6-Chloromelatonin
Catalog Number: BT-253936
CAS Number: 63762-74-3
Molecular Formula: C13H15ClN2O2
Molecular Weight: 266.72 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
Product Introduction
Description
6-Chloromelatonin is a synthetic derivative of melatonin, a hormone produced by the pineal gland in the brain. It was first synthesized in 1997 by researchers at the University of Milan, Italy. Since then, it has gained attention for its potential therapeutic and environmental applications.
Properties
CAS Number
63762-74-3
Product Name
6-Chloromelatonin
IUPAC Name
N-[2-(6-chloro-5-methoxy-1H-indol-3-yl)ethyl]acetamide
Molecular Formula
C13H15ClN2O2
Molecular Weight
266.72 g/mol
InChI
InChI=1S/C13H15ClN2O2/c1-8(17)15-4-3-9-7-16-12-6-11(14)13(18-2)5-10(9)12/h5-7,16H,3-4H2,1-2H3,(H,15,17)
InChI Key
LUINDDOUWHRIPW-UHFFFAOYSA-N
SMILES
CC(=O)NCCC1=CNC2=CC(=C(C=C21)OC)Cl
Synonyms
N-[2-(6-Chloro-5-methoxyindol-3-yl)ethyl]acetamide
Canonical SMILES
CC(=O)NCCC1=CNC2=CC(=C(C=C21)OC)Cl
Method of Synthesis or Extraction
There are several methods of synthesizing 6-Chloromelatonin, including the reaction of melatonin with thionyl chloride, the reaction of melatonin with phosphorus oxychloride, and the reaction of melatonin with chlorosulfonic acid. The efficiency and yield of each method vary, with the reaction of melatonin with thionyl chloride being the most efficient and yielding the highest amount of 6-Chloromelatonin. However, all methods require careful handling of hazardous chemicals and should be performed in a well-ventilated area with appropriate safety equipment. Environmental considerations include the disposal of hazardous waste and the potential for air and water pollution.
Chemical Structure and Biological Activity
The chemical structure of 6-Chloromelatonin is similar to that of melatonin, with the addition of a chlorine atom at the 6-position of the indole ring. This modification alters the biological activity of the molecule, increasing its potency and selectivity for certain biological targets. The mechanism of action of 6-Chloromelatonin is similar to that of melatonin, acting as an agonist for melatonin receptors in the brain and peripheral tissues. It has been shown to have antioxidant, anti-inflammatory, and immunomodulatory effects, as well as the ability to regulate circadian rhythms and sleep-wake cycles.
Biological Effects
The biological effects of 6-Chloromelatonin on cell function and signal transduction are diverse and complex. It has been shown to modulate the activity of several signaling pathways, including the MAPK/ERK, PI3K/Akt, and NF-κB pathways. It also has the potential to affect gene expression and protein synthesis, leading to changes in cellular function and behavior. In terms of therapeutic and toxic effects, 6-Chloromelatonin has been studied for its potential use in treating various diseases, including cancer, neurodegenerative disorders, and sleep disorders. However, its toxicity and side effects are not well understood and require further investigation.
Applications
In medical research, 6-Chloromelatonin has been studied for its role in drug development, with several compounds based on its structure currently in clinical trials. It has also been investigated for its potential use in treating sleep disorders, cancer, and other diseases. In environmental research, 6-Chloromelatonin has been shown to have effects on ecosystems, including the regulation of seasonal reproduction in animals and the protection of plants from environmental stressors. It has also been studied for its potential use in pollution management and sustainability, with the ability to reduce the toxicity of pollutants and improve soil health. In industrial research, 6-Chloromelatonin has been used in manufacturing processes to improve product quality and efficiency, with health and safety considerations being a primary concern.
Future Perspectives and Challenges
The use and study of 6-Chloromelatonin face several challenges, including the need for further research into its toxicity and side effects, as well as the development of more efficient and sustainable methods of synthesis or extraction. However, the potential applications of 6-Chloromelatonin in medical, environmental, and industrial research are vast, with the ability to improve human health and well-being, protect the environment, and enhance industrial processes. Future trends and prospects in the application of 6-Chloromelatonin in scientific research will depend on continued research and development, as well as the ability to balance the benefits and risks of its use.
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