Clozapine

Base Information

• Chemical Name: Clozapine
• CAS No.: 5786-21-0
• Molecular Formula: C18H19ClN4
• Molecular Weight: 326.829
• Hs Code.: 29339900
• Mol file: 5786-21-0.mol

Synonyms:Clorazil;Fazaclo;Iprox;Clozapina [INN-Spanish];8-Chloro-11-(4-methyl-1-piperazinyl)-5H-dibenzo(b,e)(1,4)diazepine;5H-Dibenzo(b,e)(1,4)diazepine, 8-chloro-11-(4-methyl-1-piperazinyl)-;Leponex;Asaleptin;Clozaril (TN);Clozapine [USAN:BAN:INN];8-chloro-11（4-methy-1-piperaziong）-5-H-dibenzo[b,e][1.4]diazepine;

Chemical Property of Clozapine

Chemical Property:

• Appearance/Colour: Yellow Crystalline Solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 182-185 °C
• Refractive Index: 1.681
• Boiling Point: 489.159 °C at 760 mmHg
• PKA: 3.70, 7.60(at 25℃)
• Flash Point: 249.635 °C
• PSA: 30.87000
• Density: 1.319 g/cm³
• LogP: 3.17210
• Storage Temp.: Store at RT
• Solubility.: ethanol: 1 mg/mL

Purity/Quality:

98% ^*data from raw suppliers

Clozapine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi,T,F
• Statements: 22-36/37/38-68-63-39/23/24/25-23/24/25-11
• Safety Statements: 26-36/37-45-16-7

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Clozapine is an atypical antipsychotic with a complex pharmacological profile, primarily acting as an antagonist at dopamine and serotonin receptors. Its unique mechanism, distinct from traditional antipsychotics, contributes to its efficacy in treatment-resistant schizophrenia while potentially reducing extrapyramidal side effects. The drug's structural similarity to butaclamol suggests shared receptor interactions, though its clinical advantages may stem from additional receptor modulation beyond dopamine antagonism. Clozapine's therapeutic benefits are accompanied by significant safety considerations, including agranulocytosis risk, necessitating careful patient monitoring. Research into structural analogs aims to retain its efficacy while mitigating adverse effects, though challenges remain in translating receptor binding properties to clinical outcomes.

Technology Process of Clozapine

There total 23 articles about Clozapine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

clozapine N-oxide → clozaril (5786-21-0)

Guidance literature:

With hydrogenchloride; titanium(III) chloride; In water; acetonitrile; at 20 ℃; for 1h;

DOI:10.1021/acs.oprd.5b00312

Reference yield: 88.0%

1-methyl-piperazine (109-01-3) + 8-chloro-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one (50892-62-1) → clozaril (5786-21-0)

Guidance literature:

With titanium tetrachloride; In 1,4-dioxane; toluene; for 2h; Heating;

DOI:10.1071/CH07197

Reference yield: 80.0%

N-(4-chloro-2-nitrophenyl)-N-{2-[(4-methylpiperazin-1-yl)carbonyl]phenyl}amine (65514-72-9) → clozaril (5786-21-0)

Guidance literature:

With tributylphosphine; at 150 ℃; for 48h; Temperature; Reagent/catalyst;

DOI:10.1021/acs.joc.8b02682

upstream raw materials:

1-methyl-piperazine

8-chloro-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one

N-(2-Amino-4-chlorophenyl)anthranilic acid

2-amino-4-chlorodiphenylamine-2'-carboxylic acid (4''-methyl)piperazide

Downstream raw materials:

N-desmethylclozapine

Refernces

Use of the butaclamol template in a search for antipsychotic agents with lessened side effects

10.1021/jm00190a009

The research focuses on the search for antipsychotic agents with reduced side effects. The study explores the molecular similarities between butaclamol and clozapine, suggesting a common mechanism of action through binding at the antagonist state of the dopamine receptor. Simplified analogues of butaclamol, namely compounds 4, 8, and 12a, were synthesized and tested for their ability to displace tritiated haloperidol in vitro. Compound 12a showed significant binding affinity, comparable to butaclamol. However, in vivo testing revealed that 12a was less potent than expected based on its in vitro results. The study highlights the challenges in correlating in vitro binding affinity with in vivo efficacy and suggests that further modifications of the butaclamol structure could lead to the development of antipsychotic agents with fewer side effects.

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