Acetamide,N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]- supplier

Name
N-ACETYL-5-HYDROXYTRYPTAMINE
EINECS 214-916-5
CAS No. 1210-83-9
Article Data29
CAS DataBase
Density 1.268 g/cm³
Solubility ethanol: 50 mg/mL
Melting Point 120-122 °C(lit.)
Formula C₁₂H₁₄N₂O₂
Boiling Point 556.8 °C at 760 mmHg
Molecular Weight 218.255
Flash Point 214-916-5
Transport Information
Appearance White to off-white or slightly pink powder
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Acetamide,N-[2-(5-hydroxyindol-3-yl)ethyl]- (6CI,7CI,8CI);5-Hydroxy-N-acetyltryptamine;5-Hydroxymelatonin;N-(2-(5-Hydroxy-1H-indol-3-yl)ethyl)acetamide;N-Acetyl-2-(5-hydroxyindol-3-yl)ethylamine;N-Acetyl-5-hydroxytryptamine;N-Acetylserotonin;Normelatonin;O-Demethylmelatonin;Serotonin, N-acetyl-;
PSA 65.12000
LogP 1.94300

Synthetic route

: 68062-88-4
N-{2-[5-(benzyloxy)-1H-indol-3-yl]ethyl}acetamide

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

Conditions

Conditions	Yield
With hydrogen; nickel In ethanol under 2068.6 Torr;	95%
With palladium 10% on activated carbon; hydrogen; ammonium formate In ethanol for 2h; Reflux; Inert atmosphere;	85%
With hydrogen; nickel
With palladium on activated charcoal; hydrogen In ethyl acetate

: 108-05-4
vinyl acetate

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

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

Conditions

Conditions	Yield
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%

: 2436-15-9
NSC 73391

: 108-24-7
acetic anhydride

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

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 50℃; under 3000.3 Torr; for 12h; Inert atmosphere;	71%

: 28026-16-6
3-(2-acetamidoethyl)-1H-indol-5-yl acetate

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

Conditions

Conditions	Yield
With potassium carbonate In methanol at 20℃; for 1.6h;	65%
With potassium carbonate In methanol at 26℃; for 2h;

: 73-31-4
5-methoxy-N-acetyl-tryptamine

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

Conditions

Conditions	Yield
With boron tribromide In dichloromethane at -78 - 20℃;	45%
Stage #1: 5-methoxy-N-acetyl-tryptamine With boron tribromide In dichloromethane at -78℃; for 1h; Stage #2: With hydrogenchloride In dichloromethane; water at -78 - 20℃;	45%

: 136788-90-4
Nb-acetyl-1-hydroxytriptamine

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

B: 176244-66-9
N,N'-diacetyl-2,2'-biindolyl-3,3'-bis(2-aminoethane)

: C24H26N4O4

Conditions

Conditions	Yield
With trifluoroacetic acid	A 13% B 17% C 33%

...Expand

: 64-18-6
formic acid

: 136788-90-4
Nb-acetyl-1-hydroxytriptamine

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

B: Nb-acetyl-1-formyl-5-hydroxytryptamine

Conditions

Conditions	Yield
for 19h; Ambient temperature;	A 17% B 19%

...Expand

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

: 75-36-5
acetyl chloride

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

Conditions

Conditions	Yield
In acetonitrile at 20℃; Acetylation;

: 971-74-4
serotonin creatinine sulfate

[14C]acetyl-CoA: [14C]acetyl-CoA

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

Conditions

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

: 20776-45-8
5-benzyloxytryptamine

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 74 percent / aq. HCl, NaOAc / 1 h 2: 95 percent / H2 / Raney nickel / ethanol / 2068.6 Torr View Scheme
Multi-step reaction with 2 steps 1: NaOAc 2: H2 / Raney Ni View Scheme
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane 2: palladium on activated charcoal; hydrogen / ethyl acetate View Scheme

: aluminum nickel

: 20776-45-8
5-benzyloxytryptamine

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

Conditions

Conditions	Yield
With sodium acetate; acetic anhydride In hydrogenchloride; methanol; ethanol

