123500-70-9

Basic information

• Product Name: (1H-indol-2-yl)-pyrrolidin-1-yl-methanone
• Synonyms: (1H-indol-2-yl)-pyrrolidin-1-yl-methanone;1H-indol-2-yl-1-pyrrolidinylmethanone
• CAS NO: 123500-70-9
• Molecular Formula: C₁₃H₁₄N₂O
• Molecular Weight: 214
• Mol File: 123500-70-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1H-indol-2-yl)-pyrrolidin-1-yl-methanone(CAS DataBase Reference)
• NIST Chemistry Reference: (1H-indol-2-yl)-pyrrolidin-1-yl-methanone(123500-70-9)
• EPA Substance Registry System: (1H-indol-2-yl)-pyrrolidin-1-yl-methanone(123500-70-9)

Safety Data

• Hazardous Substances Data: 123500-70-9(Hazardous Substances Data)

Usage

Uses

Used in Recreational Drug Industry:
2-AI is used as a recreational drug for its stimulant and entactogenic effects. It is known to provide feelings of euphoria, increased energy, and heightened sensory perception due to its action as a serotonin and dopamine reuptake inhibitor.
However, it is important to note that 2-AI also has the potential for negative side effects such as increased heart rate, hypertension, and in some cases, more serious health issues. Therefore, its use is not recommended without proper medical supervision and should be approached with caution.

Upstream product

• 123-75-1 pyrrolidine 
• 1477-50-5 Indole-2-carboxylic acid 
• 120-94-5 1-Methylpyrrolidine 
• 188837-56-1 pentafluorophenyl 1H-indole-2-carboxylate 
• 58881-45-1 Indole-2-carbonyl chloride 

Downstream Products

• 921194-90-3 2-(pyrrolidine-1-carbonyl)-1H-indole-3-carboxylic acid 
• 1374453-99-2 1-{4-[3-chloro-2-(pyrrolidine-1-carbonyl)-indol-1-yl]-phenyl}-ethanone 
• 1374454-00-8 {1-[4-(1-amino-ethyl)-phenyl]-3-chloro-1H-indol-2-yl}-pyrrolidin-1-yl-methanone 
• 1374453-97-0 1-(2,2,2-trifluoro-acetylamino)-cyclopropanecarboxylic acid (1-{4-[3-chloro-2-(pyrrolidine-1-carbonyl)-indol-1-yl]-phenyl}-ethyl)-amide 

Relevant articles and documents

A Fast and General Route to Ketones from Amides and Organolithium Compounds under Aerobic Conditions: Synthetic and Mechanistic Aspects

We report that the nucleophilic acyl substitution reaction of aliphatic and (hetero)aromatic amides by organolithium reagents proceeds quickly (20 s reaction time), efficiently, and chemoselectively with a broad substrate scope in the environmentally responsible cyclopentyl methyl ether, at ambient temperature and under air, to provide ketones in up to 93 % yield with an effective suppression of the notorious over-addition reaction. Detailed DFT calculations and NMR investigations support the experimental results. The described methodology was proven to be amenable to scale-up and recyclability protocols. Contrasting classical procedures carried out under inert atmospheres, this work lays the foundation for a profound paradigm shift of the reactivity of carboxylic acid amides with organolithiums, with ketones being straightforwardly obtained by simply combining the reagents under aerobic conditions and with no need of using previously modified or pre-activated amides, as recommended.

Discovery of a Novel Class of Negative Allosteric Modulator of the Dopamine D2 Receptor Through Fragmentation of a Bitopic Ligand

Recently, we have demonstrated that N-((trans)-4-(2-(7-cyano-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)cyclohexyl)-1H-indole-2-carboxamide (SB269652) (1) adopts a bitopic pose at one protomer of a dopamine D2 receptor (D2R) dimer to negatively modulate the binding of dopamine at the other protomer. The 1H-indole-2-carboxamide moiety of 1 extends into a secondary pocket between the extracellular ends of TM2 and TM7 within the D2R protomer. To target this putative allosteric site, we generated and characterized fragments that include and extend from the 1H-indole-2-carboxamide moiety of 1. N-Isopropyl-1H-indole-2-carboxamide (3) displayed allosteric pharmacology and sensitivity to mutations of the same residues at the top of TM2 as was observed for 1. Using 3 as an "allosteric lead", we designed and synthesized an extensive fragment library to generate novel SAR and identify N-butyl-1H-indole-2-carboxamide (11d), which displayed both increased negative cooperativity and affinity for the D2R. These data illustrate that fragmentation of extended compounds can expose fragments with purely allosteric pharmacology.

Energy-efficient green catalysis: Supported gold nanoparticle-catalyzed aminolysis of esters with inert tertiary amines by C-O and C-N bond activations

Catalyzed by supported gold nanoparticles, an aminolysis reaction between various aryl esters and inert tertiary amines by C-O and C-N bond activations has been developed for the selective synthesis of tertiary amides. Comparison studies indicated that the gold nanoparticles could perform energy-efficient green catalysis at room temperature, whereas Pd(OAc)2 could not.

Indol-3-yl-carbonyl-piperidin-benzoimidazol derivatives

The present invention relates to Indol-3-yl-carbonyl-piperidin-benzoimidazol derivatives which act as V1a receptor antagonists and which are represented by Formula I: wherein the residues R1 to R7 are as defined herein. The invention