Tianeptine FREE ACID, ≥98%

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Antidepressant, analgesic and neuroprotective.

Chemical Name7-[(3-Chloro-6,11-dihydro-6-methyl-5,5-dioxidodibenzo[c,f][1,2]thiazepin-11-yl)amino] heptanoic acid
Synonyms7-[(3-Chloro-6,11-dihydro-6-methyl-5,5-dioxidodibenzo[c,f][1,2]thiazepin-11-yl)amino] heptanoic acid
CAS #66981-73-5
FormWhite powder
Molecular FormulaC21H25ClN2O4S
Molecular Weight436.95
SolubilityInsoluble in in Water. Soluble in aqueous solutions of NaOH, KOH

The Tianeptine molecule itself, not formed into a salt. Sometimes also referred to as the "free base", although Tianeptine is mildly acidic. It is the second most common form of Tianeptine - most often used as an intermediate for further processing into various forms.
It is non-water soluble and dissolves in basic aqueous solutions.
It is also non-hygroscopic. Unlike sodium salt, this form can be exposed to atmospheric humidity for minutes to hours with no ill effect. If developed as a pharmaceutical - is absorbed gradually and to a somewhat lower extent when consumed p.o., vs. sodium salt form.
If developed as a pharmaceutical - has a sustained release tendency when consumed p.o., so concentrations rise and fall more gently.

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From $54.88

Precaution and Disclaimer:

This Material is Sold For Research Use Only. Terms of Sale Apply. Not for Human Consumption, nor Medical, Veterinary, or Household Uses.

Chemical Information:

CAS Number:66981-73-5
Purity:≥98%
Molecular Weight:458.93
Melting Point:129-131 °C
Molecular Formula:C21H24ClN2NaO4S
Synonyms: Coaxil, 7-(3-chloro-6-methyl-5,5-dioxo-6,11-dihydrodibenzo(c,f)(1,2)thiazepin-11-yl)-7-aminoheptanoic acid; tianeptine, tianeptine (+)(-) isomer
PubChem CID:68870
SMILES:CN1C2=CC=CC=C2C(C3=C(S1(=O)=O)C=C(C=C3)Cl)NCCCCCCC(=O)O

Technical Information:

Application:Used in clinical trials for major depressive disorder (MDD), bipolar disorder, and also studied for effects on asthma and irritable bowel syndrome (IBS). 
Appearance:White powder
Physical State:Solid
Solubility:Insoluble in in Water. Soluble in aqueous solutions of NaOH, KOH
Storage:Store in closed container at -20 °C in dark, dry conditions.
Stability:Tianeptine sulfate is stable for at least four years when stored as above.

Background:

Tianeptine refers to an uncommon antidepressant compound. It is said to be ‘uncommon’ because of its unique mechanism of action. In contrast to most antidepressant chemicals, which tend to regulate the monoaminergic neurotransmitter systems (acting as MAOIs), Tianeptine exerts its effects primarily on the glutamatergic system. [1] Research suggests that Tianeptine has a positive effect on 5-HT (serotonin) uptake in the brain, a mechanism of action that directly contrasts typical selective serotonin-reuptake inhibitors (SSRIs). [2]

Tianeptine free acid refers to the Tianeptine molecule itself, not formed into a salt. It is sometimes also referred to as the "free base" form, although Tianeptine is actually mildly acidic. Tianeptine free acid is the second most common form of Tianeptine - most often used as an intermediate for further processing into various forms. It is non-water soluble and dissolves in basic aqueous solutions. It is also non-hygroscopic.

Unlike Tianeptine sodium salt, Tianeptine free acid form can be exposed to atmospheric humidity for minutes to hours with no ill effect on its potency. If developed as a pharmaceutical it is important to note that the free acid is absorbed gradually and to a somewhat lower extent when consumed p.o., vs. the Tianeptine sodium salt form. It also has more of a sustained release tendency when consumed p.o., so concentrations tend to rise and fall more gently.

In some countries, Tianeptine is sold as a prescription medication (typically in the Tianeptine sodium salt form). In the United State, Tianeptine has not been patented by any pharmaceutical corporations and has not been approved by the FDA. It is therefore available for research use only. International brand names for Tianeptine include Coaxil, Stablon, Tatinol, Tianeurax, and Zinosal. These typically refer to the sodium salt form. [3]

Modes of Action:

Two of the most important modes of action for Tianeptine are a.) to increase serotonin (5-HT) uptake in the brain and in platelets; and b.) to act on the glutamatergic system. In contrast to other tricyclic antidepressants, Tianeptine is not associated with any decrease in cognitive function or in motor coordination. [4]

In contrast to SSRIs, research points to Tianeptine’s abilities to increase 5-HT uptake and act on adenosine A1 receptors. Furthermore, this mechanism is thought to have effects on the neuroplasticity hypothesis of depression. [5]

New research suggests Tianeptine’s potential to exert positive regulatory effects on m-opioid receptors (MORs). Using radio-ligand binding and cell-based functional assays, researchers were able to successful determine that Tianeptine works as a functional MOR agonist. Although at a much lower affinity, Tianeptine also has agonist-like effects at the d-opioid receptor (DOR) sites. [6]

Further Scientific research:

Please note that this is an incomplete account of the scientific research on Tianeptine to date. We have made a humble attempt to convey some of the most relevant research on the subject to date, in a variety of applications. However, there is far too much research to condense in this space. For more research, please select a topic and search through the hundreds of journal articles published in PubMed.

