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Sertraline

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Name

Sertraline

EINECS N/A
CAS No. 79617-96-2 Density 1.25 g/cm3
PSA 12.03000 LogP 5.57050
Solubility <0.1g/L(room temperature) Melting Point 246 - 249oC
Formula C17H17Cl2N Boiling Point 416.3 °C at 760 mmHg
Molecular Weight 306.235 Flash Point 205.6 °C
Transport Information N/A Appearance white to off-white powder
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 79617-96-2 (Sertraline) Hazard Symbols IrritantXi
Synonyms

1-Naphthalenamine,4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-, (1S-cis)-;(+)-Sertraline;(1S,4S)-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine;CP 51974;

Article Data 37

Sertraline Synthetic route

79559-97-0

sertraline hydrochloride

79617-96-2

Sertraline

Conditions
ConditionsYield
With sodium hydroxide In water; toluene for 0.25h; pH=> 10;93%
With sodium hydroxide In water; ethyl acetate77%
With ammonium hydroxide In water pH=10;
With sodium hydroxide In water
With potassium carbonate In water at 20℃;10.9 g

[(1S,4S)-4-(3,4-dichloro-phenyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-methyl-amine D(-)mandelate

79617-96-2

Sertraline

Conditions
ConditionsYield
With sodium hydroxide In water; ethyl acetate for 0.25h; pH=> 10;93%
With sodium hydroxide In water; ethyl acetate for 0.25h; pH=> 10;93%
1346228-89-4

benzyl (1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl(methyl)carbamate

79617-96-2

Sertraline

Conditions
ConditionsYield
With hydrogen In methanol; dichloromethane; water at 20℃; for 5h; Inert atmosphere;89%
79560-19-3, 79836-44-5, 124379-29-9

(4S)-4-(3,4-dichlorophenyl)-1-tetralone

74-89-5

methylamine

79617-96-2

Sertraline

Conditions
ConditionsYield
With titanium tetrachloride In tetrahydrofuran; diethyl ether; dichloromethane at -78 - 25℃;88%
267884-85-5

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

79617-96-2

Sertraline

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; for 1h; deacylation;85%
234448-58-9

C17H16Cl2IN

79617-96-2

Sertraline

Conditions
ConditionsYield
With tert.-butyl lithium In tetrahydrofuran; toluene at -78℃;69%

N-((1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)-N-methyl-2-(trimethylsilyl)ethane-1-sulfonamide

79617-96-2

Sertraline

Conditions
ConditionsYield
With cesium fluoride In N,N-dimethyl-formamide at 95℃; for 20h; diastereoselective reaction;65%
4229-44-1

N-methylhydroxyamine hydrochloride

79560-19-3, 79836-44-5, 124379-29-9

(4S)-4-(3,4-dichlorophenyl)-1-tetralone

79617-96-2

Sertraline

Conditions
ConditionsYield
Stage #1: N-methylhydroxyamine hydrochloride; (4S)-4-(3,4-dichlorophenyl)-1-tetralone With sodium acetate In ethanol for 15h; Reflux;
Stage #2: With Lindlar's catalyst; hydrogen In methanol; dichloromethane at 20℃; under 760.051 Torr; for 20h;
47%
79617-95-1

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

79617-96-2

Sertraline

541-41-3

chloroformic acid ethyl ester

87857-41-8

norsertraline

79617-96-2

Sertraline

Conditions
ConditionsYield
With potassium carbonate; lithium (hydro)trimethoxyaluminate 1) MeCN, 2) THF, reflux, 40 h; Yield given. Multistep reaction;

Sertraline History

  Sertraline (CAS NO.79617-96-2) is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. It was introduced to the market by Pfizer in 1991. It is primarily used to treat major depression in adult outpatients as well as obsessive–compulsive, panic, and social anxiety disorders in both adults and children. In 2007, it was the most prescribed antidepressant on the U.S. retail market, with 29,652,000 prescriptions.

