164668-08-0

Basic information

• Product Name: 4-(4'-chlorophenyl)-1-(4'-(4-fluorophenyl)butyl)piperidin-4-ol
• Synonyms: 4-(4'-chlorophenyl)-1-(4'-(4-fluorophenyl)butyl)piperidin-4-ol
• CAS NO: 164668-08-0
• Molecular Weight: 361.887
• Mol File: 164668-08-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-(4'-chlorophenyl)-1-(4'-(4-fluorophenyl)butyl)piperidin-4-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4'-chlorophenyl)-1-(4'-(4-fluorophenyl)butyl)piperidin-4-ol(164668-08-0)
• EPA Substance Registry System: 4-(4'-chlorophenyl)-1-(4'-(4-fluorophenyl)butyl)piperidin-4-ol(164668-08-0)

Safety Data

• Hazardous Substances Data: 164668-08-0(Hazardous Substances Data)

Upstream product

• 3874-54-2 4-(4-fluorophenyl)-4-oxo-n-butyl chloride 
• 39512-49-7 4-(4-chlorophenyl)-4-hydroxypiperidine 
• 54540-58-8 1-(4-chlorobutyl)-4-fluorobenzene 
• 52-86-8 haloperidol 
• 352-13-6 4-flourophenylmagnesium bromide 
• 89326-70-5 1-bromo-4-(4-fluorophenyl)-butane 
• 149069-37-4 1-fluoro-4-(4-iodobutyl)benzene 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 

Relevant articles and documents

Structure-Kinetic Profiling of Haloperidol Analogues at the Human Dopamine D2 Receptor

Haloperidol is a typical antipsychotic drug (APD) associated with an increased risk of extrapyramidal side effects (EPSs) and hyperprolactinemia relative to atypical APDs such as clozapine. Both drugs are dopamine D2 receptor (D2R) antagonists, with contrasting kinetic profiles. Haloperidol displays fast association/slow dissociation at the D2R, whereas clozapine exhibits relatively slow association/fast dissociation. Recently, we have provided evidence that slow dissociation from the D2R predicts hyperprolactinemia, whereas fast association predicts EPS. Unfortunately, clozapine can cause severe side effects independent of its D2R action. Our results suggest an optimal kinetic profile for D2R antagonist APDs that avoids EPS. To begin exploring this hypothesis, we conducted a structure-kinetic relationship study of haloperidol and revealed that subtle structural modifications dramatically change binding kinetic rate constants, affording compounds with a clozapine-like kinetic profile. Thus, optimization of these kinetic parameters may allow development of novel APDs based on the haloperidol scaffold with improved side-effect profiles.

Multi-receptor drug design: Haloperidol as a scaffold for the design and synthesis of atypical antipsychotic agents

Using haloperidol as a scaffold, new agents were designed to investigate the structural contributions of various groups to binding at CNS receptors associated with atypical antipsychotic pharmacology. It is clear that each pharmacophoric group, the butyrophenone, the piperidine and the 4-chlorophenyl moieties contributes to changes in binding to the receptors of interest. This strategy has resulted in the identification of several new agents, compounds 16, 18, 19, 23, 24 and 25, with binding profiles which satisfy our stated criteria for agents to act as potential atypical antipsychotics. This research demonstrates that haloperidol can serve as a useful lead in the identification and design of new agents that target multiple receptors associated with antipsychotic pharmacology.