Product Name

  • Name

    5-Methoxytryptamine

  • EINECS 210-153-7
  • CAS No. 608-07-1
  • Article Data68
  • CAS DataBase
  • Density 1.0815 (rough estimate)
  • Solubility
  • Melting Point 245-250 °C (dec.)(lit.)
  • Formula C11H14N2O
  • Boiling Point 380oC
  • Molecular Weight 190.245
  • Flash Point
  • Transport Information
  • Appearance White to tan crystalline powder
  • Safety 36-26
  • Risk Codes 22-36/37/38-20/21/22
  • Molecular Structure Molecular Structure of 608-07-1 (5-Methoxytryptamine)
  • Hazard Symbols HarmfulXn
  • Synonyms Indole,3-(2-aminoethyl)-5-methoxy- (6CI,8CI);2-(5-Methoxyindol-3-yl)ethylamine;2-[5-(Methyloxy)-1H-indol-3-yl]ethanamine;3-(2-Aminoethyl)-5-methoxyindole;5-MOT;5-Methoxy-1H-indole-3-ethanamine;Deacetylmelatonin;Methoxytryptamine;NSC 56422;[2-(5-Methoxy-1H-indol-3-yl)ethyl]amine;
  • PSA 51.04000
  • LogP 2.37800

Synthetic route

5-methoxy-3-(2-nitroethyl)-1H-indole
68935-49-9

5-methoxy-3-(2-nitroethyl)-1H-indole

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In methanol at 20℃;99%
With hydrogen; palladium on activated charcoal In ethanol under 2585.7 Torr; for 12h;
methyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]carbamate
67199-10-4

methyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]carbamate

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
With sodium hydroxide In methanol for 4h; Hydrolysis; decarboxylation; Heating;99%
With water Hydrolysis;
With sodium hydroxide Heating;
2-ethoxycarbonyl-3-(2-phthalimidoethyl)-5-methoxyindole
55747-53-0

2-ethoxycarbonyl-3-(2-phthalimidoethyl)-5-methoxyindole

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
Stage #1: 2-ethoxycarbonyl-3-(2-phthalimidoethyl)-5-methoxyindole With water; sodium hydroxide at 88 - 90℃;
Stage #2: With hydrogenchloride In water at 10 - 110℃; Temperature;		99%
Multi-step reaction with 2 steps
1: 10 percent aq. NaOH / 0.08 h / Heating; microwave irradiation
2: 20 percent H2SO4 / 0.17 h / Heating; microwave irradiation
View Scheme
With potassium hydroxide for 3h; Reflux;57 g
5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
With ammonium bromide; ethylenediamine at 100℃; for 7h; Microwave irradiation;89%
With sulfuric acid In water for 8h; Heating;69.7%
With sodium hydroxide In 2-methyl-propan-1-ol
2-(1-methanesulfonyl-5-methoxy-1H-indol-3-yl)ethylamine
627086-10-6

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

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
With potassium hydroxide In methanol for 9h; Heating;84%
5-methoxy-3-(2-nitro-vinyl)-indole
61675-19-2

5-methoxy-3-(2-nitro-vinyl)-indole

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 40h;73%
With lithium aluminium tetrahydride In tetrahydrofuran Heating;
Stage #1: 5-methoxy-3-(2-nitro-vinyl)-indole With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; Inert atmosphere;
Stage #2: With water In tetrahydrofuran at 0℃;
2-(1-benzyl-5-methoxy-1H-indol-3-yl)ethylamine
40619-73-6

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

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
With sodium In tetrahydrofuran; ammonia at -33℃; for 1.5h;66%
N-(2-(5-methoxy-1H-indol-3-yl)ethyl)-4-methylbenzenesulfonamide
102016-76-2

N-(2-(5-methoxy-1H-indol-3-yl)ethyl)-4-methylbenzenesulfonamide

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
With ammonia; sodium In tetrahydrofuran at -78℃; for 0.25h;65%
5-methoxylindole
1006-94-6

