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138112-76-2

Basic Information
CAS No.: 138112-76-2
Name: Agomelatine
Molecular Structure:
Molecular Structure of 138112-76-2 (Agomelatine)
Formula: C15H17NO2
Molecular Weight: 243.30098
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:
Appearance: white solid
Hazard Symbols: N
Risk Codes: 50
Safety: 61
Transport Information:
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;

2-(7-methoxynaphthalen-1-yl)ethanamine carbon dioxide adduct

108-24-7

acetic anhydride

138112-76-2

agomelatine

Conditions
ConditionsYield
With sodium acetate In methanol Reflux;91%
With sodium acetate In methanol Reflux;91%
With sodium acetate In methanol Reflux;91%
108-24-7

acetic anhydride

138113-08-3

(7-methoxy-1-naphthyl)acetonitrile

138112-76-2

agomelatine

Conditions
ConditionsYield
With hydrogen; Raney nickel In ethanol; water at 70℃; under 22502.3 Torr;89%
With hydrogen In ethanol; water at 70℃; under 22502.3 Torr;89%
With hydrogen In ethanol; water at 70℃; under 22502.3 Torr; for 1h;89%
With hydrogen In ethanol at 60℃; under 37503.8 Torr; for 4h;
Stage #1: (7-methoxy-1-naphthyl)acetonitrile With hydrogen; sodium hydroxide In methanol; water at 30℃; under 3000.3 Torr;
Stage #2: acetic anhydride In methanol at 15 - 25℃;

2-(7-methoxynaphthalen-1-yl)ethen-1-amine

108-24-7

acetic anhydride

138112-76-2

agomelatine

Conditions
ConditionsYield
With sodium acetate In ethanol; acetic anhydride at 25℃; for 1h; Temperature;88.1%

1-[2-(acetylamino)ethyl]-7-methoxynaphthalen-2-yl propane-1-sulphonate

138112-76-2

agomelatine

Conditions
ConditionsYield
With palladium 10% on activated carbon; ammonium acetate; magnesium In ethanol for 16h;87%
1352139-49-1

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

138112-76-2

agomelatine

Conditions
ConditionsYield
With acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene at 40℃; for 5h;85%
With acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene at 40℃; for 5h;
Multi-step reaction with 2 steps
1: hydrogenchloride / ethyl acetate; water / 2 h / 20 °C
2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 20 °C
View Scheme
1206788-15-9

2-(2-(7-methoxynaphthalen-1-yl)ethyl) isoindoline-1,3-dione

108-24-7

acetic anhydride

138112-76-2

agomelatine

Conditions
ConditionsYield
Stage #1: 2-(2-(7-methoxynaphthalen-1-yl)ethyl) isoindoline-1,3-dione With hydrazine hydrate In methanol; dichloromethane at 30℃; for 14h;
Stage #2: acetic anhydride With triethylamine In methanol; dichloromethane; toluene at 25℃; for 0.333333h;
85%

1-[2-(acetylamino)ethyl]-7-methoxynaphthalen-2-yl-4-methylbenzenesulphonate

138112-76-2

agomelatine

Conditions
ConditionsYield
With methanol; sodium tetrahydroborate; nickel dichloride at 20℃; for 0.5h; Sealed tube; Inert atmosphere;80%
138113-07-2

2-(2-methoxynaphthalen-8-yl)acetamide

64-19-7

acetic acid

138112-76-2

agomelatine

Conditions
ConditionsYield
With sodium tetrahydroborate In 1,4-dioxane at 95 - 98℃; for 22h;76.3%
108-24-7

acetic anhydride

185336-04-3

2-(7-methoxynaphthalen-1-yl)ethyl methanesulphonate

138112-76-2

agomelatine

Conditions
ConditionsYield
Stage #1: 2-(7-methoxynaphthalen-1-yl)ethyl methanesulphonate With ammonia In water; acetonitrile at 110℃; for 3h;
Stage #2: acetic anhydride With sodium acetate for 1h;
74%
1384261-25-9