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

A O-diacetyl serotonine: O-diacetyl serotonine

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

Conditions

Conditions	Yield
With sodium hydroxide; acetic anhydride

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

: 72-89-9
acetylcoenzyme A

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

Conditions

Conditions	Yield
With sea bream arylalkylamine N-acetyltransferase containing I157M mutation at β5 region Kinetics; Reagent/catalyst; Enzymatic reaction;
With 5,5'-dithiobis-(2-nitrobenzoic acid); Drosophila melanogaster arylalkylamine N-acetyltransferase A from E. coli In aq. buffer pH=8; Kinetics; Enzymatic reaction;
With dipyridin-4-yl disulfide; wild-type arylalkylamine N-acyltransferase from Tribolium castaneum In aq. buffer pH=8; Kinetics; Enzymatic reaction;

: 2436-15-9
NSC 73391

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; nickel(II) chloride hexahydrate / methanol / 20 h / 0 - 20 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen; ammonium formate / ethanol / 2 h / Reflux; Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / diethyl ether / 0 °C 2: triethylamine / dichloromethane 3: palladium on activated charcoal; hydrogen / ethyl acetate View Scheme

: 153-98-0
serotonin hydrochloride

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 5 h / 0 - 26 °C 2: potassium carbonate / methanol / 2 h / 26 °C View Scheme
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 14 h / 0 - 20 °C / Inert atmosphere 2: potassium carbonate / methanol / 1.6 h / 20 °C View Scheme

: N-acetylserotonine-O-sulfate

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

Conditions

Conditions	Yield
With Helix pomatia arylsulfatase In aq. acetate buffer at 21℃; for 24h; Catalytic behavior; Enzymatic reaction;
With arylsulfatase from Helix pomatia In aq. acetate buffer at 21℃; for 24h; pH=7; Enzymatic reaction;

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

: 141-78-6
ethyl acetate

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

Conditions

Conditions	Yield
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;

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

arabidopsis serotonin N-acetyltransferase-2: arabidopsis serotonin N-acetyltransferase-2

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

Conditions

Conditions	Yield
With acetylcoenzyme A In aq. phosphate buffer at 45℃; for 1h; pH=7.8; Enzymatic reaction;

: 1215-59-4
5-benzyloxy-1H-indole

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

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: acetic acid 2: N,N-dimethyl-formamide; water / 80 °C 3: lithium aluminium tetrahydride / diethyl ether / 0 °C 4: triethylamine / dichloromethane 5: palladium on activated charcoal; hydrogen / ethyl acetate View Scheme

: 1453-97-0
5-benzyloxygramine

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

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide; water / 80 °C 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: triethylamine / dichloromethane 4: palladium on activated charcoal; hydrogen / ethyl acetate View Scheme

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

: 172983-04-9
Nb-acetyltryptamine-4,5-dione

Conditions

Conditions	Yield
With potassium nitrososulfonate In methanol; water at 0℃; for 0.5h;	99%
With potassiuim nitrosodisulfonate In water for 3h;	11 mg

: 98386-81-3
(E)-3-(2-(trifluoromethyl)phenyl)acrylic acid

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

: 3-(2-acetamidoethyl)-1H-indol-5-yl (E)-3-(2-(trifluoromethyl)phenyl)acrylate

Conditions

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 3.5h; Inert atmosphere;	97%

: 943-89-5
(E)-3-(4-methoxyphenyl)acrylic acid

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

: 3-(2-acetamidoethyl)-1H-indol-5-yl (E)-3-(4-methoxyphenyl)acrylate

Conditions

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 1h; Inert atmosphere;	96%

: 186581-53-3, 908094-01-9
diazomethane

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

: 180910-62-7
Nb-acetyl-1-methoxytryptamine

Conditions

Conditions	Yield
In methanol Ambient temperature;	94%

: 6099-04-3
trans-3-methoxycinnamic acid

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

: 3-(2-acetamidoethyl)-1H-indol-5-yl (E)-3-(3-methoxyphenyl)acrylate

Conditions

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 2h; Inert atmosphere;	93%

: 107-93-7
(E)-but-2-enoic acid

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

: 3-(2-acetamidoethyl)-1H-indol-5-yl (E)-2-butenoate

Conditions

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 1.5h; Inert atmosphere;	76%

