Sertraline hydrochloride

Iupac Name：(1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine;hydrochloride

Molecular Weight：306.22958

Modify Date.: 2022-11-22 16:06

Introduction: 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. View more+

Request For Quotation

1. Names and Identifiers

1.1 Name: Sertraline hydrochloride
1.2 Synonyms: (+)-cis-(1S,4S)-1-methylamino-4-(3,4-dichlorophenyl)tetralin hydrochloride (+)-sertraline hydrochloride (1S,4S)-1-(3,4-DICHLOROPHENYL)-1,2,3,4-TETRAHYDRO-4-(METHYLAMINO)NAPHTHALENE HYDROCHLORIDE (1S,4S)-4-(3,4-dichlorophényl)-N-méthyl-1,2,3,4-tétrahydronaphtalén-1-amine chlorhydrate (1S,4S)-4-(3,4-DICHLOROPHENYL)-1,2,3,4-TETRAHYDRO-N-METHYL-1-NAPHTHALENAMINE HYDROCHLORIDE (1S,4S)-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthylamine hydrochloride (1S,4S)-4-(3,4-DICHLOROPHENYL)-1,2,3,4-TETRAHYDRO-N-METHYL-1-NAPTHALENAMINE HYDROCHLORIDE (1S,4S)-4-(3,4-Dichlorophenyl)-N-methyl-1,2,3,4-tetrahydro-1-naphthalenamine hydrochloride (1S,4S)-4-(3,4-Dichlorophenyl)-N-methyl-1,2,3,4-tetrahydro-1-naphthalenamine hydrochloride (1:1) (1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine hydrochloride (1S,4S)-4-(3,4-Dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine hydrochloride (1:1) (1S,4S)-4-(3,4-Dichlorphenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-aminhydrochlorid 1-naphthalenamine, 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-, (1S,4S)-, hydrochloride 1-Naphthalenamine, 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-, (1S,4S)-, hydrochloride (1:1) Cp 51,974-1 CP 51974-1 CP-51974-1 Lustral MFCD00895772 Sertraline (hydrochloride) SERTRALINE HCL FORM I SERTRALINE HCL FORM II SERTRALINE MANDELATE Sertraline.HCl SETRALINE HCL Zoloft

1.3 CAS No.: 79559-97-0

1.4 CID: 63009

1.5 EINECS(EC#): 616-702-0

1.6 Molecular Formula: C17H18Cl3N (isomer)

1.7 Inchi: InChI=1S/C17H17Cl2N.ClH/c1-20-17-9-7-12(13-4-2-3-5-14(13)17)11-6-8-15(18)16(19)10-11;/h2-6,8,10,12,17,20H,7,9H2,1H3;1H/t12-,17-;/m0./s1

1.8 InChkey: BLFQGGGGFNSJKA-XHXSRVRCSA-N

1.9 Canonical Smiles: CNC1CCC(C2=CC=CC=C12)C3=CC(=C(C=C3)Cl)Cl.Cl

1.10 Isomers Smiles: CN[C@H]1CC[C@H](C2=CC=CC=C12)C3=CC(=C(C=C3)Cl)Cl.Cl

2. Properties

2.1 Density: 1.37

2.1 Melting point: 246-249℃

2.1 Boiling point: 416.3 °C at 760 mmHg

2.1 Flash Point: 205.6 °C

2.1 Precise Quality: 341.05000

2.1 PSA: 12.03000

2.1 logP: 6.37250

2.1 Solubility: DMSO: ~26?mg/mL

2.2 Appearance: white solid

2.3 Chemical Properties: White or almost white, crystalline powder.

2.4 Color/Form: white

2.5 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℃)

2.6 Water Solubility: DMSO: ~26?mg/mL

2.7 Stability: Store in Freezer

2.8 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 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 disoder, panic disorder and post-traumatic stress disorder.

3.2 Usage: A selective serotonin reuptake inhibitor. Used as an antidepressant

4. Safety and Handling

4.1 Symbol: GHS02, GHS06, GHS08

4.1 Hazard Codes: Xi

4.1 Signal Word: Danger

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S22;S24/25

4.1 Hazard Class: IRRITANT

4.1 Hazard Declaration: H225-H301 + H311 + H331-H370

4.1 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

4.2 RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution

4.2 Caution Statement: P210-P260-P280-P301 + P310-P311

4.2 Formulations/Preparations: Active ingredient in the drug Zoloft produced by Pfizer (oral concentrate and oral tablets) /Sertraline hydrochloride/

4.3 WGK Germany: 3

4.3 RTECS: QJ0352070

4.3 Safety: Hazard Codes:Xi
Risk Statements:36/37/38
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements:22-24/25-36-26
22:Do not breathe dust
24/25:Avoid contact with skin and eyes
36:Wear suitable protective clothing
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany:3
HazardClass:IRRITANT

4.4 Specification

The Sertraline hydrochloride with the cas number 79559-97-0, is also called (1)(1S,4S)-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthylamine hydrochloride; (2) Adjuvin ; (3) Atruline ; (4) Gladem ; (5) Serad ; (6) Sertraline HCl ; (7) Sertraline hydrochloride ; (8) Tatig ; (9) Tresleen ; (10) Zoloft ; (11)1-Naphthalenamine, 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-, hydrochloride, (1S-cis)- . It belongs to the following product categories:(1)Pharmaceutical Intermediates; (2)Active PharmaceuticalIngredients; (3)APIs; (4)Inhibitors; (5)Intermediates & Fine Chemicals; (6)Pharmaceuticals; (7)Serotonin receptor?

