Quetiapine Sulfoxide

Base Information

• Chemical Name: Quetiapine Sulfoxide
• CAS No.: 329216-63-9
• Molecular Formula: C₂₁H₂₅N₃O₃S
• Molecular Weight: 399.514
• European Community (EC) Number: 813-652-3
• UNII: 1CW92313VM
• DSSTox Substance ID: DTXSID40439830
• Nikkaji Number: J1.487.724J
• ChEMBL ID: CHEMBL1199
• Mol file: 329216-63-9.mol

Synonyms:Quetiapine Sulfoxide;329216-63-9;Quetiapine S-Oxide;2-[2-[4-(11-oxobenzo[b][1,4]benzothiazepin-6-yl)piperazin-1-yl]ethoxy]ethanol;Ethanol, 2-[2-[4-(5-oxidodibenzo[b,f][1,4]thiazepin-11-yl)-1-piperazinyl]ethoxy]-;1CW92313VM;2-[2-[4-(5-Oxidodibenzo[b,f][1,4]thiazepin-11-yl)-1-piperazinyl]ethoxy]ethanol;2-(2-(4-(5-Oxidodibenzo(b,f)(1,4)thiazepin-11-yl)piperazin-1-yl)ethoxy)ethanol;Ethanol, 2-(2-(4-(5-oxidodibenzo(b,f)(1,4)thiazepin-11-yl)-1-piperazinyl)ethoxy)-;QuetiapineSulfoxide;Quetiapine metabolite Quetiapine sulfoxide;CHEMBL1199;UNII-1CW92313VM;SCHEMBL17524440;DTXSID40439830;HY-G0014;Quetiapine fumarate impurity S [EP];AKOS015965462;CS-4127;SULFOXIDE METABOLITE (INACTIVE);Ethanol,2-[2-[4-(5-oxidodibenzo[b,f][1,4]thiazepin-11-yl)-1-piperazinyl]ethoxy]-;MRF-0000747;AC-20385;FT-0674261;A875480;J-018937;QUETIAPINE FUMARATE IMPURITY S [EP IMPURITY];11-(4-[2-(2-Hydroxyethoxy)ethyl]piperazin-1-yl)dibenzo-[b,f][1,4]thiazepine Sulfoxide;11-[4-[2-(2-Hydroxyethoxy)ethyl]piperazino]dibenzo[b,f][1,4]thiazepine 5-oxide;2-[2-[4-(5-oxidodibenzo[b,f][1,4]thiazepin-11-yl)-1-piperazinyl]ethoxy]-ethanol;11-(4-(2-(2-Hydroxyethoxy)ethyl)piperazin-1-yl)dibenzo[b,f][1,4]thiazepine 5-oxide dihydrochloride

Chemical Property of Quetiapine Sulfoxide

Chemical Property:

• Appearance/Colour: pale yellow solid
• Vapor Pressure: 8.48E-16mmHg at 25°C
• Melting Point: ~48 °C
• Refractive Index: 1.675
• Boiling Point: 611.3 °C at 760 mmHg
• PKA: 14.41±0.10(Predicted)
• Flash Point: 323.5 °C
• PSA: 84.58000
• Density: 1.35 g/cm³
• LogP: 2.04860
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Sparingly), Methanol (Slightly), Water (Slightly)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 399.16166284
• Heavy Atom Count: 28
• Complexity: 515

Purity/Quality:

99%+, ^*data from raw suppliers

Quetiapine Sulfoxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCN1CCOCCO)C2=NC3=CC=CC=C3S(=O)C4=CC=CC=C42
• Isomeric SMILES: C1CN(CCN1CCOCCO)C2=NC3=CC=CC=C3[S@@](=O)C4=CC=CC=C42
• Uses: Quetiapine Sulfoxide is a metabolite of Quetiapine, which is used as an antipsychotic. Quetiapine Sulfoxide (Quetiapine EP Impurity S) is a metabolite of Quetiapine, which is used as an antipsychotic.

Technology Process of Quetiapine Sulfoxide

There total 5 articles about Quetiapine Sulfoxide 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: 32.0%

quetiapine N19-oxide + (2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (E)-3-phenylpropenal (14371-10-9) + Quetiapine (111974-69-7) + Quetiapine sulfoxide (329216-63-9)

Guidance literature:

With tetrapropylammonium perruthennate; In dichloromethane; for 0.5h; Molecular sieve; Inert atmosphere;

DOI:10.1055/s-0033-1338519

Reference yield: 29.0%

quetiapine N19-oxide + (2E)-3-phenyl-2-propen-1-ol (4407-36-7) → 1-phenyl-propane-1,2,3-triol (63157-81-3) + Quetiapine (111974-69-7) + Quetiapine sulfoxide (329216-63-9)

Guidance literature:

With osmium(VIII) oxide; In water; tert-butyl alcohol; at 20 ℃; for 19h; Inert atmosphere;

DOI:10.1055/s-0033-1338519

Reference yield: 6.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + quetiapine N19-oxide → phenylethane 1,2-diol (93-56-1) + quetiapine N19,S-dioxide + Quetiapine sulfoxide (329216-63-9)

Guidance literature:

With osmium(VIII) oxide; In water; tert-butyl alcohol; at 20 ℃; for 19h; Inert atmosphere;

DOI:10.1055/s-0033-1338519

upstream raw materials:

Quetiapine

styrene

(2E)-3-phenyl-2-propen-1-ol

Refernces

• 1、 Skibinski, Robert. "A study of photodegradation of quetiapine by the use of LC-MS/MS method". experimental part. p. 232 - 240. Retrieved 2012/04/10.