An internal standard for the quantification of tianeptine
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Unlabeled Version(s)
17561Tianeptine (sodium salt)
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Tianeptine-d6 (hydrochloride)

Item No. 36800

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
7-[(3-chloro-6,11-dihydro-6-methyl-5,5-dioxidodibenzo[c,f][1,2]thiazepin-11-yl)amino]-heptanoic-4,4,5,5,6,6-d6 acid, monohydrochloride
Molecular Formula
C21H19ClD6N2O4S • HCl
Formula Weight
479.5
Purity
≥99% deuterated forms (d1-d6)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Methanol: Soluble
SMILES
OC(CCC([2H])([2H])C([2H])([2H])C([2H])([2H])CNC(C1=C2C=C(Cl)C=C1)C(C=CC=C3)=C3N(C)S2(=O)=O)=O.Cl
InChi Code
InChI=1S/C21H25ClN2O4S.ClH/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);1H/i2D2,3D2,7D2;
InChi Key
VALUNVMGXVWSGM-OEZAEQEYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

    $279

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    1 mg

    $530

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    Product Description

    Tianeptine-d6 is intended for use as an internal standard for the quantification of tianeptine (Item No. 17561) by GC- or LC-MS. Tianeptine is an atypical antidepressant.1 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.1,2 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.3 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.4 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.5 It also reverses increases in extracellular glutamate levels induced by acute restraint stress in the basolateral nucleus of the amygdala in rats.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. McEwen, B.S., Chattarji, S., Diamond, D.M., et al. The neurobiological properties of tianeptine (Stablon): From monoamine hypothesis to glutamatergic modulation. Mol. Psychiatry 15(3), 237-249 (2010).

    2. Gassaway, M.M., Rives, M.L., Kruegel, A.C., et al. The atypical antidepressant and neurorestorative agent tianeptine is a μ-opioid receptor agonist. Transl. Psychiatry 4(7), e411 (2014).

    3. Samuels, B.A., Nautiyal, K.M., Kruegel, A.C., et al. The behavioral effects of the antidepressant tianeptine require the mu-opioid receptor. Neuropsychopharmacology 42(10), 2052-2063 (2017).

    4. Svenningsson, P., Bateup, H., Qi, H., et al. Involvement of AMPA receptor phosphorylation in antidepressant actions with special reference to tianeptine. Eur. J. Neurosci. 26(12), 3509-3517 (2007).

    5. Reagan, L.P., Rossell, D.R., Wood, G.E., et al. Chronic restraint stress up-regulates GLT-1 mRNA and protein expression in the rat hippocampus: Reversal by tianeptine. Proc. Natl. Acad. Sci. USA 101(7), 2179-2184 (2004).

    6. Reznikov, L.R., Grillo, C.A., Piroli, G.G., et al. Acute stress-mediated increases in extracellular glutamate levels in the rat amygdala: Differential effects of antidepressant treatment. Eur. J. Neurosci. 25(10), 3109-3114 (2007).