Seserine

Base Information

• Chemical Name: Seserine
• CAS No.: 79559-97-0
• Molecular Formula: C17H17Cl2N.HCl
• Molecular Weight: 342.696
• Hs Code.: 29214990
• Mol file: 79559-97-0.mol

Synonyms:Altruline;Apo Sertraline;Apo-Sertraline;Aremis;Besitran;Gen Sertraline;Gen-Sertraline;Gladem;Hydrochloride, Sertraline;Lustral;Novo Sertraline;Novo-Sertraline;ratio Sertraline;ratio-Sertraline;Rhoxal sertraline;Rhoxal-sertraline;Sealdin;Sertraline;Sertraline Hydrochloride;Sertraline Hydrochloride (1S-cis)-Isomer;Zoloft

Chemical Property of Seserine

Chemical Property:

• Appearance/Colour: White or white-like crystalline powder
• Vapor Pressure: 3.85E-07mmHg at 25°C
• Melting Point: 246-249 °C
• Boiling Point: 416.3 °C at 760 mmHg
• PKA: pKa (water): 9.48 ± 0.04; pKa (methanol:water, 40:60 v/v): 8.6; pKa (ethanol:water, 1:1 v/v): 8.5(at 25℃)
• Flash Point: 205.6 °C
• PSA: 12.03000
• Density: 1.37
• LogP: 6.37250
• Storage Temp.: Desiccate at RT
• Solubility.: DMSO: ~26?mg/mL
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 341.050483
• Heavy Atom Count: 21
• Complexity: 322

Purity/Quality:

99%, ^*data from raw suppliers

Sertraline, Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T,F
• Statements: 36/37/38-39/23/24/25-23/24/25-11
• Safety Statements: S22:; S24/25:

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[NH2+]C1CCC(C2=CC=CC=C12)C3=CC(=C(C=C3)Cl)Cl.[Cl-]
• Isomeric SMILES: C[NH2+][C@H]1CC[C@H](C2=CC=CC=C12)C3=CC(=C(C=C3)Cl)Cl.[Cl-]
• Description: Sertraline is the hydrochloride form of sertraliine. Sertraline belongs to the selective serotonin reuptake inhibitor (SSRI) class antidepressant drug. Sertraline is indicated for the treatment of major depressive disorder in adults as well as obsessive-compulsive disorder, post-traumatic stress disorder (PTSD), premenstrual dysphoric disorder (PMDD), panic disorder and social anxiety disorder occurring in both adults and children. Its exact mechanism of action is still not fully understand. But it is indicated that this drug can selectively inhibit the reuptake of serotonin at the presynaptic membrane, increasing serotonin levels in the synapses and enhancing serotonergic neurotransmission. This effect seems to be related to the antidepressant effect of sertraliine. Sertraline is a selective serotonin reuptake inhibitor (SSRI). It inhibits monoamine uptake by the serotonin transporter (SERT) with an IC50 value of 70 nM. It is selective for SERT over the norepinephrine and dopamine transporters (IC50s = 520 and 720 nM, respectively). Sertraline (3.2-56 mg/kg, s.c.) reduces immobility in the forced swim test in mice. Sertraline (5 μM) prevents acid sphingomyelinase activation and subsequent ceramide release induced by infection with replication-deficient vesicular stomatitis virus pseudoviral particles (pp-VSV) presenting the severe acute respiratory coronavirus 2 (SARS-CoV-2) spike protein in Vero cells, an effect that can be overcome with exogenous application of C16 ceramide. Formulations containing sertraline have been used in the treatment of depression, obsessive-compulsive disorder (OCD), premenstrual dysphoric disorder (PMDD), and various anxiety disorders. Sertraline hydrochloride is a selective serotonin reuptake inhibitor, similar mechanistically to fluoxetine, introduced initially for the maintenance and long-term treatment of depression. It is reportedly non-sedating and compared to fluoxetine has a shorter duration of action and lack of CNS activating effects such as nervousness and anxiety. Sertraline hydrochloride is currently undergoing investigation for the treatment of obesity and obsessive-compulsive disorders.
• Uses: antibacterial A selective ST inhibitor The effect of exposure of sertraline hydrochloride was studied in chronically prepared ovine fetus. It was used in glucocorticoid function assay to study the effect of antidepressants on glucocorticoid receptor function in humans.
• Therapeutic Function: Antidepressant

Technology Process of Seserine

There total 36 articles about Seserine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

sertraline 4-methoxybenzoate → sertraline hydrochloride (79559-97-0)

Guidance literature:

With hydrogenchloride; In diethyl ether; nitromethane; at 25 - 30 ℃; for 1h; Product distribution / selectivity;

Reference yield: 96.0%

Sertraline (79617-96-2) → sertraline hydrochloride (79559-97-0)

Guidance literature:

With hydrogenchloride; In propan-1-ol; at 30 ℃; for 1h; Product distribution / selectivity;

Reference yield: 95.0%

(1S-cis)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine mandelate → sertraline hydrochloride (79559-97-0)

Guidance literature:

With hydrogenchloride; In methoxypropyl acetate; at 20 - 70 ℃; for 3h; Product distribution / selectivity;

upstream raw materials:

hydrogenchloride

(1S,4S)-sertraline*(S)-mandelic acid

1S-cis-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthaleneamine-mandelate

Sertraline

Downstream raw materials:

sertraline hydrochloride acetic acid solvate

cis-(1S,4S)-N-(tert-butoxycarbonyl)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine

Refernces

• 1、 -. "Preparation method of chiral sertraline hydrochloride". Paragraph 0039; 0042-0044; 0047-0049; 0052-0054; 0057-0059. . Retrieved 2020/10/21.
• 2、 Chen, Fei,Ding, Ziyuan,He, Yanmei,Qin, Jie,Wang, Tianli,Fan, Qing-Hua. "Asymmetric hydrogenation of N-alkyl and N-aryl ketimines using chiral cationic Ru(diamine) complexes as catalysts: The counteranion and solvent effects, and substrate scope". . p. 5248 - 5257. Retrieved 2012/08/08.