Tianeptine
Also called Stablon, Coaxil, Tatinol, Tianeptine Acid
Part of the metabolic pathway of Tianeptine. See the timeline on the metabolic highway.
Dosage
Oral bands as drawn from PsychonautWiki's ranges below. The table is the source of truth.
When sources disagree, both rows are shown as published. Nothing is averaged or merged.
Oral
| Source | Threshold | Light | Common | Strong | Heavy |
|---|---|---|---|---|---|
| PsychonautWiki | 25 mg PW | 50–100 mg PW | 100–250 mg PW | 250–350 mg PW | 350 mg+ PW |
| TripSit | – | 7.5 mg TS | 12.5 mg TS | 17 mg TS | – |
Bioavailability: 99% PW
TripSit dose text
TripSit's factsheet also states its doses as text.
Light: 7.5mg Common: 12.5mg Strong: 17mg Note: Tianeptine is reported to have opioid-like effects at high doses, but this is offset by an increased risk of liver damage TS
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Duration
Oral, drawn at the midpoint of each PsychonautWiki range.
| Route · source | Onset | Come-up | Peak | Offset | Total | After-effects |
|---|---|---|---|---|---|---|
| Oral · PsychonautWiki | 30–60 minutes PW | 15–30 minutes PW | 60–90 minutes PW | 30–60 minutes PW | 2–3 hours PW | – |
TripSit factsheet
Mixing
For best safety practice, don't mix this drug with other depressants.
Why: respiratory depression. PsychonautWiki says:
- “Respiratory depression (also known as hypoventilation) can be described as a reduced urge to breathe that can be fatal depending on its intensity.” (PsychonautWiki, Respiratory depression, revision 150612)
- “... otherwise safe dosages of these compounds can become fatal when combined with even small amounts of other classes of depressant. For example, benzodiazepines combined with opioids are an extremely common cause of fatal respiratory depression. It is therefore strongly discouraged to combine these depressants at any dosage range.” (PsychonautWiki, Respiratory depression, revision 150612)
- “The most common cause of substance-related deaths is the combination of depressants (such as opiates, benzodiazepines, or alcohol) with other depressants.” (PsychonautWiki, Responsible drug use, revision 168206)
- “This combination potentiates the muscle relaxation, amnesia, sedation, and respiratory depression caused by one another. At higher doses, it can lead to a sudden, unexpected loss of consciousness along with a dangerous amount of depressed respiration.” (PsychonautWiki, dangerous interactions table, "Depressants" row, revision 156847)
Quotes from PsychonautWiki, CC BY-SA 4.0.
Acute combinations: what happens when these are taken close together. Entries backed by a medical journal or agency are listed first.
Backed by medical journals
TripSit combination chart
TripSit rates each pairing. Only pairings with a number carry a citation from TripSit. See the whole chart; TripSit's own notes are on combo.tripsit.me.
