6650-04-0

Basic information

• Product Name: 2,3,4,9-Tetrahydro-1-isopropyl-1H-pyrido[3,4-b]indole
• Synonyms: 2,3,4,9-Tetrahydro-1-(1-methylethyl)-1H-pyrido[3,4-b]indole;2,3,4,9-Tetrahydro-1-isopropyl-1H-pyrido[3,4-b]indole;ICI-49455;1-isopropyl-2,3,4,9-tetrahydro-1H-beta-carboline(SALTDATA: FREE);1-isopropyl-2,3,4,9-tetrahydro-1H-beta-carboline
• CAS NO: 6650-04-0
• Molecular Formula: C₁₄H₁₈N₂
• Molecular Weight: 214.31
• Mol File: 6650-04-0.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 377.8°C at 760 mmHg
• Flash Point: 182.3°C
• Appearance: /
• Density: 1.088g/cm³
• Vapor Pressure: 6.58E-06mmHg at 25°C
• Refractive Index: 1.606
• CAS DataBase Reference: 2,3,4,9-Tetrahydro-1-isopropyl-1H-pyrido[3,4-b]indole(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,9-Tetrahydro-1-isopropyl-1H-pyrido[3,4-b]indole(6650-04-0)
• EPA Substance Registry System: 2,3,4,9-Tetrahydro-1-isopropyl-1H-pyrido[3,4-b]indole(6650-04-0)

Safety Data

• Hazardous Substances Data: 6650-04-0(Hazardous Substances Data)

Usage

Description

2,3,4,9-Tetrahydro-1-isopropyl-1H-pyrido[3,4-b]indole is a heterocyclic organic compound with a complex molecular structure. It is a tetrahydro derivative of a pyridoindole, with an isopropyl group attached to the carbon atom at position 1. 2,3,4,9-Tetrahydro-1-isopropyl-1H-pyrido[3,4-b]indole has potential biological activity and may have medicinal uses, particularly in the field of pharmacology.

Uses

Used in Pharmaceutical Industry:
2,3,4,9-Tetrahydro-1-isopropyl-1H-pyrido[3,4-b]indole is used as a starting material for the synthesis of new drugs. Its unique molecular structure and potential biological activity make it a promising candidate for the development of novel therapeutic agents.
Used in Research Applications:
2,3,4,9-Tetrahydro-1-isopropyl-1H-pyrido[3,4-b]indole is used as a research tool for studying the mechanisms of action of psychoactive substances. Its potential to interact with neurotransmitter receptors in the brain makes it of interest for understanding the effects of psychoactive drugs and for the development of new psychoactive drugs.

InChI:InChI=1/C14H18N2/c1-9(2)13-14-11(7-8-15-13)10-5-3-4-6-12(10)16-14/h3-6,9,13,15-16H,7-8H2,1-2H3

Upstream product

• 343-94-2 tryptamine hydochloride 
• 78-84-2 isobutyraldehyde 
• 65601-08-3 1-isopropyl-4,9-dihydro-3H-pyrido[3,4-b]indole 
• 61-54-1 tryptamine 
• 146560-30-7 C₁₄H₁₈N₂ 

Downstream Products

• 903437-40-1 1-isopropyl-2-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 
• 22314-95-0 1-isopropyl-9H- pyrido[3,4-b]indole 
• 335094-05-8 (1-isopropyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indol-2-yl)(phenyl)methanone 

Relevant articles and documents

Discovery of novel liver X receptor inverse agonists as lipogenesis inhibitors

Based on the co-crystal structures of LXRβ and its agonists (spiro [pyrrolidine-3,3′-oxindole] derivatives) discovered by us previously, we designed and synthesized a compound library to explore the agonistic activities. The library was screened with luciferase reporter assays, interestingly, it resulted in the discovery of 10 LXR inverse agonists besides 5 LXR agonists. To clarify the mechanism of the actions, we conducted molecular dynamics (MD) simulations on the LXR and inverse agonists complexes, and revealed that H3, H11 and H12 configurations are the key to turn on agonism or inverse agonism status for LXR. Binding tightly with H3, pushing H11 out and destabilizing H12 could form a bigger hydrophobic groove to accommodate NCOR1 to turn on LXR inverse agonism. The inverse agonist 10rr was further studied, and found as a lipogenesis inhibitor through down-regulating LXR target genes SREBP-1c, ACC, FAS and SCD-1, and demonstrated lipid-lowering effects in 3T3-L1 cells, HepG2 cells and mice with Triton WR-1339-induced hyperlipidemia. Therefore, we have proved that LXR inverse agonists can be promising agents for hyperlipidemia treatment.

TCCA-mediated oxidative rearrangement of tetrahydro-β-carbolines: Facile access to spirooxindoles and the total synthesis of (±)-coerulescine and (±)-horsfiline

Multi-reactive centered reagents are beneficial in chemical synthesis due to their advantage of minimal material utilization and formation of less by-products. Trichloroisocyanuric acid (TCCA), a reagent with three reactive centers, was employed in the synthesis of spirooxindoles through the oxidative rearrangement of various N-protected tetrahydro-β-carbolines. In this protocol, low equivalents of TCCA were required to access spirooxindoles (up to 99% yield) with a wide substrate scope. Furthermore, the applicability and robustness of this protocol were proven for the gram-scale total synthesis of natural alkaloids such as (±)-coerulescine (1) and (±)-horsfiline (2) in excellent yields.

Spiro (3,3'-isopropylpyrrolidineoxoindole) liver X receptor regulator and preparation method and application thereof

The invention relates to a spiro (3,3'-isopropyl pyrrolidineoxoindole) liver X receptor modifier and a preparation method and application thereof, particularly provides a compound which is a compoundshown in a formula (I), or a stereoisomer, a geometric i