165950-84-5

Basic information

• Product Name: (S)-5,6,7,8-Tetrahydro-6-(propylamino)-1-naphthalenol hydrobromide
• Synonyms: (6S)-(-)-5-Hydroxy-N-propyl-2-aminotetralin hydrobromide;(S)-5,6,7,8-Tetrahydro-6-(propylamino)-1-naphthalenol hydrobromide;(S)-2-NaphthalenaMine, 1,2,3,4-tetrahydro-5-hydroxy-N-propyl-, hydrobroMide;(S)-6-(Propylamino)-5,6,7,8-tetrahydronaphthalen-1-ol hydrobromide;(2S)-2-(Propylamino)tetralin-5-ol hydrobromide;(6S)-6-(Propylamino)-5,6,7,8-tetrahydronaphthalen-1-ol hydrobromide;6S)-(-)-5-Hydroxy-N-propyl-2-aminotetralin;(6S)-6-(propylamino)-5,6,7,8-tetrahydronaphthalen-1-ol
• CAS NO: 165950-84-5
• Molecular Formula: C13H19NO.HBr
• Molecular Weight: 286
• Mol File: 165950-84-5.mol

Chemical Properties

• Appearance: /
• Density: 1.4g/cm3 at 20℃
• Vapor Pressure: 0-0Pa at 20-25℃
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: (S)-5,6,7,8-Tetrahydro-6-(propylamino)-1-naphthalenol hydrobromide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-5,6,7,8-Tetrahydro-6-(propylamino)-1-naphthalenol hydrobromide(165950-84-5)
• EPA Substance Registry System: (S)-5,6,7,8-Tetrahydro-6-(propylamino)-1-naphthalenol hydrobromide(165950-84-5)

Safety Data

• Hazardous Substances Data: 165950-84-5(Hazardous Substances Data)

Usage

Uses

Used in Neuroscience Research:
(S)-5,6,7,8-Tetrahydro-6-(propylamino)-1-naphthalenol hydrobromide is used as a research tool for investigating the role of serotonin 5-HT1A receptors in brain function and behavior. It helps scientists understand the mechanisms of serotonin signaling and neurotransmission, which are crucial for various physiological processes.
Used in Pharmaceutical Development:
In the pharmaceutical industry, (S)-5,6,7,8-Tetrahydro-6-(propylamino)-1-naphthalenol hydrobromide is used as a lead compound for developing potential therapeutic agents. Its agonistic action on serotonin 5-HT1A receptors makes it a promising candidate for the treatment of anxiety, depression, and other mood disorders. Researchers are exploring its efficacy and safety in clinical trials to advance its application in medicine.

InChI:InChI=1/C13H19NO.BrH/c1-2-8-14-11-6-7-12-10(9-11)4-3-5-13(12)15;/h3-5,11,14-15H,2,6-9H2,1H3;1H/t11-;/m0./s1

Upstream product

• 101403-25-2 (R)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-naphthalen-2-amine 
• 93601-86-6 (S)-(-)-(5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propylamine hydrochloride 
• 32940-15-1 5-methoxy-2-tetralone 
• 1352917-62-4 N-(methoxycarbonyl)-N-propyl-5-methoxy-2-aminotetralin 
• 1352917-69-1 (S)-N-(methoxycarbonyl)-N-propyl-5-methoxy-2-aminotetralin 
• 3904-24-3 (5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propylamine hydrochloride 
• 1352917-68-0 (S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-naphthalen-2-ammonium (S)-2-methoxy-2-phenylacetate 
• 1352917-67-9 (S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-naphthalen-2-ammonium (S)-2-hydroxy-3-phenylpropionate 
• 1352917-66-8 (S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-naphthalen-2-ammonium (R)-2-(2-chlorophenyl)-2-hydroxyacetate 
• 78598-91-1 2-(N-propylamino)-5-methoxytetraline 
• 3880-88-4 SKF 87967 hydrochloride 
• 101403-24-1 (S)-(5-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propylamine hydrochloride 

Downstream Products

• 125572-93-2 rotigotine hydrochloride 
• 99755-59-6 rotigotine 

Relevant articles and documents

IMPROVED PROCESS FOR THE PREPARATION OF CRYSTALLINE FORM II OF ROTIGOTINE

The present invention relates to an improved, environment friendly and cost effective process for the preparation of crystalline Form II of Rotigotine. Rotigotine, i.e. (6S)-6-{propyl[2-(2-thienyl) ethyl]amino}-5,6,7,8-tetrahydro-l-naphthalenol represented by structural formula (I), is used for the treatment of Parkinson's disease and Willis-Ekbom disease.

Novel Process for the Preparation of Nitrogen Substituted Aminotetralins Derivatives

The present invention provides an alternative synthesis of N-substituted aminotetralines comprising resolution of N-substituted aminotetralins of formula (II), wherein R1, R2 and R3 are as defined for compound of formula (I).