Risks and toxicity
The toxicity and long-term health effects of recreational tianeptine use have not been studied in any scientific context, and the exact toxic dosage is unknown. PW
Anecdotal evidence suggests that there are no negative health effects attributed to simply trying the drug by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). Independent research should always be done to ensure that a combination of two or more substances is safe before consumption. PW
It is strongly recommended that one use harm reduction practices when using this substance. PW
Lethal dosage
The LD₅₀ of tianeptine has not yet officially been established; however, it seems to have a large therapeutic index and margin of safety. In 2007, a 26-year-old man committed suicide by taking an excessive amount of tianeptine in combination with alcohol. However, the amount required to overdose is not likely to be taken on accident. To ensure safety while using tianeptine, it is advised to not exceed 100 mg in a single dose or 300 mg total in one day.[17] PW
Tolerance and addiction potential
The chronic use of tianeptine can be considered as mildly addictive and is capable of causing both physical and psychological dependence. When physical dependence has developed, withdrawal symptoms may occur if a person suddenly stops their usage. PW
Tolerance to many of the effects of tianeptine develops with prolonged use, including therapeutic effects. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about 3 - 7 days for the tolerance to be reduced to half and 1 - 2 weeks to be back at baseline (in the absence of further consumption). This compound may share a cross tolerance with other trycyclic antidepressants and opioids. PW
It is worth noting that because of tianeptine's short duration of effects, it may compel some to frequent redosing. The potential euphoric effects of high doses (> 100 mg) may cause some users to exceed recommended dosages, which could quickly raise tolerance and intensify negative side effects. In addition, tianeptine possesses certain properties as a μ-opioid agonist, possibly leading to addiction and withdrawal mechanics similar to that of opiates. However, as with most people looking to discontinue their antidepressant medications (both SSRIs and TCAs), daily users of tianeptine should taper off their usage instead of suddenly halting it. This will ensure that negative discontinuation symptoms are kept to a minimum.[8] PW
Tianeptine withdrawal can occur with as little as ~500mg per day, and increases in severity with the amount of daily dosage and time spent using the drug. Withdrawal symptoms are similar to opioids (flu-like symptoms, watery eyes, and nose, dry heaves et al.) and may include emotional instability. Due to the fact that Tianeptine generally has weaker recreational properties compared to other opioids, the withdrawal of this substance can feel significantly worse than an equally euphoric dose of a more traditional opioid. PW
Testing
Effects
Overview
Tianeptine (trade names Stablon and Coaxil) is an atypical antidepressant. While primarily a prescription drug, it is sometimes used in high doses for recreational opioid effects. It has a unique and poorly-understood mechanism of action consisting of modulation of the brain's monoaminergic and glutamatergic systems. PW
A Tricyclic antidepressant, that has quite unique pharmacological properties than others in its class. Such as the possible indirect action on NMDA/AMPA and a full agonist at the μ-opioid receptor. While abuse of this substance is uncommon, it has been shown in a few countries. TS
Tianeptine, sold under the brand names Stablon, Tatinol, and Coaxil among others, is an atypical tricyclic antidepressant which is used mainly in the treatment of major depressive disorder, although it may also be used to treat anxiety, asthma, and irritable bowel syndrome.[1–4] WP
Tianeptine has antidepressant and anxiolytic effects with a relative lack of sedative, anticholinergic, and cardiovascular side effects. 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. This may explain part of its antidepressant and anxiolytic effects; however, it is thought that tianeptine also modulates glutamate receptors, and this may also explain tianeptine's antidepressant/anxiolytic effects.[5–10] WP
Tianeptine was discovered and patented by the French Society of Medical Research in the 1960s. It was introduced for medical use in France in 1983. Currently, tianeptine is approved in France and manufactured and marketed by Laboratories Servier SA; it is also marketed in a number of other European countries under the trade name Coaxil as well as in Asia (including Singapore) and Latin America as Stablon and Tatinol but it is not available in Australia, Canada, New Zealand, Italy or the United Kingdom. In the United States, it is an unregulated drug sold under several names and some of these products have been found to be adulterated with other recreational drugs. It is commonly known by the nickname "gas station heroin". In July 2026, the United States Drug Enforcement Administration (DEA) announced its intention to make tianeptine a Schedule I controlled substance.[11–16] WP
History
History
Tianeptine was introduced for medical use in France under the brand name Stablon in 1983.[11] WP
Legal status
- Tianeptine is available by prescription in many European, Asian, and South American countries and distributed under brand names such as Stablon and Coaxil. PW
- Canada: Tianeptine is uncontrolled in Canada, meaning it is legal to possess without any sort of license or prescription. PW⚠ PsychonautWiki itself has flagged this text: citation needed.
