1134-01-6

Basic information

• Product Name: 3-(2-methylaminoethyl)-1H-indol-5-ol
• Synonyms: N-Methylserotonin;3-[2-(MethylaMino)ethyl]indol-5-ol
• CAS NO: 1134-01-6
• Molecular Formula: C₁₁H₁₄N₂O
• Molecular Weight: 190.24
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Neurochemicals;Pharmaceuticals
• Mol File: 1134-01-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 402.6°Cat760mmHg
• Flash Point: 197.3°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 4.66E-07mmHg at 25°C
• Refractive Index: 1.655
• CAS DataBase Reference: 3-(2-methylaminoethyl)-1H-indol-5-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-methylaminoethyl)-1H-indol-5-ol(1134-01-6)
• EPA Substance Registry System: 3-(2-methylaminoethyl)-1H-indol-5-ol(1134-01-6)

Safety Data

• Hazardous Substances Data: 1134-01-6(Hazardous Substances Data)

Usage

Description

3-(2-methylaminoethyl)-1H-indol-5-ol, also known as N-Methylserotonin, is a naturally occurring indole alkaloid and the N-methylated derivative of serotonin. It exhibits similar activity to serotonin and has been identified as a potential active constituent that contributes to the serotonergic activity of black cohosh.

Uses

Used in Pharmaceutical Industry:
3-(2-methylaminoethyl)-1H-indol-5-ol is used as a pharmaceutical compound for its serotonergic activity. It is particularly useful in the development of treatments for various neurological and psychiatric disorders due to its ability to modulate serotonin levels in the brain.
Used in Nutraceutical Industry:
3-(2-methylaminoethyl)-1H-indol-5-ol is used as a nutraceutical ingredient in dietary supplements and functional foods. It is valued for its potential to support mood regulation, cognitive function, and overall brain health.
Used in Research Applications:
3-(2-methylaminoethyl)-1H-indol-5-ol is used as a research tool in scientific studies to investigate the role of serotonin and its derivatives in various biological processes and disease mechanisms. It aids in understanding the molecular mechanisms underlying the therapeutic effects of serotonergic agents.

InChI:InChI=1/C11H14N2O/c1-12-5-4-8-7-13-11-3-2-9(14)6-10(8)11/h2-3,6-7,12-14H,4-5H2,1H3

Synthetic route

5-hydroxy-Nb-methoxycarbonyltryptamine (77549-09-8) → N-methylserotonin (1134-01-6)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether Heating;	65%
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether for 26h; Heating;	65%

N-methylserotonin 5-O-β-glucoside (1261074-26-3) → N-methylserotonin (1134-01-6)

Conditions	Yield
With hydrogenchloride; water at 70℃; for 1h;	57%

N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)formamide → N-methylserotonin (1134-01-6)

Conditions	Yield
Stage #1: N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)formamide With lithium aluminium tetrahydride In tetrahydrofuran at 25℃; for 4.66h; Inert atmosphere; Reflux; Stage #2: With sodium hydroxide In water at 0 - 10℃; for 0.25h; Inert atmosphere;	39.1%

benzyl-[2-(5-benzyloxy-indol-3-yl)-ethyl]-methyl-amine (4652-04-4) → N-methylserotonin (1134-01-6)

Conditions	Yield
With palladium on activated charcoal; ethanol Hydrogenation;
With ethanol; palladium on activated charcoal Hydrogenation;

[2-(5-benzyloxy-indol-3-yl)-ethyl]-methyl-amine; hydrogenoxalate (5971-62-0) → N-methylserotonin (1134-01-6)

Conditions	Yield
With methanol; magnesium hydrosilicate; palladium Hydrogenation;

3-(2-aminoethyl)-1H-indol-5-ol (50-67-9) → N-methylserotonin (1134-01-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / pyridine / dimethylformamide / 1.5 h / 0 - 20 °C 2: 65 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 26 h / Heating View Scheme

1-hydroxy-Nb-methoxycarbonyltryptamine (180910-53-6) → N-methylserotonin (1134-01-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 24 percent / H2O / 0.33 h / 20 °C 2: 65 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 26 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 40 percent / H2O / 0.33 h / 20 °C 2: 60 percent / aq. HCl / methanol / 0.33 h / 0 - 20 °C 3: 65 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 26 h / Heating View Scheme