N-[2-(4-chloro-7-methoxy-1,2-dihydro-1-naphthyl)ethyl]acetamide

138112-76-2

agomelatine

Conditions
ConditionsYield
With potassium tert-butylate In tert-butyl alcohol for 3h; Reflux;68%
1384261-27-1

N-[2-(4-bromo-7-methoxy-1,2-dihydro-1-naphthyl)ethyl]acetamide

138112-76-2

agomelatine

Conditions
ConditionsYield
With potassium tert-butylate In tert-butyl alcohol for 3h; Reflux;68%
1415243-95-6

(E)-7-methoxy-1-(2-nitrovinyl)naphthalene

108-24-7

acetic anhydride

138112-76-2

agomelatine

Conditions
ConditionsYield
With palladium 10% on activated carbon; acetic acid65%
138113-09-4

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

127-09-3

sodium acetate

138112-76-2

agomelatine

Conditions
ConditionsYield
With acetic anhydride In ethanol at 20℃; for 1h;61%
1384261-23-7

N-[2-(7-methoxy-1,2-dihydro-1-naphthyl)ethyl]acetamide

138112-76-2

agomelatine

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane for 48h;48%

1-[2-(2,5-dioxopyrrolidin-1-yl)ethyl]-7-methoxynaphthalen-2-yl propane-1-sulphonate

108-24-7

acetic anhydride

138112-76-2

agomelatine

Conditions
ConditionsYield
Stage #1: 1-[2-(2,5-dioxopyrrolidin-1-yl)ethyl]-7-methoxynaphthalen-2-yl propane-1-sulphonate With palladium 10% on activated carbon; ammonium acetate; magnesium In methanol at 30℃; for 12h;
Stage #2: acetic anhydride With sodium acetate; sodium hydroxide In ethanol; water for 1h; Sealed tube;
37%
138113-09-4

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

[14C]acetyl-CoA

[14C]acetyl-CoA

138112-76-2

agomelatine

Conditions
ConditionsYield
With sheep pineal supernatant (serotonin-N-acetyl transferase); Pargyline In phosphate buffer at 37℃; for 0.166667h; pH=6.8; Enzyme kinetics;
6836-22-2

2-(7-methoxynaphthalen-1-yl)acetic acid

138112-76-2

agomelatine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: thionyl chloride / CHCl3
2: aq. NH4OH / diethyl ether / 0 °C
3: AlH4 / diethyl ether
4: K2CO3 / H2O; CHCl3 / 0 °C
View Scheme
Multi-step reaction with 5 steps
1: thionyl chloride / CHCl3
2: aq. NH4OH / diethyl ether / 0 °C
3: (CF3CO)2O / tetrahydrofuran / 0 °C
4: H2, HCl / Ni Raney / diethyl ether
5: K2CO3 / H2O; CHCl3 / 0 °C
View Scheme
Multi-step reaction with 5 steps
1.1: thionyl chloride / dichloromethane / 2 h / Reflux
2.1: ammonia / ethyl acetate; water / Cooling with ice
3.1: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 20 °C / Cooling with ice
4.1: hydrogen; ammonia / ethanol; water / 12 h / 60 °C / 228015 Torr / Autoclave
5.1: pyridine / 40 °C
5.2: 20 °C / Cooling with ice
View Scheme
138113-07-2

2-(2-methoxynaphthalen-8-yl)acetamide

138112-76-2

agomelatine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: AlH4 / diethyl ether
2: K2CO3 / H2O; CHCl3 / 0 °C
View Scheme
Multi-step reaction with 3 steps
1: (CF3CO)2O / tetrahydrofuran / 0 °C
2: H2, HCl / Ni Raney / diethyl ether
3: K2CO3 / H2O; CHCl3 / 0 °C
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 20 °C / Cooling with ice
2.1: hydrogen; ammonia / ethanol; water / 12 h / 60 °C / 228015 Torr / Autoclave
3.1: pyridine / 40 °C
3.2: 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 3 steps
1.1: trichlorophosphate / dichloromethane; N,N-dimethyl-formamide / 2 h / 85 °C
2.1: sodium hydroxide; hydrogen / water; methanol; isopropyl alcohol / 25 - 30 °C / 7500.75 Torr
2.2: 1 h / 50 - 55 °C
3.1: sodium hydroxide / water; toluene / 0.25 h / 20 - 25 °C
3.2: 35 - 40 °C
View Scheme
138113-08-3

