6-(2-{4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl}ethyl)-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

• ChemBase ID: 103983
• Molecular Formular: C27H25F2N3OS
• Molecular Mass: 477.5687064
• Monoisotopic Mass: 477.16863988
• SMILES: Cc1c(CCN2CC/C(=C(/c3ccc(F)cc3)\c3ccc(F)cc3)/CC2)c(=O)n2ccsc2n1
• Canonical SMILES: Fc1ccc(cc1)/C(=C/1\CCN(CC1)CCc1c(C)nc2n(c1=O)ccs2)/c1ccc(cc1)F
• InChI: InChI=1S/C27H25F2N3OS/c1-18-24(26(33)32-16-17-34-27(32)30-18)12-15-31-13-10-21(11-14-31)25(19-2-6-22(28)7-3-19)20-4-8-23(29)9-5-20/h2-9,16-17H,10-15H2,1H3
• InChIKey: JUQLTPCYUFPYKE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-(2-{4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl}ethyl)-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one
• IUPAC Traditional name: ritanserin
• Synonyms: 6-[2-[4-(bis(4-Fluorophenyl)methylene]-1-piperidinyl]ethyl]-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one; Ritanserin; 6-[2-[4-[Bis(4-fluorophenyl)methylene]-1-piperidinyl]ethyl]-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one; Tiserton; 6-[2-[4-[bis (4-Fluorophenyl)-methylene]-1-piperidinyl]-ethyl]-5H-thiazolo[3,2-a]pyrimidin-5-one; RITANSERIN

Database IDs

• CAS Number: 87051-43-2
• MDL Number: MFCD00069341
• PubChem SID: 24278117; 162090977
• PubChem CID: 5074

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.8512743
• LogD (pH = 7.4): 4.6147885
• Log P: 5.3129544
• Molar Refractivity: 144.4701 cm^3
• Polarizability: 50.55729 Å^3
• Polar Surface Area: 35.91 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 2-hydroxypropyl-β-cyclodextrin: insoluble; dilute aqueous base: insoluble; DMSO: >10.1 mg/mL; H2O: insoluble; methanol: >10 mg/mL
• Apperance: white powder

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 22-26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... HTR2A(3356)rat ... Adra1a(29412), Drd2(24318), Htr1a(24473), Htr2a(29595), Htr7(65032)

DETAILS

MP Biomedicals - 02153769

5-HT2/5-HT1C serotonin antagonist

Sigma Aldrich - R103

Biochem/physiol Actions
Potent 5-HT2A serotonin receptor antagonist/inverse agonist that crosses the blood-brain barrier.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. R103.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - R533400

A potent 5-HT2A serotonin receptor antagonist/inverse agonist that crosses the blood-brain barrier.

REFERENCES

• Krajl, M., et al.: Biochem. Pharmacol., 14, 1684 (1965)
• Yura, A., et al.: Brain Res., 738, 96 (1965)
• Miorelli, S., et al.: Mutagenesis, 23, 93 (1965)