N-({4-[2-(dimethylamino)ethoxy]phenyl}methyl)-3,4-dimethoxybenzamide hydrochloride

• ChemBase ID: 155037
• Molecular Formular: C20H27ClN2O4
• Molecular Mass: 394.89238
• Monoisotopic Mass: 394.16593503
• SMILES: CN(C)CCOc1ccc(cc1)CNC(=O)c1ccc(c(c1)OC)OC.Cl
• Canonical SMILES: COc1cc(ccc1OC)C(=O)NCc1ccc(cc1)OCCN(C)C.Cl
• InChI: InChI=1S/C20H26N2O4.ClH/c1-22(2)11-12-26-17-8-5-15(6-9-17)14-21-20(23)16-7-10-18(24-3)19(13-16)25-4;/h5-10,13H,11-12,14H2,1-4H3,(H,21,23);1H
• InChIKey: ZTOUXLLIPWWHSR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-({4-[2-(dimethylamino)ethoxy]phenyl}methyl)-3,4-dimethoxybenzamide hydrochloride
• IUPAC Traditional name: itopride hydrochloride
• Synonyms: N-[[4-[2-(Dimethylamino)ethoxy]phenyl]methyl]-3,4-dimethoxy benzamidehydrochloride; N-[p-[2-(dimethylamino)ethoxy]benzyl]veratramide hydrochloride; Itopride hydrochloride; N-[[4-[2-(Dimethylamino)ethoxy]phenyl]methyl]-3,4-dimethoxy Benzamide Hydrochloride; HSR-803; HC-803; Itax; Ganaton; Itopride Hydrochloride

Database IDs

• CAS Number: 122892-31-3
• MDL Number: MFCD00881710
• PubChem SID: 162249175
• PubChem CID: 129791

CALCULATED PROPERTIES

• Acid pKa: 14.712449
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -0.7529689
• LogD (pH = 7.4): 0.93125874
• Log P: 2.317666
• Molar Refractivity: 102.0544 cm^3
• Polarizability: 39.197426 Å^3
• Polar Surface Area: 60.03 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; H2O: ≥48 mg/mL; Methanol; Water
• Apperance: White Solid; white to tan powder
• Melting Point: 194-195°C

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Nature polluting (N)
• German water hazard class: 3
• Risk Statements: 50
• Safety Statements: 61
• GHS Pictograms: GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H400
• GHS Precautionary statements: P273
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H26N2O4 ·HCl

DETAILS

Sigma Aldrich - SML0033

Biochem/physiol Actions
Itopride is an acetylcholinesterase (AChE) inhibitor and D2 dopamine receptor antagonist. Itopride is used as a gastroprokinetic agent.

Toronto Research Chemicals - I931500

Dopamine D2-receptor antagonist with anticholinesterase activity. Gastroprokinetic.

REFERENCES

• Iwanaga, Y., et al; Jpn. J. Pharmacol., 56, 261 (1991)
• Mushiroda, T., et al.: Drug Metab. Dispos., 28, 1231 (1991)