10-{4-[2-(2-hydroxyethoxy)ethyl]piperazin-1-yl}-2-thia-9-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-5-ol

• ChemBase ID: 171251
• Molecular Formular: C21H25N3O3S
• Molecular Mass: 399.5065
• Monoisotopic Mass: 399.16166268
• SMILES: N1=C(c2c(Sc3c1ccc(c3)O)cccc2)N1CCN(CC1)CCOCCO
• Canonical SMILES: OCCOCCN1CCN(CC1)C1=Nc2ccc(cc2Sc2c1cccc2)O
• InChI: InChI=1S/C21H25N3O3S/c25-12-14-27-13-11-23-7-9-24(10-8-23)21-17-3-1-2-4-19(17)28-20-15-16(26)5-6-18(20)22-21/h1-6,15,25-26H,7-14H2
• InChIKey: VEGVCHRFYPFJFO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 10-{4-[2-(2-hydroxyethoxy)ethyl]piperazin-1-yl}-2-thia-9-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-5-ol
• IUPAC Traditional name: 10-{4-[2-(2-hydroxyethoxy)ethyl]piperazin-1-yl}-2-thia-9-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-5-ol
• Synonyms: 11-[4-[2-(2-Hydroxyethoxy)ethyl]-1-piperazinyl]dibenzo[b,f][1,4]thiazepin-7-ol; ICI214227; 7-Hydroxy Quetiapine

Database IDs

• CAS Number: 139079-39-3
• PubChem SID: 164227161
• PubChem CID: 132203

CALCULATED PROPERTIES

• Acid pKa: 8.476061
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.9181366
• LogD (pH = 7.4): 2.3000615
• Log P: 2.3273635
• Molar Refractivity: 116.0663 cm^3
• Polarizability: 43.351456 Å^3
• Polar Surface Area: 68.53 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 56-60°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H953225

A metabolite of Quetiapine, a Benzothiazepine with mixed serotonin and dopamine receptor antagonistic properties used as an antipsychotic.

REFERENCES

• Newton, D., et al.: Drug Metab. Dispos., 23, 154 (1995)
• Tanaka, E., et al.: J. Clin. Pharm. Ther., 24, 7 (1999)