10-{4-[2-(2-hydroxyethoxy)ethyl]piperazin-1-yl}-2λ4-thia-9-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-one

• ChemBase ID: 177259
• Molecular Formular: C21H25N3O3S
• Molecular Mass: 399.5065
• Monoisotopic Mass: 399.16166268
• SMILES: c12c(S(=O)c3c(C(=N1)N1CCN(CC1)CCOCCO)cccc3)cccc2
• Canonical SMILES: OCCOCCN1CCN(CC1)C1=Nc2ccccc2S(=O)c2c1cccc2
• InChI: InChI=1S/C21H25N3O3S/c25-14-16-27-15-13-23-9-11-24(12-10-23)21-17-5-1-3-7-19(17)28(26)20-8-4-2-6-18(20)22-21/h1-8,25H,9-16H2
• InChIKey: FXJNLPUSSHEDON-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 10-{4-[2-(2-hydroxyethoxy)ethyl]piperazin-1-yl}-2λ^4-thia-9-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-one
• IUPAC Traditional name: 10-{4-[2-(2-hydroxyethoxy)ethyl]piperazin-1-yl}-2λ^4-thia-9-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-one
• Synonyms: 2-[2-[4-(5-Oxidodibenzo[b,f][1,4]thiazepin-11-yl)-1-piperazinyl]ethoxy]ethanol; Quetiapine S-Oxide; Quetiapine Sulfoxide

Database IDs

• CAS Number: 329216-63-9
• PubChem SID: 164233169
• PubChem CID: 10431050

CALCULATED PROPERTIES

• Acid pKa: 15.121227
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 0.4172181
• LogD (pH = 7.4): 1.2707673
• Log P: 1.3062338
• Molar Refractivity: 115.4571 cm^3
• Polarizability: 43.46567 Å^3
• Polar Surface Area: 65.37 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 45-46°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - Q510030

A metabolite of Quetiapine, which is used as an antipsychotic.

REFERENCES

• Onrust, S., et al.: CNS Drugs, 15, 329 (2001)
• Lin, S., et al.: J. Anal. Toxicol., 28, 443 (2001)
• Kirschbaum, K., et al.: Clin. Chem., 51, 1718 (2001)
• Kinon, B., et al.: J. Clin. Psychopharmacol., 26, 453 (2001)