5-(ethanesulfonyl)-N-{[1-(2H5)ethylpyrrolidin-2-yl]methyl}-2-methoxybenzamide

• ChemBase ID: 178028
• Molecular Formular: C17H26N2O4S
• Molecular Mass: 354.46434
• Monoisotopic Mass: 354.16132832
• SMILES: c1(ccc(c(c1)C(=O)NCC1CCCN1CC)OC)S(=O)(=O)CC
• Canonical SMILES: CCN1CCCC1CNC(=O)c1cc(ccc1OC)S(=O)(=O)CC
• InChI: InChI=1S/C17H26N2O4S/c1-4-19-10-6-7-13(19)12-18-17(20)15-11-14(24(21,22)5-2)8-9-16(15)23-3/h8-9,11,13H,4-7,10,12H2,1-3H3,(H,18,20)
• InChIKey: UNRHXEPDKXPRTM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(ethanesulfonyl)-N-{[1-(^2H₅)ethylpyrrolidin-2-yl]methyl}-2-methoxybenzamide
• IUPAC Traditional name: 5-(ethanesulfonyl)-N-{[1-(^2H₅)ethylpyrrolidin-2-yl]methyl}-2-methoxybenzamide
• Synonyms: N-[(1-(Ethyl-d5)-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide; (+/-)-Sultopride-d5; Barnetil-d5; LIN 1418-d5; Sultopride-d5

Database IDs

• PubChem SID: 164233938
• PubChem CID: 46782965

CALCULATED PROPERTIES

• Acid pKa: 13.224751
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -0.4231061
• LogD (pH = 7.4): 0.9364668
• Log P: 1.0802137
• Molar Refractivity: 95.1444 cm^3
• Polarizability: 37.211655 Å^3
• Polar Surface Area: 75.71 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Crystalline Solid
• Melting Point: 181-182°C

DETAILS

Toronto Research Chemicals - S790512

Labelled dopamine D2-receptor antagonist. An antipsychotic.

REFERENCES

• Lavelle, C., et al.: J. Pharmacol., 5, 58 (1974)
• Morel, D., et al.: Sem. Hop., 59, 2337 (1974)
• Kamizono, A., et al.: Biol. Pharm. Bull., 16, 1121 (1974)