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

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

Uses

Used in Neurological Medicine:
Rotigotine is used as a therapeutic agent for the treatment of Parkinson's disease, a progressive neurological disorder characterized by motor impairments. It is utilized to alleviate motor symptoms such as tremors, rigidity, and bradykinesia by mimicking the effects of dopamine, which is deficient in Parkinson's patients.
Rotigotine is also used as a treatment for restless legs syndrome, a neurological sleep disorder that causes an irresistible urge to move the legs, often accompanied by uncomfortable sensations. The medication helps to reduce the frequency and severity of symptoms, thereby improving sleep quality and overall well-being.
Used in Pharmaceutical Formulation:
Rotigotine is used as a transdermal patch for continuous and controlled delivery of the medication. This application ensures that the drug is released steadily over time, providing a consistent therapeutic effect and reducing the likelihood of side effects that may occur with fluctuating blood levels.
While Rotigotine has demonstrated effectiveness in managing the symptoms of Parkinson's disease and restless legs syndrome, it is important to note that it can cause side effects such as nausea, vomiting, dizziness, and sleep disturbances. Therefore, it should be administered with caution, particularly 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

• 1918-77-0 Thiophene-2-acetic acid 
• 32940-15-1 5-methoxy-2-tetralone 
• 78598-91-1 2-(N-propylamino)-5-methoxytetraline 
• 40412-06-4 2-(2-thienyl)ethyl tosylate 
• 78950-82-0 2-N-propylamino-1,2,3,4-tetrahydro-5-hydroxynaphthalene 
• 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.

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 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 OF PRODUCING BODY WEIGHT AND FOOD INTAKE USING A DOPAMINE D2 RECEPTOR AGONIST

This invention provides a method for treating the symptoms of obesity which comprises administering to a human or other mammal suffering from the symptoms of obesity an effective amount of a compound selected from the group consisting of the optically active compounds especially the (-) negative stereoisomers represented by the formula: STR1 wherein R 1 R 2,R 3,R 4,R 5 and R 6 are defined by the specification substituted or unsubstituted phenyls, pyridyl, hydroxyphenyl, STR2 X is oxygen or sulfur, Y is selected from the group consisting of hydroxy, nitro, cyano, azido, 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 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 3 and R 4 is H, that at least one of R. sub.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.Most preferably, R 2 is OA and A is H, and the compound is the (-) isomer.

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.

Method for treating schizophrenia

This invention provides a method for treating the symptoms of schizophrenia which comprises administering to a schizophrenic an effective amount of a compound selected from the group consisting of optically-active or racemic compounds represented by the general formula: STR1 wherein R1 is selected from the group consisting of organic radicals having fused rings, phenyl, pyridyl STR2 X is oxygen or sulfur, Y, if present, is selected from the group consisting of hydroxy, nitro, cyano, azido, 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 between zero and 3. R2, R3 and R4 are each selected from the group consising of H and OA, A is H or is selected from the group consisting of hydrocarbyl radicals, or STR3 R5 is selected from the group consisting of hydrocarbyl radicals and n is 2 or 3; with the proviso that at least one of R2, R3 and R4 is H, that at least one of R2, R3 and R4 is not H and that R2 and R4 are not both OA, except that when R1 is m-hydroxyphenyl, phenyl or 2-thienyl, the compound is optically-active.

Method and compositions for treatment of parkinsonism syndrome in mammals

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 R1 is selected from the group consisting of organic radicals methyl, substituted or unsubstituted phenyls, pyridyl, hydroxyphenyl, STR2 X is oxygen or sulfur, Y is selected from the group consisting of hydroxy, nitro, cyano, azido, 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, R2, R3 and R4 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 R5 is selected from the group consisting of hydrocarbyl radicals; n is an integer between 1 and 3; and R6 is an alkyl chain having between 1 and 3 carbon atoms with the provision that at least one of R2, R3 and R4 is H, that at least one of R2, R3 and R4 is not H, and that R2 and R4 are not both OA, and pharmaceutically acceptable salts thereof. Preferably, R2 is oxygen. Preferably, R2 is OA and A is H, and the compound is the (-) isomer.