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

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

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

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

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

Synthesis and study of pigment aggregation response of some melatonin derivatives

This study was performed to investigate the reactivity of melatonin towards various chemical reagents to produce new derivatives of melatonin containing extra- or fused heterocyclic systems such as the imidazoindole derivatives 3, 5, 6, the triazinoindole

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.

Compounds effective in the treatment of circadian rhythms and related disorders, the novel pharmaceutical preparations and novel method of application

The novel compounds of formula: STR1 in which R is isopropyl, cyclohexyl, phenyl, CH 3, Br or I; or H R 1 is CH 3 or cyclopropyl and R 2 is H or Br, and when R 1 is cyclopropyl and R 2 is H, R is other than H, and when R 1 is CH 3 and R 2 is H, R is other than H, and when R 1 is CH 3 and R 2 is H, R is other than I, and when R is CH 3 and R 2 is H, R 1 is other than CH 3, and when R is phenyl and R 2 is H, R 1 is other than CH 3, exhibit superior activity in the treatment of pathologies which interfere with the circadian rhythm. A novel method of preparation is described according to which the pharmaceutical compositions containing the novel compounds, as well as compounds already known, are administered transdermally. The novel method of administration results in sustained peripheral blood level. Novel pharmaceutical compositions are described suitable for transdermal administration.

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.