ChemicalBook--->CAS DataBase List--->66981-73-5

66981-73-5

66981-73-5 Structure

66981-73-5 Structure
IdentificationMore
[Name]

Tianeptine
[CAS]

66981-73-5
[Synonyms]

7-[(3-chloro-6,11-dihydro-6-methyldibenzo[c,f][1,2]thiazepin-11-yl)-amino]heptanoic acid s,s-dioxide
7-[(3-CHLORO-6,11-DIHYDRO-6-METHYL-DIBENZO[C,F][1,2]THIAZEPINE-11-YL)AMINO]HEPTANOIC ACID S,S DIOXIDE
TIANEPTINE
Tianeptineacid
COAXIL
7-[(3-Chloro-6,11-dihydro-6-methyldibenzo[c,f][1,2]thiazepin-11-y1)amino]heptanoic acid S,S-dioxide
[EINECS(EC#)]

614-004-0
[Molecular Formula]

C21H25ClN2O4S
[MDL Number]

MFCD00865376
[Molecular Weight]

436.95
[MOL File]

66981-73-5.mol
Chemical PropertiesBack Directory
[Appearance]

White Solid
[Melting point ]

129-131°C
[storage temp. ]

Hygroscopic, -20°C Freezer, Under inert atmosphere
[solubility ]

Freely soluble in water, in methanol and in methylene chloride.
[form ]

Solid
[color ]

White to Off-White
[Usage]

Tricyclic compound with psychostimulant, anti-ulcer and anti-emetic properties. Antidepressant
[InChIKey]

JICJBGPOMZQUBB-UHFFFAOYSA-N
[SMILES]

C(O)(=O)CCCCCCNC1C2=CC=C(Cl)C=C2S(=O)(=O)N(C)C2=CC=CC=C21
[CAS DataBase Reference]

66981-73-5(CAS DataBase Reference)
Safety DataBack Directory
[RIDADR ]

3249
[HazardClass ]

6.1(b)
[PackingGroup ]

III
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Diethyl ether-->Sodium sulfate-->Nitromethane-->Hexamethyleneimine-->Ethyl heptanoate-->7-Aminoheptanoic acid-->Ethyl7-Aminoheptanoate-->Sodium hydroxide
Hazard InformationBack Directory
[Description]

Tianeptine, a tricyclic compound, is a selective facilitator of 5-HT (serotonin; sc-201146) uptake in vitro and in vivo. Additionally, Tianeptine is reported to act as a selective inhibitor of dopamine uptake and is similar to amineptine. Tianeptine does not have a noted effect on monoamine uptake.
[Chemical Properties]

White Solid
[Originator]

Stablon,Servier,France,1983
[Uses]

Tricyclic compound with psychostimulant, anti-ulcer and anti-emetic properties. Antidepressant
[Definition]

ChEBI: Tianeptine is a racemate comprising of equimolar amounts of (R)- and (S)-tianeptine. It is an atypical antidepressant used in Europe to treat patients who respond poorly to selective serotonin reuptake inhibitors (SSRIs). It has a role as a mu-opioid receptor agonist, a second generation antipsychotic and an anxiolytic drug. It contains a (R)-tianeptine and a (S)-tianeptine.
[Manufacturing Process]

A solution of 27.6 g (0.16 mol) of freshly distilled ethyl 7-aminoheptanoate in 40 ml of nitromethane was added all at once and with mechanical stirring to a suspension of 26.2 g (0.08 mol) of 5,8-dichloro-10-dioxo-11- methyldibenzo[c,f]thiazepine(1,2) in 120 ml of nitromethane. The whole was heated to 55°C for 30 minutes, the solvent was then evaporated in vacuo and the residue was taken up in water. The crude ester was extracted with ether. After evaporation of the ether 36 g of crude ester were obtained, and 30 g (0.065 mol) there of were treated under reflux with a solution of 2.8 g (0.07 mol) of sodium hydroxide in 35 ml of ethanol and 25 ml of water. After one hour's refluxing, the alcohol was evaporated in vacuo. The residue was taken up in 150 ml of water.
The mixture was twice extracted with 75 ml of chloroform and the aqueous phase was evaporated in vacuo. The sodium salt was then dissolved in 150 ml of chloroform, the solution was dried over sodium sulfate and the product precipitated with anhydrous ether.
The salt was filtered off, washed with ether and dried at 50°C. 13 g of sodium 7-[8-chloro-10-dioxo-11-methyldibenzo[c,f]thiazepin-(1,2)-aminoheptanoate,melting with decomposition at about 180°C, were obtained.
[Therapeutic Function]

Antidepressant
[storage]

Store at -20°C
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

66981-73-5(sigmaaldrich)
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