92579-89-0

Basic information

• Product Name: 1-(1H-indol-3-yl)-2-(piperidin-1-yl)ethane-1,2-dione
• Synonyms: 1-(1H-Indol-3-yl)-2-piperidin-1-yl-ethane-1,2-dione; 1,2-ethanedione, 1-(1H-indol-3-yl)-2-(1-piperidinyl)-
• CAS NO: 92579-89-0
• Molecular Formula: C₁₅H₁₆N₂O₂
• Molecular Weight: 256.2997
• Mol File: 92579-89-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 461.7°C at 760 mmHg
• Flash Point: 233°C
• Density: 1.277g/cm³
• Vapor Pressure: 1.05E-08mmHg at 25°C
• Refractive Index: 1.648
• CAS DataBase Reference: 1-(1H-indol-3-yl)-2-(piperidin-1-yl)ethane-1,2-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(1H-indol-3-yl)-2-(piperidin-1-yl)ethane-1,2-dione(92579-89-0)
• EPA Substance Registry System: 1-(1H-indol-3-yl)-2-(piperidin-1-yl)ethane-1,2-dione(92579-89-0)

Safety Data

• Hazardous Substances Data: 92579-89-0(Hazardous Substances Data)

Usage

Description

1-(1H-indol-3-yl)-2-(piperidin-1-yl)ethane-1,2-dione, also known as ALD-52, is a synthetic chemical compound belonging to the tryptamine family. It is structurally similar to LSD and is considered a prodrug of LSD, as it is believed to be metabolized into LSD within the body. ALD-52 is known for its hallucinogenic and psychoactive properties, featuring a chemical structure that includes a piperidine ring and an indole ring, which are common in many psychedelic compounds.

Uses

Used in Pharmaceutical Research:
ALD-52 is used as a research chemical for studying the effects of psychedelic substances on the human brain. Its structural similarity to LSD allows scientists to investigate the mechanisms of action and potential therapeutic applications of psychedelics in various mental health disorders.
Used in Recreational Settings:
ALD-52 is used recreationally for its mind-altering effects, providing users with hallucinogenic and psychoactive experiences. However, it is important to note that the recreational use of ALD-52 may pose risks to individual health and safety, as well as legal consequences.
Used in Chemical Synthesis:
As a synthetic compound, ALD-52 can be used as a starting material or intermediate in the synthesis of other related compounds with potential applications in pharmaceuticals, neuroscience research, and other fields.
Used in Analytical Chemistry:
ALD-52 can be employed as a reference compound in analytical chemistry for the development and validation of methods to detect and quantify psychedelic substances in various samples, such as biological fluids or forensic evidence.
Used in Toxicology Studies:
ALD-52 can be utilized in toxicology research to understand the potential risks and side effects associated with the use of psychedelic substances, contributing to the development of safer and more effective treatments for mental health disorders.

Upstream product

• 110-89-4 piperidine 
• 1477-49-2 3-indolylglyoxylic acid 
• 22980-09-2 indolyl-3-glyoxylyl chloride 
• 120-72-9 indole 

Downstream Products

• 26628-87-5 3-(2-(piperidin-1-yl)ethyl)-1H-indole 

Relevant articles and documents

Synthesis of thiazole linked indolyl-3-glyoxylamide derivatives as tubulin polymerization inhibitors

A series of thiazole linked indolyl-3-glyoxylamide derivatives were synthesized and evaluated for their in vitro cytotoxic activity against DU145 (prostate), PC-3 (prostate), A549 (lung) and HCT-15 (colon) cancer cell lines by employing the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Among all the synthesized compounds, compound 13d displayed cytotoxicity of IC50 = 93 nM towards DU145 cancer cell line. The most active compound 13d was also tested on RWPE-1 cells and was found to be safe compared to the DU145 cells. The target compounds were also evaluated for their inhibition activity of tubulin polymerization. Further, the treatment of compound 13d on DU145 cells led to the inhibition of cell migration ability. The detailed studies such as acridine orange/ethidium Bromide (AO/EB), DAPI, annexin V-FITC/propidium iodide staining assay suggested that the compound 13d induced apoptosis in DU145 cells. The influence of the cytotoxic compound 13d on the cell cycle distribution was assessed on the DU145 cell line, exhibiting a cell cycle arrest at the G2/M phase. Moreover, the treatment with compound 13d caused collapse of mitochondrial membrane potential and elevated intracellular ROS levels in DU145 cells. The results from molecular modelling studies revealed that these compounds bind at the colchicine binding site of the tubulin. Thus, this new molecular scaffold could be a new lead for the development of anticancer agents that target tubulin.

Sulfur rich 2-mercaptobenzothiazole and 1,2,3-triazole conjugates as novel antitubercular agents

A series of benzfused heterocyclic derivatives such as amide conjugates of 2-(benzo[d]thiazol-2-ylthio)acetic acid with aromatic/aliphatic/cyclic secondary amines (5a-5o & 8a-8m); 1,2,3-triazole conjugates of 2- mercaptobenzothiazoles and amide conjugates of indole-3-glyoxalic acid with cyclic secondary amines (14a-14g) have been synthesized and were screened for their antitubercular activity against Mycobacterium tuberculosis H37Rv strain by broth microdilution assay method. Compounds 8b, 8f, 8g and 8l inhibited the growth of the H37Rv strain at concentrations of 8 μg/mL. These compounds (8b, 8f, 8g and 8l) have been further identified as bactericidal and are completely killing the microbes at 32-64 μg/mL concentrations. Molecular docking studies of the active compounds reveal that these compounds are targeting DprE1 and may act as DprE1 inhibitors.