4018-91-1

Basic information

• Product Name: 2-AMINO-5-METHOXYTETRALIN
• Synonyms: 2-AMINO-5-METHOXYTETRALIN;5-Methoxy-1,2,3,4-tetrahydronaphthalen-2-aMine;1,2,3,4-Tetrahydro-5-methoxy-2-naphthalenamine;SKF 87967;2-Amino-5-methoxy-1,2,3,4-tetrahydronaphthalene;5-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylamine
• CAS NO: 4018-91-1
• Molecular Formula: C11H15NO
• Molecular Weight: 177.2429
• Mol File: 4018-91-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 309.109°C at 760 mmHg
• Flash Point: 147.448°C
• Appearance: /
• Density: 1.056g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.548
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 10.21±0.20(Predicted)
• CAS DataBase Reference: 2-AMINO-5-METHOXYTETRALIN(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-5-METHOXYTETRALIN(4018-91-1)
• EPA Substance Registry System: 2-AMINO-5-METHOXYTETRALIN(4018-91-1)

Safety Data

• Hazardous Substances Data: 4018-91-1(Hazardous Substances Data)

Usage

Uses

5-Methoxy-1,2,3,4-tetrahydronaphthalen-2-amine is an intermediate for Rotigotine (R700700), which is a non-ergot dopamine agonist drug and is indicated for the treatment of Parkinson’s disease.

InChI:InChI=1/C11H15NO/c1-13-11-4-2-3-8-7-9(12)5-6-10(8)11/h2-4,9H,5-7,12H2,1H3

Upstream product

• 116885-79-1 (2RS)-N-(5-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide 
• 92422-31-6 5-Methoxy-3,4-dihydro-[1,2]naphthoquinone 2-oxime 
• 25677-39-8 2-(hydroxymethylene)-5-methoxy-3,4-dihydronaphthalen-1(2H)-one 
• 33892-75-0 5-Methoxy-1-tetralone 
• 3900-49-0 1,6-dimethoxynaphthalene 
• 575-44-0 1,6-dihydroxynaphthalene 
• 32940-15-1 5-methoxy-2-tetralone 
• 3899-04-5 5-methoxy-3,4-dihydro-2(1H)-naphthalenone oxime 
• 134865-81-9 2-acetamido-5-methoxy-1,2,3,4-tetrahydronaphthalene 
• 136247-07-9 2-(N-benzylamino)-5-methoxytetralin 
• 107-06-2 1,2-dichloro-ethane 

Downstream Products

• 105086-92-8 (S)-5-methoxy-2-amino-1,2,3,4-tetrahydronaphthalene 
• 244239-67-6 (S)-N-(5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propionamide 
• 101403-24-1 (S)-(5-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propylamine hydrochloride 
• 1148154-91-9 (2S)-5-methoxy-N-propyl-N-(2'-(thien-2-yl)ethyl)tetralin-2-amine 
• 99755-59-6 rotigotine 
• 75016-98-7 5,6,7,8-tetrahydro-6-amino-1-naphthol 

Relevant articles and documents

Preparation method of rotigotine

The invention relates to the technical field of medicine preparation, and discloses a preparation method of rotigotine, which comprises the following steps: by taking 5-methoxy-2-tetralone as an initial raw material, reacting with R-alpha-methylbenzylamine, performing debenzylation reduction and S-mandelic acid chiral resolution, then reacting with a propionyl chloride reagent to generate an amide compound, and then reducing by a sodium borohydride reagent to obtain the rotigotine; and finally, reacting with 2-(thiophene-2-yl) 2-nitric acid benzene sulfonic acid ethyl ester to obtain the rotigotine. The preparation process route is as follows: the rotigotine is mild in preparation condition, simple and convenient to operate, relatively high in yield of key intermediates, high in optical purity and easy for industrial large-scale production, and has a very good application prospect.

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.

Conformationally Restricted and Conformationally Defined Tyramine Analogues as Inhibitors of Phenylethanolamine N-Methyltransferase

In a search for a selective inhibitor for the epinephrine synthesizing enzyme phenylethanolamine N-methyltransferase (PNMT; EC 2.1.1.28), phenolic 2-aminotetralins (12-15 as conformationally restricted analogues of tyramine) and phenolic benzobicyclo3.2.