5-methoxylindole

L-serin
56-45-1

L-serin

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
Stage #1: 5-methoxylindole; L-serin With engineered tryptophan synthase In methanol; aq. phosphate buffer at 75℃; for 12h; pH=8.0; Enzymatic reaction;
Stage #2: With pyridoxal 5'-phosphate; Ruminococcus gnavus L-tryptophan decarboxylase In methanol; aq. phosphate buffer at 37℃; pH=8.0; Enzymatic reaction;		14%
5-methoxylindole
1006-94-6

5-methoxylindole

methyl magnesium iodide
917-64-6

methyl magnesium iodide

diethyl ether
60-29-7

diethyl ether

chloroacetonitrile
107-14-2

chloroacetonitrile

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
und Erwaermen des Reaktionsprodukts Natrium in Aethanol;
...Expand
5-methoxylindole
1006-94-6

5-methoxylindole

methyl magnesium iodide
917-64-6

methyl magnesium iodide

chloroacetonitrile
107-14-2

chloroacetonitrile

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
With diethyl ether Erwaermen des Reaktionsprodukts mit Natrium und Aethanol;
...Expand
(5-methoxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetonitrile
70351-49-4

(5-methoxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetonitrile

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
With 2-methyl-propan-1-ol; sodium
5-methoxytryptamine-2-carboxylic acid
52648-13-2

5-methoxytryptamine-2-carboxylic acid

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
With hydrogenchloride
4-Methoxyphenylhydrazine
3471-32-7

4-Methoxyphenylhydrazine

4-amino-butyraldehyde diethyl acetate

4-amino-butyraldehyde diethyl acetate

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
With zinc(II) chloride at 180℃;
5-methoxy-3-indoleglyoxylylamide
52055-22-8

5-methoxy-3-indoleglyoxylylamide

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 8h; Heating;
With lithium aluminium tetrahydride In tetrahydrofuran for 18h; Reflux;
5-methoxy-3-(2-phthalimido-ethyl)-indole-2-carboxylic acid
55747-60-9

5-methoxy-3-(2-phthalimido-ethyl)-indole-2-carboxylic acid

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
With sulfuric acid for 0.166667h; Heating; microwave irradiation;
tryptamine
61-54-1

tryptamine

phenyl halide

phenyl halide

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 100 percent / Et3N
2: Et3SiH / trifluoroacetic acid
3: 63 percent / Na2WO4*2H2O; aq. H2O2 / methanol; H2O
4: 85 percent / BF3
5: NaOH / Heating
View Scheme
methyl 2-(1-H-indol-3-yl)ethylcarbamate
58635-45-3

methyl 2-(1-H-indol-3-yl)ethylcarbamate

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Et3SiH / trifluoroacetic acid
2: 63 percent / Na2WO4*2H2O; aq. H2O2 / methanol; H2O
3: 85 percent / BF3
4: NaOH / Heating
View Scheme
Multi-step reaction with 4 steps
1: 97 percent / Et3SiH / trifluoroacetic acid / 3 h / 60 °C
2: 65 percent / H2O2 / Na2WO4*2H2O / methanol; H2O / 0.5 h / 20 °C
3: 94 percent / BF3 / 0.67 h / Heating
4: 99 percent / aq. NaOH / methanol / 4 h / Heating
View Scheme
2,3-dihydro-Nb-methoxycarbonyltryptamine
180910-64-9

2,3-dihydro-Nb-methoxycarbonyltryptamine

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 63 percent / Na2WO4*2H2O; aq. H2O2 / methanol; H2O
2: 85 percent / BF3
3: NaOH / Heating
View Scheme
Multi-step reaction with 3 steps
1: 65 percent / H2O2 / Na2WO4*2H2O / methanol; H2O / 0.5 h / 20 °C
2: 94 percent / BF3 / 0.67 h / Heating
3: 99 percent / aq. NaOH / methanol / 4 h / Heating
View Scheme
1-hydroxy-Nb-methoxycarbonyltryptamine
180910-53-6

1-hydroxy-Nb-methoxycarbonyltryptamine

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / BF3
2: NaOH / Heating
View Scheme
Multi-step reaction with 2 steps
1: 94 percent / BF3 / 0.67 h / Heating
2: 99 percent / aq. NaOH / methanol / 4 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 85 percent / BF3*MeOH / 0.17 h / Heating
2: H2O
View Scheme
5-methoxylindole
1006-94-6

