46006-95-5

Usage

Uses

Used in Pharmaceutical Research:
2-(2,3-Dihydro-1H-indol-1-yl)ethanamine is used as a research chemical for investigating its psychoactive effects and potential therapeutic applications. Its agonistic action on the 5-HT2A receptor makes it a valuable tool in studying the receptor's role in various psychiatric and neurological conditions.
Used in Neurological and Psychiatric Treatment Research:
In the field of medicine, 2-(2,3-Dihydro-1H-indol-1-yl)ethanamine is used as a compound for exploring its potential in treating a range of disorders. Its effects on the 5-HT2A receptor suggest it may have utility in managing conditions such as depression, anxiety, and other mood disorders, although further research is necessary to confirm these possibilities.
Used in Psychedelic Therapy Research:
2-(2,3-Dihydro-1H-indol-1-yl)ethanamine is also used in the study of psychedelic therapy, where its hallucinogenic properties are being investigated for their potential to facilitate breakthroughs in psychotherapy, particularly for conditions that are resistant to conventional treatments.
Used in Toxicology and Abuse Potential Studies:
Given the concerns about the recreational use and potential for abuse, 2-(2,3-Dihydro-1H-indol-1-yl)ethanamine is utilized in toxicology research to understand its side effects and mechanisms of action, which can inform the development of strategies to mitigate risks associated with its use.

InChI:InChI=1/C10H14N2/c11-6-8-12-7-5-9-3-1-2-4-10(9)12/h1-4H,5-8,11H2

Upstream product

• 13708-58-2 2-indol-1-yl-ethylamine 
• 496-15-1 1-indoline 
• 689-98-5 chloroethylamine 
• 2576-47-8 2-bromoethylamine hydrobromide 

Downstream Products

• 13708-58-2 2-indol-1-yl-ethylamine 
• 345264-15-5 S-6-(tert-butoxycarbonyl)-5,6-dihydro-6H-[1,4]diazepino[6,7,1-hi]indole 
• 28740-91-2 1,2,3,4,6,7-hexahydro-[1,4]diazepino[6,7,1-hi]indole 

Relevant academic research and scientific papers

Development of Bisindole-Substituted Aminopyrazoles as Novel GSK-3β Inhibitors with Suppressive Effects against Microglial Inflammation and Oxidative Neurotoxicity

Development of glycogen synthase kinase-3β (GSK-3β) inactivation-centric agents with polypharmacological profiles is increasingly recognized as a promising therapeutic strategy against the multifactorial etiopathology of Alzheimer's disease (AD). In this respect, a series of disubstituted aminopyrazole derivatives were designed and synthesized as a new class of GSK-3β inhibitors. Most of these derivatives possess GSK-3β inhibitory activities with IC50 values in the micromolar ranges, among which bisindole-substituted aminopyrazole derivative 6h displayed moderate GSK-3β inhibition (IC50 = 1.76 ± 0.19 μM), and alleviative effects against lipopolysaccharide (LPS)-induced glial inflammation in BV-2 cells and glutamate-induced oxidative neurotoxicity in HT-22 cells. Further in vivo studies indicated that compound 6h had potent anti-inflammatory effect, by showing markedly reduced microglial activation and astrocyte proliferation in the brain of LPS-injected mice. Overall, the simultaneous modulation of 6h on multiple dysfunctions of disease network highlights this structural distinctively bisindole-substituted aminopyrazole could be a useful prototype for the discovery of novel therapeutic agents to tackle AD and other GSK-3β associated complex neurological syndromes.

Discovery of a lead series of potent benzodiazepine 5-HT2C receptor agonists with high selectivity in functional and binding assays

A series of potential new 5-HT2 receptor scaffolds based on a simplification of the clinically studied, 5-HT2CR agonist vabicaserin, were designed. An in vivo feeding assay early in our screening process played an instrumental part in the lead identification process, leading us to focus on a 6,5,7-tricyclic scaffold. A subsequent early SAR investigation provided potent agonists of the 5-HT2C receptor that were highly selective in both functional and binding assays, had good rat PK properties and that significantly reduced acute food intake in the rat.

