Product Name

  • Name

    Serotonin hydrochloride

  • EINECS 244-464-4
  • CAS No. 153-98-0
  • Article Data2
  • CAS DataBase
  • Density
  • Solubility soluble in water
  • Melting Point 168-172 °C
  • Formula C10H12N2O.HCl
  • Boiling Point 416.1 °C at 760 mmHg
  • Molecular Weight 212.679
  • Flash Point 205.4 °C
  • Transport Information UN 2811
  • Appearance white to cream powder
  • Safety 22-26-36
  • Risk Codes 20/21/22-36/37/38
  • Molecular Structure Molecular Structure of 153-98-0 (Serotonin hydrochloride)
  • Hazard Symbols HarmfulXn, IrritantXi
  • Synonyms 1H-Indol-5-ol,3-(2-aminoethyl)-, monohydrochloride (9CI);Indol-5-ol, 3-(2-aminoethyl)-,monohydrochloride (8CI);3-(2-Aminoethyl)-1H-indol-5-ol hydrochloride;5-Hydroxytryptamine hydrochloride;Hippophaine hydrochloride;Serotoninhydrochloride;
  • PSA 62.04000
  • LogP 2.87700

Synthetic route

C10H10N2O3

C10H10N2O3

serotonin hydrochloride
153-98-0

serotonin hydrochloride

Conditions
ConditionsYield
Stage #1: C10H10N2O3 With hydrogen In methanol at 30℃; Autoclave; Industrial scale;
Stage #2: With hydrogenchloride In methanol; water Autoclave; Industrial scale;
91%
tert-butyl 2-(5-hydroxy-1H-indol-3-yl)ethylcarbamate
53157-48-5

tert-butyl 2-(5-hydroxy-1H-indol-3-yl)ethylcarbamate

serotonin hydrochloride
153-98-0

serotonin hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In methanol; water; ethyl acetate at 25℃; for 0.166667h;
4-chlorocarbonyl-piperazine-1-carboxylic acid benzyl ester
25539-27-9

4-chlorocarbonyl-piperazine-1-carboxylic acid benzyl ester

serotonin hydrochloride
153-98-0

serotonin hydrochloride

C23H26N4O4

C23H26N4O4

Conditions
ConditionsYield
With triethylamine In dichloromethane; N,N-dimethyl-formamide at 25℃; for 15h;100%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

serotonin hydrochloride
153-98-0

serotonin hydrochloride

tert-butyl 2-(5-hydroxy-1H-indol-3-yl)ethylcarbamate
53157-48-5

tert-butyl 2-(5-hydroxy-1H-indol-3-yl)ethylcarbamate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 3h;100%
With sodium hydrogencarbonate; sodium chloride In chloroform; water for 3h; Reflux;95%
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 6h;94%
2-fluoro-N-(2-methoxyethyl)-9H-purin-6-amine

2-fluoro-N-(2-methoxyethyl)-9H-purin-6-amine

serotonin hydrochloride
153-98-0

serotonin hydrochloride

3-[2-[[6-(2-methoxyethylamino)-9H-purin-2-yl]amino]ethyl]-1H-indol-5-ol

3-[2-[[6-(2-methoxyethylamino)-9H-purin-2-yl]amino]ethyl]-1H-indol-5-ol

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 110℃;100%
serotonin hydrochloride
153-98-0

serotonin hydrochloride

propionic acid anhydride
123-62-6

propionic acid anhydride

N-(2-(5-hydroxyindol-3-yl)ethyl)-3-propanamide

N-(2-(5-hydroxyindol-3-yl)ethyl)-3-propanamide

Conditions
ConditionsYield
With sodium carbonate In tetrahydrofuran at 20℃; for 2h;98%
thiophene-2-carbaldehyde
98-03-3

thiophene-2-carbaldehyde

serotonin hydrochloride
153-98-0

serotonin hydrochloride

C20H20N2OS2

C20H20N2OS2

Conditions
ConditionsYield
With sodium methylate; sodium cyanoborohydride; acetic acid In methanol at 20℃; pH=5-6; Inert atmosphere; Cooling with ice;98%
2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile
58632-95-4

