N-[(2S,3R)-1-benzyl-2-methylpyrrolidin-3-yl]-5-chloro-2-methoxy-4-(methylamino)benzamide

• ChemBase ID: 175066
• Molecular Formular: C21H26ClN3O2
• Molecular Mass: 387.90304
• Monoisotopic Mass: 387.17135477
• SMILES: [C@@H]1([C@@H](N(CC1)Cc1ccccc1)C)NC(=O)c1cc(c(cc1OC)NC)Cl
• Canonical SMILES: COc1cc(NC)c(cc1C(=O)N[C@@H]1CCN([C@H]1C)Cc1ccccc1)Cl
• InChI: InChI=1S/C21H26ClN3O2/c1-14-18(9-10-25(14)13-15-7-5-4-6-8-15)24-21(26)16-11-17(22)19(23-2)12-20(16)27-3/h4-8,11-12,14,18,23H,9-10,13H2,1-3H3,(H,24,26)/t14-,18+/m0/s1
• InChIKey: KRVOJOCLBAAKSJ-KBXCAEBGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R)-1-benzyl-2-methylpyrrolidin-3-yl]-5-chloro-2-methoxy-4-(methylamino)benzamide
• IUPAC Traditional name: N-[(2S,3R)-1-benzyl-2-methylpyrrolidin-3-yl]-5-chloro-2-methoxy-4-(methylamino)benzamide
• Synonyms: rel-5-Chloro-2-methoxy-4-(methylamino)-N-[(2R,3S)-2-methyl-1-(phennylmethyl)-3-pyrrolidinyl]benzamide; trans-5-Chloro-2-methoxy-4-(methylamino)-N-[2-methyl-1-(phennylmethyl)-3-pyrrolidinyl]benzamide; trans-Nemonapride

Database IDs

• CAS Number: 752154-64-6
• PubChem SID: 164230976
• PubChem CID: 6604906

CALCULATED PROPERTIES

• Acid pKa: 14.568861
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.36476722
• LogD (pH = 7.4): 2.137136
• Log P: 3.0746083
• Molar Refractivity: 111.112 cm^3
• Polarizability: 41.96392 Å^3
• Polar Surface Area: 53.6 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Pale Brown Solid
• Melting Point: 131-133°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N389830

trans-Nemonapride is a selective dopamine D2 receptor antagonist. trans-Nemonapride is used as an antipsychotic.

REFERENCES

• Yamamoto, M., et al.: Neuropharmacology, 21, 945 (1982)
• Grewe, C.W., et al.: Eur. J. Pharmacol., 81, 149 (1982)
• Satoh, K., et al.: Int. Clin. Psychopharmacol., 11, 279 (1996)