5-methoxylindole

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: POCl3 / 0 °C
2: NH4OAc / 70 °C
3: LiAlH4 / tetrahydrofuran / Heating
View Scheme
Multi-step reaction with 3 steps
1: diethyl ether / 6 h / Heating
2: NH3 / dioxane / 8 h / 20 °C
3: lithium aluminum hydride / tetrahydrofuran / 8 h / Heating
View Scheme
Multi-step reaction with 5 steps
1.1: BuLi / tetrahydrofuran; hexane / 0.25 h / -10 °C
1.2: tetrahydrofuran; hexane / 3 h / 0 °C
2.1: 5.4 g / NBS / tetrahydrofuran; hexane / 3 h / -78 °C
3.1: t-BuLi / pentane; diethyl ether / 0.17 h / -78 °C
3.2: CuBr*SMe2 / pentane; diethyl ether / 0.25 h / -78 °C
3.3: 50 percent / BF3*Et2O / pentane; diethyl ether / 4 h / -78 °C
4.1: 89 percent / Bu4NF / tetrahydrofuran / 0.17 h / 20 °C
5.1: 65 percent / NH3; Na / tetrahydrofuran / 0.25 h / -78 °C
View Scheme
5-methoxyindole-3-carboxaldehyde
10601-19-1

5-methoxyindole-3-carboxaldehyde

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NH4OAc / 70 °C
2: LiAlH4 / tetrahydrofuran / Heating
View Scheme
Multi-step reaction with 3 steps
1: ammonium acetate / benzene / Reflux
2: sodium tetrahydroborate / tetrahydrofuran; methanol / 20 °C
3: palladium on activated charcoal; hydrogen / methanol / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: piperidine; acetic acid / benzene / Reflux
2: lithium aluminium tetrahydride / tetrahydrofuran / Reflux
View Scheme
Multi-step reaction with 2 steps
1: ammonium acetate / 1.5 h / Reflux
2: lithium aluminium tetrahydride / tetrahydrofuran / 40 h / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: ammonium acetate / 1.5 h / Reflux; Inert atmosphere
2: lithium aluminium tetrahydride / tetrahydrofuran / 36 h / 0 - 20 °C / Inert atmosphere
View Scheme
2-iodo-4-methoxylaniline
191348-14-8

2-iodo-4-methoxylaniline

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 96 percent / 4-dimethylaminopyridine; pyridine / 14 h / 20 °C
2.1: 82 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C
3.1: tristrimethylsilylsilane; azoisobutyronitrile / toluene / 12 h / Heating
3.2: 74 percent / p-toluenesulfonic acid / toluene / 2 h / Heating
4.1: 85 percent / hydrazine monohydrate / ethanol / 3 h / Heating
5.1: 84 percent / KOH / methanol / 9 h / Heating
View Scheme
N-(2-iodo-4-methoxyphenyl)methanesulfonamide
627086-06-0

N-(2-iodo-4-methoxyphenyl)methanesulfonamide

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 82 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C
2.1: tristrimethylsilylsilane; azoisobutyronitrile / toluene / 12 h / Heating
2.2: 74 percent / p-toluenesulfonic acid / toluene / 2 h / Heating
3.1: 85 percent / hydrazine monohydrate / ethanol / 3 h / Heating
4.1: 84 percent / KOH / methanol / 9 h / Heating
View Scheme
2-[2-(1-methanesulfonyl-5-methoxy-1H-indol-3-yl)ethyl]isoindole-1,3-dione
627086-09-3

2-[2-(1-methanesulfonyl-5-methoxy-1H-indol-3-yl)ethyl]isoindole-1,3-dione

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / hydrazine monohydrate / ethanol / 3 h / Heating
2: 84 percent / KOH / methanol / 9 h / Heating
View Scheme
N-[4-(1,3-dioxodihydroisoindol-2-yl)but-2-ynyl]-N-(2'-iodo-4'-methoxyphenyl)methanesulfonamide
627086-07-1

N-[4-(1,3-dioxodihydroisoindol-2-yl)but-2-ynyl]-N-(2'-iodo-4'-methoxyphenyl)methanesulfonamide

