Product Name

  • Name

    5-Hydroxytryptamine

  • EINECS 200-058-9
  • CAS No. 50-67-9
  • Article Data43
  • CAS DataBase
  • Density 1.288 g/cm3
  • Solubility 0.5 g/100 mL (25 oC)
  • Melting Point 22-23°C(lit.)
  • Formula C10H12N2O
  • Boiling Point 416.089 °C at 760 mmHg
  • Molecular Weight 176.218
  • Flash Point 205.443 °C
  • Transport Information
  • Appearance White powder
  • Safety 36/37-45
  • Risk Codes 63-25
  • Molecular Structure Molecular Structure of 50-67-9 (5-Hydroxytryptamine)
  • Hazard Symbols T
  • Synonyms Indol-5-ol,3-(2-aminoethyl)- (6CI,8CI);3-(2-Aminoethyl)indol-5-ol;3-(b-Aminoethyl)-5-hydroxyindole;5-Hydroxy-3-(b-aminoethyl)indole;Tryptamine, 5-hydroxy-;5-Hydroxytryptamine;
  • PSA 62.04000
  • LogP 2.07500

Synthetic route

N-Benzyl-2-<5-(benzyloxy)-3-indolyl>-1-ethanamin
147918-24-9

N-Benzyl-2-<5-(benzyloxy)-3-indolyl>-1-ethanamin

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
With palladium 10% on activated carbon; ammonium formate In methanol at 70℃; for 0.75h; Inert atmosphere;100%
L-5-HTP
4350-09-8

L-5-HTP

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
With pyridoxal 5'-phosphate; aromatic L-amino acid decarboxylase In various solvent(s) at 30℃; for 48h;97%
With NH4OH-NH4Cl buffer; pyridoxal 5'-phosphate at 30℃; for 0.5h; relative rate of CO2 evolution by aromatic L-amino acid decarboxylase from Micrococcus percitreus;
With isopropyl β-D-thiogalactoside; L-tryptophan decarboxylase in recombinant Escherichia coli at 28℃;
5-hydroxy-Nb-methoxycarbonyltryptamine
77549-09-8

5-hydroxy-Nb-methoxycarbonyltryptamine

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
With sodium hydroxide In methanol Heating;73%
With sodium hydroxide In methanol for 4h; Heating;73%
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

2-(5-methoxyindol-3-yl)ethylamine

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
With boron tribromide In dichloromethane at 20℃;65%
With aluminium trichloride; benzene
5-benzyloxytryptamine
20776-45-8

5-benzyloxytryptamine

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
With methanol; palladium on activated charcoal Hydrogenation;
With palladium on activated charcoal; ethanol; water Hydrogenation;
With methanol; Pd-BaSO4 Hydrogenation;
5-benzyloxy-3-(2-nitro-ethyl)-indole
93331-75-0

5-benzyloxy-3-(2-nitro-ethyl)-indole

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
With platinum Hydrogenation;
With palladium on activated charcoal Hydrogenation;
[2-(5-benzyloxy-indol-3-yl)-ethyl]-carbamic acid benzyl ester
55895-70-0

[2-(5-benzyloxy-indol-3-yl)-ethyl]-carbamic acid benzyl ester

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
With hydrogenchloride; palladium on activated charcoal; ethanol Hydrogenation.und Wasser;
tryptamine
61-54-1

tryptamine

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
biotransformation by cell cultures of Peganum harmala;
With CYP71P1; NADPH; NADPH-P450 reductase at 30℃; for 0.166667h; pH=7.25; Kinetics; aq. phosphate buffer; Enzymatic reaction;
tryptamine hydochloride
343-94-2

tryptamine hydochloride

A

7-Hydroxytryptamine
15700-23-9

7-Hydroxytryptamine

B

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

C

6-hydroxytryptamine
443-31-2

6-hydroxytryptamine

D

4-Hydroxytryptamine
570-14-9

4-Hydroxytryptamine

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide; ascorbic acid 1.) H2O, 2.) phosphate buffer (pH= 7.2, 0.1 M), 22 deg C, 2.5 min; Multistep reaction. Title compound not separated from byproducts;
...Expand
N-Cbz-5-hydroxytryptamine
53157-50-9

N-Cbz-5-hydroxytryptamine

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol Yield given;
5-hydroxytryptophan
56-69-9

