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CasNo: 66981-73-5
Molecular Formula: C21H25ClN2O4S
Appearance: white solid
Chemical Properties |
Tianeptine, sold under the brand names Stablon, Tatinol, and Coaxil among others, is an atypical tricyclic antidepressant. |
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. It is used mainly in the treatment of major depressive disorder, although it may also be used to treat anxiety, asthma, and irritable bowel syndrome. |
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. HEALTHTIDE BIOTECH CO.,LTD. is a collection of production and sales of biotechnology companies. Our company mainly sells plant extracts, chemical raw materials,food additives,raw material of cosmetics. Our company has overseas warehouses in Vancouver and Toronto in Canada, Germany and the Netherlands in Europe, Melbourne and Sydney in Australia, and Mocheng in Mexico. |
Therapeutic Function |
Antidepressant |
InChI:InChI=1/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)
Tianeptine fully photodegrades in water after 106 h of simulated solar irradiation. Tianeptine degradation kinetics in ultrapure water and river water are very similar. Eight new transformation products of tianeptine were identified by HR MS/MS.
On further questioning, the mother revealed the use of a tianeptine-containing dietary supplement. We did not perform confirmatory toxicology testing because tianeptine is not assayed by usual urine drug screening tests. For infants with clinical signs of opioid withdrawal without known etiology, we suggest that the maternal interview should inquire about the use of neurotropic over-the-counter drugs.
ethyl 7-((3-chloro-6-methyl-5,5-dioxido-6,11-dihydrodibenzo[c,f][1,2]thiazepin-11-yl)amino)heptanoate
tianeptine
Conditions | Yield |
---|---|
With sodium hydroxide; In water; for 3h; Reflux;
|
80% |
With water; sodium hydroxide; In ethanol; at 50 ℃; for 2h; pH=>= 8;
|
75.3% |
7-(((11RS)-3-chloro-6-methyl-6,11-dihydro-dibenzo[c,f][1,2]thiazepin-11-yl)amino)heptanenitrile S,S-dioxide
tianeptine
Conditions | Yield |
---|---|
7-(((11RS)-3-chloro-6-methyl-6,11-dihydro-dibenzo[c,f][1,2]thiazepin-11-yl)amino)heptanenitrile S,S-dioxide; With hydrogenchloride; In water; Reflux;
With sodium hydroxide; In water; at 0 - 5 ℃; pH=~ 5.8 - 6.2;
|
7-(((11RS)-3-chloro-6-methyl-6,11-dihydro-dibenzo[c,f][1,2]thiazepin-11-yl)amino)heptanenitrile S,S-dioxide
8-chloro-10,10-dioxo-11-methyl-5,11-dihydrodibenzo
7-aminoheptanoic acid ethyl ester
ethyl 7-((3-chloro-6-methyl-5,5-dioxido-6,11-dihydrodibenzo[c,f][1,2]thiazepin-11-yl)amino)heptanoate
7-[(3-chloro-6,11-dihydro-6-methyldibenzo[c,f][1,2]thiazepin-11-yl)amino]heptanoic acid S,S-dioxide tosylate
ethyl 7-((3-chloro-6-methyl-5,5-dioxido-6,11-dihydrodibenzo[c,f][1,2]thiazepin-11-yl)amino)heptanoate