Facile in Vitro Biocatalytic Production of Diverse Tryptamines

Tryptamines are a medicinally important class of small molecules that serve as precursors to more complex, clinically used indole alkaloid natural products. Typically, tryptamine analogues are prepared from indoles through multistep synthetic routes. In the natural world, the desirable tryptamine synthon is produced in a single step by l-tryptophan decarboxylases (TDCs). However, no TDCs are known to combine high activity and substrate promiscuity, which might enable a practical biocatalytic route to tryptamine analogues. We have now identified the TDC from Ruminococcus gnavus as the first highly active and promiscuous member of this enzyme family. RgnTDC performs up to 96 000 turnovers and readily accommodates tryptophan analogues with substituents at the 4, 5, 6, and 7 positions, as well as alternative heterocycles, thus enabling the facile biocatalytic synthesis of >20 tryptamine analogues. We demonstrate the utility of this enzyme in a two-step biocatalytic sequence with an engineered tryptophan synthase to afford an efficient, cost-effective route to tryptamines from commercially available indole starting materials.

Salts of 2- or 3-haloalkylamines in the synthesis of N-aminoalkyl derivatives of heterocyclic and aromatic amines

Reactions of 2-haloethyl- or 3-halopropylamine salts with NH-substrates (indoline, 1,2,3,4-tetrahydroquinoline, aniline, and N-ethylaniline) in the presence of NaHCO3 in water furnished various N-aminoalkyl derivatives of heterocyclic and aromatic amines.

Electrooxidative cyclization of hydroquinolyl alcohols, hydroquinolylamines, and dimethyl aminomalonates

Several hydroquinolyl alcohols and amines were electrochemically oxidized in methanol in the presence of sodium methoxide and potassium iodide to afford the corresponding intramolecular cyclization products. Furthermore, several amino malonates were electrochemically oxidized to yield the corresponding heterocyclic compounds through an intramolecular carbon-carbon bond formation in the presence of sodium cyanide in methanol. CSIRO 2007.

Discovery of SB-705498: A potent, selective and orally bioavailable TRPV1 antagonist suitable for clinical development

Small molecule antagonists of the vanilloid receptor TRPV1 (also known as VR1) are disclosed. Pyrrolidinyl ureas such as 8 and 15 (SB-705498) emerged as lead compounds following optimisation of the previously described urea SB-452533. Pharmacological studies using electrophysiological and FLIPR-Ca2+-based assays showed that compounds such as 8 and 15 were potent antagonists versus the multiple chemical and physical modes of TRPV1 activation (namely capsaicin, acid and noxious heat). Furthermore, 15 possessed suitable developability properties to enable progression of this compound into in vivo studies and subsequently clinical development.

Properties of Bis(trifluoroacetoxy)borane as a Reducing Agent of Organic Compounds

Reactions of bis(trifluoroacetoxy)borane-THF (1) with compounds containing representative organic functional groups were studied to determine the usefulness of 1 as a selective reducing agent.Reducible functionalities were indoles, ketones, aldehydes, imines, and compounds that readily generate carbocations in trifluoroacetic acid.Many functionalities were inert to 1.Epoxides and ortho esters suffered decomposition under the reaction conditions.Olefins and acetylenes were not hydroborated, and carboxylic acids were not reduced by 1.

Reduction of indole compounds to indoline compounds

A method for reducing indole compounds to the corresponding indoline compounds substantially free of undesirable side reactions is described. The method involves contacting an indole compound with a borane complex reagent in the presence of trifluoroacetic acid. The method is rapidly and readily carried out and provides an excellent method for preparing certain indoline compounds from the corresponding indole compounds. A novel dioxyborane useful as a borane reagent is also disclosed.