5-hydroxytryptophan

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
With pyridoxal 5'-phosphate mammalian aromatic L-amino acid decarboxylase;
With Papaver somniferum tyrosine decarboxylase S372G mutant In aq. phosphate buffer at 25℃; pH=7.5; Kinetics; Reagent/catalyst; Enzymatic reaction;
2-<3-amino-1-aminomethyl-propyl>-hydroquinone dihydriodide

2-<3-amino-1-aminomethyl-propyl>-hydroquinone dihydriodide

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
With water; sodium hydrogencarbonate; potassium hexacyanoferrate(III)
2-(1-benzyl-5-methoxy-1H-indol-3-yl)ethylamine
40619-73-6

2-(1-benzyl-5-methoxy-1H-indol-3-yl)ethylamine

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 66 percent / Na / tetrahydrofuran; liquid ammonia / 1.5 h / -33 °C
2: 65 percent / BBr3 / CH2Cl2 / 20 °C
View Scheme
1-benzyl-5-methoxy-1H-indole-3-acetamide
93879-42-6

1-benzyl-5-methoxy-1H-indole-3-acetamide

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 60.5 percent / LiAlH4 / diethyl ether / 48 h / Heating
2: 66 percent / Na / tetrahydrofuran; liquid ammonia / 1.5 h / -33 °C
3: 65 percent / BBr3 / CH2Cl2 / 20 °C
View Scheme
methyl 1-benzyl-5-methoxy-1H-indole-3-acetate
419569-93-0

methyl 1-benzyl-5-methoxy-1H-indole-3-acetate

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 83 percent / NH3 / methanol / 192 h / 20 °C
2: 60.5 percent / LiAlH4 / diethyl ether / 48 h / Heating
3: 66 percent / Na / tetrahydrofuran; liquid ammonia / 1.5 h / -33 °C
4: 65 percent / BBr3 / CH2Cl2 / 20 °C
View Scheme
1-formyl-5-hydroxy-N-methoxycarbonyltryptamine
185987-04-6

1-formyl-5-hydroxy-N-methoxycarbonyltryptamine

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 76 percent / 2N NaOH / methanol
2: 73 percent / 10percent NaOH / methanol / Heating
View Scheme
(2-indol-3-yl-ethyl)-carbamic acid benzyl ester
38750-13-9

(2-indol-3-yl-ethyl)-carbamic acid benzyl ester

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) Pb(OAc)4; 2.) Zn powder / 1.) CF3COOH, CH2Cl2
2: H2 / 5percent Pd-C / methanol
View Scheme
5-benzyloxy-1H-indole
1215-59-4

5-benzyloxy-1H-indole

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: acetic acid; dioxane
2: NaCN; aqueous ethanol
3: LiAlH4; diethyl ether
4: palladium/charcoal; ethanol / Hydrogenation
View Scheme
Multi-step reaction with 4 steps
1: phosphoryl chloride / und anschliessenden Hydrolysieren mit wss.Natronlauge bzw. wss.Natriumcarbonat-Loesung
2: ammonium acetate
3: LiAlH4; diethyl ether
4: methanol; palladium/charcoal / Hydrogenation
View Scheme
Multi-step reaction with 4 steps
1: phosphoryl chloride / und anschliessenden Hydrolysieren mit wss.Natronlauge bzw. wss.Natriumcarbonat-Loesung
2: benzylamine
3: LiAlH4; THF
4: palladium/charcoal; ethanol; water / Hydrogenation
View Scheme
NSC 73391
2436-15-9

NSC 73391

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: LiAlH4; diethyl ether
2: palladium/charcoal; ethanol / Hydrogenation
View Scheme
5-Benzyloxy-2,ω-dinitro-styrol
92438-11-4

5-Benzyloxy-2,ω-dinitro-styrol

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: ethanol; acetic acid
2: acetic acid; dioxane
3: NaCN; aqueous ethanol
4: LiAlH4; diethyl ether
5: palladium/charcoal; ethanol / Hydrogenation
View Scheme
5-benzyloxygramine
1453-97-0

5-benzyloxygramine

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NaCN; aqueous ethanol
2: LiAlH4; diethyl ether
3: palladium/charcoal; ethanol / Hydrogenation
View Scheme
Multi-step reaction with 3 steps
1: NaCN; aqueous ethanol
2: LiAlH4; diethyl ether
3: platinum/charcoal; methanol / Hydrogenation
View Scheme
5-benzyloxyindole-3-acetamide
5933-28-8