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tristrimethylsilylsilane; azoisobutyronitrile / toluene / 12 h / Heating
1.2: 74 percent / p-toluenesulfonic acid / toluene / 2 h / Heating
2.1: 85 percent / hydrazine monohydrate / ethanol / 3 h / Heating
3.1: 84 percent / KOH / methanol / 9 h / Heating
View Scheme
(5-methoxy-1H-indol-3-yl)oxoacetyl chloride
2426-19-9

(5-methoxy-1H-indol-3-yl)oxoacetyl chloride

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NH3 / dioxane / 8 h / 20 °C
2: lithium aluminum hydride / tetrahydrofuran / 8 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: ammonia / 1,4-dioxane / 20 °C
2: lithium aluminium tetrahydride / tetrahydrofuran / 18 h / Reflux
View Scheme
1-benzyl-5-methoxy-1H-indole-3-acetamide
93879-42-6

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

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

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

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

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Conditions
ConditionsYield
Multi-step reaction with 3 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
View Scheme
succinic acid anhydride
108-30-5

succinic acid anhydride

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

3-<(5-methoxy-3-indolyl)ethylamino>propionic acid
58714-14-0

3-<(5-methoxy-3-indolyl)ethylamino>propionic acid

Conditions
ConditionsYield
In chloroform at 0 - 5℃; for 0.25h;100%
In dichloromethane at 20℃; for 18h;99%
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

acetic anhydride
108-24-7

acetic anhydride

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

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With pyridine In dichloromethane100%
In 1,2-dichloro-ethane at 0℃; for 1h;96%
With triethylamine95%
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

formic acid ethyl ester
109-94-4

formic acid ethyl ester

N-(2-(5-methoxy-1H-indol-3-yl)ethyl)formamide
104510-12-5

N-(2-(5-methoxy-1H-indol-3-yl)ethyl)formamide

Conditions
ConditionsYield
for 10h; Reflux;100%
for 10h; Reflux;100%
for 12h; Reflux;100%
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Trifluoroacetaldehyde ethyl hemiacetal
433-27-2

Trifluoroacetaldehyde ethyl hemiacetal

6-methoxy-1-trifluoromethyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole
126260-64-8

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

Conditions
ConditionsYield
at 110 - 120℃; for 5h;99.7%
4-methyleneoxetan-2-one
674-82-8

4-methyleneoxetan-2-one

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

N-<2-(5-methoxy-1H-indol-3-yl)ethyl>-3-oxobutyramide
112081-40-0

N-<2-(5-methoxy-1H-indol-3-yl)ethyl>-3-oxobutyramide

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 24h;99%
In dichloromethane at 0℃; for 12.5h;
phthalic anhydride
85-44-9

phthalic anhydride

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

2-(2-(5-methoxy-1H-indol-3-yl)ethyl)isoindoline-1,3-dione
55747-66-5

2-(2-(5-methoxy-1H-indol-3-yl)ethyl)isoindoline-1,3-dione

Conditions
ConditionsYield
With triethylamine In toluene for 24h; Reflux; Dean-Stark;99%
at 206℃;88%
With triethylamine In toluene for 24h; Reflux;87%
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

3-[2-[(tert-butyloxycarbonyl)amino]ethyl]-5-methoxy-1H-indole
380358-27-0

3-[2-[(tert-butyloxycarbonyl)amino]ethyl]-5-methoxy-1H-indole

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 12h;99%
With triethylamine In tetrahydrofuran at 10℃; for 1h; Inert atmosphere;99%
With triethylamine In tetrahydrofuran at 10℃; for 1h;99%
1-methyl-1H-indole-2,3-dione
2058-74-4

1-methyl-1H-indole-2,3-dione

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

(S)-6'-methoxy-1-methyl-2',3',4',9'-tetrahydrospiro[indoline-3,1'-pyrido[3,4-b]indol]-2-one
1340563-49-6

(S)-6'-methoxy-1-methyl-2',3',4',9'-tetrahydrospiro[indoline-3,1'-pyrido[3,4-b]indol]-2-one

Conditions
ConditionsYield
With (S)-3,3'-bis(2,4,6-tri-iso-propylphenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In N,N-dimethyl-formamide at 40℃; Pictet-Spengler cyclisation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;99%
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