Properties of Sertraline hydrochloride are: (1)ACD/LogP: 4.81 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): 1.77 ; (4)ACD/LogD (pH 7.4): 2.77 ; (5)ACD/BCF (pH 5.5): 2.41 ; (6)ACD/BCF (pH 7.4): 24.52 ; (7)ACD/KOC (pH 5.5): 8.89 ; (8)ACD/KOC (pH 7.4): 90.64 ; (9)#H bond acceptors: 1 ; (10)#H bond donors: 1 ; (11)#Freely Rotating Bonds: 2 ; (12)Polar Surface Area: 3.24?² ; (13)Flash Point: 205.6 °C ; (14)Enthalpy of Vaporization: 66.96 kJ/mol; (15)Boiling Point: 416.3 °C at 760 mmHg ; (16)Vapour Pressure: 3.85E-07 mmHg at 25°C

The Sertraline hydrochloride appears to be white or white-like crystalline powder. The Sertraline hydrochloride is mainly used for treatment with depression and obsessive-compulsive disorder. Usage and dosage: The usual dose is 50mg, once a day. Dose can be increased according to patient's condition within weeks, the maximum amount can reach 200mg/day. Please pay attention to using this medicine, because it can cause the following adverse effects: slight xerocheilia, nausea, indigestion, liquid stools and diarrhea. A few patients may show tremor, sweating, defering male ejaculation. Serum transaminase occasionally asymptomatically increase.

You can still convert the following datas into molecular structure :
1. SMILES: Cl.Clc1ccc(cc1Cl)[C@H]3c2c(cccc2)[C@@H](NC)CC3
2. InChI: InChI=1/C17H17Cl2N.ClH/c1-20-17-9-7-12(13-4-2-3-5-14(13)17)11-6-8-15(18)16(19)10-11;/h2-6,8,10,12,17,20H,7,9H2,1H3;1H/t12-,17-;/m0./s1

The Sertraline hydrochloride toxic data can be showed in the following sheet.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
man	TDLo	oral	2857ug/kg (2.857mg/kg)	BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" GASTROINTESTINAL: NAUSEA OR VOMITING SKIN AND APPENDAGES (SKIN): SWEATING: OTHER	Shinkei Seishin Yakuri. Neuropsychopharmacology. Vol. 19, Pg. 395, 1997.
mouse	LDLo	intraperitoneal	56mg/kg (56mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: FOOD INTAKE (ANIMAL)	Drug and Chemical Toxicology. Vol. 21, Pg. 163, 1998.
mouse	LDLo	oral	336mg/kg (336mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE BEHAVIORAL: FOOD INTAKE (ANIMAL)	Drug and Chemical Toxicology. Vol. 21, Pg. 163, 1998.
rat	LDLo	intraperitoneal	56mg/kg (56mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: FOOD INTAKE (ANIMAL)	Drug and Chemical Toxicology. Vol. 21, Pg. 163, 1998.
rat	LDLo	oral	840mg/kg (840mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: FOOD INTAKE (ANIMAL) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS	Drug and Chemical Toxicology. Vol. 21, Pg. 163, 1998.
women	TDLo	oral	7mg/kg/2W-I (7mg/kg)	BEHAVIORAL: HEADACHE MUSCULOSKELETAL: CHANGES IN TEETH AND SUPPORTING STRUCTURES SKIN AND APPENDAGES (SKIN): SWEATING: OTHER	Journal of Clinical Psychiatry. Vol. 54, Pg. 432, 1993.
women	TDLo	oral	7mg/kg/7D-I (7mg/kg)	BEHAVIORAL: EXCITEMENT	Journal of Clinical Psychiatry. Vol. 54, Pg. 321, 1993.

View all

4.5 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QJ0352070

CHEMICAL NAME :: 1-Naphthalenamine, 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-, hydrochloride, (1S-cis)-

CAS REGISTRY NUMBER :: 79559-97-0

LAST UPDATED :: 199606

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C17-H17-Cl2-N.Cl-H

MOLECULAR WEIGHT :: 342.71

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 7 mg/kg/2W-I

TOXIC EFFECTS :: Behavioral - headache Musculoskeletal - changes in teeth and supporting structures Skin and Appendages - sweating

REFERENCE :: JCLPDE Journal of Clinical Psychiatry. (Physicians Postgraduate Press, Inc., POB 240008, Memphis, TN 38124) V.39- 1978- Volume(issue)/page/year: 54,432,1993

