2-bromo-N-[2-(4-{[2-hydroxy-3-(1H-indol-4-yloxy)propyl]amino}-4-methylcyclohexyl)propan-2-yl]acetamide

• ChemBase ID: 131295
• Molecular Formular: C23H34BrN3O3
• Molecular Mass: 480.43836
• Monoisotopic Mass: 479.17835396
• SMILES: CC1(CCC(CC1)C(C)(C)NC(=O)CBr)NCC(COc1cccc2c1cc[nH]2)O
• Canonical SMILES: BrCC(=O)NC(C1CCC(CC1)(C)NCC(COc1cccc2c1cc[nH]2)O)(C)C
• InChI: InChI=1S/C23H34BrN3O3/c1-22(2,27-21(29)13-24)16-7-10-23(3,11-8-16)26-14-17(28)15-30-20-6-4-5-19-18(20)9-12-25-19/h4-6,9,12,16-17,25-26,28H,7-8,10-11,13-15H2,1-3H3,(H,27,29)
• InChIKey: KNGWXFIRAISQAP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-bromo-N-[2-(4-{[2-hydroxy-3-(1H-indol-4-yloxy)propyl]amino}-4-methylcyclohexyl)propan-2-yl]acetamide
• IUPAC Traditional name: 2-bromo-N-[2-(4-{[2-hydroxy-3-(1H-indol-4-yloxy)propyl]amino}-4-methylcyclohexyl)propan-2-yl]acetamide
• Synonyms: (±)-Pindobind; N1-Bromoacetyl-N8-3′-(4-indolyloxy)-2′-hydroxy-propyl-[Z]-1,8-diamino-p-menthane; Pindobind-5HT1A

Database IDs

• MDL Number: MFCD00082321
• PubChem SID: 162225573
• PubChem CID: 1239

CALCULATED PROPERTIES

• Acid pKa: 13.318093
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -0.1608873
• LogD (pH = 7.4): 0.51755184
• Log P: 3.0596952
• Molar Refractivity: 122.2423 cm^3
• Polarizability: 49.052 Å^3
• Polar Surface Area: 86.38 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.53 mg/mL; methanol: soluble17.3 mg/mL
• Apperance: tan solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - P150

Biochem/physiol Actions
Potent and selective 5-HT1A serotonin receptor antagonist; structural isomer of the β adrenoceptor alkylating ligand Pindobind
Caution
Hygroscopic