87857-27-0

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

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

Relevant academic research and scientific papers

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 OF PRODUCING BODY WEIGHT AND FOOD INTAKE USING A DOPAMINE D2 RECEPTOR AGONIST

This invention provides a method for treating the symptoms of obesity which comprises administering to a human or other mammal suffering from the symptoms of obesity an effective amount of a compound selected from the group consisting of the optically active compounds especially the (-) negative stereoisomers represented by the formula: STR1 wherein R 1 R 2,R 3,R 4,R 5 and R 6 are defined by the specification substituted or unsubstituted phenyls, pyridyl, hydroxyphenyl, STR2 X is oxygen or sulfur, Y 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 of from zero to 3, R 2, R 3 and R 4 are each selected from the group consisting of H and OA, A is H or is selected from the group consisting of hydrocarbyl radicals, STR3 R 5 is selected from the group consisting of hydrocarbyl radicals; n is an integer between 1 and 3; and R 6 is an alkyl chain having between 1 and 3 carbon atoms with the provision that at least one of R 2, R 3 and R 4 is H, that at least one of R. sub.2, R 3 and R 4 is not H, and that R. sub.2 and R 4 are not both OA, and pharmaceutically acceptable salts thereof. Preferably, R 2 is oxygen.Most preferably, R 2 is OA and A is H, and the compound is the (-) isomer.

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.

Method and compositions for treatment of parkinsonism syndrome in mammals

This invention provides a method for treating the symptoms of parkinsonism which comprises administering to a human or other mammal suffering from the symptoms of parkinsonism 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 methyl, substituted or unsubstituted phenyls, pyridyl, hydroxyphenyl, STR2 X is oxygen or sulfur, Y 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 of from zero to 3, R2, R3 and R4 are each selected from the group consisting of H and OA, A is H or is selected from the group consisting of hydrocarbyl radicals, STR3 R5 is selected from the group consisting of hydrocarbyl radicals; n is an integer between 1 and 3; and R6 is an alkyl chain having between 1 and 3 carbon atoms with the provision 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, and pharmaceutically acceptable salts thereof. Preferably, R2 is oxygen. Preferably, R2 is OA and A is H, and the compound is the (-) isomer.

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.