N-[(1S,7aS)-hexahydro-1H-pyrrolizin-1-ylmethyl]-4-amino-5-chloro-2-methoxybenzamide hydrochloride

• ChemBase ID: 177643
• Molecular Formular: C16H23Cl2N3O2
• Molecular Mass: 360.27872
• Monoisotopic Mass: 359.11673235
• SMILES: c1(c(cc(c(c1)C(=O)NC[C@H]1[C@H]2N(CCC2)CC1)OC)N)Cl.Cl
• Canonical SMILES: COc1cc(N)c(cc1C(=O)NC[C@@H]1CCN2[C@H]1CCC2)Cl.Cl
• InChI: InChI=1S/C16H22ClN3O2.ClH/c1-22-15-8-13(18)12(17)7-11(15)16(21)19-9-10-4-6-20-5-2-3-14(10)20;/h7-8,10,14H,2-6,9,18H2,1H3,(H,19,21);1H/t10-,14-;/m0./s1
• InChIKey: TVWDAUMNWKAMIX-LPJGFKLNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(1S,7aS)-hexahydro-1H-pyrrolizin-1-ylmethyl]-4-amino-5-chloro-2-methoxybenzamide hydrochloride
• IUPAC Traditional name: N-[(1S,7aS)-hexahydro-1H-pyrrolizin-1-ylmethyl]-4-amino-5-chloro-2-methoxybenzamide hydrochloride
• Synonyms: 4-Amino-5-chloro-N-[[(1S,7aS)-hexahydro-1H-pyrrolizin-1-yl]methyl]-2-methoxybenzamide Hydrochloride Hydrate; (1S-cis)-4-Amino-5-chloro-N-[(hexahydro-1H-pyrrolizin-1-yl)methyl]-2-methoxybenzamide Hydrochloride Hydrate; SC-53116 Hydrochloride Hydrate

Database IDs

• CAS Number: 879208-42-1
• PubChem SID: 164233553
• PubChem CID: 71752133

CALCULATED PROPERTIES

• H Donor: 2
• LogD (pH = 5.5): -2.244529
• LogD (pH = 7.4): -1.3304591
• Log P: 1.2149692
• Molar Refractivity: 88.782 cm^3
• Polarizability: 33.51238 Å^3
• Polar Surface Area: 67.59 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true
• Acid pKa: 14.503774
• H Acceptors: 4

DETAILS

Toronto Research Chemicals - S199890

SC-53116 is a 5-HT4 receptor partial agonist. SC-53116 has been shown to ameliorate scopolamine-induced impairment in learning in rats at a does of 10 μg/rat i.c.v and increase population spike amplitude in the CA1 and CA3 fields of the hippocampus at the

REFERENCES

• Robertson, D., et al.: J. Med. Chem., 29, 2 (1986)
• Hadley, M; Bioorg. Med. Chem. Lett., 9, 1147 (1986)
• Rivkin, A., et al.: Clin. Ther., 1952 (1986)