- Germany: Tianeptine is a prescription medicine, according to Anlage 1 AMVV.[18] PW
- Russia: In Russia, since 2010, tianeptine is a Schedule III controlled substance.[19] PW
- Sweden: Tianeptine is not an approved prescription medicine, and is therefore a controlled substance.[20] PW
- Switzerland: Tianeptine is not controlled under Buchstabe A, B, C and D. It could be considered legal.[21] PW
- Turkey: Tianeptine is a 'green prescription' only substance and illegal when sold or possessed without a prescription.[22] PW
- United Kingdom: Tianeptine is illegal to produce, supply, or import under the Psychoactive Substance Act, which came into effect on May 26th, 2016.[23] PW
- United States: Tianeptine is currently a federally uncontrolled substance in the United States. However, many nootropics vendors have ceased carrying it due to its recreational use and abuse potential. In March of 2018, the Michigan state legislature passed a bill to classify tianeptine sodium salt as a Schedule II controlled substance, making it the first state to schedule the drug.[24]
[25] PW
Approval and brand names
Brand names include: WP
- Coaxil (BG, CR, CZ, EE, HU, LT, LV, PL, RO, RU, SK UA) WP
- Salymbra (EE) WP
- Stablon (AR, AT, BR, FR, HK, IN, ID, MY, MX, PK, PT, SG, SK, TH, TT, TR, VE) WP
- Tatinol (CN) WP
- Tianeurax (DE) WP
- Tynept (IN) WP
- Zinosal (ES) WP
- Tianesal (PL) WP
Development
Under the code names JNJ-39823277 and TPI-1062, tianeptine was previously under development for the treatment of major depressive disorder in the United States and Belgium. Phase I clinical trials were completed in Belgium and the United States in May and June 2009, respectively. For unclear reasons development of tianeptine was discontinued in both countries in January 2012. In October 2023, Tonix Pharmaceuticals announced that it had discontinued its development of tianeptine as a monotherapy for major depressive disorder after disappointing phase-2 clinical trial results. An ongoing clinical trial, sponsored by the New York Psychiatric Institute, is examining tianeptine's use in treatment-resistant depression.[26]
U.S. National Poison Data System data on tianeptine showed a nationwide increase in tianeptine exposure calls and calls related to abuse and misuse during 2014–2017.[10] WP
Legal status
In 2003, Bahrain classified tianeptine a controlled substance due to increasing reports of misuse and recreational use.[29] WP
In Russia, tianeptine (sold under the brand name "Coaxil") is a schedule III controlled substance in the same list as the majority of benzodiazepines and barbiturates.[30] WP
On 13 March 2020, with a decree approved by the Minister of Health, Italy became the first European country to outlaw tianeptine considering it a Class I controlled substance.[31] WP
United states
In the United States, tianeptine is not considered by the Drug Enforcement Administration as a controlled substance or analogue thereof. However, its use in dietary supplements and food is unlawful. The Food and Drug Administration (FDA) has issued warnings, as recently as January 2024, about the dangers of recreational tianeptine use and the risks posed by adulterated dietary supplements containing undeclared tianeptine.[32]
On 6 April 2018, Michigan became the first US state to outlaw tianeptine sodium, classifying it as a schedule II controlled substance. The scheduling of tianeptine sodium is effective 4 July 2018.[35]
On 1 November 2019, Tianeptine became a Schedule II controlled dangerous substance as classified within the Uniform Controlled Dangerous Substances Act of the state of Oklahoma. WP
On 15 March 2021, Alabama outlawed tianeptine, initially classifying it as a schedule II controlled substance. It was later reclassified as a schedule I controlled substance on 14 November 2021.[37]
On 1 July 2022, Tennessee outlawed tianeptine and adds "any salt, sulfate, free acid, or other preparation of tianeptine, and any salt, sulfate, free acid, compound, derivative, precursor, or preparation thereof that is substantially chemically equivalent or identical with tianeptine", classifying it as a schedule II controlled substance.[39] WP