: 1866-39-3
trans-p-methylcinnamic acid

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

: 3-(2-acetamidoethyl)-1H-indol-5-yl (E)-3-(4-methylphenyl)acrylate

Conditions

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 2.5h; Inert atmosphere;	75%

: 1011-54-7
2-methoxycinnamic acid

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

: 3-(2-acetamidoethyl)-1H-indol-5-yl (E)-3-(2-methoxyphenyl)acrylate

Conditions

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 3h; Inert atmosphere;	71%

: 111-25-1
1-bromo-hexane

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

: C18H26N2O2

Conditions

Conditions	Yield
With caesium carbonate In acetonitrile at 60℃; for 4h; Reflux; Inert atmosphere;	68%

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

: 103-63-9
1-phenyl-2-bromoethane

: 1345995-63-2
C20H22N2O2

Conditions

Conditions	Yield
With caesium carbonate In acetonitrile at 60℃; for 4h; Reflux; Inert atmosphere;	65%

: 5454-83-1
5-bromovaleric acid methyl ester

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

: 5-[3-(2-acetylaminoethyl)-1H-indol-5-yloxy]pentanoic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile Reflux; Inert atmosphere;	63%

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

: 77-78-1
dimethyl sulfate

: 73-31-4
5-methoxy-N-acetyl-tryptamine

Conditions

Conditions	Yield
With sodium hydroxide In water at 26℃; for 2.25h;	61.4%

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

: 7693-46-1
4-Nitrophenyl chloroformate

: 1415303-65-9
3-[2-(acetylamino)ethyl]-1H-indol-5-yl 4-nitrophenyl carbonate

Conditions

Conditions	Yield
With 4-methyl-morpholine In tetrahydrofuran for 0.5h; Inert atmosphere;	60%
With 4-methyl-morpholine

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

: 142356-33-0
tert-butyl 6-bromohexylcarbamate

: tert-butyl N-(6-{[3-(2-acetamidoethyl)-1H-indol-5-yl]oxy}hexyl) carbamate

Conditions

Conditions	Yield
Stage #1: N-acetyl-5-hydroxytryptamine With potassium carbonate In acetonitrile for 1h; Reflux; Inert atmosphere; Stage #2: tert-butyl 6-bromohexylcarbamate With sodium iodide In acetonitrile for 20h; Reflux; Inert atmosphere;	59%

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

: 109-90-0
ethyl isocyanate

: 1269760-72-6
carbamic acid 3-(2-acetylamino-ethyl)-1H-indol-5-yl ethyl ester

Conditions

Conditions	Yield
With sodium In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	57%

: 3351-50-6
3-(1-naphthyloxy)propyl bromide

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

: C25H26N2O3

Conditions

Conditions	Yield
With caesium carbonate In acetonitrile at 60℃; for 4h; Reflux; Inert atmosphere;	57%

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

: 588-63-6
3-phenoxypropyl bromide

: 1346011-09-3
C21H24N2O3

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile for 18h; Reflux; Inert atmosphere;	56%

: 113795-28-1
4-(3-bromopropoxy)-1,1′-biphenyl

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

: C27H28N2O3

Conditions

Conditions	Yield
With caesium carbonate In acetonitrile at 60℃; for 4h; Reflux; Inert atmosphere;	55%

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

: 589-10-6
phenoxyethyl bromide

: 1346011-08-2
C20H22N2O3

Conditions

Conditions	Yield
With caesium carbonate In acetonitrile at 60℃; for 4h; Reflux; Inert atmosphere;	55%

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

: 106-95-6
allyl bromide

: 1345995-61-0
C15H18N2O2

Conditions

Conditions	Yield
With caesium carbonate In acetonitrile at 60℃; for 4h; Reflux; Inert atmosphere;	53%

