58349-23-8

Basic information

• Product Name: (S)-5-methoxy-1,2,3,4-tetrahydro-N-(phenylmethyl)- 2-Naphthalenamine (Rotigotine)
• Synonyms: (S)-5-methoxy-1,2,3,4-tetrahydro-N-(phenylmethyl)- 2-Naphthalenamine (Rotigotine);(S)-5-Methoxy-1,2,3,4-tetrahydro-N-(phenylmethyl)-2-naphthalenamine;(2S)-N-Benzyl-5-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine
• CAS NO: 58349-23-8
• Molecular Formula: C₁₈H₂₁NO
• Molecular Weight: 267.37
• Product Categories: APIs Intermediate
• Mol File: 58349-23-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 424.4±45.0 °C(Predicted)
• Appearance: /
• Density: 1.09±0.1 g/cm3(Predicted)
• Refractive Index: 1.593
• PKA: 9.19±0.20(Predicted)
• CAS DataBase Reference: (S)-5-methoxy-1,2,3,4-tetrahydro-N-(phenylmethyl)- 2-Naphthalenamine (Rotigotine)(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-5-methoxy-1,2,3,4-tetrahydro-N-(phenylmethyl)- 2-Naphthalenamine (Rotigotine)(58349-23-8)
• EPA Substance Registry System: (S)-5-methoxy-1,2,3,4-tetrahydro-N-(phenylmethyl)- 2-Naphthalenamine (Rotigotine)(58349-23-8)

Safety Data

• Hazardous Substances Data: 58349-23-8(Hazardous Substances Data)

Usage

General Description

Rotigotine, also known as (S)-5-methoxy-1,2,3,4-tetrahydro-N-(phenylmethyl)- 2-Naphthalenamine, is a synthetic dopamine agonist used for the treatment of Parkinson's disease and restless legs syndrome. It works by stimulating dopamine receptors in the brain, which helps to regulate movement and reduce the symptoms of these conditions. Rotigotine is typically administered as a transdermal patch, providing continuous delivery of the medication over a 24-hour period. It has a long half-life and is well-tolerated, making it a convenient and effective option for managing the symptoms of Parkinson's disease and restless legs syndrome. Common side effects of Rotigotine include nausea, dizziness, and application site reactions.

InChI:InChI=1/C18H21NO/c1-20-18-9-5-8-15-12-16(10-11-17(15)18)19-13-14-6-3-2-4-7-14/h2-9,16,19H,10-13H2,1H3/t16-/m0/s1

Upstream product

• 136247-07-9 2-(N-benzylamino)-5-methoxytetralin 
• 58349-24-9 C₈H₈O₃*C₁₈H₂₁NO 
• 100-46-9 benzylamine 
• 32940-15-1 5-methoxy-2-tetralone 

Downstream Products

• 1089179-55-4 (6S)-6-[benzylamino]-5,6,7,8-tetrahydronaphthalen-1-ol 
• 136247-11-5 N-((S)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-2-(4-nitro-phenyl)-N-propyl-acetamide 
• 136316-06-8 (S)-(-)-2--5-methoxytetralin 
• 129388-80-3 (S)-(-)-2--5-hydroxytetralin 
• 101470-23-9 Desthienyl-Rotigotine 
• 101403-24-1 (S)-(5-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propylamine hydrochloride 
• 101403-23-0 (-)-(2S)-2-(N-benzyl-N-n-propylamino)-5-methoxytetralin 

Relevant articles and documents

Heterocyclyl-substituted-tetrahydro-naphthalen derivatives as 5-HT7 receptor ligands

The present invention relates to heterocyclyl-substituted-tetrahydro-naphthalen compounds of general formula (I) and (Iprot), methods for their preparation, medicaments comprising these compounds as well as their use for the preparation of a medicament for the treatment of humans or animals, mediated by the receptor 5-HT7 affinity.

Fluorescent Probes for Dopamine Receptors: Synthesis and Characterization of Fluorescein and 7-Nitrobenz-2-oxa-1,3-diazol-4-yl Conjugates of D-1 and D-2 Receptor Ligands

Fluorescent probes have been designed and developed for dopamine D-1 and D-2 receptors.Fluorescein and/or NBD (7-nitrobenz-2-oxa-1,3-diazol-4-yl)derivatives of PPHT (D-2 agonist), spiperone (D-2 antagonist), SKF 38393 (D-1 agonist), and SKF 83566 (D-1 antagonist) were synthesized via their amino-functionalized analogues and all ligands were pharmacologically evaluated by measuring their ability to displace SCH 23390 and 3H)spiperone from D-1 and D-2 receptor sites in caudate putamen of monkeys (Macaca fascicularis).The fluorescein derivatives of PPHT andSKF 83566 and the NBD derivatives of spiperone and SKF 83566 retained the high affinity and selectivity of parent ligands.The NBD derivatives of PPHT showed higher D-2 receptor affinity and selectivity than their parent ligands.The enantiomers of the fluorescent derivatives of PPHT were also synthesized and were found to exhibit stereoselectivity in binding to the D-2 receptor, with the S enantiomers having a considerably higher affinity than their R analogues.In contrast to these results, the fluorescein derivative of SKF 38393 showed only a low affinity for the D-1 receptor.These fluorescein- and NBD-coupled D-1 and D-2 receptor ligands have considerable significance as potential probes in the study of distribution of the receptors at the cellular/subcellular level and of their mobility in membranes in normal/diseased states by use of fluorescence microscopic and fluorescence photobleaching recovery techniques, respectively.The development of these novel fluorescent probes should also provide new leads for the design and synthesis of additional fluorescent ligands with better fluorescent properties and/or higher affinity/selectivity for the DA receptors.