85696-95-3

Usage

Uses

Used in Pharmaceutical Industry:
1H-Indol-4-amine,1-methylis used as a precursor in the synthesis of various pharmaceutical compounds for its role in the production of serotonin and melatonin. These neurotransmitters and hormones are crucial for mood regulation, sleep patterns, and overall mental health.
Used in Neuroscientific Research:
In the field of neuroscientific research, 1H-Indol-4-amine,1-methylis utilized for studying the effects of neurotransmitters and neuromodulators on the central nervous system. Its role in mood regulation, cognition, and sleep makes it a valuable compound for understanding the complex interactions within the brain.
Used in Psychedelic Therapy:
1H-Indol-4-amine,1-methylis used as a component in psychedelic therapy, where its psychoactive effects are harnessed to facilitate deep introspection, emotional healing, and personal growth. It is being explored for potential use in the treatment of various mental health conditions, including depression, anxiety, and post-traumatic stress disorder (PTSD).
Used in Dietary Supplements:
As a naturally occurring compound, 1H-Indol-4-amine,1-methylis sometimes used in dietary supplements for its potential benefits in mood enhancement, cognitive function, and sleep regulation. However, it is essential to note that the use of tryptamine in supplements should be approached with caution due to its psychoactive properties and potential for misuse.
Used in Forensic Toxicology:
In forensic toxicology, 1H-Indol-4-amine,1-methylis analyzed to detect its presence in biological samples, such as blood or urine, to identify cases of drug abuse or intoxication. Its psychoactive effects and potential for misuse make it a relevant compound for toxicological analysis in legal and medical investigations.

InChI:InChI=1/C9H10N2/c1-11-6-5-7-8(10)3-2-4-9(7)11/h2-6H,10H2,1H3

Upstream product

• 91482-63-2 1-methyl-4-nitro-1H-indole 
• 85696-93-1 4-N-methylaminoindole 
• 4769-97-5 4-nitro-1H-indoIe 
• 603-83-8 3-nitro-o-tolylamine 
• 115118-93-9 N-(2-methyl-3-nitrophenyl)ethoxymethylenimine 

Downstream Products

• 852715-69-6 3-phenyl-3-(1-methylindol-4-ylamino)acrylic acid ethyl ester 
• 4375-14-8 octahydro-1H-indole 
• 13618-91-2 4,5,6,7-tetrahydroindole 
• 1429041-91-7 tert-butyl ((1S,2R)-2-(6-carbamoyl-5-(1-methyl-1H-indol-4-ylamino)-1,2,4-triazin-3-ylamino)cyclohexyl)carbamate 
• 1429041-90-6 ethyl 3-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-5-(1-methyl-1H-indol-4-ylamino)-1,2,4-triazine-6-carboxylate 
• 1438423-75-6 tert-butyl (1S,2R)-2-(5-cyano-6-(1-methyl-1H-indol-4-ylamino)pyrazin-2-ylamino)cyclohexylcarbamate 
• 1438419-29-4 5-((1R,2S)-2-aminocyclohexylamino)-3-(1-methyl-1H-indol-4-ylamino)pyrazine-2-carboxylic acid amide 
• 1438423-76-7 5-((1R,2S)-2-aminocyclohexylamino)-3-(1-methyl-1H-indol-4-ylamino)pyrazine-2-carbonitrile 
• 401916-34-5 2-[(1-methyl-1H-indol-4-yl)amino]-3-nitrobenzoic acid 

Relevant academic research and scientific papers

Regioselective Radical Arene Amination for the Concise Synthesis ofortho-Phenylenediamines

The formation of arene C-N bonds directly from C-H bonds is of great importance and there has been rapid recent development of methods for achieving this through radical mechanisms, often involving reactiveN-centered radicals. A major challenge associated with these advances is that of regiocontrol, with mixtures of regioisomeric products obtained in most protocols, limiting broader utility. We have designed a system that utilizes attractive noncovalent interactions between an anionic substrate and an incoming radical cation in order to guide the latter to the areneorthoposition. The anionic substrate takes the form of a sulfamate-protected aniline and telescoped cleavage of the sulfamate group after amination leads directly toortho-phenylenediamines, key building blocks for a range of medicinally relevant diazoles. Our method can deliver both free amines and monoalkyl amines allowing access to unsymmetrical, selectively monoalkylated benzimidazoles and benzotriazoles. As well as providing concise access to valuableortho-phenylenediamines, this work demonstrates the potential for utilizing noncovalent interactions to control positional selectivity in radical reactions.

