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Tianeptine

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Tianeptine Basic information

Product Name:
Tianeptine
Synonyms:
  • (±)-7-[(3-chloro-6,11-dihydro-6-methyldibenzo[c,f][1,2]thiazepin-11-yl)amino]heptanoic acid S,S-dioxide
  • (1)-7-((3-Chloro-6,11-dihydro-6-methyldibenzo(C,F)(1,2)thiazepin-11-yl)amino)heptanoic acid S,S-dioxide
  • Einecs 276-851-9
  • 7-((3-chloro-6-methyl-5,5-dioxido-6,11-dihydrodibenzo[c,f][1,2]thiazepin-11-yl)amino)heptanoic acid
  • 7-[(3-Chloro-6,11-dihydro-6-methyl-5,5-dioxidodibenzo[c,f][1,2]thiazepin-11-yl)amino]heptanoic acid
  • Tianeptin
  • JNJ-39823277
  • TPI-1062
CAS:
72797-41-2
MF:
C21H25ClN2O4S
MW:
436.95
EINECS:
276-851-9
Product Categories:
  • Amines
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Sulfur & Selenium Compounds
Mol File:
72797-41-2.mol
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Tianeptine Chemical Properties

Melting point:
129-131?C
Boiling point:
609.2±65.0 °C(Predicted)
Density 
1.38±0.1 g/cm3(Predicted)
vapor pressure 
0.001Pa at 25℃
storage temp. 
Refrigerator, Under Inert Atmosphere
pka
4.75±0.10(Predicted)
form 
solid
InChIKey
JICJBGPOMZQUBB-UHFFFAOYSA-N
SMILES
C(O)(=O)CCCCCCNC1C2=CC=C(Cl)C=C2S(=O)(=O)N(C)C2=CC=CC=C21
LogP
2.162 at 25℃ and pH6
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Safety Information

WGK Germany 
3
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Tianeptine Usage And Synthesis

Chemical Properties

White Solid

Uses

Tricyclic compound with psychostimulant, anti-ulcer and anti-emetic properties. It is used mainly in the treatment of major depressive disorder and may also be used to treat anxiety, asthma, and irritable bowel syndrome. It has been found to act as an atypical agonist of the μ-opioid receptor with clinically negligible effects on the δ- and κ-opioid receptors. Tianeptine prevents chronic stress-induced morphological changes in the hippocampus and amygdala and blocks the effects of acute stress on synaptic plasticity in the hippocampus and PFC.

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.

brand name

Stablon, Tatinol, and Coaxil among others

Mechanism of action

Current research suggests that tianeptine produces its antidepressant effects through the modulation of glutamate receptor activity (for example, AMPA receptors and NMDA receptors) and affect the release of brain-derived neurotrophic factor (BDNF), which impacts neural plasticity.

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