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 7 mg/kg/7D-I

TOXIC EFFECTS :: Behavioral - excitement

REFERENCE :: JCLPDE Journal of Clinical Psychiatry. (Physicians Postgraduate Press, Inc., POB 240008, Memphis, TN 38124) V.39- 1978- Volume(issue)/page/year: 54,321,1993 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 56 mg/kg

SEX/DURATION :: female 5 week(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - breasts, lactation (prior to or during pregnancy)

REFERENCE :: AJPSAO American Journal of Psychiatry. (American Psychiatric Assoc., Circulation Dept., 1400 K St., NW, Washington, DC 20005) V.78- 1921- Volume(issue)/page/year: 150,1269,1993

View all

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H400 Very toxic to aquatic life
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P273 Avoid release to the environment.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P391 Collect spillage.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

Predict 1H proton NMR

7. Synthesis Route

79559-97-0Total: 21 Synthesis Route

95-50-1 34 Suppliers

79559-97-0 265 Suppliers

Literatures:
Chemistry - A European Journal, , vol. 17, # 4 p. 1109 - 1113
Yield: null

90-15-3 324 Suppliers

79559-97-0 265 Suppliers

Literatures:
Chemistry - A European Journal, , vol. 17, # 4 p. 1109 - 1113
Yield: null

79617-96-2 130 Suppliers

79559-97-0 265 Suppliers

Literatures:
RECORDATI SA Patent: WO2005/12224 A1, 2005 ; Location in patent: Page/Page column 7 ;
Yield: ~97%

View all

8. Precursor and Product

precursor:

1346228-89-4

79560-19-3

1186422-36-5

928057-24-3

928057-23-2

167026-37-1

928057-20-9

79617-96-2

928057-22-1

95-50-1

1357380-69-8

244223-89-0

267884-85-5

836597-67-2

64-19-7

312620-93-2

90-15-3

1346228-87-2

1346228-88-3

254731-40-3

View all

product :

79617-96-2

9. Other Information

9.0 Collision Cross Section: 168.1 ?2 [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

9.1 Mesh: Compounds that specifically inhibit the reuptake of serotonin in the brain. (See all compounds classified as Serotonin Uptake Inhibitors.)|Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems. (See all compounds classified as Antidepressive Agents.)

9.2 Mesh Entry Terms: Altruline

9.3 Use Classification: Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

9.4 Merck: 14,8467

9.5 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.

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

9.7 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.

9.8 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.

9.9 Chemical Properties: White or almost white, crystalline powder.

9.10 Originator: Pfizer (USA)

9.11 Uses: A selective serotonin reuptake inhibitor. Used as an antidepressant

9.12 Uses: antibacterial

9.13 Uses: A selective ST inhibitor

9.14 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.

10. Computational chemical data

Molecular Weight: 306.22958g/mol
Molecular Formula: C₁₇H₁₈Cl₃N
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 341.050483
Monoisotopic Mass: 341.050483
Complexity: 322
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 1
Topological Polar Surface Area: 12
Heavy Atom Count: 21
Defined Atom Stereocenter Count: 2
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 2
CACTVS Substructure Key Fingerprint: AAADceB6AAAGAAAAAAAAAAAAAAAAAAAAAAAwYMAAAAAAAADBQAAAHAIQAAAADSrBGCQyAILAAACAAiBCAACCAAAgBQAIisAIBogIICKBkxGEIAhgkAAIiAcQgMAOhAAAIAAQAAQYAATAACQACAAAAAAAAA==

11. Recommended Suppliers

Global251SuppliersView all >>

Chengdu Aupone Pharmaceutical Co., Ltd. Diamond member

-122YR

Products:Cetirizine hydrochloride,Sertraline hydrochloride,Terbinafine Hydrochloride,Loratadine,Iron succinate,Midodrine hydrochloride,Cenobamate
Tel:+86-28-65506537
Email:Alanchen@aupone.com

Sertraline hydrochloride

Purity:99%Packing: 200kg/bag FOB
Price:
Time: 2023/04/26

Inquire

Wuhan Fortuna Chemical Co., Ltd. Diamond member

-113YR

Products:API,fine chemical&its intermediates,biological chemistry
Tel:0086-27-59207850
Email:info@fortunachem.com

Good quality Sertraline hydrochloride CAS 79559-97-0 supplied by manufacturer

Purity:99%Packing: 200kg/bag FOB
Price: 500 USD/kilogram
Time: 2023/06/05

Inquire

Hebei Fanggan New Material Technology Co., LTD Diamond member

-121YR

Products:chemicals
Tel:0311-18503114-031178503114
Email:andy@rilonchem.com

CAS 79559-97-0,Sertraline hydrochloride，99.99%

Purity:99%Packing: 200kg/bag FOB
Price: 45 USD/kg
Time: 2023/06/05

Inquire

Hebei Chengcai Biotechnology Co., LTD Diamond member

-122YR

Products:We are engaged in the development, marketing and sales of apis, intermediates, natural products (extracts), fine chemicals, food additives, agricultural chemicals and other products.
Tel:0086-0319-19131200228
Email:17610795226@chengcaibio.com

Factory Wholesale Sertraline hydrochloride