(7-methoxy-1-naphthyl)acetonitrile

138112-76-2

agomelatine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2, HCl / Ni Raney / diethyl ether
2: K2CO3 / H2O; CHCl3 / 0 °C
View Scheme
Multi-step reaction with 2 steps
1.1: hydrogen; ammonia / ethanol; water / 12 h / 60 °C / 228015 Torr / Autoclave
2.1: pyridine / 40 °C
2.2: 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydroxide; hydrogen / water; methanol; isopropyl alcohol / 25 - 30 °C / 7500.75 Torr
1.2: 1 h / 50 - 55 °C
2.1: sodium hydroxide / water; toluene / 0.25 h / 20 - 25 °C
2.2: 35 - 40 °C
View Scheme
Multi-step reaction with 2 steps
1.1: ammonia; hydrogen / methanol / 15 - 55 °C / 3750.38 Torr / Autoclave
1.2: 1 h / 0 - 5 °C
2.1: triethylamine / dichloromethane / 0.5 h / 25 - 35 °C
2.2: 1 h / 10 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: ammonia; hydrogen / ethanol / 24 h / 30 - 40 °C / 2250.23 - 3000.3 Torr / Autoclave
2: triethylamine / toluene / 0.5 h / 0 - 30 °C
View Scheme
6836-23-3

(7-methoxy-1-naphthyl)acetic acid chloride

138112-76-2

agomelatine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aq. NH4OH / diethyl ether / 0 °C
2: AlH4 / diethyl ether
3: K2CO3 / H2O; CHCl3 / 0 °C
View Scheme
Multi-step reaction with 4 steps
1: aq. NH4OH / diethyl ether / 0 °C
2: (CF3CO)2O / tetrahydrofuran / 0 °C
3: H2, HCl / Ni Raney / diethyl ether
4: K2CO3 / H2O; CHCl3 / 0 °C
View Scheme
Multi-step reaction with 4 steps
1.1: ammonia / ethyl acetate; water / Cooling with ice
2.1: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 20 °C / Cooling with ice
3.1: hydrogen; ammonia / ethanol; water / 12 h / 60 °C / 228015 Torr / Autoclave
4.1: pyridine / 40 °C
4.2: 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 4 steps
1.1: ammonia / toluene / 0 - 5 °C / pH 10 - 11
2.1: trichlorophosphate / dichloromethane; N,N-dimethyl-formamide / 2 h / 85 °C
3.1: sodium hydroxide; hydrogen / water; methanol; isopropyl alcohol / 25 - 30 °C / 7500.75 Torr
3.2: 1 h / 50 - 55 °C
4.1: sodium hydroxide / water; toluene / 0.25 h / 20 - 25 °C
4.2: 35 - 40 °C
View Scheme
138112-76-2

agomelatine

110-16-7

maleic acid

1403960-82-6

agomelatine maleic acid

Conditions
ConditionsYield
In ethanol for 0.75h;100%
In methanol; ethyl acetate at 20℃; for 168h; Product distribution / selectivity;
for 1h;
138112-76-2

agomelatine

77-92-9

citric acid

1403960-81-5

agomelatine citric acid

Conditions
ConditionsYield
In acetone at 20℃;100%
In methanol; ethyl acetate at 2 - 5℃; Product distribution / selectivity; Reflux;
In methanol at 20℃; for 20h; Product distribution / selectivity;
490-79-9

2,5-dihydroxybenzoic acid.