Unexpected synthesis of azepino[4,3,2-cd]indoles from 4-aminoindoles

Unexpected regioselectivity for the Skraup-Doebner-Von Miller reaction was observed during the synthesis of quinolines from 4-aminoindoles and acetone in the presence of hydrochloric acid as a catalyst. The products were unambiguously assigned as 1-alkyl-

7H-PYRROLO[2,3-H]QUINAZOLINE COMPOUNDS, THEIR USE AS mTOR KINASE AND PI3 KINASE INHIBITORS, AND THEIR SYNTHESIS

A 7H-pyrrolo[2,3-h]quinazoline compound of the formula I wherein Ar, R1, R2, R7, R8, R9, R10, R11, R12, and n are as defined in the specification, and methods for maki

Synthesis and in vitro and in vivo antitumor activity of 2-phenylpyrroloquinolin-4-ones

In our search for potential new anticancer drugs, we designed and synthesized a series of tricyclic compounds containing the antimitotic 2-phenylazaflavone chromophore fused to a pyrrole ring in a pyrroloquinoline structure. Compounds 8, 18, 19, 22, 23, 25 and 26, when tested against a panel of fourteen human tumor cell lines, showed poor in vitro cytotoxic activity, whereas 20, 21 and 24 showed significant activity (IC50 0.7 to 50 μM). Steroid hormone-sensitive ovary, liver, breast and adrenal gland adenocarcinoma cell lines displayed the highest sensitivity (IC50 0.7 to 8 μM). Compound 24 blocked cells in the G2/M phase of the cell cycle and induced a significant increase in apoptotis. Compounds 20, 21 and 24 proved to alter microtubule assembly and stability, displaying a cytoplasmic microtubule network similar to that caused by Vincristine. In vivo, administration of compound 24 to Balb/c mice inhibited the growth of a syngenic hepatocellular carcinoma.

Discovery of a New Class of Anilinoquinazoline Inhibitors with High Affinity and Specificity for the Tyrosine Kinase Domain of c-Src

Deregulated activity of the nonreceptor tyrosine kinase c-Src is believed to result in signal transduction, cytoskeletal and adhesion changes, ultimately promoting a tumor-invasive phenotype. We report here the discovery of a new class of anilinoquinazoline inhibitors with high affinity and specificity for the tyrosine kinase domain of the c-Src enzyme. Special attention was directed toward finding inhibitors selective against KDR tyrosine kinase in order to ensure that the in vivo profile of a specific Src inhibitor could be determined. The 4-aminobenzodioxole quinazoline series gave compounds with excellent potency and selectivity. The most interesting compounds were evaluated in vivo and displayed good pharmacokinetics following oral dosing. Compounds such as the aminobenzodioxoles were shown to be potent inhibitors of tumor growth in a c-Src-transformed 3T3 xenograft model in vivo, resulting in more than 90% growth inhibition at doses as low as 6 mg/kg po once daily. Src tyrosine kinase inhibitors such as these may provide a novel therapeutic modality for targeting cancer invasion and metastasis.

Cell proliferation inhibitors

Compounds having formula (I) inhibit cellular proliferation. Processes for the preparation of the compounds, pharmaceutical compositions containing the compounds, and methods of treatment using the compounds are disclosed.

Methods for dyeing keratinous fibres with aminoindoles, compositions and devices for use

Method for dyeing keratinous fibres, in particular human keratinous fibres, such as hair, characterized in that a composition (A) containing, in a medium appropriate for dyeing, at least one aminoindole corresponding to the formula: STR1 in which: R1 and R3, independently of one another, represent a hydrogen atom or a C1 -C4 alkyl group; R2 denotes hydrogen or a C1 -C4 alkyl group or COOR', R' being a hydrogen atom or a C1 -C4 alkyl group; R4 represents a hydrogen atom or a C1 -C4 alkyl, C1 -C4 hydroxyalkyl or C2 -C4 polyhydroxyalkyl group; Z1 represents a hydrogen or halogen atom or a C1 -C4 alkyl group or OR; R being a hydrogen atom or a C1 -C4 alkyl group; and Z2 represents a hydrogen atom or a C1 -C4 alkyl group; and its salts is applied to said fibres, the colour being developed with the aid of an oxidizing system.

A SYNTHESIS OF (-)-INDOLACTAM V

(-)-Indolactam V (1) was synthesized in 14 steps from 2,6-dinitrotoluene in 15 percent overall yield via enantiospecific SN2 displacement of a chiral triflate with the 4-amino group of a 4-aminoindole and coupling of 3-bromomethylindole with Schoellkopf's asymmetric bislactim ether.

An Unexpected Rearrangement of 4-Alkylaminoindoles

4-Alkylaminoindoles rearrange in good yield to the corresponding 1-alkyl-4-aminoindoles in the presence of 10 molpercent hydrated toluene-p-sulphonic acid in boiling toluene.