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

serotonin hydrochloride
153-98-0

serotonin hydrochloride

tert-butyl 2-(5-hydroxy-1H-indol-3-yl)ethylcarbamate
53157-48-5

tert-butyl 2-(5-hydroxy-1H-indol-3-yl)ethylcarbamate

Conditions
ConditionsYield
With TEA In 1,4-dioxane; water at 45℃; for 1h;97.8%
7-phenylheptanoic acid
40228-90-8

7-phenylheptanoic acid

serotonin hydrochloride
153-98-0

serotonin hydrochloride

C23H28N2O2

C23H28N2O2

Conditions
ConditionsYield
Stage #1: 7-phenylheptanoic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 0 - 20℃; for 1.25h;
Stage #2: serotonin hydrochloride With triethylamine In N,N-dimethyl-formamide at 20℃; for 16h; Further stages.;
92%
8-phenyloctanoic acid
26547-51-3

8-phenyloctanoic acid

serotonin hydrochloride
153-98-0

serotonin hydrochloride

C24H30N2O2
1002100-52-8

C24H30N2O2

Conditions
ConditionsYield
Stage #1: 8-phenyloctanoic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 0 - 20℃; for 1.25h;
Stage #2: serotonin hydrochloride With triethylamine In N,N-dimethyl-formamide at 20℃; for 16h; Further stages.;
92%
(9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid
463-40-1

(9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid

serotonin hydrochloride
153-98-0

serotonin hydrochloride

(Z,Z,Z)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-octadeca-9,12,15-trienamide
345663-12-9

(Z,Z,Z)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-octadeca-9,12,15-trienamide

Conditions
ConditionsYield
Stage #1: (9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 0 - 20℃; for 1.25h;
Stage #2: serotonin hydrochloride With triethylamine In N,N-dimethyl-formamide at 20℃; for 16h; Further stages.;
88%
C10H6(2)H2Cl2O4
1445606-13-2

C10H6(2)H2Cl2O4

serotonin hydrochloride
153-98-0

serotonin hydrochloride

C20H16(2)H2Cl2N2O4
1441642-15-4

C20H16(2)H2Cl2N2O4

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;88%
2,2-Dichloropropionic acid
75-99-0

2,2-Dichloropropionic acid

serotonin hydrochloride
153-98-0

serotonin hydrochloride

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;88%
lauric acid
143-07-7

lauric acid

serotonin hydrochloride
153-98-0

serotonin hydrochloride

C22H34N2O2
73452-35-4

C22H34N2O2

Conditions
ConditionsYield
Stage #1: lauric acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 0 - 20℃; for 1.25h;
Stage #2: serotonin hydrochloride With triethylamine In N,N-dimethyl-formamide at 20℃; for 16h; Further stages.;
87%
serotonin hydrochloride
153-98-0

serotonin hydrochloride

Thioctic acid
1077-28-7, 62-46-4

Thioctic acid

C18H24N2O2S2
1002100-46-0

C18H24N2O2S2

Conditions
ConditionsYield
Stage #1: Thioctic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 0 - 20℃; for 1.25h;
Stage #2: serotonin hydrochloride With triethylamine In N,N-dimethyl-formamide at 20℃; for 16h; Further stages.;
86%
3-(1,3-benzodioxol-5-yl)-2,2-dichloropropanoic acid
1309659-13-9

3-(1,3-benzodioxol-5-yl)-2,2-dichloropropanoic acid

serotonin hydrochloride
153-98-0

serotonin hydrochloride

3-(1,3-benzodioxol-5-yl)-2,2-dichloro-N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)propanamide
1309659-14-0

3-(1,3-benzodioxol-5-yl)-2,2-dichloro-N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)propanamide

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;86%
Stage #1: serotonin hydrochloride In N,N-dimethyl-formamide at 0℃; for 3h;
Stage #2: 3-(1,3-benzodioxol-5-yl)-2,2-dichloropropanoic acid With diphenylphosphoranyl azide In N,N-dimethyl-formamide at 20℃; for 36h;
84%
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;181 mg
linoleic acid
60-33-3

linoleic acid

serotonin hydrochloride
153-98-0

serotonin hydrochloride

C28H42N2O2
623174-83-4

C28H42N2O2

Conditions
ConditionsYield
Stage #1: linoleic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 0 - 20℃; for 1.25h;
Stage #2: serotonin hydrochloride With triethylamine In N,N-dimethyl-formamide at 20℃; for 16h; Further stages.;
85%
undecylenic acid
112-37-8

