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

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

Uses

Used in Pharmaceutical Industry:
1H-Indole-4-ethanamine is used as a precursor in the synthesis of various pharmaceutical compounds for its role in the production of serotonin and other related substances. Its involvement in neurotransmission makes it a key component in the development of medications targeting mood disorders and other neurological conditions.
Used in Research Applications:
In the scientific community, 1H-Indole-4-ethanamine is utilized as a research tool to study the effects of neurotransmitters on the central nervous system, particularly in the context of mood regulation, sleep, and arousal. Its psychoactive properties also make it valuable for investigating the mechanisms of hallucinogenic substances and their impact on cognitive and perceptual processes.
Used in Forensic and Toxicological Analysis:
Due to its status as a regulated substance with potential for abuse, 1H-Indole-4-ethanamine is employed in forensic and toxicological analyses to detect and monitor its presence in biological samples. This helps in identifying cases of substance abuse and supporting legal and medical interventions.
Used in Recreational Settings:
Although not a recommended or legal application in many jurisdictions, 1H-Indole-4-ethanamine is sometimes used recreationally for its hallucinogenic and mind-altering effects. Its use in this context, however, carries significant risks related to health and safety, and is subject to strict regulation and control.

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

Downstream Products

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

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.

4-Indolyl-N-hydroxyphenylacrylamides as potent HDAC class I and IIB inhibitors in?vitro and in?vivo

A series of 4,5-indolyl-N-hydroxyphenylacrylamides, as HDAC inhibitors, has been synthesized and evaluated in?vitro and in?vivo. 4-Indolyl compounds 13 and 17 functions as potent inhibitors of HDAC1 (IC50 1.28?nM and 1.34?nM) and HDAC 2 (ICsub

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.

PROCESS FOR THE PREPARATION OF ROPINIROLE

A new process for the preparation of Ropinirole (1) and pharmaceutically acceptable hydrochloride salt thereof comprising reacting the compound V with nitromethane to obtain the compound of formula 11, which is reduced to compound III and alkylated to obtain compound IV. The oxidation of the indole ring provides the compound of formula (I).

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.

1,9-Alkano-Bridged 2,3,4,5-Tetrahydro-1H-3-benzazepines with Affinity for the α2-Adrenoceptor and the 5-HT1A Receptor

A number of 1,9-alkano-bridged 2,3,4,5-tetrahydro-1H-3-benzazepines were prepared and evaluated for 5-HT1A receptor and α2-adrenoceptor affinity by using radioligand receptor binding techniques.Several compounds displayed 5-HT1A receptor affinity comparable to, or greater than, the known 5-HT1A ligand buspirone.The highest affinity 5-HT1A receptor ligands were N-alkyl-, N-allyl-5-chloro-, and 5-methoxy-1,2,3,4,8,9,10,10a-octahydronaphthazapines (4c, 4m, 4n), which had pKi values of 7.9-8.1.The S enantiomer of 4c had a higher affinity for the 5-HT1A receptor than the corresponding R isomer (pKi of 8.2 for (S)-4c vs 7.7 for (R)-4c).These compounds had a relatively low affinity for the α2-adrenoceptor (pKi of 7 or less).On the other hand, the closely related 5-chloro-2-methyl-2,3,4,8,9,9a-hexahydro-1H-indenoazepine (3b) had high affinity for both the α2-adrenoceptor (pKi=8.1) and 5-HT1A receptor (pKi=7.6).These results indicate that the two receptors may share common recognition sites.