6,7-ADTN hydrobromide

Base Information

• Chemical Name: 6,7-ADTN hydrobromide
• CAS No.: 13575-86-5
• Molecular Formula: BrH*C₁₀H₁₃NO₂
• Molecular Weight: 260.131
• European Community (EC) Number: 634-387-8
• NSC Number: 287353
• UNII: U1P469341B
• DSSTox Substance ID: DTXSID501017128
• Wikidata: Q27290569
• ChEMBL ID: CHEMBL1255656
• Mol file: 13575-86-5.mol

Synonyms:D 002;D-002

Chemical Property of 6,7-ADTN hydrobromide

Chemical Property:

• Vapor Pressure: 1.69E-06mmHg at 25°C
• Melting Point: 270-271 °C
• Boiling Point: 385.6°Cat760mmHg
• Flash Point: 187°C
• PSA: 66.48000
• Density: 1.273g/cm³
• LogP: 2.57220
• Storage Temp.: 2-8°C
• Solubility.: Soluble in Water (up to 25 mg/ml)
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 259.02079
• Heavy Atom Count: 14
• Complexity: 186

Purity/Quality:

98% ^*data from raw suppliers

(+/-)-2-Amino-6,7-dihydroxy-1,2,3,4-tetrahydronaphthaleneHydrobromide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC2=CC(=C(C=C2CC1N)O)O.Br
• Description: 6,7-ADTN HBr (13575-86-5) is a broad spectrum dopamine receptor agonist.1,2? Demonstrates a marked selectivity for the human dopamine D3 receptor.3 6,7-ADTN and psychostimulants such as cocaine and amphetamine reduce excitatory synaptic transmission in the nucleus accumbens by activating presynaptic dopamine receptors.4

Technology Process of 6,7-ADTN hydrobromide

There total 16 articles about 6,7-ADTN hydrobromide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

6,7-dimethoxy-1,2,3,4-tetrahydro-2-naphthylamine hydrochloride (13917-16-3) → ADTN hydrobromide (13575-86-5,73304-33-3)

Guidance literature:

With hydrogen bromide; In water; Heating;

DOI:10.1002/hlca.200390272

Reference yield: 75.0%

2-Acetylamino-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen (13575-85-4) → ADTN hydrobromide (13575-86-5,73304-33-3)

Guidance literature:

With hydrogen bromide; for 8h; Heating;

Reference yield:

1,2,3,4-tetrahydro-6,7-dimethoxynaphthalene-2-carboxylic acid (80054-06-4) → ADTN hydrobromide (13575-86-5,73304-33-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: (PhO)2P(O)N₃; Et₃N / benzene / Heating

1.2: 86 percent / benzene / Heating

2.1: 95 percent / H₂ / Pd-C / methanol; CHCl₃ / 24 h / 20 °C

3.1: 80 percent / HBr / H₂O / Heating

With diphenyl phosphoryl azide; hydrogen bromide; hydrogen; triethylamine; palladium on activated charcoal; In methanol; chloroform; water; benzene; 1.2: Curtius rearrangement;

DOI:10.1002/hlca.200390272

upstream raw materials:

2-Acetylamino-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen

6,7-dimethoxy-1,2,3,4-tetrahydro-2-naphthylamine hydrochloride

2-amino-6,7-diacetoxy-1,2,3,4-tetrahydronaphthalene hydrobromide

6,7-dimethoxy-2-acetylnaphthalene

Downstream raw materials:

2-amino-6,7-di(benzoyloxy)-1,2,3,4-tetrahydronaphthalene

2-amino-6,7-diacetoxy-1,2,3,4-tetrahydronaphthalene hydrobromide

Refernces

• 1、 Horn, A. S.,Griever-Kazemier, H.,Dijkstra, D.. "Brain Levels and Metabolism of the Dopaminergic Agonist 2-Amino-6,7-dihydroxytetrahydronaphthalene After Administration of Various Prodrugs". . p. 993 - 996. Retrieved 2007/10/02.
• 2、 Narula, Anubhav P.S.,Schuster, David I.. "A NEW SYNTHESIS OF 2-AMINO-6,7-DIHYDROXY-TETRAHYDRONAPHTHALENE (ADTN) VIA FUNCTIONALIZED ARYL-LITHIUM REAGENTS AND METHYL 2-TRIMETHYLSILYLACRYLATE - A NEW ANNULATION SEQUENCE". . p. 3707 - 3710. Retrieved 2007/10/02.