1-formyl-5-hydroxy-N-methoxycarbonyltryptamine (185987-04-6) → N-methylserotonin (1134-01-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 76 percent / 8 percent aq. NaOH / methanol / 0.17 h / 60 °C 2: 65 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 26 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 76 percent / 2N NaOH / methanol 2: 65 percent / LiAlH4 / diethyl ether; tetrahydrofuran / Heating View Scheme

5-formyloxy-N-methoxycarbonyltryptamine (329764-36-5) → N-methylserotonin (1134-01-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / aq. HCl / methanol / 0.33 h / 0 - 20 °C 2: 65 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 26 h / Heating View Scheme

(5-benzyloxy-indol-3-yl)-acetic acid-(benzyl-methyl-amide) (725227-53-2) → N-methylserotonin (1134-01-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4; THF 2: ethanol; palladium/charcoal / Hydrogenation View Scheme

N-methylserotonin (1134-01-6) + acetaldehyde (75-07-0) → 3,4,5,6-tetrahydro-7-hydroxy-5,6-dimethyl-1H-azepino[5,4,3-cd]indole

Conditions	Yield
With oxygen; triethylamine In methanol at 20℃; for 4h;	80%

N-methylserotonin (1134-01-6) + triethylamine (121-44-8) → 3,4,5,6-tetrahydro-7-hydroxy-5,6-dimethyl-1H-azepino[5,4,3-cd]indole

Conditions	Yield
With oxygen In methanol for 20h; Heating;	23%

N-methylserotonin (1134-01-6) + trifluoroacetic anhydride (407-25-0) → Trifluoro-acetic acid 3-{2-[methyl-(2,2,2-trifluoro-acetyl)-amino]-ethyl}-1-(2,2,2-trifluoro-acetyl)-1H-indol-5-yl ester

Conditions	Yield
In dichloromethane at 60℃; for 0.166667h; Acylation;

Upstream product

• 5971-62-0 [2-(5-benzyloxy-indol-3-yl)-ethyl]-methyl-amine; hydrogenoxalate 
• 77549-09-8 5-hydroxy-Nb-methoxycarbonyltryptamine 
• 1261074-26-3 N-methylserotonin 5-O-β-glucoside 
• 329764-36-5 5-formyloxy-N-methoxycarbonyltryptamine 
• 185987-04-6 1-formyl-5-hydroxy-N-methoxycarbonyltryptamine 
• 180910-53-6 1-hydroxy-N_b-methoxycarbonyltryptamine 
• 4652-04-4 benzyl-[2-(5-benzyloxy-indol-3-yl)-ethyl]-methyl-amine 
• 725227-53-2 (5-benzyloxy-indol-3-yl)-acetic acid-(benzyl-methyl-amide) 
• 50-67-9 3-(2-aminoethyl)-1H-indol-5-ol 

Relevant articles and documents

Isolation of N,N-dimethyl and N-methylserotonin 5-0-ss-glucosides from immature zanthoxylum piperitum seeds

Two serotonin derivatives, N,N-dimethylserotonin 5-O-ss-glucoside (la) and N-methylserotonin 5-O-ss-glucoside (lb) were isolated from immature seeds of Zanthoxylum piperitum. Their structures were determined by multi-step conversion reactions and spectro-scopic analyses. Immature seeds of Z. piperitum contained extremely high levels of compounds la and lb of approximately 0.29% and 0.15% (w/w), respectively.

The chemistry of indoles. CIII. Simple syntheses of serotonin, N-methylserotonin, bufotenine, 5-methoxy-N-methyltryptamine, bufobutanoic acid, N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine, and lespedamine based on 1-hydroxyindole chemistry

Application of regioselective nucleophilic substitution reactions of 1-hydroxytryptamines to novel and simple syntheses of serotonin (1a), N-methylserotonin (1b), bufotenine (1c), 5-methoxy-N-methyltryptamine (2a), bufobutanoic acid (3a), N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine (4), and lespedamine (5) are described. Effective syntheses of 5-benzyloxytryptamine and 1-methoxy-2-oxindoles are also reported.