Tianeptine sodium salt

Iupac Name：sodium;7-[(3-chloro-6-methyl-5,5-dioxo-11H-benzo[c][2,1]benzothiazepin-11-yl)amino]heptanoate

Molecular Weight：458.933

Modify Date.: 2022-10-25 19:18

Introduction: Tianeptine sodium salt is a salt of Tianeptine. Tianeptine is an atypical antidepressant. It is an agonist of the μ-opioid receptor (MOR; EC50s = 194 and 641 nM for human and mouse receptors, respectively, in a BRET assay for G protein activation) and also has effects on the glutamate system. Tianeptine (30 mg/kg) decreases immobility in the forced swim test in wild-type, but not MOR knockout mice, indicating antidepressant-like activity dependent on MORs. It increases locomotor activity at a dose of 30, but not 10 mg/kg, in the open field test and increases paw withdrawal latency in the hot-plate test in mice. Tianeptine modulates AMPA receptor activity by increasing phosphorylation of the AMPA receptor GluR1 subunit in the frontal cortex and hippocampal CA3 region in mice. It prevents increases in glial glutamate transporter 1 (GLT-1) expression induced by chronic restraint stress in the hippocampal CA3 region in rats when administered at a dose of 10 mg/kg per day for 21 days.5It also reverses increases in extracellular glutamate levels induced by acute restraint stress in the basolateral nucleus of the amygdala in rats. View more+

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1. Names and Identifiers

1.1 Name: Tianeptine sodium salt
1.2 Synonyms: [7-[(3-Chloro-6,11-dihydro-6-methyldibenzo[c,f][1,2]thiazepine 5,5-dioxide)-11-ylamino]heptanoic acid]sodium salt 3-Chloro-6,11-dihydro-6-methyl-11-[6-(sodiooxycarbonyl)hexylamino]dibenzo[c,f][1,2]thiazepine 5,5-dioxide 7-[(3-Chloro-6,11-dihydro-6-methyldibenzo[c,f][1,2]thiazepin-11-yl)amino]heptanoic Acid S,S-Dioxide Sodium Salt 7-[(3-chloro-6,11-dihydro-6-methyl-dibenzo[c,f][1,2]thiazepine-11-yl)amino]heptanoic acid s,s dioxide sodium salt EINECS 250-059-3 Heptanoic acid, 7-[(3-chloro-6,11-dihydro-6-methyl-5,5-dioxidodibenzo[c,f][1,2]thiazepin-11-yl)amino]-, sodium salt (1:1) MFCD00879851 S-1574 Sodium 7-[(3-chloro-6-methyl-5,5-dioxido-6,11-dihydrodibenzo[c,f][1,2]thiazepin-11-yl)amino]heptanoate Stablon Tianeptine (sodium salt) TIANEPTINE SODIUM Tianeptine Sodium Salt Hydrate Tianeptine sodium salt,7-[(3-Chloro-6,11-dihydro-6-methyl-5,5-dioxidodibenzo[c,f][1,2]thiazepin-11-yl)amino]heptanoicacidsodiumsalt UNII:7LI031265R UNII:ROJ48D5596 UNII:YG0E19592I

1.3 CAS No.: 30123-17-2

1.4 CID: 23663953

1.5 EINECS(EC#): 250-059-3

1.6 Molecular Formula: C21H24ClN2NaO4S (isomer)

1.7 Inchi: InChI=1S/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/p-1

1.8 InChkey: ZLBSUOGMZDXYKE-UHFFFAOYSA-M

1.9 Canonical Smiles: CN1C2=CC=CC=C2C(C3=C(S1(=O)=O)C=C(C=C3)Cl)NCCCCCCC(=O)[O-].[Na+]

1.10 Isomers Smiles: CN1C2=CC=CC=C2C(C3=C(S1(=O)=O)C=C(C=C3)Cl)NCCCCCCC(=O)[O-].[Na+]

2. Properties

2.1 Density: 1.38

2.1 Melting point: 1800C

2.1 Boiling point: 609.2 °C at 760 mmHg

2.1 Flash Point: 322.2 °C

2.1 Precise Quality: 458.10400

2.1 PSA: 97.92000

2.1 logP: 4.39460

2.1 Solubility: DMSO: ≥20mg/mL

2.2 Appearance: solid

2.3 Storage: Desiccate at RT

2.4 Chemical Properties: White to Yellowish Powder

2.5 Color/Form: white to tan

2.6 StorageTemp: Desiccate at RT

3. Use and Manufacturing

3.1 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 4 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 1 of 4 companies. For more detailed information, please visit ECHA C&L website

Of the 3 notification(s) provided by 3 of 4 companies with hazard statement code(s):

