 (3R)-quinuclidin-3-amine dihydrochloride 
• 74-11-3 para-chlorobenzoic acid 
• 122-01-0 4-chloro-benzoyl chloride 

Relevant articles and documents

Discovery and structure-activity relationship of quinuclidine benzamides as agonists of α7 nicotinic acetylcholine receptors

A library of benzamides was tested for α7 nicotinic acetylcholine receptor (nAChR) agonist activity using a chimeric receptor in a functional, cell-based, high-throughput assay. From this library, quinuclidine benzamides were found to have α7 nAChR agonist activity. The SAR diverged from the activity of this compound class verses the 5-HT3 receptor, a structural homologue of the α7 nAChR. PNU-282987, the most potent compound from this series, was also shown to open native α7 nAChRs in cultured rat neurons and to reverse an amphetamine-induced gating deficit in rats.

Method of treating or preventing schizophrenia and/or psychosis using S-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamides and thiobenzamides

Compounds of general formula I STR1 wherein: X represents oxygen or sulphur; each of R1 and R3 independently represents hydrogen or a C1 -C4 alkyl group; Ar represents: a phenyl ring optionally substituted by one, two or three C1 -C4 alkoxy groups and/or by one or two halogen atoms; a phenyl ring of the general formula STR2 wherein R2 represents halogen, 4,5-benzo, C1 -C8 alkoxy, C1 -C4 alkylcarbonyl or Am, wherein Am represents amino, methylamino or dimethylamino, R4 represents C1 -C8 alkyl, n is 1 or 2; or a pyrimidinyl moiety of the general formula STR3 wherein R5 is C1 -C4 alkyl; and their N-oxides and pharmaceutically acceptable salts are useful as antischizophrenic and/or antipsychotic agents. A preferred compound is S(-)-4-amino-N-(1-azabicyclo[2.2.2]oct-3-yl)-5-chloro-2-methoxybenzamide.