5-benzyloxyindole-3-acetamide

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: LiAlH4; diethyl ether
2: palladium/charcoal; ethanol / Hydrogenation
View Scheme
Multi-step reaction with 2 steps
1: LiAlH4; diethyl ether
2: platinum/charcoal; methanol / Hydrogenation
View Scheme
(5-benzyloxy-indol-3-yl)-glyoxylic acid amide
22424-62-0

(5-benzyloxy-indol-3-yl)-glyoxylic acid amide

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: LiAlH4; diethyl ether; THF
2: palladium/BaSO4; methanol / Hydrogenation
View Scheme
2-(5-(benzyloxy)-1H-indol-3-yl)-2-oxoacetyl chloride
22424-61-9

2-(5-(benzyloxy)-1H-indol-3-yl)-2-oxoacetyl chloride

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aqueous NH3 <28percent >
2: LiAlH4; diethyl ether; THF
3: palladium/BaSO4; methanol / Hydrogenation
View Scheme
3-(5-benzyloxy-indol-3-yl)-propionic acid
7394-76-5

3-(5-benzyloxy-indol-3-yl)-propionic acid

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: methanol. HCl
2: ethanol; N2H4+H2O
3: benzene; NaNO2; aqueous acetic acid / Erwaermen des Reaktionsprodukts in Benzol mit Benzylalkohol
4: palladium/charcoal; HCl; ethanol / Hydrogenation.und Wasser
View Scheme
3-(5-benzyloxy-indol-3-yl)-propionic acid methyl ester
101890-43-1

3-(5-benzyloxy-indol-3-yl)-propionic acid methyl ester

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ethanol; N2H4+H2O
2: benzene; NaNO2; aqueous acetic acid / Erwaermen des Reaktionsprodukts in Benzol mit Benzylalkohol
3: palladium/charcoal; HCl; ethanol / Hydrogenation.und Wasser
View Scheme
3-(5-benzyloxy-indol-3-yl)-propionic acid hydrazide
101783-03-3

3-(5-benzyloxy-indol-3-yl)-propionic acid hydrazide

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: benzene; NaNO2; aqueous acetic acid / Erwaermen des Reaktionsprodukts in Benzol mit Benzylalkohol
2: palladium/charcoal; HCl; ethanol / Hydrogenation.und Wasser
View Scheme
5-benzyloxy-3-(2-carboxy-ethyl)-indole-2-carboxylic acid
7358-97-6

5-benzyloxy-3-(2-carboxy-ethyl)-indole-2-carboxylic acid

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: tetralin
2: methanol. HCl
3: ethanol; N2H4+H2O
4: benzene; NaNO2; aqueous acetic acid / Erwaermen des Reaktionsprodukts in Benzol mit Benzylalkohol
5: palladium/charcoal; HCl; ethanol / Hydrogenation.und Wasser
View Scheme
5-benzyloxyindole-3-carboxaldehyde
6953-22-6

5-benzyloxyindole-3-carboxaldehyde

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ammonium acetate
2: LiAlH4; diethyl ether
3: methanol; palladium/charcoal / Hydrogenation
View Scheme
Multi-step reaction with 3 steps
1: benzylamine
2: LiAlH4; THF
3: palladium/charcoal; ethanol; water / Hydrogenation
View Scheme
3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-2-propenamide
68573-23-9

(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-2-propenamide

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide99%
Stage #1: (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 3-(2-aminoethyl)-1H-indol-5-ol With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; Inert atmosphere;		57%
Stage #1: 3-(2-aminoethyl)-1H-indol-5-ol; (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid With pyridine; dicyclohexyl-carbodiimide at 20℃; for 24h;
Stage #2: With potassium hydroxide In methanol at 20℃; for 4h;
3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Trifluoroacetaldehyde ethyl hemiacetal
433-27-2

Trifluoroacetaldehyde ethyl hemiacetal

6-hydroxy-1-trifluoromethyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole
126260-67-1

6-hydroxy-1-trifluoromethyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole

