25390-67-4

Basic information

• Product Name: N,N-Dimethyl-5-(benzyloxy)-1H-indole-3-ethanamine
• Synonyms: 5-(Benzyloxy)-3-[2-(dimethylamino)ethyl]-1H-indole;N,N-Dimethyl-5-(benzyloxy)-1H-indole-3-ethanamine;N,N-Dimethyl-5-(phenylmethoxy)-1H-indole-3-ethanamine;O-Benzylbufotenine
• CAS NO: 25390-67-4
• Molecular Formula: C₁₉H₂₂N₂O
• Molecular Weight: 294.39
• Mol File: 25390-67-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 472.9°C at 760 mmHg
• Flash Point: 239.8°C
• Appearance: /
• Density: 1.133g/cm³
• Vapor Pressure: 4.13E-09mmHg at 25°C
• Refractive Index: 1.628
• CAS DataBase Reference: N,N-Dimethyl-5-(benzyloxy)-1H-indole-3-ethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Dimethyl-5-(benzyloxy)-1H-indole-3-ethanamine(25390-67-4)
• EPA Substance Registry System: N,N-Dimethyl-5-(benzyloxy)-1H-indole-3-ethanamine(25390-67-4)

Safety Data

• Hazardous Substances Data: 25390-67-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C19H22N2O/c1-21(2)11-10-16-13-20-19-9-8-17(12-18(16)19)22-14-15-6-4-3-5-7-15/h3-9,12-13,20H,10-11,14H2,1-2H3

Upstream product

• 108-01-0 2-(N,N-dimethylamino)ethanol 
• 1215-59-4 5-benzyloxy-1H-indole 
• 66521-34-4 N,N-dimethyl-2-<5-(benzyloxy)-1H-indol-3-yl>glyoxalylamide 
• 7757-82-6 sodium sulfate 
• 22424-61-9 2-[5-(benzyloxy)-1H-indol-3-yl]-2-oxoacetyl chloride 
• 20776-45-8 5-benzyloxytryptamine 
• 74-88-4 methyl iodide 
• 50-00-0 formaldehyd 
• 52055-23-9 5-benzyloxytryptamine hydrochloride 
• 409111-49-5 (5-benzyloxy-indol-3-yl)-acetic acid dimethylamide 

Downstream Products

• 297751-69-0 benzyloxy-3-[2-(dimethylamino)ethyl]-1H-indole-1-carboxylic acid tert-butyl ester 
• 297751-67-8 [5-benzyloxy-3-[2-(dimethylamino)ethyl]-1H-indol-1-yl]phenylmethanone 
• 5787-02-0 5-hydroxy-N,N-dimethyltryptamine iodomethylate 
• 330851-85-9 3-(dimethylaminoethyl)-5-hydroxy-1-phenylindole 
• 330851-67-7 5-benzyloxy-3-dimethylaminoethyl-1-phenylindole 
• 297751-70-3 5-benzyloxy-3-dimethylaminoethyl-1-phenylindole 
• 487-93-4 bufotenin 
• 112626-00-3 [2-(5-benzyloxy-indol-3-yl)-ethyl]-trimethyl-ammonium; iodide 

Relevant articles and documents

Observations concerning the synthesis of tryptamine homologues and branched tryptamine derivatives via the borrowing hydrogen process: Synthesis of psilocin, bufotenin, and serotonin

Observations concerning the synthesis of substituted tryptamine derivatives starting from indoles and 1,n-amino alcohols via the borrowing hydrogen process are discussed. This catalytic, single-step, and modular approach to tryptamines and homotryptamines allows the synthesis of branched and nonbranched tryptamines as well as tryptamine-based natural products such as psilocin, bufotenin, and serotonin.

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.

5-HT(1D) receptor agonist properties of novel 2-[5- [[(trifluoromethyl)sulfonyl]oxy]indolyl]ethylamines and their use as synthetic intermediates

2-[5-[[(Trifluoromethyl)sulfonyl]oxy]-1H-indol-3-yl]ethylamine (18), its N,N'-di-n-propyl (12), N,N-diethyl (13), and N,N-dimethyl (14) derivatives, and 4-[3-[2-(N,N-dimethylamino)ethyl]-1H-indol-3-yl]-N-(p- methoxybenzyl)acrylamide (GR46611, 19) were syn