142959-59-9

Basic information

• Product Name: 2-BROMOMELATONIN
• Synonyms: N-[2-(2-BROMO-5-METHOXY-1H-INDOL-3-YL)ETHYL]ACETAMIDE;2-BROMOMELATONIN;N-[2-(2-bromo-5-methoxy-1H-indol-3-yl)ethyl]ethanamide;N-Acetyl-2-broMo-5-MethoxytryptaMine;NSC 674637
• CAS NO: 142959-59-9
• Molecular Formula: C₁₃H₁₅BrN₂O₂
• Molecular Weight: 311.17
• EINECS: 604-604-1
• Product Categories: Agro Products;Agonist;Amines;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 142959-59-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 138-140°C
• Boiling Point: 556.8 °C at 760 mmHg
• Flash Point: 290.5 °C
• Appearance: yellow solid
• Density: 1.455 g/cm³
• Vapor Pressure: 1.96E-12mmHg at 25°C
• Refractive Index: 1.622
• Storage Temp.: -20°C Freezer
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly)
• CAS DataBase Reference: 2-BROMOMELATONIN(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMOMELATONIN(142959-59-9)
• EPA Substance Registry System: 2-BROMOMELATONIN(142959-59-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 142959-59-9(Hazardous Substances Data)

Usage

Description

2-Bromomelatonin is a melatonin agonist that exhibits high affinity for chicken brain membrane melatonin receptors, as demonstrated by its low Ki value of 0.031nM in a competition radioligand binding assay using 2-[125I]iodomelatonin. It is a yellow solid with unique chemical properties that make it suitable for various applications.

Uses

Used in Pharmaceutical Industry:
2-Bromomelatonin is used as a pharmaceutical agent for its high affinity to melatonin receptors. Its application in this industry is due to its potential role in modulating melatonin receptor activity, which can have implications for the treatment of various conditions related to melatonin dysregulation, such as sleep disorders, mood disorders, and certain neurological conditions.
Used in Research and Development:
2-Bromomelatonin is used as a research compound for studying the function and role of melatonin receptors in various biological processes. Its application in this field is due to its high affinity for melatonin receptors, making it a valuable tool for understanding the mechanisms of melatonin action and for the development of new drugs targeting these receptors.
Used in Veterinary Medicine:
2-Bromomelatonin is used as a veterinary medicine for the treatment of conditions in chickens and other animals that may be affected by melatonin receptor dysregulation. Its application in this industry is due to its high affinity for chicken brain membrane melatonin receptors, suggesting potential therapeutic benefits for animals with melatonin-related disorders.
Used in Drug Delivery Systems:
2-Bromomelatonin can be used as a component in drug delivery systems, particularly for targeting melatonin receptors. Its application in this field is due to its high affinity for these receptors, which could enhance the specificity and efficacy of drug delivery to cells expressing melatonin receptors, potentially improving treatment outcomes for various conditions.

InChI:InChI=1/C13H15BrN2O2/c1-8(17)15-6-5-10-11-7-9(18-2)3-4-12(11)16-13(10)14/h3-4,7,16H,5-6H2,1-2H3,(H,15,17)

Upstream product

• 214416-47-4 2,4-dibromomelatonin 
• 128-08-5 N-Bromosuccinimide 
• 73-31-4 5-methoxy-N-acetyl-tryptamine 
• 67199-10-4 methyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]carbamate 
• 180910-53-6 1-hydroxy-N_b-methoxycarbonyltryptamine 
• 180910-64-9 2,3-dihydro-Nb-methoxycarbonyltryptamine 
• 58635-45-3 methyl 2-(1-H-indol-3-yl)ethylcarbamate 
• 608-07-1 2-(5-methoxyindol-3-yl)ethylamine 

Downstream Products

• 151889-03-1 2-phenylmelatonin 

Relevant articles and documents

Substituted melatonin derivatives, process for their preparation, and methods of use

The invention provides 2 aryl substituted derivatives of melatonin. The invention further provides pharmaceutical compositions comprising such derivatives, methods for preparing such derivatives, and methods of using such derivatives to induce general ane

Syntheses of melatonin and its derivatives

Two simple synthetic methods for melatonin are newly developed from tryptamine through intermediates, which are promising lead compounds for drug developing research. Novel chemical reactivities of melatonin in its bromination, lithiation, and acylation are also reported.

Pharmaceutical compositions active in the therapy of sleep disorders

The present invention relates to new pharmaceutical compositions active in the therapy of sleep disorders comprising N-acetyl-5-methoxy-triptamine (melatonin) or one of its derivatives, preferably 2-iodo-N-acetyl-5-methoxy-triptamine (2-iodomelatonin), 2-bromo-N-acetyl-5-methoxy-triptamine (2-bromomelatonin), 2-chloro-N-acetyl-5-methoxy-triptamine (2-chloromelatonin) or 6-chloro-N-acetyl-5-methoxy-triptamine (6-chloromelatonin), at a dosage comprised between 10 and 100 mg, preferably comprised respectively between 20 and 80 mg between 10 and 20 mg and between 10 and 40 mg alone or in association with a benzodiazepinic derivative at a dosage comprised between 0.06 and 25 mg.