87857-27-0

Basic information

• Product Name: 2-(N-phenethyl-N-propyl)amino-5-hydroxytetralin
• Synonyms: 2-(N-phenethyl-N-propyl)amino-5-hydroxytetralin;2-[(Phenethyl)(propyl)amino]-5-hydroxy-1,2,3,4-tetrahydronaphthalene;N-0434;PPHT;5,6,7,8-Tetrahydro-6-[(2-phenylethyl)propylamino]-1-naphthalenol;1-Naphthalenol,5,6,7,8-tetrahydro-6-[(2-phenylethyl)propylamino]-
• CAS NO: 87857-27-0
• Molecular Formula: C₂₁H₂₇NO
• Molecular Weight: 309.45
• Mol File: 87857-27-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 468°C at 760 mmHg
• Flash Point: 228.6°C
• Appearance: /
• Density: 1.09g/cm³
• Vapor Pressure: 2.22E-09mmHg at 25°C
• Refractive Index: 1.599
• CAS DataBase Reference: 2-(N-phenethyl-N-propyl)amino-5-hydroxytetralin(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(N-phenethyl-N-propyl)amino-5-hydroxytetralin(87857-27-0)
• EPA Substance Registry System: 2-(N-phenethyl-N-propyl)amino-5-hydroxytetralin(87857-27-0)

Safety Data

• Hazardous Substances Data: 87857-27-0(Hazardous Substances Data)

Usage

Chemical structure

The compound has a 5-hydroxytetralin nucleus, with N-phenethyl and N-propyl amine substituents.

Function

It is used as a serotonin receptor agonist in research and scientific studies.

Potential pharmacological effects

The compound has been studied for its potential effects on the central nervous system.

Value in research

Its chemical properties and structure make it a valuable tool in the study of neurotransmitters and their role in brain function and behavior.

Potential applications

The compound may have applications in the development of new medications for conditions such as depression, anxiety, and other neurological disorders.

InChI:InChI=1/C21H27NO/c1-2-14-22(15-13-17-7-4-3-5-8-17)19-11-12-20-18(16-19)9-6-10-21(20)23/h3-10,19,23H,2,11-16H2,1H3

Upstream product

• 78950-82-0 2-N-propylamino-1,2,3,4-tetrahydro-5-hydroxynaphthalene 
• 103-82-2 phenylacetic acid 
• 32940-15-1 5-methoxy-2-tetralone 
• 78598-91-1 2-(N-propylamino)-5-methoxytetraline 

Relevant articles and documents

Affinity for dopamine D2, D3, and D4 receptors of 2-aminotetralins. Relevance of D2 agonist binding for determination of receptor subtype selectivity.

A series of 2-aminotetralins, substituted with a methoxy or a hydroxy group on the 5- or 7-position, and with varying N-alkyl or N-arylalkyl substituents, were prepared and evaluated in binding assays for human dopamine (DA) D2, D3, and D4 receptors. Some members of this series were prepared in former studies, but were never tested in vitro with single receptor subtypes, and these were examined again. None of the tested 2-aminotetralins showed high affinity for the dopamine D4 receptor. However, a number of the 2-aminotetralins showed high affinity for both the D2 and the D3 DA receptors, as exemplified by compounds 11-15 and 21-26, while some had a reasonable selectivity for the DA D3 receptors. The affinities of the 2-aminotetralins for the D21, receptor depended on the type of radioligand (agonist or antagonist) used. The agonist affinity data, obtained by using the agonist ligand [3H]N-0437, are thought to be more relevant for calculating DA receptor subtype selectivity.

Method for treating schizophrenia

This invention provides a method for treating the symptoms of schizophrenia which comprises administering to a schizophrenic an effective amount of a compound selected from the group consisting of optically-active or racemic compounds represented by the general formula: STR1 wherein R1 is selected from the group consisting of organic radicals having fused rings, phenyl, pyridyl STR2 X is oxygen or sulfur, Y, if present, is selected from the group consisting of hydroxy, nitro, cyano, azido, amino, acylamino, carboxyamido, trifluoromethyl, sulfate, sulfonamido halogen, hydrocarbyl and hetero atom-substituted hydrocarbyl radicals, wherein said heteroatoms are selected from the group consisting of halogen, nitrogen, oxygen, sulfur and phosphorus and said hydrocarbyl radicals comprise from 1 to 12 carbon atoms, and a is an integer between zero and 3. R2, R3 and R4 are each selected from the group consising of H and OA, A is H or is selected from the group consisting of hydrocarbyl radicals, or STR3 R5 is selected from the group consisting of hydrocarbyl radicals and n is 2 or 3; with the proviso that at least one of R2, R3 and R4 is H, that at least one of R2, R3 and R4 is not H and that R2 and R4 are not both OA, except that when R1 is m-hydroxyphenyl, phenyl or 2-thienyl, the compound is optically-active.

Structure-Activity Relationships of Dopaminergic 5-Hydroxy-2-aminotetralin Derivatives with Functionalized N-Alkyl Substituents

5-Hydroxy-2-aminotetralin derivatives in which one N-alkyl substituent carries a functional group have been prepared and their dopaminergic activities compared with those of 5-hydroxy-2-(di-n-propylamino)tetralin (5-OH-DPAT) and known ergolines.Several members of the series demonstrated high affinities in dopamine (DA) receptor binding and DA agonist properties in the rotational behavior model in the range of known potent ergolines.The results suggests that the accessory binding site for the larger N-alkyl substituent of the 5-hydroxy-2-aminotetralins can accommodate various neutral and bulky functionalities and is probably identical with the site(s) to which the 8-substituents of the ergolines bind.