5-bromo-N-{[(2S)-1-ethylpyrrolidin-2-yl]methyl}-2,3-dimethoxybenzamide hydrobromide

• ChemBase ID: 168994
• Molecular Formular: C16H24Br2N2O3
• Molecular Mass: 452.18136
• Monoisotopic Mass: 450.01536664
• SMILES: C1C[C@H](N(C1)CC)CNC(=O)c1c(c(cc(c1)Br)OC)OC.Br
• Canonical SMILES: CCN1CCC[C@H]1CNC(=O)c1cc(Br)cc(c1OC)OC.Br
• InChI: InChI=1S/C16H23BrN2O3.BrH/c1-4-19-7-5-6-12(19)10-18-16(20)13-8-11(17)9-14(21-2)15(13)22-3;/h8-9,12H,4-7,10H2,1-3H3,(H,18,20);1H/t12-;/m0./s1
• InChIKey: AOEBIEBXGASRIN-YDALLXLXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-bromo-N-{[(2S)-1-ethylpyrrolidin-2-yl]methyl}-2,3-dimethoxybenzamide hydrobromide
• IUPAC Traditional name: 5-bromo-N-{[(2S)-1-ethylpyrrolidin-2-yl]methyl}-2,3-dimethoxybenzamide hydrobromide
• Synonyms: (S)-5-Bromo-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2,3-dimethoxybenzamide Monohydrobromide; Isoremoxipride Hydrobromide; FLB 457 Hydrobromide

Database IDs

• CAS Number: 107188-92-1
• PubChem SID: 162263126
• PubChem CID: 46781582

CALCULATED PROPERTIES

• Acid pKa: 13.474005
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.5202022
• LogD (pH = 7.4): 1.233687
• Log P: 2.3419893
• Molar Refractivity: 90.5612 cm^3
• Polarizability: 34.69842 Å^3
• Polar Surface Area: 50.8 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F375000

Potential antipsychotic agent; antidopaminergic.

REFERENCES

• Hoegberg, T., et al.: J. Med. Chem., 33, 2305 (1990)
• 3) Glase, S., et al.: J. Med. Chem., 40, 1771 (1990)
• Hansch, C., et al.: Bioorg. Med. Chem., 11, 2075 (1990)
• Kulkarni, S., et al.: J. Med. Chem., 47, 3388 (1990)
• Verma, R., et al.: Bioorg. Med. Che