7-({tricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,12,14-hexaen-2-yl}amino)heptanoic acid

• ChemBase ID: 130418
• Molecular Formular: C22H27NO2
• Molecular Mass: 337.45528
• Monoisotopic Mass: 337.20417911
• SMILES: O=C(O)CCCCCCNC1c2ccccc2CCc2c1cccc2
• Canonical SMILES: OC(=O)CCCCCCNC1c2ccccc2CCc2c1cccc2
• InChI: InChI=1S/C22H27NO2/c24-21(25)13-3-1-2-8-16-23-22-19-11-6-4-9-17(19)14-15-18-10-5-7-12-20(18)22/h4-7,9-12,22-23H,1-3,8,13-16H2,(H,24,25)
• InChIKey: ONNOFKFOZAJDHT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-({tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3,5,7,12,14-hexaen-2-yl}amino)heptanoic acid; 7-({tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}amino)heptanoic acid
• IUPAC Traditional name: amineptine
• Synonyms: Amineptine; 7-[(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)amino]heptanoic Acid; Survector

Database IDs

• CAS Number: 57574-09-1
• PubChem SID: 162224697
• PubChem CID: 34870
• CHEBI ID: 32499
• ATC CODE: N06AA19
• CHEMBL: 418995
• Chemspider ID: 32091
• DrugBank ID: DB04836
• KEGG ID: D07335
• Unique Ingredient Identifier: 27T1I13L6G
• Wikipedia Title: Amineptine

CALCULATED PROPERTIES

• Acid pKa: 4.41307
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.717727
• LogD (pH = 7.4): 2.742191
• Log P: 2.7436762
• Molar Refractivity: 101.211 cm^3
• Polarizability: 39.503975 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Admin Routes: Oral
• Excretion: Renal
• Half Life: 48 mins (original drug); 2.5 hours (metabolites)
• Metabolism: Hepatic
• Legal Status: United Nations: Schedule II; Canada: Schedule III; USA: Unscheduled; UK: Schedule 2; Germany: Anlage II (not prescribable)

DETAILS

Toronto Research Chemicals - A634280

Amineptine is used as an atypical tricyclic antidepressant. Amineptine selectively inhibits the reuptake of dopamine and to a lesser extent norepinephrine.

REFERENCES

• Vaugeois J.M. et al.: Pharmacol. Biochem. Behav., 63, 285 (1999)
• Chanelet, J. et al.: Pharmatherapeutica, 1, 593 (1999)
• Hall, H. et al.: Acta Pharmacol. Toxicol., 54, 379 (1999)