undecylenic acid

serotonin hydrochloride
153-98-0

serotonin hydrochloride

C21H32N2O2
1002100-48-2

C21H32N2O2

Conditions
ConditionsYield
Stage #1: undecylenic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 0 - 20℃; for 1.25h;
Stage #2: serotonin hydrochloride With triethylamine In N,N-dimethyl-formamide at 20℃; for 16h; Further stages.;
85%
formaldehyd
50-00-0

formaldehyd

serotonin hydrochloride
153-98-0

serotonin hydrochloride

bufotenin
487-93-4

bufotenin

Conditions
ConditionsYield
With sodium methylate; sodium cyanoborohydride; acetic acid In methanol; water at 20℃; for 2h; pH=5 - 9; Inert atmosphere;85%
With sodium methylate; sodium cyanoborohydride; acetic acid In methanol; water at 20℃;
3-(4-hydroxy-3-methoxyphenyl)propionic acid
1135-23-5

3-(4-hydroxy-3-methoxyphenyl)propionic acid

serotonin hydrochloride
153-98-0

serotonin hydrochloride

C20H22N2O4
1246613-20-6

C20H22N2O4

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; Inert atmosphere;85%
succinic acid anhydride
108-30-5

succinic acid anhydride

serotonin hydrochloride
153-98-0

serotonin hydrochloride

bufobutanoic acid

bufobutanoic acid

Conditions
ConditionsYield
With pyridine In N,N-dimethyl-formamide at 20℃; for 10h;84%
With pyridine In N,N-dimethyl-formamide at 20℃; for 24h;62%
With pyridine In N,N-dimethyl-formamide at 20℃; for 24h;62%
4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

serotonin hydrochloride
153-98-0

serotonin hydrochloride

N-[2-(5-Hydroxy-1H-indol-3-yl)-ethyl]-3-(4-hydroxy-phenyl)-propionamide

N-[2-(5-Hydroxy-1H-indol-3-yl)-ethyl]-3-(4-hydroxy-phenyl)-propionamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; Inert atmosphere;83.7%

Serotonin hydrochloride Specification

The IUPAC name of Serotonin hydrochloride is 3-(2-aminoethyl)-1H-indol-5-ol hydrochloride. With the CAS registry number 153-98-0, it is also named as 5-Hydroxytryptamine hydrochloride. The product's categories are Tryptamines; Indoles. I is white to cream powder which is stable, but light sensitive and hygroscopic. It is also incompatible with strong oxidizing agents. In addition, this chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.21; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 3; (4)#H bond donors: 4; (5)#Freely Rotating Bonds: 4; (6)Polar Surface Area: 17.4 Å2; (7)Flash Point: 205.4 °C; (8)Enthalpy of Vaporization: 69.52 kJ/mol; (9)Boiling Point: 416.1 °C at 760 mmHg; (10)Vapour Pressure: 1.63E-07 mmHg at 25°C; (11)Rotatable Bond Count: 2; (12)Tautomer Count: 9; (13)Exact Mass: 212.071641; (14)MonoIsotopic Mass:212.071641; (15)Topological Polar Surface Area: 62; (16)Heavy Atom Count: 14; (17)Complexity: 174.

Preparation of Serotonin hydrochloride: It is a biochemical messenger and regulator, synthesized from the essential amino acid L-tryptophan.

Uses of Serotonin hydrochloride: It can react with fluoroacetic acid to get 2-fluoro-N-[2-(5-hydroxy-1H-indol-3-yl)-ethyl]-acetamide. This reaction needs reagent DCC and solvents H2O, tetrahydrofuran at ambient temperature. The yield is 71.5%.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. So people should not breathe dust. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

People can use the following data to convert to the molecule structure. 
1. SMILES:Cl.Oc1cc2c(cc1)ncc2CCN
2. InChI:InChI=1/C10H12N2O.ClH/c11-4-3-7-6-12-10-2-1-8(13)5-9(7)10;/h1-2,5-6,12-13H,3-4,11H2;1H 
3. InChIKey:MDIGAZPGKJFIAH-UHFFFAOYAF

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