COMPOSITIONS AND METHODS FOR TREATMENT OF NEUROLOGIC DISEASES

Provided are compounds, pharmaceutical acceptable salts, polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising the compounds may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup or injection, and may be used for the treatment of neurologic diseases, such as depression, Alzheimer's disease, multiple sclerosis, Batten disease, Parkinson's disease and restless legs syndrome.

NOVEL PROCESS FOR THE PREPARATION OF NITROGEN SUBSTITUTED AMINOTETRALINS DERIVATIVES

The present invention provides an alternative synthesis of N-substituted aminotetralines comprising resolution of N-substituted aminotetralins of formula (II), wherein R1, R2 and R3 are as defined for compound of formula (I).

PROCESS FOR THE PREPARATION OF ROTIGOTINE

A process for the preparation of Rotigotine (I) and of pharmaceutically acceptable salts thereof, which comprises the reductive amination of an amine of formula 6 with the 2-thienylacetic acid-sodium boron hydride complex and which makes use of hydrobromide 5 as an intermediate (II) The process is advantageous from the industrial point of view in that it allows to obtain Rotigotine with high enantiomeric purity starting from optically active 5,6,7,8-tetrahydro-6-(S)-N-propylamino-1-methoxy-naphthalene (2), avoiding the use of dangerous reactives, the need for difficult chromatographic separation or the formation of by-products. Furthermore, two novel crystalline forms are disclosed.

A PROCESS FOR THE PREPARATION OF ROTIGOTINE

A process for the preparation of Rotigotine (I) and of pharmaceutically acceptable salts thereof, which comprises the reductive amination of an amine of formula 6 with the 2-thienylacetic acid- sodium boron hydride complex and which makes use of hydrobromide 5 as an intermediate (II) The process is advantageous from the industrial point of view in that it allows to obtain Rotigotine with high enantiomeric purity starting from optically active 5,6,7,8-tetrahydro-6-(S)-N-propylamino-l-methoxy- naphthalene (2), avoiding the use of dangerous reactives, the need for difficult chromatographic separation or the formation of by-products. Furthermore, two novel crystalline forms are disclosed.

PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE (S)-(-)-2-(N-PROPYLAMINO)-5-METHOXYTETRALINE AND (S)-(-)-2-(N-PROPYLAMINO)-5-HYDROXYTETRALINE COMPOUNDS

The present invention describes a novel process for the preparation of optically active (S)-(-)-2-(N-propylamino)-5-methoxytetraline and (S)-(-)-2-(N-propylamino)-5- hydroxytetraline compounds based on the optical resolution of mixtures of the enantiomers of 2-(N-propylamino)-5-methoxytetraline and 2-(N-propylamino)-5- hydroxytetraline respectively. This process comprises (a) reacting a mixture of the enantiomers of said compounds with an optically active organic acid to form diastereoisomeric salts and separating the salts by crystallization. Said compounds are useful in the preparation of (6S)-(-)-5,6,7,8-tetrahydro-6-[propyl-(2- thienyl)ethyl]amino-1 -naphthol (Rotigotine). Rotigotine is a dopamine agonist and is indicated for the treatment of Parkinson's disease.

Substituted 2-aminotetralins

Optically active or racemic compounds represented by the formula STR1 where R2 is OA and R3 is selected from the group consisting of H and OA; where A is H or is selected from the group consisting of hydrocarbyl radicals comprising b

Synthesis and evaluation of pharmacological and pharmacokinetic properties of monopropyl analogs of 5-, 7-, and 8-[[(trifluoromethyl)sulfonyl]oxy]-2- aminotetralins: Central dopamine and serotonin receptor activity

In order to explore further the structure-activity relationships of serotonergic and dopaminergic ligands, a series of enantiopure 5-, 7-, or 8- triflate (-OTf)-substituted 2-(monopropylamino)-tetralins have been synthesized and evaluated in in vitro binding and in vivo biochemical and behavioral assays in rats. Consequently, the 8-OTf-substituted compound R- (+)-6 was found to be a potent and selective 5-HT(1A) (5-hydroxytryptamine) receptor agonist inducing a full-blown 5-HT syndrome in normal rats, while the corresponding 5-OTf-substituted compound S-(-)-12 was found to be a preferential dopamine (DA) autoreceptor agonist. A partial 5-HT syndrome was also observed for S-(-)-12, while the corresponding R-(+)-12 was found to be inactive at the DA and 5-HT receptors both in vitro and in vivo. Compounds 6 and 12 were found to be major urinary metabolites following oral administration of their dipropyl analogs (2 and 13, respectively). Thus 6 was proposed to be the metabolite responsible for the full-blown 5-HT syndrome seen after oral (but not subcutaneous) administration of 2. Similarly, 12 was proposed to be the metabolite responsible for the partial 5-HT syndrome seen after oral (but not subcutaneous) administration of 13. The bioavailability of R-(+)-6 (7.6 ± 1.1%) appeared to be slightly lower than that of 2 (11.2 ± 5.2%), although the in vitro metabolism of R-(+)-6 appeared to be slower than that of 2. Therefore first-pass metabolism was not thought to be the reason for the lower bioavailability of R-(+)-6, as compared to 2.