(2R,3R)-2,3-dihydroxybutanedioic acid; 3-{2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl}-1,2,3,4-tetrahydroquinazoline-2,4-dione

• ChemBase ID: 132715
• Molecular Formular: C26H28FN3O9
• Molecular Mass: 545.5136232
• Monoisotopic Mass: 545.18095771
• SMILES: c1ccc2c(c1)c(=O)n(c(=O)[nH]2)CCN1CCC(CC1)C(=O)c1ccc(cc1)F.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O
• Canonical SMILES: OC(=O)[C@@H]([C@H](C(=O)O)O)O.Fc1ccc(cc1)C(=O)C1CCN(CC1)CCn1c(=O)[nH]c2c(c1=O)cccc2
• InChI: InChI=1S/C22H22FN3O3.C4H6O6/c23-17-7-5-15(6-8-17)20(27)16-9-11-25(12-10-16)13-14-26-21(28)18-3-1-2-4-19(18)24-22(26)29;5-1(3(7)8)2(6)4(9)10/h1-8,16H,9-14H2,(H,24,29);1-2,5-6H,(H,7,8)(H,9,10)/t;1-,2-/m.1/s1
• InChIKey: KMTLTEVOQLMYRS-LREBCSMRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2,3-dihydroxybutanedioic acid; 3-{2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl}-1,2,3,4-tetrahydroquinazoline-2,4-dione
• IUPAC Traditional name: L(+)-tartaric acid; ketanserin
• Synonyms: 3-(2-[4-(4-Fluorobenzoyl)-1-piperidinyl]ethyl)-2,4(1H,3H)-quinazolinedione (+)-tartrate salt; R 41468 (+)-tartrate salt; Ketanserin (+)-tartrate salt

Database IDs

• CAS Number: 83846-83-7
• EC Number: 281-062-8
• MDL Number: MFCD00084651
• PubChem SID: 24278121; 162226992
• PubChem CID: 16219944

CALCULATED PROPERTIES

• Acid pKa: 11.424021
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.8247793
• LogD (pH = 7.4): 3.361728
• Log P: 3.6093197
• Molar Refractivity: 109.1073 cm^3
• Polarizability: 40.334778 Å^3
• Polar Surface Area: 69.72 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: soluble6 mg/mL; DMSO: soluble52 mg/mL; ethanol: soluble3.3 mg/mL
• Apperance: white solid

Safety Information

• RTECS: VA1411195
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 22-36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... HTR2A(3356), HTR2B(3357), HTR2C(3358)

Product Information

• Purity: ≥97%; ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C22H22FN3O3 · C4H6O6

DETAILS

Sigma Aldrich - S006

Biochem/physiol Actions
Selective 5-HT2 serotonin receptor antagonist. Ketanserin significantly reduces nicotine self-administration in rats, supporting an unexpected involvement of serotonin in nicotine addiction.1

Sigma Aldrich - 15850

Biochem/physiol Actions
Selective 5-HT2 serotonin receptor antagonist. Ketanserin significantly reduces nicotine self-administration in rats, supporting an unexpected involvement of serotonin in nicotine addiction.1