Natrium-7-[(3-chlor-6,11-dihydro-6-methyldibenzo[c,f][1,2]thiazepin-11-yl)amino]heptanoat-S,S-dioxid

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Tianeptine sodium salt Chemische Eigenschaften,Einsatz,Produktion Methoden

• Beschreibung

  Tianeptine sodium salt is a structurally novel, serotonin specific antidepressant. It is useful in the treatment of neurotic and reactive depressions, as well as depressive states accompanied by anxiety. Tianeptine (sodium salt) is an analytical reference standard categorized as an opioid. Tianeptine has been abused and associated with overdose and death. Formulations containing tianeptine have been used in the treatment of depression. This product is intended for use in analytical forensic applications. This product is also available as a general research tool .

• Originator

  Sci. Union et Cie (France)

• Verwenden

  Tianeptine sodium salt is a tricyclic compound with psychostimulant, anti-ulcer and anti-emetic properties. Tianeptine sodium salt hydrate has been used as a selective serotonin reuptake enhancer (SSRE) positive control during serotonin transporter (SERT) assay in human embryonic kidney 293 cell lines. Tianeptine (INN) (Stablon, Coaxil, Tatinol) is a SSRE drug used for treating major depressive episodes (mild, moderate, or severe). Tianeptine commonly used for depression. It is also used for pain, asthma, anxiety, and many other conditions, but there is no good scientific evidence to support these other uses.

• Manufacturing Process

  A solution of 27.6 g (0.16 mol) of freshly distilled ethyl 7-aminoheptanoate in 40 ml of nitromethane was added all at once and with mechanical stirring to a suspension of 26.2 g (0.08 mol) of 5,8-dichloro-10-dioxo-11- methyldibenzo[c,f]thiazepine(1,2) in 120 ml of nitromethane. The whole was heated to 55°C for 30 minutes, the solvent was then evaporated in vacuo and the residue was taken up in water. The crude ester was extracted with ether. After evaporation of the ether 36 g of crude ester were obtained, and 30 g (0.065 mol) there of were treated under reflux with a solution of 2.8 g (0.07 mol) of sodium hydroxide in 35 ml of ethanol and 25 ml of water. After one hour's refluxing, the alcohol was evaporated in vacuo. The residue was taken up in 150 ml of water.
  The mixture was twice extracted with 75 ml of chloroform and the aqueous phase was evaporated in vacuo. The sodium salt was then dissolved in 150 ml of chloroform, the solution was dried over sodium sulfate and the product precipitated with anhydrous ether.
  The salt was filtered off, washed with ether and dried at 50°C. 13 g of sodium 7-[8-chloro-10-dioxo-11-methyldibenzo[c,f]thiazepin-(1,2)-aminoheptanoate,melting with decomposition at about 180°C, were obtained.

• Trademarks

  STABLON

• Therapeutic Function

  Antidepressant

• Allgemeine Beschreibung

  Tianeptine is a μ-opioid receptor (MOR) as well as a δ-opioid receptor (DOR) agonist.

• Biologische Aktivität

  Selective facilitator of 5-HT uptake in vitro and in vivo . Has no affinity for a wide range of receptors, including 5-HT and dopamine (IC 50 > 10 μ M) and has no effect on noradrenalin or dopamine uptake. Antidepressant, analgesic and neuroprotective following systemic administration in vivo .

• Biochem/physiol Actions

  Tianeptine is a tricyclic antidepressant that enhances serotonin uptake. This drug can affect neuroprotection, neuronal excitability, memory and anxiety. However, tianeptine is not linked to adverse psychomotor, cognitive, cardiovascular, sleep and bodyweight effects. The drug has a low tendency for abuse and has a positive pharmacokinetic profile.

• Einzelnachweise

  1)?Mennini?et al. (1987),?Tianeptine, a selective enhancer of serotonin uptake in rat brain; ?Naunyn-Schmied. Arch. Pharmacol.,?336?478 2)?Kato and Weitsch (1988),?Neurochemical profile of tianeptine, a new antidepressant drug; ?Clin. Neuropharmacol.,?11?S43 3)?Plaisant?et al. (2003),?Neuroprotective properties of tianeptine: interactions with cytokines; Neuropharmacology,?44?801 4)?Seo?et al. (2016),?Tianeptine induces mTORC1 activation in rat hippocampal neurons under toxic conditions; ?Psychopharmacology (Berl.),?233?2617 5)?Slusarczyk?et al. (2017),?Anti-inflammatory properties of tianeptine on lipopolysaccharide-induced changes in microglial cells involve toll-like receptor-related pathways; ?J. Neurochem.,?136?958

Tianeptine sodium salt Upstream-Materialien And Downstream Produkte

Natrium-7-[(3-chlor-6,11-dihydro-6-methyldibenzo[c,f][1,2]thiazepin-11-yl)amino]heptanoat-S,S-dioxid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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