Sertraline hydrochloride Chemical Properties

Melting point:

246-249°C

alpha 

D23 +37.9° (c = 2 in methanol)

Density 

1.37

Flash point:

9℃

storage temp. 

2-8°C

solubility 

DMSO: ~26 mg/mL

form 

solid

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℃)

color 

white

Merck 

14,8467

Stability:

Store in Freezer

CAS DataBase Reference

79559-97-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T,F

Risk Statements 

36/37/38-39/23/24/25-23/24/25-11

Safety Statements 

22-24/25-36-26-45-36/37-16-7

RIDADR 

UN1230 - class 3 - PG 2 - Methanol, solution

WGK Germany 

3

RTECS 

QJ0352070

HazardClass 

IRRITANT

HS Code 

29214990

MSDS

• Language:English Provider:SigmaAldrich

Sertraline hydrochloride Usage And Synthesis

Description

Sertraline(79559-97-0) 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.

References

https://en.wikipedia.org/wiki/Sertraline
https://www.drugbank.ca/drugs/DB01104

Description

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.

Description

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.

Chemical Properties

White or almost white, crystalline powder.

Originator

Pfizer (USA)

Uses

A selective serotonin reuptake inhibitor. Used as an antidepressant

Uses

antibacterial

Uses

A selective ST inhibitor

Uses

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.

Definition

ChEBI: A hydrochloride resulting from the reaction of equimolar amounts of sertraline and hydrogen chloride. A selective serotonin-reuptake inhibitor (SSRI), it is administered orally as an antidepressant for the treatment of depression, obsessive-compulsive diso der, panic disorder and post-traumatic stress disorder.

Manufacturing Process

Manufacturing process for Sertraline hydrochloride includes these steps as follows: Preparation of hot ethyl acetate-pentane, Preparation of an analytical sample of 3-ethoxycarbonyl-4-(3,4- dichlorophenyl)-4-phenylbut-3-enoic acid; Preparation of 4-(3,4- dichlorophenyl)-4-phenylbut-3-enoic acid; Preparation of an analytical sample of the 4-(3,4-dichlorophenyl)-4-phenylbutanoic acid, 4-(3,4-dichlorophenyl)-3,4-dihydro-1-(2H)- naphthalenone; Preparation of a white precipitate, containing about 70% cis-racemate and 30% tras-racemate of N-methyl-4-(3,4- dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine hydrochloride; Preparation of cis-(1S)(1R)-N-methyl-4-(3,4- dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine hydrochloride; Preparation of cis-(1S)-N-methyl-4- (3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine mandelate. The mandelate salt were suspended in ethyl acetate (about 2 L). The ethyl acetate suspension was treated with 10% aqueous NaOH solution, thereby converting the amine to the free base. The resulting ethyl acetate solution was then dried, diluted with ether (2 L) and then treated with excess gaseous hydrogen chloride to give a gelatinous suspension which crystallized overnight. The crystalline HCl salt product was separated by filtration, washed with ether and air dried. The cis-(1S)-N-methyl-4-(3,4-dichlorophenyl)- 1,2,3,4-tetrahydro-1-naphthalenamine hydrochloride 25.96 g, 39% yield, with melting point 243°-245°C.

brand name

Zoloft (Pfizer);Lustral.

Therapeutic Function

Antidepressant

General Description

Sertraline, marketed as the brand drug Zoloft^?, is an SSRI antidepressant used in the treatment of major depression as well as obsessive-compulsive, panic, and social anxiety disorders. This Certified Snap-N-Spike^? Solution is applicable for use in LC/MS or GC/MS applications for urine drug testing, clinical toxicology, and forensic analysis.

Biological Activity

Potent, orally active selective serotonin re-uptake inhibitor (SSRI) used clinically to treat depression.

Biochem/physiol Actions

Selective serotonin reuptake inhibitor, antidepressant.

storage

Desiccate at RT

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