Tianeptine sodium salt
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Product Description
Tianeptine sodium, also known as tianeptine sodium salt, is an atypical tricyclic antidepressant with a unique mechanism of action. Unlike traditional SSRIs, it enhances serotonin reuptake and modulates glutamate receptor activity, offering neuroprotective, anxiolytic, and antidepressant properties. Structurally, it is a modified tricyclic compound with enhanced water solubility due to its sodium salt form. It is approved in some countries, such as France and Russia, for treating major depressive disorder, with a typical dosage of 12.5 mg three times daily. However, it is not approved by the FDA in the U.S. due to concerns about its potential for abuse and opioid-like dependence, especially at high doses. Misuse can lead to severe adverse effects, including neurological, cardiovascular, and gastrointestinal symptoms, and withdrawal can cause significant distress.
Synthesis Methods
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Patented Synthesis: Originally patented by Malen et al. at the French Society of Medical Research in 1973.
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Commercial Synthesis: The patent for the synthesis of tianeptine was issued to Biophore India Pharmaceuticals in 2010.
Analytical Methods
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Spectrophotometry: A simple, sensitive, and cost-effective extraction visible spectrophotometric method has been developed for the determination of tianeptine sodium in bulk and tablet dosage forms. The method involves the formation of a colored ion-association complex with Tropaelin OOO (orange dye II) in an acid medium, with an absorption maximum of 489 nm.
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HPLC: High-performance liquid chromatography (HPLC) methods have been reported for the determination of tianeptine sodium in biological fluids and formulations.
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Other Methods: Other analytical techniques include potentiometric titration, flow injection analysis, spectrofluorometry, voltametry, and gas chromatography (GC).
Common Applications
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Medical Uses:
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Antidepressant: Tianeptine sodium salt is primarily used as an atypical antidepressant.
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Anxiolytic: It has anxiolytic properties, helping to reduce anxiety.
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Neuroprotective: Exhibits neuroprotective effects.
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Anti-ulcer and Anti-emetic: Demonstrates anti-ulcer and anti-emetic properties.
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Psycho-stimulant: Acts as a psycho-stimulant.
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Mood-brightening: Enhances mood.
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Research Uses:
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Anti-invasive Agent: Studies suggest that tianeptine sodium salt can suppress tumor invasion by reducing the expression of matrix metalloproteinase-9 (MMP-9) via inhibition of the PI3K/Akt-mediated NF-κB pathway.
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Serotonin Reuptake Enhancer: Acts as a selective facilitator of serotonin reuptake, enhancing presynaptic reuptake of serotonin without affecting noradrenaline or dopamine uptake.
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Properties
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Molecular Formula: C₂₁H₂₄ClN₂NaO₄S
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Molecular Weight: 458.9 g/mol
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IUPAC Name: Sodium;7-[(3-chloro-6-methyl-5,5-dioxo-11H-benzo[c][2,1]benzothiazepin-11-yl)amino]heptanoate
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Chemical Structure: Tianeptine sodium salt is a tricyclic compound with a dibenzothiazepine core and a heptanoic acid side chain. It contains a chlorine atom and a sodium ion associated with the sulfonate group.
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Solubility: Freely soluble in water, methanol, and methylene chloride.
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Isomers: Exists as two isomers, with the levorotatory isomer being the therapeutically active form.
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Metabolism: Primarily metabolized via β-oxidation of its heptanoic side chain, with major metabolites being pentanoic (MC5) and propionic (MC3) acid side chain derivatives found in urine and plasma.
Regulatory and Safety Information
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FDA Status: Not approved by the U.S. Food and Drug Administration (FDA) for medical use in the United States due to concerns about its potential for abuse and dependence.
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Controlled Substance: Classified as a Schedule II controlled substance in some U.S. states (e.g., Michigan, Alabama, Minnesota, Tennessee, and Oklahoma).
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Side Effects: Common side effects include nausea, dizziness, constipation, and risk of dependence at supratherapeutic doses.
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Withdrawal Symptoms: Severe withdrawal symptoms can occur, including agitation, depression, muscle pain, chills, and sweating.
Environmental and Toxicological Information
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Anti-invasive Effects: Tianeptine sodium salt has been shown to reduce the invasive potential of tumor cells by suppressing the expression of MMP-9 via the PI3K/Akt-mediated NF-κB pathway.
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Carcinoma Cell Studies: Studies have demonstrated that tianeptine sodium salt can significantly attenuate invasive rates in TNF-α-stimulated carcinoma cells, suggesting its potential as an anti-invasive agent in cancer treatment.