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138112-76-2

Basic Information
CAS No.: 138112-76-2
Name: Agomelatine
Article Data: 50
Cas Database
Molecular Structure:
Molecular Structure of 138112-76-2 (Agomelatine)
Formula: C15H17NO2
Molecular Weight: 243.305
Synonyms: Thymanax;N-[2-(7-Methoxy-1-naphthyl)ethyl]acetamide;S 20098;Valdoxan;Acetamide, N-(2-(7-methoxy-1-naphthalenyl)ethyl)-;
EINECS: 629-727-7
Density: 1.109 g/cm3
Melting Point: 107-109 °C
Boiling Point: 478.8 °C at 760 mmHg
Flash Point: 243.4 °C
Solubility: N/A
Appearance: white solid
Hazard Symbols: N
Risk Codes: 50
Safety: 61
Transport Information: N/A
PSA: 38.33000
LogP: 2.91790
Synthetic route
139525-77-2

2-(7-methoxynaphthalen-1-yl)ethanamine hydrochloride

108-24-7

acetic anhydride

138112-76-2

agomelatine

Conditions
ConditionsYield
With sodium acetate In ethanol for 1h; Reflux;99.5%
With sodium acetate In Isopropyl acetate99%
With sodium acetate In ethanol for 1h; Reflux;95%
1331869-01-2

2-(2-methoxynaphthalen-8-yl)acetaldehyde oxime

138112-76-2

agomelatine

Conditions
ConditionsYield
With hydrogen; acetic anhydride In tetrahydrofuran at 50℃; under 7500.75 Torr; for 6h; Autoclave; Inert atmosphere;98%

N,N-dibenzyl-2-(7-methoxynaphthalen-1-yl)ethanamine

108-24-7

acetic anhydride

138112-76-2

agomelatine

Conditions
ConditionsYield
Stage #1: N,N-dibenzyl-2-(7-methoxynaphthalen-1-yl)ethanamine With 20% palladium hydroxide-activated charcoal; hydrogen In ethanol; water; ethyl acetate under 3750.38 Torr; for 30h; Autoclave;
Stage #2: acetic anhydride With sodium acetate for 4h;
98%
138113-09-4

2-(7-methoxynaphth-1-yl)ethylamine

108-24-7

acetic anhydride

138112-76-2

agomelatine

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃; for 6h; Concentration; Temperature;97.5%
With sodium acetate In ethanol at 65℃; Green chemistry;92%
With triethylamine In toluene at 20 - 30℃;90%
138113-09-4

2-(7-methoxynaphth-1-yl)ethylamine

75-36-5

acetyl chloride

138112-76-2

agomelatine

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 5℃;95%
In pyridine92%
With pyridine for 0.5h; Product distribution / selectivity; Cooling with ice;92%
77-78-1

dimethyl sulfate

152302-45-9

N-[2-(7-Hydroxy-1-naphthyl)ethyl]-acetamide

138112-76-2

agomelatine

Conditions
ConditionsYield
With potassium carbonate In acetone for 5h; Reflux;94.5%
1424944-40-0

1-(2-nitroethyl)-7-methoxynaphthalene

108-24-7

acetic anhydride

138112-76-2

agomelatine

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen In water; ethyl acetate at 20℃;92%
1384536-35-9

1-[2-(7-methoxynahthalen-1-yl)-ethyl]-2λ5-triaz-1-en-2-yne

108-24-7

acetic anhydride

138112-76-2

agomelatine

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In water; ethyl acetate at 20℃;92%
1352139-51-5

N-[2-(7-methoxy-3,4-dihydro-naphthalen-1-yl)ethyl]acetamide

138112-76-2

agomelatine

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃;91.8%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone for 4h; Product distribution / selectivity; Reflux;90%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran at 20℃; Product distribution / selectivity;80%
139525-77-2

2-(7-methoxynaphthalen-1-yl)ethanamine hydrochloride

75-36-5

acetyl chloride

138112-76-2

agomelatine

Conditions
ConditionsYield
With potassium carbonate In dichloromethane; water at 0 - 20℃; for 2h;91%
Stage #1: 2-(7-methoxynaphthalen-1-yl)ethanamine hydrochloride With triethylamine In dichloromethane at 25 - 35℃; for 0.5h;
Stage #2: acetyl chloride In dichloromethane at 10 - 20℃; for 1h;
90%
With potassium carbonate In chloroform; water for 0.5h; Ambient temperature;89%
With potassium carbonate In chloroform; water at 0℃;
Stage #1: 2-(7-methoxynaphthalen-1-yl)ethanamine hydrochloride With potassium carbonate In water; ethyl acetate at 20℃; Schotten-Baumann reaction;
Stage #2: acetyl chloride In water; ethyl acetate at 0 - 20℃; for 1h; Schotten-Baumann reaction;
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    Product Name: AGOMELATINE CAS: 138112-76-2 MF: C15H17NO2 MW: 243.3 EINECS: 629-727-7 Mol File: 138112-76-2.mol AGOMELATINE Structure AGOMELATINE Chemical Properties Melting point 107-109°C Boiling point 478.8±28.

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Specification

1. Introduction of Agomelatine
Agomelatine is one kind of off-white or white crystalline powder or white solid. The IUPAC Name of this chemical is N-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide. This chemical belongs to Aromatics Compounds;Aromatics;Neurochemicals;APIS. It should be store at -20°C Freezer. Agomelatine Solubility: Soluble in Chloroform and Methanol. DMSO ≥49mg/mL Water <1mg/mL Ethanol ≥49mg/mL.

Its Classification Code is Central Nervous System Agents; Central Nervous System; Depressants; Drug / Therapeutic Agent; Hypnotics and sedatives.

2. Properties of Agomelatine
Physical properties about Agomelatine are:
(1)Melting Point: 107-109°C; (2)Boiling point: 478.8 °C at 760 mmHg; (3)Flash Point: 243.4 °C ; (4)Density: 1.109 g/cm3; (5)Surface Tension: 41.5 dyne/cm ; (6)Enthalpy of Vaporization: 74.3 kJ/mol ; (7)Vapour Pressure: 2.49E-09 mmHg at 25°C; (8)XLogP3-AA: 2.7; (9)H-Bond Donor: 1; (10)H-Bond Acceptor: 2.

3. Structure Descriptors of Agomelatine
(1)Canonical SMILES: CC(=O)NCCC1=CC=CC2=C1C=C(C=C2)OC;
(2)InChI: InChI=1S/C15H17NO2/c1-11(17)16-9-8-13-5-3-4-12-6-7-14(18-2)10-15(12)13/h3-7,10H,8-9H2,1-2H3,(H,16,17) ;
(3)InChIKey: YJYPHIXNFHFHND-UHFFFAOYSA-N.

4. Toxicity of Agomelatine

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral > 1gm/kg (1000mg/kg)   United States Patent Document. Vol. #5318994,

5. Uses of Agomelatine
As a Pharmaceutical Intermediates, Agomelatine is used in the treatment of major depressive disorder, emotional disorder. Agomelatine is used in the treatment of major depressive disorder, emotional disorder. The drug substance for Nervous system. Antidepressant, anxiolytic, adjusting the rhythm of sleep and regulating biological clock. Agomelatine is a melatoninergic agonist and selective antagonist of 5-ht2c receptors. Agomelatine is an antidepressant drug. It is classified as a norepinephrine-dopamine disinhibitor (NDDI) due to its antagonism of the 5-HT2C receptor. Agomelatine is also a potent agonist at melatonin receptors which makes it the first melatonergic antidepressant.