Amineptine

Title: Amineptine
CAS Registry Number: 57574-09-1
CAS Name: 7-[(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)amino]heptanoic acid
Molecular Formula: C22H27NO2
Molecular Weight: 337.46
Percent Composition: C 78.30%, H 8.06%, N 4.15%, O 9.48%
Literature References: Dopamine uptake blocker. Prepn: C. Malen et al., DE 2011806; eidem, US 3758528 (1970, 1973 both to Sci. Union et Cie Soc. Franc. Recher. Med.). Biochemical and pharmacological study: R. Samanin et al., J. Pharm. Pharmacol. 29, 555 (1977). Effect on dopamine uptake: N. B. Mercuri et al., Br. J. Pharmacol. 104, 700 (1991). Metabolism: L. Grislain et al., Eur. J. Drug Metab. Pharmacokinet. 15, 339 (1990). HPLC determn in plasma: P. P. Rop et al., J. Chromatogr. 532, 351 (1990). Clinical trial in depression: M. Paes de Sousa, J. Tropa, Clin. Neuropharmacol. 12, Suppl. 2, S77 (1989).
Derivative Type: Hydrochloride
CAS Registry Number: 30272-08-3
Manufacturers' Codes: S-1694
Trademarks: Maneon (Poli); Survector (Eutherapie)
Molecular Formula: C22H27NO2.HCl
Molecular Weight: 373.92
Percent Composition: C 70.67%, H 7.55%, N 3.75%, O 8.56%, Cl 9.48%
Properties: Crystals from distilled water, mp 226-230°.
Melting point: mp 226-230°
Therap-Cat: Antidepressant.
Keywords: Antidepressant; Tricyclics.
Aminitrozole Aminoacetonitrile Aminoacetophenone Aminocarb Aminochlorthenoxazin

Amineptine
Amineptine2DACS.svg
Amineptine3Dan.gif
Amineptine chemical structure
Systematic (IUPAC) name
7-[(10,11-dihydro-5H-dibenzo[a,d]-cyclohepten-5-yl)amino]heptanoic acid
Clinical data
Pregnancy cat.  ?
Legal status Unscheduled (AU) United Nations: Schedule II
Canada: Schedule III
USA: Unscheduled
UK: Schedule 2[1]
Germany: Anlage II (not prescribable)
Routes Oral
Pharmacokinetic data
Bioavailability  ?
Metabolism Hepatic
Half-life 48 mins (original drug)
2.5 hours (metabolites)[2]
Excretion Renal
Identifiers
CAS number 57574-09-1 YesY
ATC code N06AA19
PubChem CID 34870
DrugBank DB04836
ChemSpider 32091 YesY
UNII 27T1I13L6G YesY
KEGG D07335 YesY
ChEBI CHEBI:32499 YesY
ChEMBL CHEMBL418995 YesY
Chemical data
Formula C22H28NO2 
Mol. mass 338.4653 g/mol
 YesY (what is this?)  (verify)

Amineptine was developed by the French Society of Medical research in the 1960s.[3] Under the trade-names (Survector, Maneon, Directim, Neolior, Provector, Viaspera) is used as an atypical tricyclic antidepressant (TCA) that selectively inhibits the reuptake of dopamine[4] and to a lesser extent norepinephrine, thus exerting a fast-acting antidepressant effect.[citation needed]

Introduced in France in 1978 by the pharmaceutical company Servier[5] and marketed under the trade name Survector, amineptine soon gained a reputation for abuse due to its short-lived, but pleasant, stimulant effect experienced by some patients. (This is to be distinguished from its antidepressant effect, which appears in approximately seven days after commencing treatment.)

After its release into the European market, cases of hepatotoxicity emerged, some serious. This, along with the potential for abuse, led to the suspension of the French marketing authorization for Survector in 1999.[6]

Amineptine was never approved by the U.S. Food and Drug Administration (FDA) for marketing in the United States, meaning that it is not legal to market or sell amineptine for any medical uses in the US.