Sertraline Specification

The Sertraline, with the CAS registry number 79617-96-2, is also known as (1S-cis)-1,2,3,4-Tetrahydro-4-(3,4-dichlorophenyl)-N-methyl-1-naphthalenamine. It belongs to the product categories of Amines; (intermediate of sertraline hcl); Sertraline. This chemical's molecular formula is C17H17Cl2N and molecular weight is 306.22958. Its IUPAC name is called (1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine. This chemical's classification codes are Antidepressive agents; Central Nervous System Agents; Drug / Therapeutic Agent; Human Data; Neurotransmitter Agents; Neurotransmitter Uptake Inhibitors; Psychotropic Drugs; Serotonin Agents; Serotonin uptake inhibitors.

Physical properties of Sertraline: (1)ACD/LogP: 4.81; (2)ACD/LogD (pH 5.5): 1.77; (3)ACD/LogD (pH 7.4): 2.77; (4)ACD/BCF (pH 5.5): 2.41; (5)ACD/BCF (pH 7.4): 24.52; (6)ACD/KOC (pH 5.5): 8.89; (7)ACD/KOC (pH 7.4): 90.64; (8)#H bond acceptors: 1; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.621; (12)Molar Refractivity: 85.82 cm3; (13)Molar Volume: 243.9 cm3; (14)Surface Tension: 48.8 dyne/cm; (15)Density: 1.25 g/cm3; (16)Flash Point: 205.6 °C; (17)Enthalpy of Vaporization: 66.96 kJ/mol; (18)Boiling Point: 416.3 °C at 760 mmHg; (19)Vapour Pressure: 3.85E-07 mmHg at 25°C.

Sertraline hydrochloride is an antidepressant of the selective serotonin reuptake inhibitor class. Sertraline is primarily used to treat major depression in adult outpatients as well as obsessive–compulsive, panic, and social anxiety disorders in both adults and children. Similarly to other antidepressants, the use of sertraline for depression may be associated with a higher rate of suicidal behavior. Due to the rarity of this side effect, statistically significant data are difficult to obtain, and suicidal behavior continues to be a subject of controversy.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc1ccc(cc1Cl)[C@H]3c2c(cccc2)[C@@H](NC)CC3
(2)InChI: InChI=1/C17H17Cl2N/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/t12-,17-/m0/s1
(3)InChIKey: VGKDLMBJGBXTGI-SJCJKPOMBV

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 5714ug/kg/9D- (5.714mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: EXCITEMENT
Journal of Clinical Psychiatry. Vol. 55, Pg. 316, 1994.
man TDLo oral 3571mg/kg/5D- (3571mg/kg) ENDOCRINE: ANTIDIURESIS American Journal of Psychiatry. Vol. 152, Pg. 809, 1995.
women TDLo oral 2mg/kg/2D-I (2mg/kg) BEHAVIORAL: EXCITEMENT Journal of the American Academy of Child and Adolescent Psychiatry. Vol. 35, Pg. 975, 1996.
women TDLo oral 6mg/kg/4D-I (6mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

ENDOCRINE: ANTIDIURESIS
American Journal of Psychiatry. Vol. 152, Pg. 809, 1995.
women TDLo oral 10500ug/kg/3W (10.5mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

ENDOCRINE: ANTIDIURESIS
Annals of Internal Medicine. Vol. 123, Pg. 811, 1995.
women TDLo oral 28mg/kg/4W-I (28mg/kg) BLOOD: AGRANULOCYTOSIS Postgraduate Medical Journal. Vol. 72, Pg. 446, 1996.
women TDLo oral 63mg/kg/10W-I (63mg/kg) BLOOD: TUMORS American Journal of Psychiatry. Vol. 153, Pg. 443, 1996.
women TDLo oral 70mg/kg/7W-I (70mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD American Journal of Psychiatry. Vol. 153, Pg. 732, 1996.

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