On 22 December 2022, Ohio outlawed tianeptine, classifying it as a schedule I controlled substance with Ohio Governor Mike DeWine referencing the widespread availability of the chemical there as "gas-station heroin".[40] WP
On 23 March 2023, Kentucky outlawed tianeptine, classifying it as a schedule I substance by an order of the Governor of Kentucky.[41]
On 20 September 2023, Florida outlawed tianeptine, classifying it as a schedule I substance by an administrative edict issued by the Florida Attorney General.[14]
In July 2026, the United States Drug Enforcement Administration (DEA) announced its intention to make tianeptine a Schedule I controlled substance.[16] WP
Pharmacology
Atypical μ-opioid receptor agonist
In 2014, tianeptine was found to be a μ-opioid receptor (MOR) full agonist using human proteins. It was also found to act as a full agonist of the δ-opioid receptor (DOR), although with approximately 200-fold lower potency. The same researchers subsequently found that the MOR is required for the acute and chronic antidepressant-like behavioral effects of tianeptine in mice and that its primary metabolite had similar activity as a MOR agonist but with a much longer elimination half-life. Moreover, in mice, although tianeptine produced other opioid-like behavioral effects such as analgesia and reward, it did not result in tolerance or withdrawal. The authors suggested that tianeptine may be acting as a biased agonist of the MOR and that this may be responsible for its atypical profile as a MOR agonist. However, there are reports that suggest that withdrawal effects resembling those of other typical opioid drugs (including but not limited to depression, insomnia, and cold/flu-like symptoms) do manifest following prolonged use at dosages far beyond the medical range. In addition to its therapeutic effects, activation of the MOR is likely to also be responsible for the abuse potential of tianeptine at high doses that are well above the normal therapeutic range and efficacy threshold.[8]
In rats, when co-administered with morphine, tianeptine prevents morphine-induced respiratory depression without impairing analgesia. In humans, however, tianeptine was found to increase respiratory depression when administered in conjunction with the potent opioid remifentanil.[49]
Glutamatergic, neurotrophic, and neuroplastic modulation
Research suggests that tianeptine produces its antidepressant effects through indirect alteration and inhibition of glutamate receptor activity (i.e., AMPA receptors and NMDA receptors) and release of BDNF (brain-derived neurotrophic factor), in turn affecting neural plasticity. Some researchers hypothesize that tianeptine has a protective effect against stress induced neuronal remodeling. There is also action on the NMDA and AMPA receptors. In animal models, tianeptine inhibits the pathological stress-induced changes in glutamatergic neurotransmission in the amygdala and hippocampus. It may also facilitate signal transduction at the CA3 commissural associational synapse by altering the phosphorylation state of glutamate receptors. With the discovery of the rapid and novel antidepressant effects of drugs such as ketamine, many believe the efficacy of antidepressants is related to promotion of synaptic plasticity. This may be achieved by regulating the excitatory amino acid systems that are responsible for changes in the strength of synaptic connections as well as enhancing BDNF expression, although these findings are based largely on preclinical studies.[7]
Serotonin reuptake enhancer
Tianeptine is no longer labelled a selective serotonin reuptake enhancer (SSRE) antidepressant.
