4-[4-(2-{[3-(2-aminoethyl)-1H-indol-5-yl]oxy}acetyl)piperazin-1-yl]benzonitrile hydrochloride

• ChemBase ID: 154971
• Molecular Formular: C23H26ClN5O2
• Molecular Mass: 439.93784
• Monoisotopic Mass: 439.17750278
• SMILES: c1cc(ccc1C#N)N1CCN(CC1)C(=O)COc1ccc2c(c1)c(c[nH]2)CCN.Cl
• Canonical SMILES: NCCc1c[nH]c2c1cc(OCC(=O)N1CCN(CC1)c1ccc(cc1)C#N)cc2.Cl
• InChI: InChI=1S/C23H25N5O2.ClH/c24-8-7-18-15-26-22-6-5-20(13-21(18)22)30-16-23(29)28-11-9-27(10-12-28)19-3-1-17(14-25)2-4-19;/h1-6,13,15,26H,7-12,16,24H2;1H
• InChIKey: ZXENQGQAPOYDOJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[4-(2-{[3-(2-aminoethyl)-1H-indol-5-yl]oxy}acetyl)piperazin-1-yl]benzonitrile hydrochloride
• IUPAC Traditional name: 4-[4-(2-{[3-(2-aminoethyl)-1H-indol-5-yl]oxy}acetyl)piperazin-1-yl]benzonitrile hydrochloride
• Synonyms: Donitriptan monohydrochloride

Database IDs

• CAS Number: 170911-68-9
• MDL Number: MFCD09027358
• PubChem SID: 162249109
• PubChem CID: 197705

CALCULATED PROPERTIES

• Acid pKa: 16.506659
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.9665461
• LogD (pH = 7.4): -0.23556067
• Log P: 2.041495
• Molar Refractivity: 116.8065 cm^3
• Polarizability: 45.43437 Å^3
• Polar Surface Area: 98.38 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >20 mg/mL
• Apperance: white to off-white

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 20/21-25-36/37/38
• Safety Statements: 26-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H312-H315-H319-H332-H335
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C23H25N5O2 · HCl

DETAILS

Sigma Aldrich - D9071

Biochem/physiol Actions
Donitriptan is a potent, selective 5-HT1B/1D agonist.