105086-80-4

Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-AMINO-5-METHOXYTETRALIN HYDROCHLORIDE is used as a research chemical for the development of new medications targeting the dopamine D3 receptor. Its agonistic activity on this receptor makes it a valuable tool in the study and treatment of neurological and psychiatric disorders.
Used in Neurological Disorder Treatment:
In the field of neurology, (S)-2-AMINO-5-METHOXYTETRALIN HYDROCHLORIDE is used as a potential therapeutic agent for the treatment of Parkinson's disease. Its interaction with the dopamine D3 receptor may contribute to the management of motor symptoms associated with this condition.
Used in Psychiatric Disorder Treatment:
Within psychiatry, (S)-2-AMINO-5-METHOXYTETRALIN HYDROCHLORIDE is utilized as a candidate for the development of treatments for schizophrenia. Its influence on the dopamine D3 receptor could help in addressing the positive and negative symptoms of the disorder.
Used in Addiction Treatment:
(S)-2-AMINO-5-METHOXYTETRALIN HYDROCHLORIDE is also considered in the domain of addiction medicine as a potential aid in the treatment of drug addiction. Its agonistic effect on the dopamine D3 receptor may play a role in managing cravings and addictive behaviors.
Each of these applications underscores the importance of (S)-2-AMINO-5-METHOXYTETRALIN HYDROCHLORIDE's interaction with the dopamine D3 receptor and its implications for advancing treatments in various areas of medicine.

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/t9-/m0/s1

Upstream product

• 3899-04-5 5-methoxy-3,4-dihydro-2(1H)-naphthalenone oxime 
• 575-44-0 1,6-dihydroxynaphthalene 
• 3900-49-0 1,6-dimethoxynaphthalene 
• 32940-15-1 5-methoxy-2-tetralone 
• 4018-91-1 2-Amino-5-methoxy-1,2,3,4-tetrahydronaphthalene 
• 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 
• 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 

Downstream Products

• 75016-98-7 5,6,7,8-tetrahydro-6-amino-1-naphthol 
• 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 
• 244239-68-7 (R)-N-(5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propionamide 
• 68643-08-3 (2S)-5-hydroxy-2-(di-n-propylamino)tetralin 

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.

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.

Synthesis and antifungal activities of novel 2-aminotetralin derivatives

Novel 2-aminotetralin derivatives were synthesized as antifungal agents. The 2-aminotetralin scaffold was chemically designed to mimic the tetrahydroisoquinoline ring of the lead molecule described before. Their antifungal activities were evaluated in vitro by measuring the minimal inhibitory concentrations (MICs). Compounds 10a, 12a, 12c, 13b, and 13d are more potent than fluconazole against seven testing human fungal pathogens. Compound 10b exhibits much higher antifungal activities against all of the four fluconazole-resistant clinic Candida albicans strains than the control drugs including amphotericin B, terbinafine, ketoconazole, and itraconazole. The mode of action of some compounds to the potential receptor lanosterol 14α-demethylase (CYP51) was investigated by molecular docking. The studies presented here provide a new structural type for the development of novel antifungal compounds. Furthermore, 10b was evaluated in vivo by a rat vaginal candidiasis model, and it was found that 10b significantly decreases the number of fungal colony counts.

2-Amido-8-methoxytetralins: A Series of Nonindolic Melatonin-like Agents

A series of unsubstituted and methoxy-substituted 2-amidotetralins (4a-q) was prepared and evaluated for their ability to complete for 2-iodomelatonin binding to chicken retinal membranes and for their potency to inhibit the calcium-dependent release of dopamine from rabbit retina.The lead compound, 2-acetamido-8-methoxytetralin (4j), showed a moderate affinity (Ki = 46 nM) and potency (IC50 = 1.4 nM) at the melatonin receptor.The structural requirements necessary for optimal agonistic activity at the melatonin receptor are as follows.First, the amido group, which should have a small, nonbranched alkyl group, is essential for affinity, and second, the methoxy substituent at the 8-position of the 2-amidotetralin ring is essential for optimal agonistic activity at the melatonin receptor.We concluded that this series of unsubstituted and methoxy-substituted 2-amidotetralins constitutes a class of nonindolic melatonin-like agents that can be used as pharmacological tools to further characterize melatonin receptors and to elucidate the mode of action of melatonin.

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.

Aminotetralin derivatives

This invention related to new aminotetralin derivatives of formula I STR1 wherein STR2 B is methylene or, when A is --CH2 --CH2 --, --CH=CH--, --NH--CO-- or --CH2 --CO--, B can also be carbonyl or thiocarbonyl; E is a C2 -C4 straight-chain alkylene, optionally substituted by a C1 -C3 alkyl, or is 2-hydroxy-n-propylene, 2-hydroxy-n-butylene or 3-hydroxy-n-butylene; R1 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl, nitro, amino, C1 -C3 alkylamino, C1 -C3 dialkylamino, C1 -C3 alkyl, C1 -C3 alkylthio, hydroxy, C1 -C3 alkoxy or phenyl C1 -C3 alkoxy; R2 is hydrogen, chlorine, bromine, hydroxy, C1 -C3 alkoxy phenyl C1 -C3 alkoxy, or C1 -C3 alkyl or, together with R1, can be a C1 -C2 alkylenedioxy; R3 and R4 are each independently selected from hydrogen, fluorine, chlorine, bromine, C1 -C3 alkyl, hydroxy, C1 -C3 alkoxy, nitro, amino, C1 -C3 alkylamino, or C1 -C3 dialkylamino, or together can be methylenedioxy; and R5 is hydrogen, C3 -C5 alkenyl, C1 -C3 alkyl, or phenyl C1 -C3 alkyl, and nontoxic, pharmaceutically acceptable addition salts thereof which have valuable pharmacological properties, particularly a long-lasting heart rate lowering effect and the effect of reducing the O2 requirement of the heart.