Product Name

  • Name

    Agomelatine

  • EINECS 629-727-7
  • CAS No. 138112-76-2
  • Article Data50
  • CAS DataBase
  • Density 1.109 g/cm3
  • Solubility
  • Melting Point 107-109 °C
  • Formula C15H17NO2
  • Boiling Point 478.8 °C at 760 mmHg
  • Molecular Weight 243.305
  • Flash Point 243.4 °C
  • Transport Information
  • Appearance white solid
  • Safety 61
  • Risk Codes 50
  • Molecular Structure Molecular Structure of 138112-76-2 (Agomelatine)
  • Hazard Symbols N
  • Synonyms Thymanax;N-[2-(7-Methoxy-1-naphthyl)ethyl]acetamide;S 20098;Valdoxan;Acetamide, N-(2-(7-methoxy-1-naphthalenyl)ethyl)-;
  • PSA 38.33000
  • LogP 2.91790

Synthetic route

2-(7-methoxynaphthalen-1-yl)ethanamine hydrochloride
139525-77-2

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

acetic anhydride
108-24-7

acetic anhydride

agomelatine
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%
2-(2-methoxynaphthalen-8-yl)acetaldehyde oxime
1331869-01-2

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

agomelatine
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

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

acetic anhydride
108-24-7

acetic anhydride

agomelatine
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%
2-(7-methoxynaphth-1-yl)ethylamine
138113-09-4

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

acetic anhydride
108-24-7

acetic anhydride

agomelatine
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%
2-(7-methoxynaphth-1-yl)ethylamine
138113-09-4

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

acetyl chloride
75-36-5

acetyl chloride

agomelatine
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%
dimethyl sulfate
77-78-1

dimethyl sulfate

N-[2-(7-Hydroxy-1-naphthyl)ethyl]-acetamide
152302-45-9

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

agomelatine
138112-76-2

agomelatine

Conditions
ConditionsYield
With potassium carbonate In acetone for 5h; Reflux;94.5%
1-(2-nitroethyl)-7-methoxynaphthalene
1424944-40-0

1-(2-nitroethyl)-7-methoxynaphthalene

acetic anhydride
108-24-7

acetic anhydride

agomelatine
138112-76-2

agomelatine

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen In water; ethyl acetate at 20℃;92%
1-[2-(7-methoxynahthalen-1-yl)-ethyl]-2λ5-triaz-1-en-2-yne
1384536-35-9

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

acetic anhydride
108-24-7

acetic anhydride

agomelatine
138112-76-2

agomelatine

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In water; ethyl acetate at 20℃;92%
N-[2-(7-methoxy-3,4-dihydro-naphthalen-1-yl)ethyl]acetamide
1352139-51-5

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

agomelatine
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%
2-(7-methoxynaphthalen-1-yl)ethanamine hydrochloride
139525-77-2

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

acetyl chloride
75-36-5

acetyl chloride

agomelatine
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

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

acetic anhydride
108-24-7

acetic anhydride

agomelatine
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%
acetic anhydride
108-24-7

acetic anhydride

(7-methoxy-1-naphthyl)acetonitrile
138113-08-3

(7-methoxy-1-naphthyl)acetonitrile

agomelatine
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

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

acetic anhydride
108-24-7

acetic anhydride

agomelatine
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

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

agomelatine
138112-76-2

agomelatine

Conditions
ConditionsYield
With palladium 10% on activated carbon; ammonium acetate; magnesium In ethanol for 16h;87%
N-[2-(1-hydroxyl-7-methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)ethyl]-acetamide
1352139-49-1

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

agomelatine
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
2-(2-(7-methoxynaphthalen-1-yl)ethyl) isoindoline-1,3-dione
1206788-15-9

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

acetic anhydride
108-24-7

acetic anhydride

agomelatine
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

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

agomelatine
138112-76-2

agomelatine

Conditions
ConditionsYield
With methanol; sodium tetrahydroborate; nickel dichloride at 20℃; for 0.5h; Sealed tube; Inert atmosphere;80%
2-(2-methoxynaphthalen-8-yl)acetamide
138113-07-2

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

acetic acid
64-19-7

acetic acid

agomelatine
138112-76-2

agomelatine

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

acetic anhydride

2-(7-methoxynaphthalen-1-yl)ethyl methanesulphonate
185336-04-3

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

agomelatine
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%
N-[2-(4-chloro-7-methoxy-1,2-dihydro-1-naphthyl)ethyl]acetamide
1384261-25-9