5-bromo-1-methyl-1H-indole-2,3-dione
2058-72-2

5-bromo-1-methyl-1H-indole-2,3-dione

5-bromo-6'-methoxy-1-methyl-2',3',4',9'-tetrahydrospiro[indoline-3,1'-pyrido[3,4-b]indol]-2-one
904501-92-4

5-bromo-6'-methoxy-1-methyl-2',3',4',9'-tetrahydrospiro[indoline-3,1'-pyrido[3,4-b]indol]-2-one

Conditions
ConditionsYield
With scandium(III) chloride; sodium sulfate In dichloromethane at 23℃; Pictet-Spengler cyclisation; Inert atmosphere;99%
3-methylbutyric acid
503-74-2

3-methylbutyric acid

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

C16H22N2O2

C16H22N2O2

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine at 20℃; for 18h;99%
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

acetyl chloride
75-36-5

acetyl chloride

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

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
In dichloromethane at 25 - 30℃; Temperature;98.3%
With triethylamine In dichloromethane at 20℃;
With triethylamine In dichloromethane at 0 - 20℃; for 5h;
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

2-bromoallyl bromide
513-31-5

2-bromoallyl bromide

2-bromo-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]prop-2-en-1-amine
1036862-81-3

2-bromo-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]prop-2-en-1-amine

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 20℃;98%
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

2-(2'-phenylethynyl)benzoic acid
1084-95-3

2-(2'-phenylethynyl)benzoic acid

3-benzyl-3-hydroxy-2-(2-(5-methoxy-1H-indol-3-yl)ethyl)isoindolin-1-one
1246168-38-6

3-benzyl-3-hydroxy-2-(2-(5-methoxy-1H-indol-3-yl)ethyl)isoindolin-1-one

Conditions
ConditionsYield
Stage #1: 2-(2'-phenylethynyl)benzoic acid With tetrabutylammonium acetate In water at 100℃; for 0.166667h; Microwave irradiation; Inert atmosphere;
Stage #2: 2-(5-methoxyindol-3-yl)ethylamine In water at 100℃; for 0.166667h; Microwave irradiation; Inert atmosphere; regioselective reaction;		98%
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

benzaldehyde
100-52-7

benzaldehyde

N-benzyl-2-(5-methoxy-1H-indol-3-yl)ethan-1-amine
25119-60-2

N-benzyl-2-(5-methoxy-1H-indol-3-yl)ethan-1-amine

Conditions
ConditionsYield
Stage #1: 2-(5-methoxyindol-3-yl)ethylamine; benzaldehyde In methanol at 20℃; for 36h;
Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 1h;		98%
Stage #1: 2-(5-methoxyindol-3-yl)ethylamine; benzaldehyde In methanol at 20℃;
Stage #2: With sodium tetrahydroborate at 20℃; Borch Reduction;		98%
Stage #1: 2-(5-methoxyindol-3-yl)ethylamine; benzaldehyde In methanol at 20℃; for 36h;
Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 1h;
Stage #1: 2-(5-methoxyindol-3-yl)ethylamine; benzaldehyde With sodium sulfate In methanol for 12h;
Stage #2: With sodium tetrahydroborate In methanol at 0℃;
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

Glyoxilic acid
298-12-4

Glyoxilic acid

6-methoxy-2,3,4,9-tetrahydro-1H-β-carboline-1-carboxylic acid
17952-63-5

6-methoxy-2,3,4,9-tetrahydro-1H-β-carboline-1-carboxylic acid

Conditions
ConditionsYield
With potassium carbonate In water; ethyl acetate at 20℃; for 24h; pH=5; Pictet-Spengler Synthesis;98%
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

2-((4-methoxyphenyl)ethynyl)benzoic acid
859829-95-1

2-((4-methoxyphenyl)ethynyl)benzoic acid

3-hydroxy-2-(2-(5-methoxy-1H-indol-3-yl)ethyl)-3-(4-methoxybenzyl)isoindolin-1-one
1246168-42-2

3-hydroxy-2-(2-(5-methoxy-1H-indol-3-yl)ethyl)-3-(4-methoxybenzyl)isoindolin-1-one

