2-{1-azabicyclo[2.2.2]octan-3-yl}-2-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaene

• ChemBase ID: 177307
• Molecular Formular: C21H24N2
• Molecular Mass: 304.42866
• Monoisotopic Mass: 304.19394878
• SMILES: C1Cc2c(N(c3c1cccc3)C1C3CCN(C1)CC3)cccc2
• Canonical SMILES: c1ccc2c(c1)N(C1CN3CCC1CC3)c1ccccc1CC2
• InChI: InChI=1S/C21H24N2/c1-3-7-19-16(5-1)9-10-17-6-2-4-8-20(17)23(19)21-15-22-13-11-18(21)12-14-22/h1-8,18,21H,9-15H2
• InChIKey: JCBQCKFFSPGEDY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{1-azabicyclo[2.2.2]octan-3-yl}-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaene
• IUPAC Traditional name: quinupramine
• Synonyms: 5-(1-Azabicyclo[2.2.2]oct-3-yl)-10,11-dihydro-5H-dibenz[b,f]azepine; 10,11-Dihydro-5-(3-quinuclidinyl)-5H-dibenz[b,f]azepine; Kevopril; Kinupril; LM 208; Quinupramine

Database IDs

• CAS Number: 31721-17-2
• PubChem SID: 164233217
• PubChem CID: 93154

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.5420302
• LogD (pH = 7.4): 3.2438414
• Log P: 4.5756135
• Molar Refractivity: 95.6914 cm^3
• Polarizability: 36.878677 Å^3
• Polar Surface Area: 6.48 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - Q796700

Quinupramine is an analog of Imipramine (I465980). Quinupramine is used as an antidepressant.

REFERENCES

• Nakanishi, M., et al.: J. Med. Chem., 16, 214 (1973)
• Omen, G., et al.: Toxicology, 102, 23 (1973)
• Stevens, J., et al.: Chem. Res. Toxicol., 19, 1393 (1973)