Tianeptine had been found to bind to the same allosteric site on the serotonin transporter (SERT) as conventional TCAs. However, whereas conventional TCAs inhibit serotonin reuptake by the SERT, tianeptine appeared to enhance it. This seems to be because of the unique C3 amino heptanoic acid side chain of tianeptine, which, in contrast to other TCAs, is thought to lock the SERT in a conformation that increases affinity for and reuptake (Vₘₐₓ) of serotonin. As such, tianeptine was thought to act a positive allosteric modulator of the SERT, or as a "serotonin reuptake enhancer".[7]
Although tianeptine was originally found to have no effect in vitro on monoamine reuptake, release, or receptor binding, upon acute and repeated administration, tianeptine decreased the extracellular levels of serotonin in rat brain without a decrease in serotonin release, leading to a theory of tianeptine enhancing serotonin reuptake. The (−)-enantiomer is more active in this sense than the (+)-enantiomer. However, more recent studies found that long-term administration of tianeptine does not elicit any marked alterations (neither increases nor decreases) in extracellular levels of serotonin in rats. However, coadministration of tianeptine and the selective serotonin reuptake inhibitor fluoxetine inhibited the effect of tianeptine on long-term potentiation in hippocampal CA1 area. This is considered an argument for the opposite effects of tianeptine and fluoxetine on serotonin uptake, although it has been shown that fluoxetine can be partially substituted for tianeptine in animal studies. In any case, the collective research suggests that direct modulation of the serotonin system is unlikely to be the mechanism of action underlying the antidepressant effects of tianeptine.[7]
Other actions
Tianeptine modestly enhances the mesolimbic release of dopamine and potentiates CNS D₂ and D₃ receptors. Tianeptine has no affinity for the dopamine transporter or the dopamine receptors. CREB-TF (CREB, cAMP response element-binding protein) is a cellular transcription factor. It binds to certain DNA sequences called cAMP response elements (CRE), thereby increasing or decreasing the transcription of the genes. CREB has a well-documented role in neuronal plasticity and long-term memory formation in the brain. Cocaine- and amphetamine-regulated transcript, also known as CART, is a neuropeptide protein that in humans is encoded by the CARTPT gene. CART appears to have roles in reward, feeding, stress, and it has the functional properties of an endogenous psychostimulant. Taking into account that CART production is upregulated by CREB, it could be hypothesized that due to tianeptine's central role in BDNF and neuronal plasticity, this CREB may be the transcription cascade through which this drug enhances mesolimbic release of dopamine.[51]
Research indicates possible anticonvulsant (anti-seizure) and analgesic (painkilling) activity of tianeptine via downstream modulation of adenosine A₁ receptors (as the effects could be experimentally blocked by antagonists of this receptor). Tianpetine is also weak histone deacetylase (HDAC) inhibitor, specifically of HDAC1 and HDAC2 but not of HDAC3, and analogues with greatly increased potency such as tianeptinaline have been developed.[68]
Tianeptine has been shown to be a high-efficacy agonist of PPAR-delta, a nuclear receptor.[70] WP
Pharmacokinetics
The bioavailability of tianeptine is approximately 99%. Its plasma protein binding is about 95%. The metabolism of tianeptine is hepatic, via β-oxidation. CYP enzymes are not involved, which limits the potential for drug-drug interactions. Maximal concentration is reached in about an hour and the elimination half-life is 2.5 to 3 hours. The elimination half-life has been found to be increased to 4 to 9 hours in the elderly. Tianeptine is usually packaged as a sodium salt but can also be found as tianeptine sulfate, a slower-releasing formulation patented by Janssen in 2012. In 2022 Tonix Pharmaceuticals received permission from the US FDA to conduct phase II clinical trials on tianeptine hemioxalate extended-release tablets designed for once-daily use. The project was discontinued in late 2023 because of disappointing results in clinical trials.[6]