Conditions
ConditionsYield
at 110 - 120℃; for 5h;98.8%
3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

methyl chloroformate
79-22-1

methyl chloroformate

5-hydroxy-Nb-methoxycarbonyltryptamine
77549-09-8

5-hydroxy-Nb-methoxycarbonyltryptamine

Conditions
ConditionsYield
With pyridine In N,N-dimethyl-formamide at 0 - 20℃; for 1.5h;94%
(2R,4R)-2-[2-[4-fluoro-2-[2-(4-fluoro-3-methoxyphenyl)ethyl]phenoxy]ethyl]-4-hydroxy-1-methylpyrrolidine
195299-77-5

(2R,4R)-2-[2-[4-fluoro-2-[2-(4-fluoro-3-methoxyphenyl)ethyl]phenoxy]ethyl]-4-hydroxy-1-methylpyrrolidine

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

lauric anhydride
645-66-9

lauric anhydride

(2R,4R)-2-[2-[4-fluoro-2-[2-(4-fluoro-3-methoxyphenyl)ethyl]phenoxy]ethyl]-4-lauroyloxy-1-methylpyrrolidine

(2R,4R)-2-[2-[4-fluoro-2-[2-(4-fluoro-3-methoxyphenyl)ethyl]phenoxy]ethyl]-4-lauroyloxy-1-methylpyrrolidine

Conditions
ConditionsYield
With pyridine; dmap91%
...Expand
3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

(Z)-2-hydroxy-3-phenyl-acrylic acid
5801-57-0, 52178-60-6

(Z)-2-hydroxy-3-phenyl-acrylic acid

1-benzyl-1,2,3,4-tetrahydro-8-hydroxy-β-carboline-1-carboxylic acid
17994-22-8

1-benzyl-1,2,3,4-tetrahydro-8-hydroxy-β-carboline-1-carboxylic acid

Conditions
ConditionsYield
In ethanol for 48h;90%
3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

2,2-Dichloropropionic acid
75-99-0

2,2-Dichloropropionic acid

C13H14Cl2N2O2
1388185-92-9

C13H14Cl2N2O2

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 24h;89%
3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

Arachidic acid
506-30-9

Arachidic acid

N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)icosanamide
21249-34-3

N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)icosanamide

Conditions
ConditionsYield
With benzotriazol-1-ol; triethylamine In N,N-dimethyl-formamide at 20℃; Reagent/catalyst; Solvent;88%
diethylenetriaminepentaacetic dianhydride
23911-26-4

diethylenetriaminepentaacetic dianhydride

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

bis-5-hydroxytriptamide-DPTA
875429-83-7

bis-5-hydroxytriptamide-DPTA

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 48h;87%
With triethylamine In N,N-dimethyl-formamide at 20℃; for 48h;58%
Stage #1: diethylenetriaminepentaacetic dianhydride; 3-(2-aminoethyl)-1H-indol-5-ol With pyridine; ascorbic acid In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: With water
vinyl acetate
108-05-4

vinyl acetate

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

N-acetyl-5-hydroxytryptamine
1210-83-9

N-acetyl-5-hydroxytryptamine

Conditions
ConditionsYield
With agarose immobilized acetyltransferase from Mycobacterium smegmatis (MsAcT) In aq. phosphate buffer; dimethyl sulfoxide at 25℃; under 760.051 Torr; for 0.0833333h; pH=8.0; Flow reactor; Enzymatic reaction; chemoselective reaction;85%
3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

benzyl chloroformate
501-53-1

benzyl chloroformate

N-Cbz-5-hydroxytryptamine
53157-50-9

N-Cbz-5-hydroxytryptamine

Conditions
ConditionsYield
With sodium carbonate In water for 6h; Ambient temperature;84%
3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

<5,6,8,9,11,12,14,15-3H8>arachidonic acid
66753-05-7

<5,6,8,9,11,12,14,15-3H8>arachidonic acid

N-[5,6,8,9,11,12,14,15-3H8]arachidonoyl5-hydroxytryptamine

N-[5,6,8,9,11,12,14,15-3H8]arachidonoyl5-hydroxytryptamine

Conditions
ConditionsYield
Stage #1: <5,6,8,9,11,12,14,15-3H8>arachidonic acid With triethylamine; isobutyl chloroformate In acetonitrile at 23℃; for 2h;
Stage #2: 3-(2-aminoethyl)-1H-indol-5-ol In N,N-dimethyl-formamide at 23℃; for 20h;		83%
3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

