30218-58-7

Usage

Uses

Used in Pharmaceutical Industry:
5-Methylgramine is used as a potential therapeutic agent for mood enhancement and stimulation due to its psychoactive properties and its interaction with neurotransmitter systems like dopamine and serotonin.
Used in Antitumor Applications:
5-Methylgramine is used as a potential antitumor agent, with research indicating its potential to target and inhibit the growth of cancer cells.
Used in Antiviral Applications:
5-Methylgramine is used as a potential antiviral agent, with its properties being studied for possible use in treating viral infections.
Used in Neurological Disorders Treatment:
5-Methylgramine is used as a potential therapeutic agent for neurological disorders, given its effects on the central nervous system and its interaction with neurotransmitters.
Used in Research and Development:
5-Methylgramine is used in research and development for further exploration of its pharmacological effects, potential medical applications, and the development of novel drug delivery systems to enhance its therapeutic outcomes.

InChI:InChI=1/C12H16N2/c1-9-4-5-12-11(6-9)10(7-13-12)8-14(2)3/h4-7,13H,8H2,1-3H3

Upstream product

• 50-00-0 formaldehyd 
• 614-96-0 5-methyl-1H-indole 
• 124-40-3 dimethyl amine 

Downstream Products

• 951-55-3 5-methyl-DL-tryptophan 
• 114872-67-2 acetylamino-(5-methyl-indol-3-ylmethyl)-malonic acid diethyl ester 
• 65881-14-3 2-(5-methyl-1H-indol-3-yl)acetonitrile 
• 52562-50-2 5-methylindole-3-carboxaldehyde 

Relevant academic research and scientific papers

Rhodium-Catalyzed Stereoselective Cyclization of 3-Allenylindoles and N-Allenyltryptamines to Functionalized Vinylic Spiroindolenines

Herein, we report a highly enantio- and diastereoselective rhodium-catalyzed cyclization of N-allenyltryptamines and 3-allenylindoles to 6-membered spirocyclic indolenines. This allylic addition methodology offers the advantage of using a comparably cheap commercially available ligand with low loadings of an affordable rhodium precursor. The products can be converted into functionalized spirooxindoles and spiroindolines, which are regarded as important building blocks for the synthesis of a lot of natural products with biological activities.

Catalyst-Controlled Regiodivergence in Rearrangements of Indole-Based Onium Ylides

We have developed catalyst-controlled regiodivergent rearrangements of onium-ylides derived from indole substrates. Oxonium ylides formed in situ from substituted indoles selectively undergo [2,3]- and [1,2]-rearrangements in the presence of a rhodium and a copper catalyst, respectively. The combined experimental and density functional theory (DFT) computational studies indicate divergent mechanistic pathways involving a metal-free ylide in the rhodium catalyzed reaction favoring [2,3]-rearrangement, and a metal-coordinated ion-pair in the copper catalyzed [1,2]-rearrangement that recombines in the solvent-cage. The application of our methodology was demonstrated in the first total synthesis of the indole alkaloid (±)-sorazolon B, which enabled the stereochemical reassignment of the natural product. Further functional group transformations of the rearrangement products to generate valuable synthetic intermediates were also demonstrated.

I2-induced cascade cyclization and dearomatization of indoles for the highly efficient synthesis of iodinated and vinylic spiroindolenines

The spiroindolenine framework is a privileged heterocyclic motif and is widely present in numerous indole alkaloids. Herein, we develop a metal-free and environmentally friendly approach for the intramolecular cascade cyclization and dearomatization of indole derivatives to selectively afford iodinated and vinylic spiroindolenines by a substrate-controlled strategy. Simple operation, mild conditions, and high yield make this strategy a green and attractive pathway to construct functionalizable spiroindolenine scaffolds, which could be converted into diverse useful spiroindolenine derivatives.

Rhodium-Catalyzed Enantioselective Cyclization of 3-Allenyl-indoles: Access to Functionalized Tetrahydrocarbazoles

A highly selective rhodium-catalyzed cyclization of tethered 3-allenylindoles is reported. In a smooth reaction, 1-vinyltetrahydrocarbazoles are obtained in excellent yields and enantioselectivities. Aside from a great functional group tolerance, this method requires neither the Schlenk technique nor the use of anhydrous solvents. Preliminary mechanistic investigations proved that the reaction proceeds via an intermediary formed spiroindolenine which rapidly undergoes an acid-catalyzed stereospecific migration.

Rhodium-Catalyzed Diastereo- And Enantioselective Tandem Spirocyclization/Reduction of 3-Allenylindoles: Access to Functionalized Vinylic Spiroindolines

A highly selective rhodium-catalyzed tandem spirocyclization/reduction of 3-allenylindoles is reported. By employing a Hantzsch ester as reductant, vinylic spiroindolines are obtained in excellent yields as well as diastereo- and enantioselectivity. In addition, the reaction's synthetic utility is highlighted by broad functional group compatibility and exemplified by a gram scale reaction with subsequent assorted transformations.

Enantioselective gold-catalyzed allylic alkylation of indoles with ALcohols: An efficient route to functionalized tetrahydrocarbazoles

[Chemical equation presented] Breaking the taboo: The direct use of allylic alcohols in catalytic and enantioselective Friedel-Crafts alkylation is described for the first time In the presence of chiral gold complexes. This intramolecular Friedel-Crafts reaction was used to prepare a broad range of functionalized tetrahydrocarbazoles (see scheme; X=Me, F, Br, Cl, OMe; R=Me, Et, tBu; R′=H, Me).