13575-86-5

Basic information

• Product Name: 6-aminotetralin-2,3-diol
• Synonyms: 6-aminotetralin-2,3-diol;6-Amino-5,6,7,8-tetrahydro-2,3-naphthalenediolhydrobromide
• CAS NO: 13575-86-5
• Molecular Formula: BrH*C₁₀H₁₃NO₂
• Molecular Weight: 0
• Product Categories: Dopamine
• Mol File: 13575-86-5.mol

Chemical Properties

• Melting Point: 270-271 °C
• Boiling Point: 385.6°Cat760mmHg
• Flash Point: 187°C
• Appearance: /
• Density: 1.273g/cm³
• Vapor Pressure: 1.69E-06mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: Soluble in Water (up to 25 mg/ml)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in distilled water may be stored at -20°C for up to 1 week.
• CAS DataBase Reference: 6-aminotetralin-2,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 6-aminotetralin-2,3-diol(13575-86-5)
• EPA Substance Registry System: 6-aminotetralin-2,3-diol(13575-86-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 13575-86-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-aminotetralin-2,3-diol is used as a pharmaceutical compound for its agonistic effects on dopamine receptors, particularly the human dopamine D3 receptor. Its selectivity and broad-spectrum activity make it a valuable tool in the development of treatments for various neurological and psychiatric disorders.
Used in Research and Development:
In the field of research and development, 6-aminotetralin-2,3-diol is used as a research tool to study the function and role of dopamine receptors in the central nervous system. Its ability to modulate synaptic transmission in the nucleus accumbens makes it a valuable asset in understanding the underlying mechanisms of various neurological conditions and the development of novel therapeutic strategies.
Used in Drug Interaction Studies:
6-aminotetralin-2,3-diol is also used in studying the interactions between psychostimulants such as cocaine and amphetamine and dopamine receptors. This helps in understanding the effects of these substances on the central nervous system and their potential for addiction and abuse, leading to the development of more effective treatments and interventions for substance use disorders.

References

1) List et al. (1982), Striatal binding of 2-amino-6,7-[3H]dihydroxy-1,2,3,4-tetrahydronaphthalene to two dopaminergic sites distinguished by their low and high affinity for neuroleptics; J. Neurosci., 2 895 2) Templeton et al. (1982), Binding of [3H]ADTN to rat striatal membranes; Biochem. Pharmacol., 31 1629 3) Freedman et al. (1994), Expression and pharmacological characterization of the human D3 dopamine receptor; Curr. J. Pharmacol. Exp. Ther., 268 417 4) Nicola et al. (1996), Psychostimulants depress excitatory synaptic transmission in the nucleus accumbens via presynaptic D1-like dopamine receptors; J. Neurosci., 16 1591

InChI:InChI=1/C10H13NO2.BrH/c11-8-2-1-6-4-9(12)10(13)5-7(6)3-8;/h4-5,8,12-13H,1-3,11H2;1H

Upstream product

• 13917-16-3 6,7-dimethoxy-1,2,3,4-tetrahydro-2-naphthylamine hydrochloride 
• 82205-66-1 2-amino-6,7-diacetoxy-1,2,3,4-tetrahydronaphthalene hydrobromide 
• 289507-36-4 2-(2-bromo-4,5-dimethoxyphenyl)ethyl alcohol 
• 80536-55-6 6,7-Dimethoxy-2-trimethylsilanyl-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid methyl ester 
• 7417-21-2 2-(3,4-dimethoxyphenyl)ethyl alcohol 
• 69327-12-4 1-bromo-2-(2-bromoethyl)-4,5-dimethoxybenzene 
• 2470-77-1 trans-2-Acetylamino-1-hydroxy-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen 
• 2470-81-7 2-Acetylamino-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-1-on 
• 92-44-4 2,3-naphthalenediol 
• 80536-56-7 benzyl N-(1,2,3,4-tetrahydro-6,7-dimethoxynaphthalene-2-yl)carbamate 
• 80054-06-4 1,2,3,4-tetrahydro-6,7-dimethoxynaphthalene-2-carboxylic acid 
• 37707-78-1 6,7-Dimethoxy-naphthalene-2-carboxylic Acid 
• 10103-06-7 2,3-dimethoxynaphthalene 
• 37707-72-5 6,7-dimethoxy-2-acetylnaphthalene 

Downstream Products

• 70172-52-0 2-amino-6,7-di(benzoyloxy)-1,2,3,4-tetrahydronaphthalene 
• 82205-66-1 2-amino-6,7-diacetoxy-1,2,3,4-tetrahydronaphthalene hydrobromide 

Relevant articles and documents

A Concise Synthesis of 2-Amino-1,2,3,4-tetrahydronaphthalene-6,7-diol ('6,7-ADTN') from Naphthalene-2,3-diol

2-Amino-1,2,3,4-tetrahydronaphthalene-6,7-diol (2; 6,7-ADTN) was synthesized starting from naphthalene-2,3-diol in seven steps and with an overall yield of 44%. Methylation of naphthalene-2,3-diol with dimethyl sulfate, followed by Friedel-Crafts acylatio

Brain Levels and Metabolism of the Dopaminergic Agonist 2-Amino-6,7-dihydroxytetrahydronaphthalene After Administration of Various Prodrugs

The synthesis of four prodrug diesters (diacetyl, diisobutyryl, dipivaloyl, and dibenzoyl) of the potent dopaminergic agonist 2-amino-6,7-dihydroxytetrahydronaphthalene (6,7-ADTN) is described.The effects of prodrug structure on the levels of 6,7-ADTN in the rat corpus striatum and cerebellum, as well as the levels of the metabolite, 6-hydroxy-7-methoxy-2-aminotetralin, in the corpus striatum, have been determined after intraperitoneal administration.In addition, the stratial levels of 6,7-ADTN after administration of the dibenzoyl analogue via intraperitoneal, subcutaneous, and oral routes have been measured.These prodrugs produce a significant improvement in the penetration and accumulation of 6,7-ADTN in the brain.

A NEW SYNTHESIS OF 2-AMINO-6,7-DIHYDROXY-TETRAHYDRONAPHTHALENE (ADTN) VIA FUNCTIONALIZED ARYL-LITHIUM REAGENTS AND METHYL 2-TRIMETHYLSILYLACRYLATE - A NEW ANNULATION SEQUENCE

A new high yield synthesis of a potent dopamine agonist, 2-amino-6,7-dihydroxy-tetrahydronaphthalene, is described utilizing a new annulation sequence.