127253-44-5

Basic information

• Product Name: (S)-(-)-8-METHOXY 2-AMINOTETRALIN
• Synonyms: (S)-(-)-8-METHOXY 2-AMINOTETRALIN;(S)-8-METHOXY-2-AMINOTETRALIN;(S)-2-Amino-8-methoxy-1,2,3,4-tetrahydronaphthalene
• CAS NO: 127253-44-5
• Molecular Formula: C11H15NO
• Molecular Weight: 177.24
• Mol File: 127253-44-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 309.1 ºC at 760 mmHg
• Flash Point: 147.4ºC
• Appearance: /
• Density: 1.056 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.548
• CAS DataBase Reference: (S)-(-)-8-METHOXY 2-AMINOTETRALIN(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-8-METHOXY 2-AMINOTETRALIN(127253-44-5)
• EPA Substance Registry System: (S)-(-)-8-METHOXY 2-AMINOTETRALIN(127253-44-5)

Safety Data

• Hazardous Substances Data: 127253-44-5(Hazardous Substances Data)

Usage

General Description

(S)-(-)-8-METHOXY 2-AMINOTETRALIN, also known as (S)-8-MeO-2-AT, is a chemical compound with potential pharmacological properties. It is a potent and selective agonist for the serotonin 5-HT1A receptor, which is involved in the regulation of mood, anxiety, and stress. (S)-(-)-8-METHOXY 2-AMINOTETRALIN has been studied for its potential use in the treatment of psychiatric disorders such as depression and anxiety. Its ability to modulate serotonin neurotransmission makes it a promising candidate for the development of novel medications for mood and anxiety disorders. Additionally, (S)-(-)-8-METHOXY 2-AMINOTETRALIN has been investigated for its potential antidepressant and anxiolytic effects in preclinical research, demonstrating its potential as a valuable pharmacological tool in the study of serotonin 5-HT1A receptor function and the development of novel therapeutics for mental health disorders.

InChI:InChI=1/C11H15NO/c1-13-11-4-2-3-8-5-6-9(12)7-10(8)11/h2-4,9H,5-7,12H2,1H3/t9-/m0/s1

Upstream product

• 460740-24-3 (2R)-2-azido-8-methoxy-1,2,3,4-tetrahydronaphthalene 
• 121-44-8 triethylamine 
• 135-02-4 ortho-anisaldehyde 
• 3880-73-7 8-(methyloxy)-3,4-dihydro-2(1H)-naphthalenone oxime 
• 5309-19-3 8-methoxy-2-tetralone 
• 460740-20-9 (2S)-8-methoxy-2-p-toluenesulphonyloxy-1,2,3,4-tetrahydronaphthalene 
• 460740-13-0 (1R,2S)-1,2-dihydroxy-8-methoxy-1,2,3,4-tetrahydronaphthalene 
• 460740-16-3 (2S)-2-hydroxy-8-methoxy-1,2,3,4-tetrahydronaphthalene 
• 5309-18-2 1,7-dimethoxynaphthalene 
• 575-38-2 1,7-Dihydroxynaphthalene 
• 81185-19-5 N-benzyl-8-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine 
• 90266-01-6 1-diazo-4-(2'-methoxyphenyl)butan-2-one 
• 22955-75-5 3-(2-methoxyphenyl)propionyl chloride 
• 1011-54-7 2-methoxycinnamic acid 

Downstream Products

• 81998-18-7 1,2,3,4-tetrahydro-8-methoxy-5-(methylthio)-2-naphthalenamine 
• 119432-89-2 (S)-8-Methoxy-DPAT 
• 119432-88-1 ((R)-8-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-dipropyl-amine 
• 80270-68-4 N-(1,2,3,4-tetrahydro,8-methoxy-2-naphthalenyl)-acetamide 

Relevant articles and documents

Radioligand binding study of a series of 5-HT(1A) receptor agonists and definition of a steric model of this site

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A chemoenzymatic synthesis of (2R)-8-substituted-2-aminotetralins

(2R)-2-Amino-8-methoxy-1,2,3,4-tetrahydronaphthalene, a useful precursor of the 5-hydroxytryptamine receptor agonist 8-OH-DPAT ((2R)-2-(dipropylamino)-8-hydroxytetrahydronaphthalene), has been synthesized from 1-methoxynaphthalene through a chemoenzymatic protocol. The same protocol has been subsequently applied to the synthesis of other (2R)-2-amino-1,2,3,4-tetrahydronaphthalenes.

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.