Conditions
ConditionsYield
Stage #1: 2-((4-methoxyphenyl)ethynyl)benzoic acid With tetrabutylammonium acetate In water at 100℃; for 0.166667h; Microwave irradiation; Inert atmosphere;
Stage #2: 2-(5-methoxyindol-3-yl)ethylamine In water at 100℃; for 0.166667h; Microwave irradiation; Inert atmosphere; regioselective reaction;		97%
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

dimethyl 2-ketoglutarate
13192-04-6

dimethyl 2-ketoglutarate

methyl 8-methoxy-2,3,5,6,11,11b-hexahydro-3-oxo-1H-indolizino<8,7-b>indole-11b-carboxylate
129968-05-4

methyl 8-methoxy-2,3,5,6,11,11b-hexahydro-3-oxo-1H-indolizino<8,7-b>indole-11b-carboxylate

Conditions
ConditionsYield
With acetic acid for 4h; Reflux; Inert atmosphere;97%
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

potassium thioacetate
10387-40-3

potassium thioacetate

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

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate In ethyl acetate at 20℃; Electrochemical reaction;97%
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

n-valeryl chloride
638-29-9

n-valeryl chloride

N-<2-(5-methoxy-1H-indol-3-yl)ethyl>pentanamide

N-<2-(5-methoxy-1H-indol-3-yl)ethyl>pentanamide

Conditions
ConditionsYield
In toluene for 1h; Ambient temperature;96%
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

7-(trifluoromethyl)-3,4,5,6-tetrahydro-2H-azepine
1146222-77-6

7-(trifluoromethyl)-3,4,5,6-tetrahydro-2H-azepine

5-(6-methoxy-1-(trifluoromethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)pentan-1-amine

5-(6-methoxy-1-(trifluoromethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)pentan-1-amine

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; for 168h; Pictet-Spengler Synthesis;96%
formaldehyd
50-00-0

formaldehyd

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

pinoline
20315-68-8

pinoline

Conditions
ConditionsYield
With chloro-trimethyl-silane95%
With acetic acid In methanol at 80℃; for 1h;83%
With sulfuric acid Erhitzen des Reaktionsprodukts mit wss. H2SO4;
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tetra(n-butyl)ammonium hydrogen sulfate

tetra(n-butyl)ammonium hydrogen sulfate

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

3-[2-[(tert-butyloxycarbonyl)amino]ethyl]-5-methoxy-1H-indole
380358-27-0

3-[2-[(tert-butyloxycarbonyl)amino]ethyl]-5-methoxy-1H-indole

A

1-(benzenesulfonyl)-3-[2-[(tert-butyloxycarbonyl)amino]ethyl]-5-methoxy-1H-indole
297751-49-6

1-(benzenesulfonyl)-3-[2-[(tert-butyloxycarbonyl)amino]ethyl]-5-methoxy-1H-indole

B

2-[1-(benzenesulfonyl)-5-methoxy-1H-indol-3-yl]ethylamine hydrochloride

2-[1-(benzenesulfonyl)-5-methoxy-1H-indol-3-yl]ethylamine hydrochloride

Conditions
ConditionsYield
With sodium hydroxide In dichloromethaneA n/a
B 95%
...Expand
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

1-benzylisatin
1217-89-6

1-benzylisatin

(S)-1-benzyl-6'-methoxy-2',3',4',9'-tetrahydrospiro[indoline-3,1'-pyrido[3,4-b]indol]-2-one
1340563-51-0

(S)-1-benzyl-6'-methoxy-2',3',4',9'-tetrahydrospiro[indoline-3,1'-pyrido[3,4-b]indol]-2-one

Conditions
ConditionsYield
With (S)-3,3'-bis(2,4,6-tri-iso-propylphenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In N,N-dimethyl-formamide at 40℃; Pictet-Spengler cyclisation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;95%
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

1-cyclohexyl-6-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

1-cyclohexyl-6-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; Pictet-Spengler Synthesis;95%
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

N-(2-(5-methoxy-1H-indol-3-yl)ethyl)-4-nitrobenzenesulfonamide

N-(2-(5-methoxy-1H-indol-3-yl)ethyl)-4-nitrobenzenesulfonamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; Schlenk technique;95%
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

