158985-00-3

Basic information

• Product Name: L-745,870 TRIHYDROCHLORIDE
• Synonyms: 3-(4-[4-CHLOROPHENYL]PIPERAZIN-1-YL)-METHYL-1H-PYRROLO[2,3-B]PYRIDINE TRIHYDROCHLORIDE;L-745,870 TRIHYDROCHLORIDE;3HCl;L 745870;3-[[4-(4-Chlorophenyl)-1-piperazinyl]methyl]-1H-pyrrolo[2,3-b]pyridine
• CAS NO: 158985-00-3
• Molecular Formula: C18H22Cl4N4
• Molecular Weight: 436.21
• Mol File: 158985-00-3.mol

Chemical Properties

• Boiling Point: 590.8°Cat760mmHg
• Flash Point: 311.1°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 3.05E-14mmHg at 25°C
• Storage Temp.: Desiccate at +4°C
• CAS DataBase Reference: L-745,870 TRIHYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: L-745,870 TRIHYDROCHLORIDE(158985-00-3)
• EPA Substance Registry System: L-745,870 TRIHYDROCHLORIDE(158985-00-3)

Safety Data

• Hazardous Substances Data: 158985-00-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
L-745,870 TRIHYDROCHLORIDE is used as a dopamine receptor antagonist for its potential antipsychotic effects. It was initially developed to target the D4 subtype of dopamine receptors, which are believed to be involved in the pathophysiology of certain psychiatric disorders. The compound has shown promise in animal models, but its effectiveness in human trials has not been established.
Used in Research and Development:
In the field of research and development, L-745,870 TRIHYDROCHLORIDE is used as a tool to study the role of dopamine D4 receptors in various physiological and pathological processes. This can help scientists better understand the mechanisms underlying psychiatric disorders and potentially develop more effective treatments in the future.

Biological Activity

A highly potent and selective D 4 dopamine receptor antagonist; L-745,870 has K i values of 0.51, 2300 and 960 nM for D 4 , D 3 and D 2 subtypes respectively and > 1000-fold selectivity over 5-HT 2 , D 1 and D 5 receptors.

InChI:InChI=1/C18H19ClN4.3ClH/c19-15-3-5-16(6-4-15)23-10-8-22(9-11-23)13-14-12-21-18-17(14)2-1-7-20-18;;;/h1-7,12H,8-11,13H2,(H,20,21);3*1H

Upstream product

• 38212-33-8 4-(4-chlorophenyl) piperazine 
• 5654-92-2 7-azagramine 

Relevant articles and documents

Regioselective Functionalization of 7-Azaindole by Controlled Annular Isomerism: The Directed Metalation-Group Dance

The regioselective functionalization of 7-azaindole by controlled annular isomerism employing a directed metalation-group migration is reported. The N7 carbamoyl azaindoles undergo regioselective metalation and quenching with an electrophile to furnish C6-substituted derivatives which, in the presence of a catalytic amount of ClCONR2 promotes a carbamoyl group shift or dance from N7 to N1. A second directed metalation/electrophile quench sequence leads to 2,6-substituted azaindoles. Optimization of the metalation conditions for C2 and C6, separately and iteratively, is presented. Using the directed metalation group dance strategy, a late-stage deuteration of an antipsychotic drug is described. Overall, the controlled migration of the carbamoyl directing group allows multiple functionalization events of the bioactive azaindole scaffold.

Pyrrolo-pyridine derivatives

A class of pyrrolo[2,3-b]pyridine derivatives, substituted at the 3-position by a substituted piperazinylmethyl moiety, are antagonists of dopamine receptor subtypes within the brain, having a selective affinity for the dopamine D 4 receptor subtype over other dopamine receptor subtypes, and are accordingly of benefit in the treatment and/or prevention of psychotic disorders such as schizophrenia while manifesting fewer side-effects than those associated with classical neuroleptic drugs.