Basic information
- CAS
57574-09-1- Standard SMILES
O=C(O)CCCCCCNC1c2ccccc2CCc2ccccc21- InChIKey
ONNOFKFOZAJDHT-UHFFFAOYSA-N- Molecular formula
- C22H27NO2
- Average molar mass
- 337.5 g/mol
- Monoisotopic mass
- 337.2041791
Overview
Amineptine is a carbocyclic fatty acid that is 5-aminoheptanoic acid in which one of the hydrogens attached to the nitrogen is replaced by a 10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-yl group. A tricyclic antidepressant, it was never approved in the US and was withdrawn from the French market in 1999 due to concerns over abuse, dependence and severe acne. It has a role as an antidepressant and a dopamine uptake inhibitor. It is an amino acid, a carbocyclic fatty acid, a carbotricyclic compound and a secondary amino compound. It derives from a hydride of a dibenzo[a,d][7]annulene.
Names & identifiers
- Preferred name
- Amineptine
- IUPAC
- 7-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylamino)heptanoic acid
Names & synonyms
AmineptineAmineptin57574-09-1AmineptinoAmineptinumamineptinaDTXSID104883127T1I13L6G7-((10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-5-yl)amino)heptanoic acid7-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylamino)heptanoic acidDTXCID4028757CHEBI:32499
Show more names
7-[(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)amino]heptanoic Acid7-(10,11-dihydro-5H-dibenzo(a,d)cyclohepten-5-ylamino)heptanoic acid10,11-dihydrodibenzo(a,d)cyclohept-5-enyl-7-aminoheptanoic acidRefChem:111994N06AA19260-818-0Amineptine [INN]Amineptine (INN)
Database identifiers
- CAS
57574-09-1- PubChem CID
- 34870
- DTXSID
DTXSID1048831- ChEMBL
CHEMBL418995- ChEBI
CHEBI:32499- UNII
- 27T1I13L6G
- EC Number
- 260-818-0
- Nikkaji
- J11.860E
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 49.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 8
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 387
Experimental & physicochemical properties
Drugs
DEA Schedule I Controlled Substance -> Stimulants
Pharmaceuticals -> Listed in ZINC15
Human DrugsPharmaceuticals
Melting Point226-230
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory InformationDEA schedule I controlled substance
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Amineptine
vMost-DILI-concern
8
Withdrawn
DOI:10.1016/j.drudis.2016.02.015
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
PharmacodynamicsAmineptine is an atypical tricyclic antidepressant.
Mechanism of ActionAmineptine selectively inhibits the reuptake of dopamine and to a lesser extent norepinephrine, thus exerting a powerful and fast-acting antidepressant effect.
Biological Half-Life48 minutes for the parent drug and 2.5 hours for the metabolites.
Metabolism/MetabolitesHepatic.
MeSH Pharmacological Classification
Substances that contain a fused three-ring moiety and are used in the treatment of depression. These drugs block the uptake of norepinephrine and serotonin into axon terminals and may block some subtypes of serotonin, adrenergic, and histamine receptors. However, the mechanism of their antidepressant effects is not clear because the therapeutic effects usually take weeks to develop and may reflect compensatory changes in the central nervous system.
A loosely defined grouping of drugs that have effects on psychological function. Here the psychotropic agents include the antidepressive agents, hallucinogens, and tranquilizing agents (including the antipsychotics and anti-anxiety agents).
Uses & manufacturing
Use ClassificationPharmaceuticals
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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