(4-fluorophenyl)glyoxal
403-32-7

(4-fluorophenyl)glyoxal

(4-fluorophenyl)(6-methoxy-9H-pyrido[3,4-b]indol-1-yl)methanone
1148028-92-5

(4-fluorophenyl)(6-methoxy-9H-pyrido[3,4-b]indol-1-yl)methanone

Conditions
ConditionsYield
Stage #1: 2-(5-methoxyindol-3-yl)ethylamine; (4-fluorophenyl)glyoxal In dichloromethane
Stage #2: With montmorillonite K-10; palladium 10% on activated carbon In methanol; dichloromethane for 0.0833333h; Pictet-Spengler cyclisation;
Stage #3: at 130℃; for 0.116667h; Microwave irradiation;		94%
With 5%-palladium/activated carbon; montmorillonite K10 Clay at 130℃; Microwave irradiation;
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

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

levulinic acid
123-76-2

levulinic acid

8-Methoxy-2,3,5,6,11,11b-hexahydro-3-oxo-11b-methyl-1H-indolizino<8,7-b>indole
734-15-6

8-Methoxy-2,3,5,6,11,11b-hexahydro-3-oxo-11b-methyl-1H-indolizino<8,7-b>indole

Conditions
ConditionsYield
at 180℃; under 11251.1 Torr; for 0.0333333h; Pictet-Spengler condensation; Microwave irradiation; Neat (no solvent);94%

5-Methoxytryptamine Chemical Properties

Molecular Structure:

Molecular Formula: C11H10NO3
Molecular Weight: 204.202
IUPAC Name: 2-(5-Methoxy-1H-indol-3-yl)ethanamine
Synonyms of 5-Methoxytryptamine (CAS NO.608-07-1): 3-(2-Aminoethyl)-5-methoxyindole ; 5-22-12-00018 (Beilstein Handbook Reference) ; 5-Mot ; 5MOT ; BRN 0145587 ; EINECS 210-153-7 ; Meksamin (free base) ; Methoxytryptamine ; Mexamine ; Mexamine base ; NSC 56422 ; 1H-Indole-3-ethanamine, 5-methoxy- (9CI) ; 2-(5-Methoxyindol-3-yl)ethylamine ; Indole, 3-(2-aminoethyl)-5-methoxy-
CAS NO: 608-07-1
Classification Code: Drug / Therapeutic Agent ; Mutation data ; Reproductive Effect
Melting point: 245-250 °C 
Storage temp.: 2-8°C
Form: crystalline
Color: white
Merck: 13,6032

5-Methoxytryptamine Uses

 5-Methoxytryptamine (CAS NO.608-07-1) is used as intermediates in organic synthesis.

5-Methoxytryptamine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 176mg/kg (176mg/kg)   Journal of Toxicology and Environmental Health. Vol. 1, Pg. 515, 1976.
mouse LD50 intravenous 106mg/kg (106mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)		 Farmakologiya i Toksikologiya Vol. 27, Pg. 681, 1964.

5-Methoxytryptamine Safety Profile

Safety Information of 5-Methoxytryptamine (CAS NO.608-07-1):
Hazard Codes:Xn
Risk Statements:22-36/37/38-20/21/22
22:Harmful if swallowed
36/37/38:Irritating to eyes, respiratory system and skin
20/21/22:Harmful by inhalation, in contact with skin and if swallowed
Safety Statements:36-26
36:Wear suitable protective clothing
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany:3
RTECS:NL4110000
F:8
Poison by intravenous and intraperitoneal routes. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

5-Methoxytryptamine Specification

First Aid Measures of 5-Methoxytryptamine (CAS NO.608-07-1):
Ingestion:If swallowed, wash out mouth with water provided person is conscious. Call a physician.
Inhalation:If inhaled, remove to fresh air. If not breathing give artificial respiration. If breathing is difficult, give oxygen.
Skin:In case of skin contact, flush with copious amounts of water for at least 15 minutes. Remove contaminated clothing and shoes. Call a physician.
Eyes:In case of contact with eyes, flush with copious amounts of water for at least 15 minutes. Assure adequate flushing by separating the eyelids with fingers. Call a physician.
Storage of 5-Methoxytryptamine (CAS NO.608-07-1):
Keep tightly closed.

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