Tianeptine has two active metabolites, MC5 (a pentanoic acid derivative of the parent compound) and MC3 (a propionic acid derivative). MC5 has a longer elimination half-life of approximately 7.6 hours, and takes about a week to reach steady-state concentration under daily-dosing. MC5 is a mu-opioid agonist but not delta-opioid agonist, with EC50 at the mu-opioid receptor of 0.545 μM (vs 0.194 μM for tianeptine). MC3 is a very weak mu-opioid agonist, with an EC50 of 16 μM. Tianeptine is excreted 65% in the urine and 15% in feces.[6]
Receptor binding · Wikipedia
Tianeptine
| Site | Kᵢ (nM) | Species |
|---|---|---|
| MOR (μ-Opioid receptor) | 383–768 (Kᵢ); 194 (EC₅₀ (Half-maximal effective concentration)) | Human[8] |
| DOR (δ-Opioid receptor) | 10000+ (Kᵢ); 37400 (EC₅₀ (Half-maximal effective concentration)) | Human[8] |
| KOR (κ-Opioid receptor) | 10000+ (Kᵢ); 100000+ (EC₅₀ (Half-maximal effective concentration)) | Human[8] |
| SERT (Serotonin transporter) | 10000+ | Human[45] WP |
| NET (Norepinephrine transporter) | 10000+ | Human[45] WP |
| DAT (Dopamine transporter) | 10000+ | Human[45] WP |
| 5-HT1A | 10000+ | Human[45] WP |
| 5-HT1B | 10000+ | Human[45] WP |
| 5-HT1D | 10000+ | Human[45] WP |
| 5-HT1E | 10000+ | Human[45] WP |
| 5-HT2A | 10000+ | Human[45] WP |
| 5-HT2B | 10000+ | Human[45] WP |
| 5-HT2C | 10000+ | Human[45] WP |
| 5-HT₃ | 10000+ | Human[45] WP |
| 5-HT5A | 10000+ | Human[45] WP |
| 5-HT₆ | 10000+ | Human[45] WP |
| 5-HT₇ | 10000+ | Human[45] WP |
| α1A | 10000+ | Human[45] WP |
| α1B | 10000+ | Human[45] WP |
| α2A | 10000+ | Human[45] WP |
| α2B | 10000+ | Human[45] WP |
| α2C | 10000+ | Human[45] WP |
| β₁ | 10000+ | Human[45] WP |
| β₂ | 10000+ | Human[45] WP |
| D₁ | 10000+ | Human[45] WP |
| D₂ | 10000+ | Human[45] WP |
| D₃ | 10000+ | Human[45] WP |
| D₄ | 10000+ | Human[45] WP |
| D₅ | 10000+ | Human[45] WP |
| H₁ | 10000+ | Human[45] WP |
| H₂ | 10000+ | Human[45] WP |
| H₃ | 10000+ | Human[45] WP |
| H₄ | 10000+ | Human[45] WP |
| mACh (Muscarinic acetylcholine receptor) | 10000+ | Human[45] WP |
| σ₁ | 10000+ | Guinea pig[45] WP |
| σ₂ | 10000+ | Rat[45] WP |
| I₁ | 10000+ | Human[45] WP |
| A₁ | 10000+ (EC₅₀ (Half-maximal effective concentration)) | Human[8] |
| VDCC (Voltage-dependent calcium channel) | 10000+ | Human[45] WP |
Chemistry
- Formula
- C21H25ClN2O4S PC
- CAS number
- 72797-41-2 PC
- Molar mass (g/mol)
- 437.0 PC
- IUPAC name (computed by PubChem)
- 7-
[(3- PCchloro- 6- methyl- 5, 5- dioxo- 11H- benzo[c] [2, 1] benzothiazepin- 11- yl) amino] heptanoic acid - SMILES
- CN1C2=CC=CC=C2C(C3=C(S1(=O)
=O) PCC=C(C=C3) Cl) NCCCCCCC(=O) O - InChIKey
- JICJBGPOMZQUBB-
UHFFFAOYSA- PCN - PubChem CID
- 68870
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References
- Journal / agency Nishio Y, Lindsley CW, Bender AM. Classics in Chemical Neuroscience: Tianeptine. ACS Chem Neurosci. November 2024. doi:10.1021/acschemneuro.4c00519 · PMID 39382192 · PMC11587517
- Other Elks J. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. 14 November 2014
- Other Index Nominum 2000: International Drug Directory. 2000
- Other Tianeptine (International database)
- Journal / agency Defrance R, Marey C, Kamoun A. Antidepressant and anxiolytic activities of tianeptine: an overview of clinical trials. Clinical Neuropharmacology. 1988. PMID 2902922
- Journal / agency Wagstaff AJ, Ormrod D, Spencer CM. Tianeptine: a review of its use in depressive disorders. CNS Drugs. March 2001. doi:10.2165/00023210-200115030-00006 · PMID 11463130
- Journal / agency Kasper S, McEwen BS. Neurobiological and clinical effects of the antidepressant tianeptine. CNS Drugs. 2008. doi:10.2165/00023210-200822010-00002 · PMID 18072812
- Journal / agency Gassaway MM, Rives ML, Kruegel AC, Javitch JA, Sames D. The atypical antidepressant and neurorestorative agent tianeptine is a μ-opioid receptor agonist. Translational Psychiatry. July 2014. doi:10.1038/tp.2014.30 · PMID 25026323 · PMC4119213
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- Other Psychoactive Substances Act 2016
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