21489-50-9

Usage

Chemical Class

Naphthalenamines

Molecular Structure

Tetrahydro-2-naphthalenyl with two methoxy groups and an amine group attached

Organic Compound

Contains carbon and hydrogen atoms

Potential Pharmacological Properties

Can act as an agonist or antagonist at certain receptors in the central nervous system

Medicinal Chemistry Applications

May have potential for drug development due to unique structural features and biological activity

Further Research Needed

To fully understand the properties and potential uses of 1,2,3,4-Tetrahydro-5,6-dimethoxy-2-naphthalenamine.

InChI:InChI=1/C12H17NO2/c1-14-11-6-3-8-7-9(13)4-5-10(8)12(11)15-2/h3,6,9H,4-5,7,13H2,1-2H3

Upstream product

• 52704-56-0 1,2,3,4-Tetrahydro-5,6-dimethoxy-2(1H)-naphthalinon-O-methyloxim 
• 24039-89-2 5,6-dimethoxy-1-tetralone 
• 52643-99-9 1-Hydroxy-5,6-dimethoxy-1,2,3,4-tetrahydronaphthalin 
• 52644-00-5 5,6-dimethoxy-1,2-dihydronaphthalene 
• 52644-01-6 5,6-dimethoxy-2-tetralone 
• 126674-76-8 5,6-dimethoxy-2-naphthalenecarboxylic acid 
• 885058-66-2 1,2,3,4-tetrahydro-5,6-dimethoxynaphthalene-2-carboxylic acid 
• 885058-67-3 phenylmethyl (1,2,3,4-tetrahydro-5,6-dimethoxynaphthalen-2-yl)carbamate 

Downstream Products

• 124399-93-5 5,6-dimethoxy-2-phthalimido-1,2,3,4-tetrahydronaphthalene 

Relevant academic research and scientific papers

Cerebral dopamine agonist properties of some 2-aminotetralin derivatives after peripheral and intracerebral administration.

A series of variously N-substituted 2-aminotetralins having OH groups at 5 and 6 and at 6 and 7 positions, as well as nonoxygenated systems, has been evaluated for central dopaminergic effects. Stereotypical behavioral effects (sniffing, compulsive gnawing, and hyperactivity) produced by direct intracerebral administration of some of the agents were shown to differ strikingly from responses resulting from peripheral administration. The centrally mediated responses of hyperactivity and sterotypical gnawing-biting head and limb movements were shown to be separable in some test compounds. An improved route to 2-aminotetralin systems has been utilized for some of the compounds, which involves Pummerer rearrangement and cyclization of beta-keto sulfoxides and reductive amination of beta-tetralones with a NaBH4-carboxylic acid complex.

An alternative synthesis of the dopaminergic drug 2-amino-1,2,3,4- tetrahydronaphthalene-5,6-diol (5,6-ADTN)

Racemic 2-amino-1,2,3,4-tetrahydronaphthalene-5,6-diol (5,6-ADTN; 4) was synthesized from 5,6-dimethoxynaphthalene-2-carboxylic acid (14) in four steps (60% overall yield; Scheme). The crucial steps of the synthesis are Birch reduction of 14 to the valuable synthon 15, Curtius reaction and carbamate formation (16), hydrogenolysis (17), and demethylation to the biologically active hydrobromide salt 18 of 4.