30123-17-2 Usage
Description
Tianeptine sodium salt is a tricyclic compound and an atypical antidepressant. It is a selective serotonin reuptake enhancer (SSRE) and an agonist of the μ-opioid receptor (MOR) and δ-opioid receptor (DOR). Tianeptine sodium salt also modulates the glutamate system and has psychostimulant, anti-ulcer, and anti-emetic properties.
Used in Pharmaceutical Industry:
Tianeptine sodium salt is used as an antidepressant for treating major depressive episodes (mild, moderate, or severe). It is particularly useful in the treatment of neurotic and reactive depressions, as well as depressive states accompanied by anxiety.
Used in Research Applications:
Tianeptine sodium salt is used as a selective serotonin reuptake enhancer (SSRE) positive control during serotonin transporter (SERT) assay in human embryonic kidney 293 cell lines. It serves as an analytical reference standard and a research tool for studying its effects on the glutamate system and opioid receptors.
Used in Forensic Applications:
Tianeptine sodium salt is used in analytical forensic applications due to its association with abuse, overdose, and death. Formulations containing tianeptine have been used in the treatment of depression, and this product helps in understanding its potential risks and implications.
Chemical Properties:
Tianeptine sodium salt appears as a white to yellowish powder and is a white to pale yellow solid in its branded form, such as under the brand name STABILON.
biological activity
Tianeptine sodium salt is a selective facilitator of 5-HT uptake in vitro and in vivo. IC50 Value:Target: 5-HT ReceptorTianeptine has no affinity for a wide range of receptors, including 5-HT and dopamine (IC50 > 10 μM) and has no effect on noradrenalin or dopamine uptake. Antidepressant, analgesic and neuroprotective following systemic administration in vivo.
Biochem/physiol Actions
Tianeptine is a tricyclic antidepressant that enhances serotonin uptake. This drug can affect neuroprotection, neuronal excitability, memory and anxiety. However, tianeptine is not linked to adverse psychomotor, cognitive, cardiovascular, sleep and bodyweight effects. The drug has a low tendency for abuse and has a positive pharmacokinetic profile.
Tianeptine is least involved in drug interaction as it is not metabolized by cytochrome P450 system in the liver. In hippocampus and amygdala, tianeptine is involved in glutamatergic transmission processes and elicits neuroplasticity.
Biochem/physiol Actions
Tianeptine is a tricyclic antidepressant that enhances serotonin uptake. This drug can affect neuroprotection, neuronal excitability, memory and anxiety. However, tianeptine is not linked to adverse psychomotor, cognitive, cardiovascular, sleep and bodyweight effects. The drug has a low tendency for abuse and has a positive pharmacokinetic profile.
Laboratory Procedures
Tianeptine (sodium salt) is supplied as a crystalline solid. A stock solution may be made by dissolving the tianeptine (sodium salt) in the solvent of choice. Tianeptine (sodium salt) is soluble in organic solvents such as ethanol, DMSO, and dimethyl formamide, which should be purged with an inert gas. The solubility of tianeptine (sodium salt) in these solvents is approximately 10, 20, and 30 mg/ml, respectively. Further dilutions of the stock solution into aqueous buffers or isotonic saline should be made prior to performing biological experiments. Ensure that the residual amount of organic solvent is insignificant, since organic solvents may have physiological effects at low concentrations. Organic solvent-free aqueous solutions of tianeptine (sodium salt) can be prepared by directly dissolving the crystalline solid in aqueous buffers. The solubility of tianeptine (sodium salt) in PBS, pH 7.2, is approximately 10 mg/ml. We do not recommend storing the aqueous solution for more than one day.
Originator
Sci. Union et Cie (France)
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
Selective facilitator of 5-HT uptake in vitro and in vivo . Has no affinity for a wide range of receptors, including 5-HT and dopamine (IC 50 > 10 μ M) and has no effect on noradrenalin or dopamine uptake. Antidepressant, analgesic and neuroprotective following systemic administration in vivo .
References
1)?Mennini?et al. (1987),?Tianeptine, a selective enhancer of serotonin uptake in rat brain; ?Naunyn-Schmied. Arch. Pharmacol.,?336?478
2)?Kato and Weitsch (1988),?Neurochemical profile of tianeptine, a new antidepressant drug; ?Clin. Neuropharmacol.,?11?S43
3)?Plaisant?et al. (2003),?Neuroprotective properties of tianeptine: interactions with cytokines; Neuropharmacology,?44?801
4)?Seo?et al. (2016),?Tianeptine induces mTORC1 activation in rat hippocampal neurons under toxic conditions; ?Psychopharmacology (Berl.),?233?2617
5)?Slusarczyk?et al. (2017),?Anti-inflammatory properties of tianeptine on lipopolysaccharide-induced changes in microglial cells involve toll-like receptor-related pathways; ?J. Neurochem.,?136?958
Check Digit Verification of cas no
The CAS Registry Mumber 30123-17-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,0,1,2 and 3 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 30123-17:
(7*3)+(6*0)+(5*1)+(4*2)+(3*3)+(2*1)+(1*7)=52
52 % 10 = 2
So 30123-17-2 is a valid CAS Registry Number.
InChI:InChI=1/C21H25ClN2O4S.Na/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);/q;+1
