| Identification | More | [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 Properties | Back 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) |
| Hazard Information | Back 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 | [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.
| [storage]
Store at -20°C |
|
|