H301 (33.33%): Toxic if swallowed [Danger Acute toxicity, oral]
H302 (66.67%): Harmful if swallowed [Warning Acute toxicity, oral]
H312 (33.33%): Harmful in contact with skin [Warning Acute toxicity, dermal]
H332 (33.33%): Harmful if inhaled [Warning Acute toxicity, inhalation]
H361 (33.33%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
H362 (33.33%): May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]
H373 (33.33%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P260, P261, P263, P264, P270, P271, P280, P281, P301+P310, P301+P312, P302+P352, P304+P312, P304+P340, P308+P313, P312, P314, P321, P322, P330, P363, P405, and P501

3.2 Usage: Tianeptine sodium salt hydrate has been used as a selective serotonin reuptake enhancer (SSRE) positive control during serotonin transporter (SERT) assay in human embryonic kidney 293 cell lines.

4. Safety and Handling

4.1 WGK Germany: 3

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Other Information

7.0 Merck: 14,9420

7.1 Target: Value

7.2 Description: Tianeptine sodium salt is a salt of Tianeptine. Tianeptine is an atypical antidepressant. It is an agonist of the μ-opioid receptor (MOR; EC50s = 194 and 641 nM for human and mouse receptors, respectively, in a BRET assay for G protein activation) and also has effects on the glutamate system. Tianeptine (30 mg/kg) decreases immobility in the forced swim test in wild-type, but not MOR knockout mice, indicating antidepressant-like activity dependent on MORs. It increases locomotor activity at a dose of 30, but not 10 mg/kg, in the open field test and increases paw withdrawal latency in the hot-plate test in mice. Tianeptine modulates AMPA receptor activity by increasing phosphorylation of the AMPA receptor GluR1 subunit in the frontal cortex and hippocampal CA3 region in mice. It prevents increases in glial glutamate transporter 1 (GLT-1) expression induced by chronic restraint stress in the hippocampal CA3 region in rats when administered at a dose of 10 mg/kg per day for 21 days.5It also reverses increases in extracellular glutamate levels induced by acute restraint stress in the basolateral nucleus of the amygdala in rats.

7.3 Appearance: White to pale yellow solid.

7.4 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.

7.5 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.

7.6 Uses: Tianeptine sodium salt hydrate has been used as a selective serotonin reuptake enhancer (SSRE) positive control during serotonin transporter (SERT) assay in human embryonic kidney 293 cell lines.

7.7 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.

7.8 Description: Tianeptine (sodium salt) (Item No. 25950) is an analytical reference standard categorized as an opioid. Tianeptine has been abused and associated with overdose and death. Formulations containing tianeptine have been used in the treatment of depression. This product is intended for use in analytical forensic applications. This product is also available as a general research tool (Item No. 17561).

7.9 Description: Tianeptine sodium is a structurally novel, serotonin specific antidepressant. It is useful in the treatment of neurotic and reactive depressions, as well as depressive states accompanied by anxiety.

7.10 Chemical Properties: White to Yellowish Powder

7.11 Originator: Sci. Union et Cie (France)

7.12 Uses: Tianeptine Sodium Salt is a tricyclic compound with psychostimulant, anti-ulcer and anti-emetic properties. Antidepressant.

7.13 Uses: Tricyclic compound with psychostimulant, anti-ulcer and anti-emetic properties. Antidepressant.
Tianeptine sodium salt hydrate has been used as a selective serotonin reuptake enhancer (SSRE) positive control during serotonin transporter (SERT) assay in human embryonic kidney 293 cell lines.

7.14 Uses: Tianeptine (INN) (Stablon, Coaxil, Tatinol) is a selective serotonin reuptake enhancer (SSRE) drug used for treating major depressive episodes (mild, moderate, or severe). Unlike conventional tricyclic antidepressants, tianeptine enhances the reuptake of

7.15 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.

7.16 Brand name: STABLON

7.17 Therapeutic Function: Antidepressant

7.18 General Description: Tianeptine is a μ-opioid receptor (MOR) as well as a δ-opioid receptor (DOR) agonist.

8. Computational chemical data

Molecular Weight: 458.933g/mol
Molecular Formula: C₂₁H₂₄ClN₂NaO₄S
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 458.1043004
Monoisotopic Mass: 458.1043004
Complexity: 660
Rotatable Bond Count: 8
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 6
Topological Polar Surface Area: 97.9
Heavy Atom Count: 30
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 1
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 2
CACTVS Substructure Key Fingerprint: AAADceB7OCBEAAAAAAAAAAAAAAAAAAAAAAAwYAAABYAAAAABQAAAHgYQQAAADCrB2CQyyYLAAAKIAiTSSHDCABAhBwAIiJkIZogIIDLB05GEIAhkkADIyAeYyOCOBAAAABAGAAAIAAAAIAwAAAAAAAAAAA==

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