92206-54-7

Basic information

• Product Name: Rotigotine
• Synonyms: 6-(propyl-(2-thiophen-2-ylethyl)amino)tetralin-1-ol;6-(Propyl(2-(2-thienyl)ethyl)amino)-5,6,7,8-tetrahydro-1-naphthalenol;N 0437;5,6,7,8-Tetrahydro-6-[propyl[2-(2-thienyl)ethyl]amino]-1-naphthalenol;(R)-2-[Propyl[2-(2-thienyl)ethyl]amino]tetralin-5-ol;[2R,(+)]-2-[Propyl[2-(2-thienyl)ethyl]amino]tetralin-5-ol;[R,(+)]-2-[Propyl[2-(2-thienyl)ethyl]amino]tetralin-5-ol;N-0924
• CAS NO: 92206-54-7
• Molecular Formula: C₁₉H₂₅NOS
• Molecular Weight: 315.4729
• Mol File: 92206-54-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 470.1 °C at 760 mmHg
• Flash Point: 238.1 °C
• Appearance: /
• Density: 1.15
• Vapor Pressure: 1.84E-09mmHg at 25°C
• Refractive Index: 1.611
• PKA: 10.49±0.40(Predicted)
• CAS DataBase Reference: Rotigotine(CAS DataBase Reference)
• NIST Chemistry Reference: Rotigotine(92206-54-7)
• EPA Substance Registry System: Rotigotine(92206-54-7)

Safety Data

• Hazardous Substances Data: 92206-54-7(Hazardous Substances Data)

Usage

General Description

Rotigotine is a dopamine agonist used in the treatment of Parkinson's disease and restless legs syndrome. It works by stimulating dopamine receptors in the brain, leading to improved motor function and reduced symptoms of movement disorders. It is available as a transdermal patch for continuous delivery of the medication, providing steady blood levels and minimizing side effects. Rotigotine has been shown to be effective in reducing motor symptoms and improving quality of life in patients with Parkinson's disease, as well as reducing the symptoms of restless legs syndrome. However, it can cause side effects such as nausea, vomiting, dizziness, and sleep disturbances, and should be used with caution in patients with a history of cardiovascular disease.

InChI:InChI=1/C19H25NOS/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/t16-/m0/s1

Upstream product

• 40412-06-4 2-(2-thienyl)ethyl tosylate 
• 78950-82-0 2-N-propylamino-1,2,3,4-tetrahydro-5-hydroxynaphthalene 
• 78598-91-1 2-(N-propylamino)-5-methoxytetraline 
• 32940-15-1 5-methoxy-2-tetralone 
• 1918-77-0 Thiophene-2-acetic acid 
• 101945-65-7 2-(N-n-propyl-N-2-[2-thienyl]ethylamino)-5-methoxytetralin 

Relevant articles and documents

METHOD FOR INDUSTRIALLY PREPARING NITROGEN SUBSTITUTED AMINO-5,6,7,8-TETRAHYDRONAPHTHOL

A method for industrially preparing a nitrogen substituted 6-amino-5,6,7,8-tetrahydronaphthol is disclosed. The method comprises includes reacting a nitrogen substituted amino-5,6,7,8-tetrahydronaphthol compound of formula (II) with a 2-substituted ethyl sulfonate compound of formula (III) under an alkaline condition and in the presence of a sulfite.

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.

METHOD AND COMPOSITIONS FOR TREATMENT OF PARKINSONISM SYNDROME IN MAMMELS

This invention provides a method for treating the symptoms of parkinsonism which comprises administering to a human or other mammal suffering from the symptoms of parkinsonism an effective amount of a compound selected from the group consisting of optically-active or racemic compounds represented by the general formula: STR1 wherein R. sub.1 is selected from the group consisting of organic radicals methyl, substituted or unsubstituted phenyls, pyridyl, hydroxphenyl, STR2 X is oxygen or sulfur, Y is selected from the group consisting of hydroxy, nitro, cyano, axido, amino, acylamino, carboxyamido, trifluoromethyl, sulfate, sulfonamido, halogen, hydrocarbyl and hetero atom-substituted hydrocarbyl radicals, wherein said heteroatoms are selected from the group consisting of halogen, nitrogen, oxygen, sulfur and phosphorus and said hydrocarbyl radicals comprise from 1 to 12 carbon atoms, and a is an integer of from zero to 3,R 2, R 3 and R 4 are each selected from the group consisting of H and OA, A is H or is selected from the group consisting of hydrocarbyl radicals, STR3 R. sub.5 is selected from the group consisting of hydrocarbyl radicals; n is an integer between 1 and 3; and R 6 is an alkyl chain having between 1 and 3 carbon atoms with the provision that at least one of R 2, R. sub.3 and R 4 is H, that at least one of R 2, R 3 and R 4 is not H, and that R. sub.2 and R 4 are not both OA, and pharmaceutically acceptable salts thereof. Preferably, R 2 is oxygen. Preferably, R 2 is OA and A is H, and the compound is the (-) isomer.