N-p-coumaroylserotonin
68573-24-0

N-p-coumaroylserotonin

Conditions
ConditionsYield
Stage #1: p-Coumaric Acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 3-(2-aminoethyl)-1H-indol-5-ol With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; Inert atmosphere;		82%
With benzotriazol-1-ol; dicyclohexyl-carbodiimide79%
Stage #1: 3-(2-aminoethyl)-1H-indol-5-ol; p-Coumaric Acid With pyridine; dicyclohexyl-carbodiimide at 20℃; for 24h;
Stage #2: With potassium hydroxide In methanol at 20℃; for 4h;		0.14 mmol
(Z)-9-octadecenoyl chloride
112-77-6

(Z)-9-octadecenoyl chloride

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

(Z)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-9-octadecenamide
1002100-44-8

(Z)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-9-octadecenamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 5h; Cooling with ice;82%
3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

(S)-2-((tert-butoxycarbonyl)amino)-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
119768-45-5

(S)-2-((tert-butoxycarbonyl)amino)-3-(5-hydroxy-1H-indol-3-yl)propanoic acid

(S)-tert-butyl (3-(5-hydroxy-1H-indol-3-yl)-1-((2-(5-hydroxy-1H-indol-3-yl)ethyl)amino)-1-oxopropan-2-yl)carbamate

(S)-tert-butyl (3-(5-hydroxy-1H-indol-3-yl)-1-((2-(5-hydroxy-1H-indol-3-yl)ethyl)amino)-1-oxopropan-2-yl)carbamate

Conditions
ConditionsYield
Stage #1: (S)-2-((tert-butoxycarbonyl)amino)-3-(5-hydroxy-1H-indol-3-yl)propanoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 0.166667h;
Stage #2: 3-(2-aminoethyl)-1H-indol-5-ol In N,N-dimethyl-formamide for 2h;		82%
Stage #1: (S)-2-((tert-butoxycarbonyl)amino)-3-(5-hydroxy-1H-indol-3-yl)propanoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #2: 3-(2-aminoethyl)-1H-indol-5-ol In N,N-dimethyl-formamide at 20℃; for 2h;		390 mg
3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

2-(phenylamino)benzoic acid
91-40-7

2-(phenylamino)benzoic acid

N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)-2-(phenylamino)benzamide

N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)-2-(phenylamino)benzamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 8h;75%
3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

mefenamic Acid
61-68-7

mefenamic Acid

2-((2,3-dimethylphenyl)amino)-N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)benzamide

2-((2,3-dimethylphenyl)amino)-N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)benzamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 8h;75%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 8h;75%
3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

piperic acid chloride
4711-72-2

piperic acid chloride

N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-5-(3,4-methylenedioxyphenyl)-2E,4E-pentadienamide

N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-5-(3,4-methylenedioxyphenyl)-2E,4E-pentadienamide

Conditions
ConditionsYield
With triethylamine at 20℃; for 5h; Cooling with ice;70%
3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

2,5,7,8-tetramethyl-6-(oxiran-2-ylmethoxy)-2-(4,8,12-trimethyltridecyl)chroman
153821-44-4

2,5,7,8-tetramethyl-6-(oxiran-2-ylmethoxy)-2-(4,8,12-trimethyltridecyl)chroman

C42H66N2O4

C42H66N2O4

Conditions
ConditionsYield
Stage #1: 3-(2-aminoethyl)-1H-indol-5-ol at -10℃; for 1h; Alkaline conditions;
Stage #2: 2,5,7,8-tetramethyl-6-(oxiran-2-ylmethoxy)-2-(4,8,12-trimethyltridecyl)chroman In dichloromethane at -10℃; for 12h; regioselective reaction;		70%
isoalantolactone
470-17-7

isoalantolactone

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

(3aR,8aR,9aR)-3-{[2-(5-hydroxy-1H-indol-3-yl)ethylamino]methyl}-8a-methyl-5-methylidene-decahydronaphtho[2,3-b]furan-2-one hydrochloride
1353868-49-1

(3aR,8aR,9aR)-3-{[2-(5-hydroxy-1H-indol-3-yl)ethylamino]methyl}-8a-methyl-5-methylidene-decahydronaphtho[2,3-b]furan-2-one hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In methanol at 20℃; Michael type reaction; stereospecific reaction;68%
3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

