117946-91-5

Basic information

• Product Name: LUZINDOLE
• Synonyms: N-ACETYL-2-BENZYLTRYPTAMINE;N-0774;LUZINDOLE;n-[2-[2-(phenylmethyl)-1h-indol-3-yl]ethyl]acetamide;N-[2-[2-(Phenylmethyl)-1H-indol-3-yl]ethyl]acetamide, N-Acetyl-2-benzyltryptamine;LuzindoleN-Acetyl-2-benzyltryptamine;N-(2-(2-benzyl-1H-indol-3-yl)ethyl)acetamide;2-Benzyl-N-acetyltryptaMine
• CAS NO: 117946-91-5
• Molecular Formula: C₁₉H₂₀N₂O
• Molecular Weight: 292.37
• Product Categories: Aromatics Compounds;Aromatics;Melatonin receptor
• Mol File: 117946-91-5.mol

Chemical Properties

• Melting Point: 44-46°C
• Boiling Point: 434.31°C (rough estimate)
• Flash Point: 292.2°C
• Appearance: /
• Density: 1.1045 (rough estimate)
• Vapor Pressure: 1.49E-12mmHg at 25°C
• Refractive Index: 1.6140 (estimate)
• Storage Temp.: −20°C
• Solubility: DMSO: 5 mg/mL
• PKA: 16.36±0.46(Predicted)
• Water Solubility: Soluble in DMSO (100 mM), ethanol (100 mM), chloroform, methanol, and water.
• Stability: Store at -20°C
• CAS DataBase Reference: LUZINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: LUZINDOLE(117946-91-5)
• EPA Substance Registry System: LUZINDOLE(117946-91-5)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: AC7765700
• Hazardous Substances Data: 117946-91-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
LUZINDOLE is used as a research compound for studying the roles of melatonin receptor signaling in various pathways, including circadian rhythms, animal behavior, and melanophore response. It is particularly useful in both in vitro and in vivo experiments to evaluate the functions of melatonin receptor signaling.
Used in Pain Management Research:
LUZINDOLE is used as an antagonist in the study of melatonin-mediated antinociception, suggesting that MEL-1B-R plays a role as a mediator of melatonin modulation of pain signaling. This application aids in understanding the underlying mechanisms of pain relief and the potential therapeutic applications of melatonin receptor antagonists.
Used in Anticancer Applications:
Although not explicitly mentioned in the provided materials, LUZINDOLE has been studied for its potential use in cancer research, particularly in the context of understanding the role of melatonin receptors in tumor growth and progression. Further research may reveal its potential applications in this field.

Biological Activity

Melatonin antagonist.

Biochem/physiol Actions

Luzindole is a melatonin (mel) receptor antagonist. It has higher affinity towards the Mel 1b receptor than the Mel 1a receptor subtype.

InChI:InChI=1/C19H20N2O/c1-14(22)20-12-11-17-16-9-5-6-10-18(16)21-19(17)13-15-7-3-2-4-8-15/h2-10,21H,11-13H2,1H3,(H,20,22)

Upstream product

• 61-54-1 tryptamine 
• 3790-45-2 1-phenyl-2,3,4,9-tetrahydro-1H-beta-carboline 
• 100-52-7 benzaldehyde 
• 3584-41-6 1-(1-phenyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indol-2-yl)ethan-1-one 
• 108-88-3 toluene 
• 221044-05-9 N-(2-pyrimidyl)indole 
• 3377-72-8 2-benzylindole 
• 142-26-7 2-acetylaminoethanol 
• 62005-48-5 N-acetylaminoacetaldehyde dimethyl acetal 

Relevant articles and documents

Iodine-Catalyzed Metal-Free Oxidative Ring Opening of 1-Aryltetrahydro-β-carbolines: Facile Synthesis of C-2 Aroyl and Aryl Methanimino Indole Derivatives

Indole derivatives bearing C-2 substituents have garnered a lot of attention due to their diverse biological activities. Various methods forthe synthesis of these compounds have been reported. Inspired by the hydrolysis of imines, an oxidative ring-opening reaction of 1-aryltetrahydro-β-carbolines with catalytic iodine in aqueous hydrogen peroxide, and also in the presence of appropriate amines, is described for the generation of 2-aroyl and arylmethanimine indole derivatives. The reaction proceeds under mild reaction conditions with ethanol as the solvent or under solvent-free conditions, respectively. This metal-free strategy facilitates the formation of the desired substituted C-2 indoles in moderate to excellent yields. The utility of this reaction is demonstrated by a facile multigram-scale synthesis of Luzindole, a selective melatonin receptor antagonist and an investigational drug against depression and disruption of the circadian rhythm.

Nickel-Catalyzed C(sp2)-H/C(sp3)-H Oxidative Coupling of Indoles with Toluene Derivatives

Nickel-catalyzed oxidative C(sp2)-H/C(sp3)-H coupling of indoles with toluene derivatives is successfully achieved in the presence of 2-iodobutane as the oxidant. This method allows the selective C-2 benzylation of indoles with toluene derivatives over the alkylation with 2-iodobutane and permits the coupling of diversified indoles via the monochelation assistance. The reaction proceeded through a single-electron-transfer (SET) process, wherein both the C-H nickelation of indole and the C-H activation of toluene derivatives have a significant effect on the entire reaction rate. The synthetic utility of this nickel-catalyzed protocol is demonstrated by the facile removal of the directing group and by the convenient synthesis of the melatonin receptor antagonist Luzindole derivatives.

Iridium-catalyzed direct synthesis of tryptamine derivatives from indoles: Exploiting N-protected β-amino alcohols as alkylating agents

The selective C3-alkylation of indoles with N-protected ethanolamines involving the "borrowing hydrogen" strategy is described. This method provides convenient and sustainable access to several tryptamine derivatives.

Synthesis of tryptamine derivatives via a direct, one-pot reductive alkylation of indoles

An efficient, one-pot reductive alkylation of indoles with N-protected aminoethyl acetals in the presence of TES/TFA is reported. It represents the first general method for the direct synthesis of tryptamine derivatives from indoles and nitrogen-functionalized acetals. This convergent and versatile approach employs safe and inexpensive reagents, proceeds under mild conditions, and tolerates several functional groups. The new procedure was efficiently applied to a gram-scale synthesis of both luzindole, a reference MT2-selective melatonin receptor antagonist, and melatonin.

2-ARYL SUBSTITUTED N-ACETYLTRYPTAMINES AND PROCESS OF PREPARING SUCH

This invention relates to novel melatonin derivatives, such as 2-aryl substituted N-acetyltryptamines, having pharmacological activity, e.g., melatonin antagonist activity, and methods for the synthesis thereof.

Compounds useful as antiproliferative agents

Melatonin compounds are disclosed of the formula STR1 where R is hydrogen or C1 to C6 linear or branched alkylene substituted with phenyl; R1 is hydrogen, substituted benzyl, naphthylmethyl or taken together with R2/

ANTIDEPRESSANT AGENTS

2-aryl substituted N-acetyl tryptamines are utilized as antidepressant agents.