3671-00-9

Usage

Uses

Used in Research Applications:
3-(1-Methyl-3-pyrrolidinyl)-1H-indole is used as a research chemical for studying the effects of psychoactive substances on the central nervous system. Its high affinity for the 5-HT2A, 5-HT2C, and 5-HT2B receptors makes it a valuable tool for investigating the mechanisms of action and potential therapeutic applications of psychedelic drugs.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 3-(1-Methyl-3-pyrrolidinyl)-1H-indole is used as a lead compound for the development of new medications targeting the serotonergic system. Its potent agonist activity at the 5-HT2A receptor and related receptors may offer insights into the treatment of various mental health disorders and neurological conditions.
Used in Forensic Toxicology:
3-(1-Methyl-3-pyrrolidinyl)-1H-indole is utilized in forensic toxicology as a reference substance for the identification and analysis of designer drugs and new psychoactive substances. Its presence in biological samples can be detected using various analytical techniques, aiding in the investigation of drug-related crimes and public health concerns.

InChI:InChI=1/C13H16N2/c1-15-7-6-10(9-15)12-8-14-13-5-3-2-4-11(12)13/h2-5,8,10,14H,6-7,9H2,1H3

Upstream product

• 3670-94-8 3-(1H-indole-3-yl)-1-methylpyrrolidine-2,5-dione 
• 10184-94-8 (3-Indolyl)bernsteinsaeure 
• 120-72-9 indole 
• 930-88-1 N-methylmaleimide 

Relevant academic research and scientific papers

Synthesis and structure activity relationship of rigidized indolyl pyrrolidine derivatives as 5-HT6 receptor ligands

A novel series of rigidized indolyl pyrrolidine derivatives have been designed by constraining the tryptamine nitrogen through a and b carbons. All the synthesized derivatives have shown moderate affinities at 5-HT6R when tested in in vitro binding assay.

Rigidized 1-aryl sulfonyl tryptamines: Synthesis and pharmacological evaluation as 5-HT6 receptor ligands

A series of N1-arylsulfonyl-3-(pyrrolidin-3-yl)-1H-indole and N1-arylsulfonyl-3-(4-chloro-2,5-dihydro-1H-pyrrol-3-yl)-1H-indole derivatives (tryptamine derivatives with rigidized side chain) have been prepared and tested for their binding affinity to 5-HT6 receptor. Several compounds displayed potent binding affinity for the 5-HT6 receptor when tested in in vitro binding assay. The primary SAR indicates that rigidification of dimethylamino alkyl chain at C3 of indole carbon maintains the binding affinity to 5-HT6R. The lead compound N 1-benzenesulfonyl-3-(4-chloro-1-methyl-2,5-dihydro-1H-pyrrol-3-yl) -1H-indole, 10a (Kb = 0.1 nM) has shown excellent in vitro affinity and was active in animal models of cognition like NORT and water maze.

Conformationally constrained N1-arylsulfonyltryptamine derivatives as 5-HT6 receptor antagonists

Several series of conformationally constrained N1- arylsulfonyltryptamine derivatives were prepared and tested for 5-HT6 receptor binding affinity and ability to modulate cAMP production in a cyclase assay. The 3-piperidin-3-yl-, 3-(1-methylpyrrolidin-2-ylmethyl)-, and 3-pyrrolidin-3-yl-1H-indole arrays (8-13) appear to be able to adopt a conformation that allows high affinity 5-HT6 receptor binding, while the β-carboline array 14 binds with a significantly weaker (10- to 100-fold) affinity. N1-Benzenesulfonyl-3-piperidin-3-yl-1H-indole 9a is a high affinity full agonist with EC50 = 24 nM. Several of the N1-arylsulfonyl-3-(1-methylpyrrolidin-2-ylmethyl)-1H-indole derivatives behave as very potent antagonists ((S)-11r, (S)-11t; IC50 = 0.8, 1.0 nM).

3-(PYROLIDIN-3-L) INDOLES AS 5-HT6 RECEPTOR MODULATORS

The present invention describes 3-(Heterocyclic)indoles with the Formula (I), its stereoisomers and salts, wherein the substituents such as R, R1, R2, R3, R4, R10, R11, R12, R13, and R14 are described in the specification. The invention also provides a method to prepare compound with formula (I), pharmaceutical composition containing such compounds and method to manufacture a medicament. These compounds are useful in the treatment of various CNS disorders, hematological disorders, eating disorders, diseases associated with pain, respiratory disease, genito-urological disorders, cardio vascular diseases and cancer.

Heterocyclylindazole and -azaindazole compounds as 5-hydroxytryptamine-6 ligands

The present invention provides a compound of formula I and the use thereof in the therapeutic treatment of disorders related to or affected by the 5-HT6 receptor.

A direct synthesis of 3-(pyrrolidin-3-yl)indoles for use as conformationally restricted analogs of tryptamines

An efficient, two step synthesis of-(pyrrolidin-3-yl)indoles 4 is described. Indoles react with maleimides in refluxing acetic acid affording 3-(indol-3-yl)succinimides 6. Reaction times and yields depend on the substituents on the indole 5. Direct reduct