125572-93-2

Basic information

• Product Name: (6S)-6-(propyl-(2-thiophen-2-ylethyl)amino)tetralin-1-ol hydrochloride
• Synonyms: (6S)-6-(propyl-(2-thiophen-2-ylethyl)amino)tetralin-1-ol hydrochloride;(S)-5,6,7,8-Tetrahydro-6-[propyl[2-(2-thienyl)ethyl]amino]-1-naphthalenol hydrochloride;Rotigotine hydrochloride;(6S)-5,6,7,8-Tetrahydro-6-[propyl[2-(2-thienyl)ethyl]amino]-1-naphthalenolhydrochloride;(S)-6-(propyl(2-(thiophen-2-yl)ethyl)amino)-5,6,7,8-tetrahydronaphthalen-1-ol hydrochloride;(6S)-;8-tetrahydro-6-[propyl[2-(2-thienyl)ethyl]aMino]-;rotigotine HCl
• CAS NO: 125572-93-2
• Molecular Formula: C₁₉H₂₅NOS*ClH
• Molecular Weight: 351.93
• EINECS: 1592732-453-0
• Product Categories: APIs;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 125572-93-2.mol
• Article Data: 13

Chemical Properties

• Melting Point: 114-117°C
• Boiling Point: 470.1 °C at 760 mmHg
• Flash Point: 238.1 °C
• Appearance: Almost white to white crystalline powder
• Density: 1.2g/cm3 at 20℃
• Vapor Pressure: 1.84E-09mmHg at 25°C
• Storage Temp.: Desiccate at RT
• Solubility: Acetone (Slightly, Heated, Sonicated), DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (6S)-6-(propyl-(2-thiophen-2-ylethyl)amino)tetralin-1-ol hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (6S)-6-(propyl-(2-thiophen-2-ylethyl)amino)tetralin-1-ol hydrochloride(125572-93-2)
• EPA Substance Registry System: (6S)-6-(propyl-(2-thiophen-2-ylethyl)amino)tetralin-1-ol hydrochloride(125572-93-2)

Safety Data

• WGK Germany: 2
• Hazardous Substances Data: 125572-93-2(Hazardous Substances Data)

Usage

Description

(6S)-6-(propyl-(2-thiophen-2-ylethyl)amino)tetralin-1-ol hydrochloride is a non-ergot dopamine agonist drug, characterized by its white to off-white solid appearance. It is primarily used for the treatment of Parkinson's disease, offering a therapeutic option for patients suffering from this neurodegenerative disorder.

Uses

Used in Pharmaceutical Industry:
(6S)-6-(propyl-(2-thiophen-2-ylethyl)amino)tetralin-1-ol hydrochloride is used as a therapeutic agent for the treatment of Parkinson's disease. It functions as a dopamine agonist, helping to alleviate the motor symptoms associated with the condition by mimicking the effects of dopamine in the brain.
As a non-ergot derivative, this compound offers an alternative to ergot-based dopamine agonists, potentially reducing the risk of certain side effects and complications. Its use in the pharmaceutical industry is specifically aimed at improving the quality of life for individuals living with Parkinson's disease by providing a medication that can manage the symptoms and slow the progression of the illness.

Biochem/physiol Actions

Rotigotine is a dopamine receptor agonist with preference for D3 receptors over D2 and D1. As such, it is an effective anti-Parkinsonian agent. Racemic rotigotine is about 50 times as potent as quinpirole, the gold standard D2 agonist.

InChI:InChI=1/C19H25NOS.ClH/c1-2-11-20(12-10-17-6-4-13-22-17)16-8-9-18-15(14-16)5-3-7-19(18)21;/h3-7,13,16,21H,2,8-12,14H2,1H3;1H/t16-;/m0./s1

Upstream product

• 1148154-91-9 (2S)-5-methoxy-N-propyl-N-(2'-(thien-2-yl)ethyl)tetralin-2-amine 
• 1232344-37-4 (2S)-5-methoxy-N-propyl-N-(2'-(thien-2-yl)ethyl)tetralin-2-amine hydrochloride 
• 39098-97-0 2-thienylacetic acid chloride 
• 32940-15-1 5-methoxy-2-tetralone 
• 1918-77-0 Thiophene-2-acetic acid 
• 165950-84-5 (S)-1,2,3,4-tetrahydro-5-hydroxy-N-propyl-naphthalen-2-ammonium hydrobromide 
• 3904-24-3 (5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propylamine hydrochloride 
• 101403-25-2 (R)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-naphthalen-2-amine 
• 1352917-68-0 (S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-naphthalen-2-ammonium (S)-2-methoxy-2-phenylacetate 
• 93601-86-6 (S)-(-)-(5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propylamine hydrochloride 
• 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 
• 5402-55-1 2-thiophenethanol 

Downstream Products

• 99755-59-6 rotigotine 

Relevant articles and documents

Novel Process for Preparation of Rotigotine and Intermediates Thereof

The present invention relates to a novel process for the preparation of Rotigotine of formula (I) and intermediates thereof.

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.

S-5-SUBSTITUENT-N-2'-(THIOPHENE-2-YL)ETHYL-TETRALIN-2-AMINE OR CHIRAL ACID SALTS THEREOF AND USE FOR PREPARING ROTIGOTINE

The chiral compound S-5-substituted-N-2-(thienyl-2-yl-)ethyl-tetralin-2-amine or its chiral acid salts and preparation method thereof are disclosed, and the method for preparing Rotigotine by using the chiral compound is also disclosed. Racemic 5-substituted-N-2'-(thien-2-yl-)ethyl-tetralin-2-amine (compound 1) is resolved by using a conventional chiral acid to obtain an optically pure chiral acid salt of S-5-substituted-N,2'-(thien-2-yl-)ethyl-tetralin-2-amine, which is then dissociated to obtain S-5-substituted-N-2'-(thien-2-yl-)ethyl-tetralin-2-amine (compound 2). The compound 2 or chiral acid salt thereof is alkylated and deprotected to produce rotigotine (compound 5).