66012-82-6

Usage

InChI:InChI=1/C14H18N2O2/c1-3-14(17)15-7-6-10-9-16-13-5-4-11(18-2)8-12(10)13/h4-5,8-9,16H,3,6-7H2,1-2H3,(H,15,17)

Upstream product

• 608-07-1 2-(5-methoxyindol-3-yl)ethylamine 
• 802294-64-0 propionic acid 
• 123-62-6 propionic acid anhydride 
• 61675-19-2 5-methoxy-3-(2-nitroethylenyl)-1H-indole 
• 66-83-1 5-methoxytryptamine hydrochloride 
• 79-03-8 propionyl chloride 

Relevant academic research and scientific papers

Potential radioprotective agents. 1. Homologs of melatonin

Homologs of melatonin were prepared by acylation of 5-methoxytryptamine with the appropriate acid chloride or anhydride. The products were administered as solutions or suspensions in soybean oil by ip injection to mice 30 min prior to irradiation with 950 cGy of 6 mV photons. Protection was achieved with all compounds, survival rate being maximal for mice treated with the hexanoic amide 5 and the octanoic amide 6.

Synthesis and antioxidant properties of some indole ethylamine derivatives as melatonin analogs

The synthesis and lipid peroxidation (LP) inhibition activity of several novel indole melatonin analogues are reported. Compounds have shown variable antioxidant features depending on the substitution pattern. Melatonin and the antioxidant reference compound butyl hydroxy toluen (BHT) were used to compare the antioxidant capability of the compounds synthesized.

2-Amido-8-methoxytetralins: A Series of Nonindolic Melatonin-like Agents

A series of unsubstituted and methoxy-substituted 2-amidotetralins (4a-q) was prepared and evaluated for their ability to complete for 2-iodomelatonin binding to chicken retinal membranes and for their potency to inhibit the calcium-dependent release of dopamine from rabbit retina.The lead compound, 2-acetamido-8-methoxytetralin (4j), showed a moderate affinity (Ki = 46 nM) and potency (IC50 = 1.4 nM) at the melatonin receptor.The structural requirements necessary for optimal agonistic activity at the melatonin receptor are as follows.First, the amido group, which should have a small, nonbranched alkyl group, is essential for affinity, and second, the methoxy substituent at the 8-position of the 2-amidotetralin ring is essential for optimal agonistic activity at the melatonin receptor.We concluded that this series of unsubstituted and methoxy-substituted 2-amidotetralins constitutes a class of nonindolic melatonin-like agents that can be used as pharmacological tools to further characterize melatonin receptors and to elucidate the mode of action of melatonin.