343-93-1

Usage

Uses

Used in Pharmaceutical Industry:
6-Fluorogramine is used as a potential pharmaceutical compound for its bioactive properties. The presence of the fluorine atom may enhance the compound's reactivity and interaction with biological systems, making it a candidate for the development of new drugs.
Used in Psychoactive Drug Research:
6-Fluorogramine is used as a research chemical in the field of psychoactive drugs. The tryptamine structure, along with the fluorine atom, may contribute to its psychoactive effects, making it a subject of interest for scientists studying the effects of such compounds on the human brain and behavior.

InChI:InChI=1/C11H13FN2/c1-14(2)7-8-6-13-11-5-9(12)3-4-10(8)11/h3-6,13H,7H2,1-2H3

Upstream product

• 399-51-9 6-fluoro-1H-indole 
• 50-00-0 formaldehyd 
• 124-40-3 dimethyl amine 
• 462-95-3 formaldehyde diethyl acetal 

Downstream Products

• 2341-25-5 2-(6-fluoro-1H-indol-3-yl)acetonitrile 
• 467458-02-2 [2-(6-fluoro-1H-indol-3-yl)ethyl]({[3-(2,2,3,3-tetrafluoropropoxy)phenyl]methyl})amine HCl salt 
• 61-54-1 tryptamine 
• 575-85-9 6-fluorotryptamine 
• 443-75-4 2-(6-fluoro-1H-indol-3-yl)acetic acid 

Relevant academic research and scientific papers

Synthesis and Preclinical Evaluation of 6-[18F]Fluorine-α-methyl- l -tryptophan, a Novel PET Tracer for Measuring Tryptophan Uptake

The positron emission tomography (PET) radioligand α-[11C]methyl-l-tryptophan ([11C]AMT) has been used to assess tryptophan metabolism in cancer, epilepsy, migraine, and autism. Despite its extensive application, the utility of this tracer is currently hampered by the short half-life of the radionuclide used for its labeling (11C, t1/2 = 20.4 min). We herein report the design, synthesis, radiolabeling, and initial in vivo evaluation of a fluorine-18 (18F, t1/2 = 109.7 min) labeled analogue that is fluorinated in the 6-position of the aromatic ring ([18F]6-F-AMTr). In a head-to-head comparison between [18F]6-F-AMTr and [11C]AMT in mice using PET, peak brain radioactivity, regional brain distribution, and kinetic profiles were similar between the two tracers. [18F]6-F-AMTr was however not a substrate for IDO1 or TPH as determined in in vitro enzymatic assays. The brain uptake of the tracer is thus more likely related to LAT1 transport over the blood-brain barrier than metabolism along the serotonin or kynurenine pathways.

General Synthesis of Unsymmetrical 3,3′-(Aza)diindolylmethane Derivatives

Diindolylmethane (DIM) and its derivatives have recently been in the focus of interest due to their significant biological activities, specifically in cancer prevention and therapy. Molecular targets of DIM have been identified, e.g., the immunostimulatory G protein-coupled receptor GPR84. However, most of the reported and investigated DIM derivatives are symmetrical because general methods for obtaining unsymmetrical DIMs have been lacking. To optimize the interaction of DIM derivatives with their protein targets, unsymmetrical substitution is required. In the present study we developed a new, mild and efficient access to unsymmetrically substituted 3,3′-DIMs by reaction of (3-indolylmethyl)trimethylammonium iodides with a wide range of substituted indole derivatives. 7-Azaindole also led to the 3,3′-connected DIM analogue, while 4- and 5-azaindoles reacted at the N1-nitrogen atom as confirmed by X-ray crystallography. The reactions were performed in water without the requirement of a catalyst or other additives. Wide substrate scope, operational simplicity, environmentally benign workup, and high yields are further advantages of the new method. The synthetic protocol proved to be suitable for upscaling to yield gram amounts for pharmacological studies. This procedure will allow the preparation of a broad range of novel, unsymmetrical DIM derivatives to exploit their potential as novel drugs.

PROCESS FOR THE MANUFACTURE OF IDALOPIRDINE

Disclosed herein is a process for the preparation of idalopirdine and pharmaceutically acceptable salts thereof.

Ru-catalysed C-H silylation of unprotected gramines, tryptamines and their congeners

Selective Ru-catalysed C2-H silylation of heteroarenes is presented. The transformation works with or without directing group assistance and requires no protecting groups. Gramines and tryptamines may be converted efficiently whilst avoiding deleterious elimination side-reactions. Mechanistic studies reveal an unusual activation of the indole C4-H bond by an electron-rich metal.

PROCESSES FOR THE MANUFACTURE OF A PHARMACEUTICALLY ACTIVE AGENT

Disclosed herein are processes for the preparation of a pharmaceutically active agent and pharmaceutically acceptable salts thereof.

1,2,3,6-TETRAHYDROAZEPINO[4,5-B]INDOLE-5-CARBOXYLATE NUCLEAR RECEPTOR INHIBITORS

Provided are certain 1,2,3,6- tetrahydroazepino[4,5-b]indole-5-carboxylate compounds which are useful for modulating the activity of nuclear receptors, such as farnesoid X receptors, and/or for the treatment, prevention, or amelioration diseases or disorders related to the activity of these receptors.