Quetiapine

Base Information

• Chemical Name: Quetiapine
• CAS No.: 111974-69-7
• Molecular Formula: C21H25N3O2S
• Molecular Weight: 383.514
• Hs Code.: 2934999090
• European Community (EC) Number: 601-143-7
• NSC Number: 758918
• UNII: BGL0JSY5SI
• DSSTox Substance ID: DTXSID9023546
• Nikkaji Number: J386.371I
• Wikipedia: Quetiapine
• Wikidata: Q408535
• NCI Thesaurus Code: C61917
• RXCUI: 51272
• Pharos Ligand ID: KT7VY43USC7W
• Metabolomics Workbench ID: 38707
• ChEMBL ID: CHEMBL716
• Mol file: 111974-69-7.mol

Synonyms:2-(2-(4-dibenzo(b,f)(1,4)thiazepine-11-yl-1-piperazinyl)ethoxy)ethanol;Ethanol, 2-(2-(4-dibenzo(b,f)(1,4)thiazepin-11-yl-1-piperazinyl)ethoxy)-, (E)-2-butenedioate (2:1) (salt);ICI 204,636;ICI 204636;ICI-204636;ICI204636;quetiapine;quetiapine fumarate;Seroquel

Chemical Property of Quetiapine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 3.22E-13mmHg at 25°C
• Melting Point: 172 - 174oC
• Boiling Point: 556.5 °C at 760 mmHg
• PKA: 14.41±0.10(Predicted)
• Flash Point: 290.4 °C
• PSA: 73.60000
• Density: 1.27 g/cm³
• LogP: 2.16740
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 383.16674822
• Heavy Atom Count: 27
• Complexity: 496

Purity/Quality:

99% ^*data from raw suppliers

Quetiapine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antipsychotic Agents
• Canonical SMILES: C1CN(CCN1CCOCCO)C2=NC3=CC=CC=C3SC4=CC=CC=C42
• Recent ClinicalTrials: A Study to Test the Effect of Different Doses of BI 1358894 and Quetiapine in People With Depression
• Recent EU Clinical Trials: Cognitive effects of adjuntive Vortioxetine in early Schizophrenia
• Recent NIPH Clinical Trials: Efficacy and safety of zotepine in critically ill patients with agitation: A prospective, cohort observational study
• Uses: antiviral Labelled Quetiapine (Q510000). Used as an antipsychotic.
• Biological Functions: Quetiapine is a dibenzothiazepine with a brain receptor–binding profile similar to that of clozapine. Quetiapine binds most effectively to histaminergic H1, adrenergic a1 and a2, and serotonergic 5-HT2A receptors in the brain and has even lower affinity than clozapine for dopaminergic D2 receptors. Unlike clozapine, however, quetiapine also has very low affinity for muscarinic receptors.
• Clinical Use: Schizophrenia Mania in bipolar disorder Depression in bipolar disorder
• Drug interactions: Potentially hazardous interactions with other drugs Anaesthetics: enhanced hypotensive effect. Analgesics: increased risk of convulsions with tramadol; enhanced hypotensive and sedative effects with opioids; increased risk of ventricular arrhythmias with methadone. Anti-arrhythmics: increased risk of ventricular arrhythmias. Antibacterials: concentration possibly increased by macrolides - avoid. Antidepressants: concentration of tricyclics possibly increased. Antiepileptics: antagonism of convulsive threshold; metabolism accelerated by carbamazepine and phenytoin; concentration possibly increased by valproate. Antifungals: concentration possibly increased by imidazoles and triazoles - avoid. Antimalarials: manufacturer advises avoid use with artemether and lumefantrine. Antipsychotics: possible increased risk of ventricular arrhythmias with risperidone. Antivirals: concentration possibly increased by atazanavir, boceprevir, darunavir, fosamprenavir, indinavir, lopinavir, ritonavir, saquinavir, telaprevir and tipranavir - avoid. Anxiolytics and hypnotics: enhanced sedative effects. Atomoxetine: increased risk of ventricular arrhythmias. Cytotoxics: increased risk of ventricular arrhythmias with arsenic trioxide. Grapefruit juice: concentration of quetiapine possibly increased - avoid.

Technology Process of Quetiapine

There total 43 articles about Quetiapine 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: 99.0%

1-[2-(2-hydroxyethoxy)ethyl]piperazine (13349-82-1) + 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) → Quetiapine (111974-69-7)

Guidance literature:

In toluene; at 105 - 107 ℃;

DOI:10.1080/10426507.2014.965813

Reference yield: 98.2%

11-piperazin-1-yldibenzo[b,f][1,4]thiazepine hydrochloride (753475-15-9,111974-74-4) + 2-(2-Chloroethoxy)ethanol (628-89-7) → Quetiapine (111974-69-7)

Guidance literature:

With sodium carbonate; sodium iodide; tetrabutylammomium bromide; In toluene; at 115 - 120 ℃; for 17h; Heating / reflux;

Reference yield: 95.0%

11-{4-[2-(2-tritiloxiethoxy)ethyl]piperazine-1-yl}dibenzo[b,f][1,4]thiazepine (844639-06-1) → Quetiapine (111974-69-7)

Guidance literature:

11-{4-[2-(2-tritiloxiethoxy)ethyl]piperazine-1-yl}dibenzo[b,f][1,4]thiazepine; With toluene-4-sulfonic acid; In methanol; toluene; for 4h; Heating / reflux;

With hydrogenchloride; In water; toluene;

With sodium hydroxide; In water; toluene; pH=9.5; Product distribution / selectivity;

upstream raw materials:

1-[2-(2-hydroxyethoxy)ethyl]piperazine

11-chloro-dibenzo[b,f][1,4]thiazepine

dibenzo[b,f][1,4]thiazepin-11-one

11-piperazin-1-yldibenzo[b,f][1,4]thiazepine hydrochloride

Downstream raw materials:

11-(4-[2-(2-hydroxyethoxy)ethyl]-1-piperazinyl)dibenzo[b,f]-1,4-thiazepine tosylate

11-(1-piperazinyl)dibenzo[b,f][1,4]thiazepine

1-[2-(2-hydroxyethoxy)ethyl]piperazine

2-[2-(1-oxidopiperazin-1-yl)ethoxy]ethanol

Refernces

• 1、 Koerber, Jochen,Loeffler, Stefan,Schollmeyer, Dieter,Nubbemeyer, Udo. "Synthesis and oxidant properties of phase 1 benzepine N-oxides of common antipsychotic drugs". . p. 2875 - 2887. Retrieved 2013.
• 2、 Li, Mingliang,Wang, Jun Joelle. "Cobalt-Catalyzed Direct C-H Thiolation of Aromatic Amides with Disulfides: Application to the Synthesis of Quetiapine". . p. 6490 - 6493. Retrieved 2018.
• 3、 -. "Synthesis method of quetiapine". Paragraph 0070-0072. . Retrieved 2022/04/06.
• 4、 Li, Chen,Ge, Min-Tong,Bai, Liang,Xia, Ai-Bao,Xu, Dan-Qian,Xu, Zhen-Yuan. "Direct: N -alkylation of sulfur-containing amines". supporting information. p. 4478 - 4482. Retrieved 2021/05/31.