N,N'-bis-Boc-S-methyl-isothiourea
322474-21-5

N,N'-bis-Boc-S-methyl-isothiourea

N',N''-bis(tert-butoxycarbonyl)-N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)guanidine

N',N''-bis(tert-butoxycarbonyl)-N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)guanidine

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃;67%
3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

alepterolic acid

alepterolic acid

(E)-N-(2-[5-hydroxy-1H-indol-3-yl]ethyl)-5-([1R,4aS,6R,8aS]-6-hydroxy-5,5,8a-trimethyl-2-methylenedecahydronaphthalene-1-yl)-3-methylpent-2-enamide

(E)-N-(2-[5-hydroxy-1H-indol-3-yl]ethyl)-5-([1R,4aS,6R,8aS]-6-hydroxy-5,5,8a-trimethyl-2-methylenedecahydronaphthalene-1-yl)-3-methylpent-2-enamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃;65%
3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

C18H16O7
1448991-74-9

C18H16O7

Dimethyl-3-(2-hydroxybenzoyl)-9-hydroxy-6,7,12,12b-tetrahydroindolo[2,3-a]quinolizine-1,12b-dicarboxylate
1355043-50-3

Dimethyl-3-(2-hydroxybenzoyl)-9-hydroxy-6,7,12,12b-tetrahydroindolo[2,3-a]quinolizine-1,12b-dicarboxylate

Conditions
ConditionsYield
Stage #1: 3-(2-aminoethyl)-1H-indol-5-ol; C18H16O7 With trimethyl orthoformate In dichloromethane at 20℃; Inert atmosphere;
Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; Inert atmosphere;		64%
3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

2-nitrobenzenesulfenyl chloride
7669-54-7

2-nitrobenzenesulfenyl chloride

3-(2-Amino-ethyl)-2-(2-nitro-phenylsulfanyl)-1H-indol-5-ol
102250-06-6

3-(2-Amino-ethyl)-2-(2-nitro-phenylsulfanyl)-1H-indol-5-ol

Conditions
ConditionsYield
In acetic acid at 0℃; for 3h;63%
3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

1-acetyl-2-methylsulfanyl-4-imidazolidinone
291519-12-5

1-acetyl-2-methylsulfanyl-4-imidazolidinone

1-acetyl-2-[2-(5-hydroxy-1H-indol-3-yl)ethylamino]-4,5-dihydroimidazol-4-one

1-acetyl-2-[2-(5-hydroxy-1H-indol-3-yl)ethylamino]-4,5-dihydroimidazol-4-one

Conditions
ConditionsYield
In ethanol for 96h; Reflux;60%
3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

2,2-dichloro-3-(6-methyl-2-oxo-2H-chromen-4-yl)propanoic acid

2,2-dichloro-3-(6-methyl-2-oxo-2H-chromen-4-yl)propanoic acid

2,2-dichloro-N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)-3-(6-methyl-2-oxo-2H-chromen-4-yl)propanamide

2,2-dichloro-N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)-3-(6-methyl-2-oxo-2H-chromen-4-yl)propanamide

Conditions
ConditionsYield
Stage #1: 2,2-dichloro-3-(6-methyl-2-oxo-2H-chromen-4-yl)propanoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide for 0.333333h; Inert atmosphere;
Stage #2: 3-(2-aminoethyl)-1H-indol-5-ol In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;		60%
(-)-(S)-3-(benzyloxycarbonylamino-methyl)-5-methyl-hexanoic acid
949890-75-9

(-)-(S)-3-(benzyloxycarbonylamino-methyl)-5-methyl-hexanoic acid

3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

C26H33N3O4
1224700-50-8

C26H33N3O4

Conditions
ConditionsYield
Stage #1: (-)-(S)-3-(benzyloxycarbonylamino-methyl)-5-methyl-hexanoic acid With N-ethylmorpholine;; isobutyl chloroformate In tetrahydrofuran at -15℃; for 0.0333333h;
Stage #2: 3-(2-aminoethyl)-1H-indol-5-ol In tetrahydrofuran; water at -15 - 20℃; for 24.1667h;		56%

Serotonin History

 Serotonin as originally discovered by Italian Vittorio Erspamer in Rome in 1935 and American scientists in the late 1940s. In 1948, it was isolated and named by Maurice M. Rapport, Arda Green, and Irvine Page of the Cleveland Clinic. It was initially identified as a vasoconstrictor substance in blood serum – hence serotonin, a serum agent affecting vascular tone. Serotonin was later chemically identified as 5-hydroxytryptamine (5-HT) by Rapport, and, as the broad range of physiological roles were elucidated, 5-HT became the preferred name in the pharmacological field.