Clinical Reviews

Please note that this selection of clinical review refers to the clinically used Tianeptine sodium. There have not yet been any meta-analyses or reviews of data on Tianeptine free acid form due to its lack of use in clinical trials.

  1. Studies published in 1988 and in 2001 found that Tianeptine was clinically effective for a number of applications. Both studies attested to Tianeptine’s antidepressant activity and its ability to be well-tolerated with the participants. Dosages used were around 25-50mg/day. [2] [7]
  2. More recently, a review published in 2010 indicated Tianeptine’s activity on the glutamatergic system. According to the authors of the study, these results are consistent with growing data pointing to glutamate’s function in neuroplasticity and depression. [5]

Human studies:

  1. Three double-blind studies, published simultaneously in 1997, examined Tianeptine’s efficacy in treatment major depressive disorder. Two of the studies indicated that Tianeptine had clinically applicable results when compared to placebo and other antidepressants. The third study had an overly high rate of placebo-responders and no conclusion could be made. [4][8]
  2. A study published in 1995 confirmed Tianeptine’s effects on serotonin uptake. The authors suggested that Tianeptine had the ability to reduce hyptothalamic-pituitary-adrenal response to stress and also to reduce stress-related behavior and changes in cerebral morphology. [8]
  3. A study published in 2004 looked into Tianeptine’s potential benefits on patients suffering from bronchial asthma. The study included data from numerous clinical trials, including an open study that lasted over 7 years and was conducted on over 25’000 asthmatic participants. The research pointed to significant efficacy in improving asthmatic symptoms, which was hypothesized to be due to Tianeptine’s improvement of serotonin uptake by platelets and serotonergic axons. [9]

Toxicity cases:

  1. In 2015, a young man from Texas passed away after consuming a large acute dose of Tianeptine. The company from whom he purchased the product sold it for household use and did not attach any warning or instructions on how to take the compound. Please note that all NewMind chemicals are sold for research and laboratory purposes only and are strictly not for human consumption. [10]
  2. In 1994, a case was reported of a patient who developed hepatitis after using Tianeptine for 8 weeks. He managed a complete recovery after discontinuing Tianeptine use. Authors of the study suggested possible hypersensitivity and immune-allergic mechanisms in the hepatotoxic response to Tianeptine. [11]

Animal studies: 

As a result of the application of Tianeptine in human studies, animal studies on Tianeptine Free Acid have been excluded from this section. For more information pertaining to animal studies, please refer to PubMed or descriptions for our other available forms of Tianeptine. 

WARNING:
Accidental or Intentional Ingestion or Administration of Quantities of Tianeptine Exceeding 100mg Can Result in Serious Toxicity or DEATH. Store Securely, and Handle with Maximum Caution using Appropriate Equipment!

References:

  • [1] Uzbay, T.I. (2007). Tianeptine: potential influences on neuroplasticity and novel pharmacological effects, Prog Neuropsychopharmaco Biol Psychiatry. 2008 May 15;32(4):915-24. 
  • [2] Wagstaff, A.J., Ormrod, D., Spencer, C.M. (2001). Tianeptine: a review of its use in depressive disorders, CNS Drugs.15(3):231-59.
  • [3] Tianeptine, CID 68870, Compound Summary on PubChem: Open Chemistry Database, US National Library of Medicine, available online at:  https://pubchem.ncbi.nlm.nih.gov/compound/Tianeptine [Accessed 16 October, 2017]
  • [4] Defrance, R., Marey, C., Kamoun, A. (1988). Antidepressant and anxiolytic activities of tianeptine: an overview of clinical trials., Clinical Neuropharmacology, Suppl 2:S74-82.
  • [5] McEwan, B.S., et al. (2010). The neurobiological properties of tianeptine (Stablon): from monoamine hypothesis to glutamatergic modulation, Molecular Psychiatry. 15(3):237-49. 
  • [6] Cooper, C.M., et al. (2015) Tianeptine in an experimental medicine model of antidepressant action, Journal of Psychopharmacology. 29(5):582-90. 
  • [7] Ginestet, D. (1997). Efficacy of tianeptine in major depressive disorders with or without melancholia, Eur Neuropsychopharmacol. Suppl 3:S341-5.
  • [8] Wilde, M.I., Benfield, P., Tianeptine. (1995). A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in depression and coexisting anxiety and depression, Drugs, 49(3):411-39.
  • [9] Lechin, F., vd Dijs, B., Lechin A.E. (2004). Treatment of bronchial asthma with tianeptine, Methods Find Exp Clin Pharmacol, 26(9):697-701.
  • [10] Harris County couple alleges lack of warnings on antidepressant led to son's death, by John Suayan, SE Texas Record online, Nov. 29, 2016
  • [11] Le Brizquir, Y., et al. (1994). Tianeptine--an instance of drug-induced hepatotoxicity predicted by prospective experimental studies, Journal of Hepatol, 21(5):771-3.

Precaution and Disclaimer:

This Material is Sold For Research Use Only. Terms of Sale Apply. Not for Human Consumption, nor Medical, Veterinary, or Household Uses.

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