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

: 1345995-64-3
C21H24N2O2

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile for 18h; Reflux; Inert atmosphere;	50%

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

: 939-26-4
2-bromomethylnaphthyl bromide

: 1345995-62-1
N-{2-[5-(naphthalen-2-ylmethoxy)-1H-indol-3-yl]ethyl}-acetamide

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile for 18h; Reflux; Inert atmosphere;	47%

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

: 142356-35-2
8-amino>octyl bromide

: tert-butyl N-(8-{[3-(2-acetamidoethyl)-1H-indol-5-yl]oxy}octyl) carbamate

Conditions

Conditions	Yield
Stage #1: N-acetyl-5-hydroxytryptamine With potassium carbonate In acetonitrile for 1h; Reflux; Inert atmosphere; Stage #2: 8-amino>octyl bromide With sodium iodide In acetonitrile for 20h; Reflux; Inert atmosphere;	47%

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

: 109-64-8
1,3-dibromo-propane

: C15H19BrN2O2

Conditions

Conditions	Yield
Stage #1: N-acetyl-5-hydroxytryptamine With sodium hydride In ethanol for 0.5h; Stage #2: 1,3-dibromo-propane In ethanol at 60℃; for 3h; Inert atmosphere;	46%

: 3245-62-3
2-(3-bromopropoxy)naphthalene

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

: C25H26N2O3

Conditions

Conditions	Yield
With caesium carbonate In acetonitrile at 60℃; for 4h; Reflux; Inert atmosphere;	43%

Acetamide,N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]- Chemical Properties

Molecular Structure of Acetamide,N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]- (CAS No.1210-83-9):

Molecular Formula: C₁₂H₁₄N₂O₂
Molecular Weight: 218.2518
IUPAC Name: N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]acetamide
CAS No: 1210-83-9
EINECS: 214-916-5
H bond acceptors: 4
H bond donors: 3
Freely Rotating Bonds: 4
Polar Surface Area: 34.47 Å²
Index of Refraction: 1.651
Molar Refractivity: 62.84 cm³
Molar Volume: 172 cm³
Surface Tension: 58 dyne/cm
Density: 1.268 g/cm³
Flash Point: 290.6 °C
Enthalpy of Vaporization: 86.98 kJ/mol
Boiling Point: 556.8 °C at 760 mmHg
Melting Point： 120-122 °C(lit.)
Vapour Pressure: 5.25E-13 mmHg at 25°C
Solubility: Ethanol: 50 mg/mL
Appearance: White to off-white or slightly pink powder
Product Categories: Tryptamines;Amino Acids;Heterocyclic Compounds;Various Metabolites and Impurities;Indoles;Intermediates Fine Chemicals;Metabolites Impurities;Pharmaceuticals
Canonical SMILES: CC(=O)NCCC1=CNC2=C1C=C(C=C2)O
InChI: InChI=1S/C12H14N2O2/c1-8(15)13-5-4-9-7-14-12-3-2-10(16)6-11(9)12/h2-3,6-7,14,16H,4-5H2,1H3,(H,13,15)
InChIKey: MVAWJSIDNICKHF-UHFFFAOYSA-N

Acetamide,N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]- Uses

Acetamide,N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]- (CAS No.1210-83-9) can be used as metabolite of Melatonin .

Acetamide,N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]- Safety Profile

Safety Information of Acetamide,N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]- (CAS No.1210-83-9):
Safety Statements 22-24/25
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
WGK Germany 3

Acetamide,N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]- Specification

Acetamide,N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]- (CAS No.1210-83-9), it also can be called 5-Hydroxy-N-acetyltryptamine ; N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]acetamid .It should be avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.And it should be stored in a tightly closed container. Store in a dry area. Keep refrigerated.

Product Name

N-ACETYL-5-HYDROXYTRYPTAMINE

Synthetic route

Acetamide,N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]- Chemical Properties

Acetamide,N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]- Uses

Acetamide,N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]- Safety Profile

Acetamide,N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]- Specification

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