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

agomelatine
138112-76-2

agomelatine

Conditions
ConditionsYield
With potassium tert-butylate In tert-butyl alcohol for 3h; Reflux;68%
N-[2-(4-bromo-7-methoxy-1,2-dihydro-1-naphthyl)ethyl]acetamide
1384261-27-1

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

agomelatine
138112-76-2

agomelatine

Conditions
ConditionsYield
With potassium tert-butylate In tert-butyl alcohol for 3h; Reflux;68%
(E)-7-methoxy-1-(2-nitrovinyl)naphthalene
1415243-95-6

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

acetic anhydride
108-24-7

acetic anhydride

agomelatine
138112-76-2

agomelatine

Conditions
ConditionsYield
With palladium 10% on activated carbon; acetic acid65%
2-(7-methoxynaphth-1-yl)ethylamine
138113-09-4

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

sodium acetate
127-09-3

sodium acetate

agomelatine
138112-76-2

agomelatine

Conditions
ConditionsYield
With acetic anhydride In ethanol at 20℃; for 1h;61%
N-[2-(7-methoxy-1,2-dihydro-1-naphthyl)ethyl]acetamide
1384261-23-7

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

agomelatine
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

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

acetic anhydride
108-24-7

acetic anhydride

agomelatine
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%
2-(7-methoxynaphth-1-yl)ethylamine
138113-09-4

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

[14C]acetyl-CoA

[14C]acetyl-CoA

agomelatine
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;
2-(7-methoxynaphthalen-1-yl)acetic acid
6836-22-2

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

agomelatine
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
2-(2-methoxynaphthalen-8-yl)acetamide
138113-07-2

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

agomelatine
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
(7-methoxy-1-naphthyl)acetonitrile
138113-08-3

(7-methoxy-1-naphthyl)acetonitrile

agomelatine
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
(7-methoxy-1-naphthyl)acetic acid chloride
6836-23-3

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

agomelatine
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
agomelatine
138112-76-2

agomelatine

maleic acid
110-16-7

maleic acid

agomelatine 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;
agomelatine
138112-76-2

agomelatine

citric acid
77-92-9

citric acid

agomelatine 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;
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

agomelatine
138112-76-2

agomelatine

agomelatine gentisic acid
1419379-42-2

agomelatine gentisic acid

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

ethylene glycol

agomelatine
138112-76-2

agomelatine

C2H6O2*C15H17NO2
1259393-47-9

C2H6O2*C15H17NO2

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

isonicotinamide

agomelatine
138112-76-2

agomelatine

agomelatine isonicotinamide adduct
1366181-84-1

agomelatine isonicotinamide adduct

Conditions
ConditionsYield
at 135℃; Neat (no solvent);98%
methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

agomelatine
138112-76-2

agomelatine

agomelatine methyl 4-hydroxybenzoate adduct
1366181-85-2

agomelatine methyl 4-hydroxybenzoate adduct

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

agomelatine

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

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℃;
acetic acid
64-19-7

acetic acid

agomelatine
138112-76-2

agomelatine

agomelatine 1:1 cocrystal with acetic acid
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;
agomelatine
138112-76-2

agomelatine

urea
57-13-6

urea

agomelatine urea adduct
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%
agomelatine
138112-76-2

agomelatine

benzenesulfonic acid
98-11-3

benzenesulfonic acid

N-[2-(7-methoxyl-1-naphthyl)ethyl]acetamide 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;
toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

agomelatine
138112-76-2

agomelatine

agomelatine p-toluenesulfonic acid monohydrate

agomelatine p-toluenesulfonic acid monohydrate

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

agomelatine

N-[2-(7-Hydroxy-1-naphthyl)ethyl]-acetamide
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%
glycolic Acid
79-14-1

glycolic Acid

agomelatine
138112-76-2

agomelatine

agomelatine glycolic acid adduct
1366181-83-0

agomelatine glycolic acid adduct

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

agomelatine

N [2-(7-methoxynaphthalen-1-yl)ethyl]acetamide hydrochloride
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%
toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

agomelatine
138112-76-2

agomelatine

agomelatine p-toluenesulfonic acid

agomelatine p-toluenesulfonic acid

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

agomelatine

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

Agomelatine 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.

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