138112-76-2

agomelatine

1419379-42-2

agomelatine gentisic acid

Conditions
ConditionsYield
In toluene for 0.75h;100%
107-21-1

ethylene glycol

138112-76-2

agomelatine

1259393-47-9

C2H6O2*C15H17NO2

Conditions
ConditionsYield
at 110 - 130℃; for 5h;98%
1453-82-3

isonicotinamide

138112-76-2

agomelatine

1366181-84-1

agomelatine isonicotinamide adduct

Conditions
ConditionsYield
at 135℃; Neat (no solvent);98%
99-76-3

methyl 4-hydroxylbenzoate

138112-76-2

agomelatine

1366181-85-2

agomelatine methyl 4-hydroxybenzoate adduct

Conditions
ConditionsYield
at 110℃; Neat (no solvent);98%
138112-76-2

agomelatine

N-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide hydrogen sulfate

Conditions
ConditionsYield
With sulfuric acid In acetone at 10 - 20℃; Solvent; Temperature;96.9%
With sulfuric acid In acetone at 10 - 20℃; Solvent; Temperature;13.6 g
With sulfuric acid In ethyl acetate at 20℃;
64-19-7

acetic acid

138112-76-2

agomelatine

1259393-46-8

agomelatine 1:1 cocrystal with acetic acid

Conditions
ConditionsYield
In diethyl ether for 48h;96%
at 20 - 45℃; for 480h; Sealed tube;
138112-76-2

agomelatine

1366181-82-9

agomelatine urea adduct

Conditions
ConditionsYield
at 120℃; for 0.333333h; Neat (no solvent);96%
In ethanol at 20℃; for 2h; Time;70%
In isopropyl alcohol at 20℃; for 20h;41%
138112-76-2

agomelatine

98-11-3

benzenesulfonic acid

1402317-73-0

N-[2-(7-methoxyl-1-naphthyl)ethyl]acetamide benzenesulfonic acid

Conditions
ConditionsYield
In acetone at 25℃; Solvent; Temperature;95.8%
In methanol; ethyl acetate at 2 - 20℃; Product distribution / selectivity;
In dichloromethane at 10 - 20℃; Solvent; Temperature;15.6 g
In methanol; ethyl acetate Heating;
104-15-4

toluene-4-sulfonic acid

138112-76-2

agomelatine

agomelatine p-toluenesulfonic acid monohydrate

Conditions
ConditionsYield
In tetrahydrofuran; hexane for 0.5h; Solvent; Temperature; Reflux;95.8%
138112-76-2

agomelatine

152302-45-9

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

Conditions
ConditionsYield
With boron tribromide In dichloromethane at -10 - 20℃; for 2h;93.3%
Stage #1: agomelatine With boron tribromide In dichloromethane at 0℃; for 2h;
Stage #2: With water In dichloromethane at 0℃;
80%
With hydrogenchloride In water at 80℃;74.8%
79-14-1

glycolic Acid

138112-76-2

agomelatine

1366181-83-0

agomelatine glycolic acid adduct

Conditions
ConditionsYield
In acetonitrile for 2h; Reflux;93%
for 0.25h;
138112-76-2

agomelatine

1176316-99-6

N [2-(7-methoxynaphthalen-1-yl)ethyl]acetamide hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water; ethyl acetate at 10℃; Product distribution / selectivity;88.7%
With hydrogenchloride In water; ethyl acetate at 10℃; for 1h;88.7%
With hydrogenchloride In water; ethyl acetate at 10℃; for 1h;88.7%
104-15-4

toluene-4-sulfonic acid

138112-76-2

agomelatine

agomelatine p-toluenesulfonic acid

Conditions
ConditionsYield
In acetone at 0 - 10℃;88.2%
In acetone at 0 - 10℃;1.5 g
138112-76-2

agomelatine

1176317-02-4

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

Conditions
ConditionsYield
With hydrogen bromide In water; ethyl acetate at 20℃; for 1h; Product distribution / selectivity;85.3%
With hydrogen bromide In water; ethyl acetate at 20℃; for 1h; Temperature;85.3%
With hydrogen bromide In water; ethyl acetate for 1h;85.3%
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  •  Wuhan Fortuna Chemical Co.,Ltd

     China (Mainland)  |  Contact Details

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  • high purity Valdoxan CAS 138112-76-2

  • Casno:

    138112-76-2

    high purity Valdoxan CAS 138112-76-2

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  •  Chemtn Biological Technology Limited

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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.