Serotonin Specification

The Serotonin, with the CAS registry number 50-67-9, is also known as 5-Hydroxytryptamine. It belongs to the product categories of Tryptamines; Standards - 13C & 2H for GC-Mass Spectrometry. Its EINECS number is 200-058-9. This chemical's molecular formula is C10H12N2O and molecular weight is 176.21. What's more, its systematic name is 3-(2-Aminoethyl)-1H-indol-5-ol. Its classification codes are: (1)Drug / Therapeutic Agent; (2)Neurotransmitter Agents; (3)Reproductive Effect; (4)Serotonin Agents; (5)Serotonin Receptor Agonists. This chemical is a monoamine neurotransmitter. It is used as a boiler water softener, degreasing detergent, metal corrosion inhibitor or anti-rust agent.

Physical properties of Serotonin are: (1)ACD/LogP: 0.545; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.53; (4)ACD/LogD (pH 7.4): -1.74; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 3; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 62.04 Å2; (13)Index of Refraction: 1.711; (14)Molar Refractivity: 53.495 cm3; (15)Molar Volume: 136.796 cm3; (16)Polarizability: 21.207×10-24cm3; (17)Surface Tension: 67.0 dyne/cm; (18)Density: 1.288 g/cm3; (19)Flash Point: 205.443 °C; (20)Enthalpy of Vaporization: 69.524 kJ/mol; (21)Boiling Point: 416.089 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be prepared by 2-(5-methoxy-indol-3-yl)-ethylamine at the temperature of 20 °C. This reaction will need reagent BBr3 and solvent CH2Cl2. The yield is about 65%.

Serotonin can be prepared by 2-(5-methoxy-indol-3-yl)-ethylamine at the temperature of 20 °C

Uses of Serotonin: it can be used to produce N-Benzyloxycarbonyl-5-hydroxytryptamin at the ambient temperature. It will need reagent Na2CO3 and solvent H2O with the reaction time of 6 hours. The yield is about 84%.

Serotonin can be used to produce N-Benzyloxycarbonyl-5-hydroxytryptamin at the ambient temperature

You can still convert the following datas into molecular structure:
(1)SMILES: c1cc2c(cc1O)c(c[nH]2)CCN
(2)Std. InChI: InChI=1S/C10H12N2O/c11-4-3-7-6-12-10-2-1-8(13)5-9(7)10/h1-2,5-6,12-13H,3-4,11H2
(3)Std. InChIKey: QZAYGJVTTNCVMB-UHFFFAOYSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 5mg/kg (5mg/kg) CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Farmakologiya i Toksikologiya Vol. 26, Pg. 10, 1963.
guinea pig LD50 intravenous 12800ug/kg (12.8mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 168, Pg. 373, 1967.
mouse LD50 intramuscular 750mg/kg (750mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 112, Pg. 319, 1957.
mouse LD50 intraperitoneal 160mg/kg (160mg/kg)   Indian Journal of Physiology and Pharmacology. Vol. 17, Pg. 31, 1973.
mouse LD50 intravenous 81mg/kg (81mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Farmakologiya i Toksikologiya Vol. 26, Pg. 10, 1963.
mouse LD50 oral 60mg/kg (60mg/kg)   Meditsinskii Zhurnal Uzbekistana. Vol. (3), Pg. 61, 1985.
mouse LD50 subcutaneous 601mg/kg (601mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 Farmakologiya i Toksikologiya Vol. 26, Pg. 10, 1963.
mouse LD50 unreported 250mg/kg (250mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 8(1), Pg. 122, 1982.
rat LD50 intravenous 30mg/kg (30mg/kg)   Psychopharmacology Service Center, Bulletin. Vol. 2, Pg. 17, 1963.
rat LD50 subcutaneous 285mg/kg (285mg/kg)   Psychopharmacology Service Center, Bulletin. Vol. 2, Pg. 17, 1963.

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