4-amino-5-chloro-N-[2-(ethylamino)ethyl]-2-methoxybenzamide

• ChemBase ID: 166229
• Molecular Formular: C12H18ClN3O2
• Molecular Mass: 271.74322
• Monoisotopic Mass: 271.10875451
• SMILES: c1(c(cc(c(c1)C(=O)NCCNCC)OC)N)Cl
• Canonical SMILES: COc1cc(N)c(cc1C(=O)NCCNCC)Cl
• InChI: InChI=1S/C12H18ClN3O2/c1-3-15-4-5-16-12(17)8-6-9(13)10(14)7-11(8)18-2/h6-7,15H,3-5,14H2,1-2H3,(H,16,17)
• InChIKey: RTQMQUZXBADBGJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-5-chloro-N-[2-(ethylamino)ethyl]-2-methoxybenzamide
• IUPAC Traditional name: 4-amino-5-chloro-N-[2-(ethylamino)ethyl]-2-methoxybenzamide
• Synonyms: 4-Amino-5-chloro-N-[2-(ethylamino)ethyl]-2-methoxybenzamide; 4-Amino-5-chloro-N-[2-(ethylamino)ethyl]-o-anisamide; N-(Ethylaminoethyl)-2-methoxy-4-amino-5-chlorobenzamide; N-Desethyl Metoclopramide

Database IDs

• CAS Number: 27260-19-1
• PubChem SID: 162260362
• PubChem CID: 33761

CALCULATED PROPERTIES

• Acid pKa: 14.490871
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -2.5348506
• LogD (pH = 7.4): -1.5591966
• Log P: 0.6574142
• Molar Refractivity: 73.4745 cm^3
• Polarizability: 27.613148 Å^3
• Polar Surface Area: 76.38 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D289385

A novel Metoclopramide (M338685) metabolite in humans.

REFERENCES

• Bateman, D., et al.: Clin. Pharmacokinet., 8, 523 (1983)
• Vlase, L., et al.: Biopharm. Drug Dispos., 27, 285 (1983)
• Gunduz, M., et al.: Drug Metab. Dispos., 38, 361 (1983)