16176-73-1

Basic information

• Product Name: 1H-INDOLE-4-ETHANAMINE
• Synonyms: 1H-INDOLE-4-ETHANAMINE;2-(1H-Indol-4-yl)ethylamine;2-(1H-indol-4-yl)ethanamine;Indole-4-ethylamine
• CAS NO: 16176-73-1
• Molecular Formula: C₁₀H₁₂N₂
• Molecular Weight: 160.22
• Mol File: 16176-73-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 342.5 °C at 760 mmHg
• Flash Point: 187.7 °C
• Appearance: /
• Density: 1.157 g/cm³
• Vapor Pressure: 7.51E-05mmHg at 25°C
• Refractive Index: 1.668
• CAS DataBase Reference: 1H-INDOLE-4-ETHANAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-INDOLE-4-ETHANAMINE(16176-73-1)
• EPA Substance Registry System: 1H-INDOLE-4-ETHANAMINE(16176-73-1)

Safety Data

• Hazardous Substances Data: 16176-73-1(Hazardous Substances Data)

Usage

General Description

1H-Indole-4-ethanamine, also known as tryptamine, is a natural monoamine alkaloid that is found in animals, plants, and fungi. It is a derivative of the amino acid tryptophan and is a precursor to the neurotransmitter serotonin as well as the psychedelic drug DMT. Tryptamine has a variety of physiological and psychoactive effects, including acting as a neurotransmitter in the central nervous system, playing a role in regulating mood, and potentially influencing sleep and arousal. It is also known for its hallucinogenic properties and is sometimes used recreationally for its mind-altering effects. Tryptamine is a highly regulated substance in many countries due to its potential for abuse and its impact on mental health.

InChI:InChI=1/C10H12N2/c11-6-4-8-2-1-3-10-9(8)5-7-12-10/h1-3,5,7,12H,4,6,11H2

Upstream product

• 30933-66-5 4-(cyanomethyl)indole 
• 1074-85-7 (1H-indol-4-yl)methanol 
• 39830-66-5 methyl 1H-indole-4-carboxylate 
• 87149-48-2 4-(2-nitroethyl)-1H-indole 
• 49839-99-8 4-(2-nitroethenyl)-1H-indole 
• 1074-86-8 4-formyl indole 
• 49839-99-8 4-(2-nitrovinyl)indole 

Downstream Products

• 1217181-09-3 2,6,7,9,10,14b-hexahydroindolo[3',4':3,4,5]azepino[2,1-a]isoquinoline 
• 76149-15-0 4-<2-(N,N-di-n-propylamino)ethyl>indole 
• 94980-84-4 (2-indol-4-yl-ethyl)-methyl-amine 

Relevant articles and documents

Synthesis of 2-Oxindoles from Substituted Indoles by Hypervalent-Iodine Oxidation

A practical conversion of indoles into the corresponding 2-oxindoles is achieved efficiently using a hypervalent iodine reagent. This oxidation is amenable to different substituted indoles, and allows the synthesis of a wide range of synthetically valuable substituted 2-oxindoles in up to 90 % yield. Furthermore, Ropinirole, a drug used to alleviate the symptoms of Parkinson's disease, was synthesized in three steps in an overall yield of 44 % using this method.

Dopamine receptor ligands. Part 18: Modification of the structural skeleton of indolobenzazecine-type dopamine receptor antagonists

On the basis of the D1/5-selective dopamine antagonist LE 300 (1), an indolo[3,2-f]benzazecine derivative, we changed the annulation pattern of the heterocycles. The target compounds represent novel heterocyclic ring systems. The most constrained indolo[4,3a,3-ef]benzazecine 2 was inactive, but the indolo[4,3a,3-fg]benzazacycloundecene 3 showed antagonistic properties (functional Ca2+ assay) with nanomolar affinities (radioligand binding) for all dopamine receptor subtypes, whereas the indolo[2,3-f] benzazecine 4 displayed a selectivity profile similar to 3 but with decreased affinities.

Azepinoindole derivatives with high affinity for brain dopamine and serotonin receptors

We synthesized 20 and 21 as conformationally constrained analogues of the dopamine receptor antagonist SKF-83742, as well as analogues 6-9, 16, and 18-22. Although 20 and 21 were inactive, 7, 9, and 19 showed strong binding to D-1, D-2, S-2, and α-1 receptors, as well as antipsychotic activity in vivo.