Tianeptine Chemical Properties

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

InChI

InChI=1S/C21H25ClN2O4S/c1-24-18-9-6-5-8-16(18)21(23-13-7-3-2-4-10-20(25)26)17-12-11-15(22)14-19(17)29(24,27)28/h5-6,8-9,11-12,14,21,23H,2-4,7,10,13H2,1H3,(H,25,26)

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 Information

RIDADR 

3249

HazardClass 

6.1(b)

PackingGroup 

III

Tianeptine Usage And Synthesis

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

Tianeptine is used in the treatment of reactive and neurotic depression, as well as in the treatment of anxious states.

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

Biological Activity

Tianeptine was identified as an efficacious MOR full agonist, binding to the human MOR with a Ki of 383 ± 183 nM. Tianeptine was also found to act as a full agonist at the DOR, although it had much lower potency and was inactive at the KOR. The MOR was required for the acute and chronic antidepressant-like effects of tianeptine in mice. Although tianeptine also produced behavioural effects, including analgesia and reward, its effects were distinct from morphine in that it did not produce tolerance or withdrawal.

Tianeptine(66981-73-5)Related Product Information

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• 6-Methyl-5-hepten-2-one
• Dihydromyrcenol
• N,N-Dimethyl-1,4-phenylenediamine
• Tolyltriazole
• ALTRENOGEST
• Glycine
• Tris(hydroxymethyl)aminomethane
• 5-Methyl-1H-benzotriazole
• N-Methyl-2-pyrrolidone
• TIANEPTINE SODIUM SALT,TIANEPTINE SODIUM
• Tianeptine Ethyl Ester
• tianeptine sulfate
• Difluorochloromethane
• Heptanoic acid
• TIANEPTINE SODIUM - REFERENCE SPECTRUM
• TIANEPTINE IMPURITY A
• TIANEPTINE FOR SYSTEM SUITABILITY