79559-97-0 Usage
Description
Sertraline HCL, also known as Zoloft, is a selective serotonin reuptake inhibitor (SSRI) antidepressant used in the treatment of major depressive disorder, obsessive-compulsive disorder, post-traumatic stress disorder (PTSD), premenstrual dysphoric disorder (PMDD), panic disorder, and social anxiety disorder in both adults and children. It selectively inhibits the reuptake of serotonin at the presynaptic membrane, increasing serotonin levels in the synapses and enhancing serotonergic neurotransmission, which is related to its antidepressant effect.
Uses
Used in Pharmaceutical Industry:
Sertraline HCL is used as an antidepressant for the treatment of major depressive disorder, obsessive-compulsive disorder, post-traumatic stress disorder (PTSD), premenstrual dysphoric disorder (PMDD), panic disorder, and social anxiety disorder.
Used in Clinical Toxicology and Forensic Analysis:
Sertraline HCL is used as a selective serotonin reuptake inhibitor (SSRI) in LC/MS or GC/MS applications for urine drug testing, clinical toxicology, and forensic analysis.
Used in Antimicrobial Applications:
Sertraline HCL is used as an antibacterial agent, exhibiting potential antimicrobial properties.
Used in Selective Serotonin Transporter Inhibition:
Sertraline HCL is used as a selective serotonin transporter (SERT) inhibitor, with an IC50 value of 70 nM, selectively inhibiting monoamine uptake by the serotonin transporter.
Used in Glucocorticoid Function Assay:
Sertraline HCL is used in glucocorticoid function assays to study the effect of antidepressants on glucocorticoid receptor function in humans.
Used in Research on Antidepressant Effects:
The effect of exposure to sertraline hydrochloride has been studied in chronically prepared ovine fetus, providing insights into the effects of antidepressants on fetal development.
Used in Treatment of Anxiety Disorders:
Formulations containing sertraline have been used in the treatment of various anxiety disorders, including panic disorder and social anxiety disorder.
Used in Investigational Treatment of Obesity:
Sertraline hydrochloride is currently undergoing investigation for the treatment of obesity, in addition to its established use in treating obsessive-compulsive disorders.
References
https://en.wikipedia.org/wiki/Sertraline
https://www.drugbank.ca/drugs/DB01104
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.
Therapeutic Function
Antidepressant
Biological Activity
Potent, orally active selective serotonin re-uptake inhibitor (SSRI) used clinically to treat depression.
Biochem/physiol Actions
Selective serotonin reuptake inhibitor, antidepressant.
Check Digit Verification of cas no
The CAS Registry Mumber 79559-97-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,9,5,5 and 9 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 79559-97:
(7*7)+(6*9)+(5*5)+(4*5)+(3*9)+(2*9)+(1*7)=200
200 % 10 = 0
So 79559-97-0 is a valid CAS Registry Number.
79559-97-0Relevant articles and documents
Catalytic Lewis and Br?nsted acid syn-diastereoselective benzylic substitutions of α-hydroxy-β-nitro- and α-hydroxy-β-azido-alkyl arenes
Chénard, étienne,Cusson, Jean-Philippe,Hanessian, Stephen,Hensienne, Rapha?l
, p. 292 - 306 (2020/06/17)
A series of alkyl and alkenyl p-methoxy arenes containing α,β-disubstituted diamino and amino alcohol groups were synthesized from β-nitro and β-azido benzylic alcohols in the presence of AuCl3 as catalyst. The formation of predominantly syn-disubstituted products were rationalized on the basis of mechanistic considerations and transition state models relying on A1,3-allylic strain. The products could have utility in the design of medicinally relevant compounds and as chiral ligands for asymmetric catalysis. A new synthesis of (+)-sertraline (Zoloft) was achieved.
Concise enantioselective synthesis of (+)-sertraline and (-)-CP-52002 using proline catalysis
Kalshetti, Rupali,Venkataramasubramanian,Kamble, Sanjay,Sudalai, Arumugam
supporting information, p. 1053 - 1055 (2016/02/16)
A short enantioselective synthesis of (+)-sertraline and its C4 epimer (-)-CP-52002 with an overall yield of 30%, respectively, as its hydrochloride has been described. The key steps are the proline catalyzed Mannich reaction of acetaldehyde and acid catalyzed intramolecular Friedel-Crafts' alkylation reaction of olefin proceeding with high optical purities.
Stereoselective amination of chiral benzylic ethers using chlorosulfonyl isocyanate: Total synthesis of (+)-Sertraline
Lee, Sang Hwi,Kim, In Su,Li, Qing Ri,Dong, Guang Ri,Jeong, Lak Shin,Jung, Young Hoon
experimental part, p. 10011 - 10019 (2012/02/05)
The stereoselective amination of various chiral benzylic ethers using chlorosulfonyl isocyanate is developed, and the application of this method to the total synthesis of a potent antidepressant, (+)-sertraline, from readily available 1-naphthol is also described (Figure presented).