67292-68-6

Basic information

• Product Name: 5-MeO-2,N,N-trimethyltryptamine
• Synonyms: (2-(5-methoxy-2-methyl-1H-indol-3-yl)-1-methyl-ethyl)dimethylamine;2-(5-methoxy-2-methyl-1H-indol-3-yl)-N,N-dimethylethanamine;2-Me-5-Meo-dmt;3-(2-(Dimethylamino)ethyl)-5-methoxy-2-methyl-indole;5-MeO-2,N,N-trimethyltryptamine;INDOLE,3-(2-(DIMETHYLAMINO)ETHYL)-5-METHOXY-2-METHYL-
• CAS NO: 67292-68-6
• Molecular Formula: C₁₄H₂₀N₂O
• Molecular Weight: 232.3214
• Mol File: 67292-68-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 374.49°C (rough estimate)
• Flash Point: 185.8°C
• Appearance: /
• Density: 1.0151 (rough estimate)
• Vapor Pressure: 4.32E-06mmHg at 25°C
• Refractive Index: 1.5110 (estimate)
• CAS DataBase Reference: 5-MeO-2,N,N-trimethyltryptamine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-MeO-2,N,N-trimethyltryptamine(67292-68-6)
• EPA Substance Registry System: 5-MeO-2,N,N-trimethyltryptamine(67292-68-6)

Safety Data

• Hazardous Substances Data: 67292-68-6(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline powder

InChI:InChI=1/C14H20N2O/c1-10-12(7-8-16(2)3)13-9-11(17-4)5-6-14(13)15-10/h5-6,9,15H,7-8H2,1-4H3

Synthetic route

formaldehyd (50-00-0) + 2-(5-methoxy-2-methyl-1H-indol-3-yl)ethan-1-amine hydrochloride (28089-03-4) → [2-(5-methoxy-2-methyl-indol-3-yl)-ethyl]-dimethyl-amine (67292-68-6)

Conditions	Yield
With sodium methylate; sodium cyanoborohydride; acetic acid In methanol; water	80%

N,N-dimethyl-4-oxopentanamine hydrochloride (79098-38-7) + 4-methoxyphenylhydrazine hydrochloride (19501-58-7) → [2-(5-methoxy-2-methyl-indol-3-yl)-ethyl]-dimethyl-amine (67292-68-6)

Conditions	Yield
Stage #1: N,N-dimethyl-4-oxopentanamine hydrochloride; 4-methoxyphenylhydrazine hydrochloride With sulfuric acid; acetic acid at 40 - 60℃; for 3.5 - 4.5h; Heating / reflux; Stage #2: With sodium carbonate In water pH=10;	78.2%

(5-methoxy-2-methyl-indol-3-yl)-acetic acid dimethylamide (100722-77-8) → [2-(5-methoxy-2-methyl-indol-3-yl)-ethyl]-dimethyl-amine (67292-68-6)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

2-(5-Methoxy-2-methyl-1H-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide (189884-58-0) → [2-(5-methoxy-2-methyl-indol-3-yl)-ethyl]-dimethyl-amine (67292-68-6)

Conditions	Yield
With lithium aluminium tetrahydride

5-methoxy-2-methyl-1H-indole (1076-74-0) → [2-(5-methoxy-2-methyl-indol-3-yl)-ethyl]-dimethyl-amine (67292-68-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: diethyl ether 2: H2O; CHCl3 3: LiAlH4 View Scheme

2-(5-methoxy-2-methyl-1H-indol-3-yl)-2-oxoacetyl chloride (1026388-93-1) → [2-(5-methoxy-2-methyl-indol-3-yl)-ethyl]-dimethyl-amine (67292-68-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2O; CHCl3 2: LiAlH4 View Scheme

5-Methoxy-2-methylindole-3-acetic acid (2882-15-7) → [2-(5-methoxy-2-methyl-indol-3-yl)-ethyl]-dimethyl-amine (67292-68-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 195 °C 2: LiAlH4; diethyl ether View Scheme

2-(5-methoxy-2-methyl-1H-indol-3-yl)ethan-1-amine hydrochloride (28089-03-4) → [2-(5-methoxy-2-methyl-indol-3-yl)-ethyl]-dimethyl-amine (67292-68-6)

Conditions	Yield
With sodium hydroxide; formaldehyd; sodium methylate; sodium cyanoborohydride; acetic acid In methanol	1.215 g (80%)

[2-(5-methoxy-2-methyl-indol-3-yl)-ethyl]-dimethyl-amine (67292-68-6) + methyl iodide (74-88-4) → [2-(2-ethyl-5-methoxy-1H-indol-3-yl)-ethyl]-dimethyl-amine

Conditions	Yield
Multistep reaction.;	16%

[2-(5-methoxy-2-methyl-indol-3-yl)-ethyl]-dimethyl-amine (67292-68-6) + benzenesulfonyl chloride (98-09-9) → N,N-dimethyl 2-[(1-benzenesulphonyl)-5-methoxy-2-methyl-1H-indol-3-yl]ethylamine

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate In dichloromethane at 20℃; for 0.333333h;

[2-(5-methoxy-2-methyl-indol-3-yl)-ethyl]-dimethyl-amine (67292-68-6) → 2-ethyl-5-methoxy-N,N-dimethyltryptamine maleate

Conditions	Yield
With hydrogenchloride; n-butyllithium; N2; CO2 In tetrahydrofuran; diethyl ether

[2-(5-methoxy-2-methyl-indol-3-yl)-ethyl]-dimethyl-amine (67292-68-6) → N,N-dimethyl-2-(1-benzenesulfonyl-5-methoxy-2-methyl-1H-indol-3-yl)ethylamine oxalate

Upstream product

• 28089-03-4 2-(5-methoxy-2-methyl-1H-indol-3-yl)ethan-1-amine hydrochloride 
• 79098-38-7 N,N-dimethyl-4-oxopentanamine hydrochloride 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 2882-15-7 5-Methoxy-2-methylindole-3-acetic acid 
• 189884-58-0 2-(5-Methoxy-2-methyl-1H-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide 
• 50-00-0 formaldehyd 
• 100722-77-8 (5-methoxy-2-methyl-indol-3-yl)-acetic acid dimethylamide 
• 1026388-93-1 2-(5-methoxy-2-methyl-1H-indol-3-yl)-2-oxoacetyl chloride 
• 1076-74-0 5-methoxy-2-methyl-1H-indole 

Relevant articles and documents

PREPARATION OF 3-AMINOALKYL-SUBSTITUTED INDOLE DERIVATIVES FROM PHENYLHYDRAZINES AND AMINOKETONES

The present invention relates to a process for the preparation of indole derivatives, particularly those, which are useful as pharmaceutical intermediates. The process involves formation of hydrazone derivative between a phenyl hydrazine and a ketone amine, followed by cyclisation to give desired 2,3-substituted indole derivative in the presence of acid catalyst.

Indole and indoline derivatives as 5-HT6 selective ligands

Three classes of indole and indoline derivatives are disclosed as ligands selective for the 5-HT6receptors, and hence of value in the treatment or prevention of CNS disorders, including Alzheimer's disease, Parkinson's disease, schizophrenia, depression and anxiety. A particular class, 1-substituted-4-(ω-N,N-dialkyl-aminoalkyl)indoles, are claimed as novel compounds.