(6S)-6-{propyl[2-(thiophen-2-yl)ethyl]amino}-5,6,7,8-tetrahydronaphthalen-1-ol hydrochloride

• ChemBase ID: 153672
• Molecular Formular: C19H26ClNOS
• Molecular Mass: 351.93384
• Monoisotopic Mass: 351.14236314
• SMILES: CCCN(CCc1cccs1)[C@H]1CCc2c(cccc2O)C1.Cl
• Canonical SMILES: CCCN([C@H]1CCc2c(C1)cccc2O)CCc1cccs1.Cl
• InChI: InChI=1S/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
• InChIKey: CEXBONHIOKGWNU-NTISSMGPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6S)-6-{propyl[2-(thiophen-2-yl)ethyl]amino}-5,6,7,8-tetrahydronaphthalen-1-ol hydrochloride
• IUPAC Traditional name: neupro hydrochloride
• Synonyms: (-)-(S)-5,6,7,8-Tetrahydro-6-(propyl(2-(2-thienyl)ethyl)amino)-1-naphthol hydrochloride; (-)-N 0437; N 0923; Neupro; SPM 962; Rotigotine hydrochloride; (6S)-5,6,7,8-Tetrahydro-6-[propyl[2-(2-thienyl)ethyl]amino]-1-naphthalenol Hydrochloride Salt; (-)-N 0437 Hydrochloride Salt; N 0923 Hydrochloride Salt; Neupro Hydrochloride Salt; SPM 962 Hydrochloride Salt; Rotigotine Hydrochloride; Rotigotine Hydrochloride

Database IDs

• CAS Number: 99755-59-6; 125572-93-2
• MDL Number: MFCD00906149
• PubChem SID: 162247811
• PubChem CID: 180335

CALCULATED PROPERTIES

• Polarizability: 36.32044 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true
• Acid pKa: 10.030946
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.758364
• LogD (pH = 7.4): 2.214749
• Log P: 4.339128
• Molar Refractivity: 94.5579 cm^3

PROPERTIES

Physical Property

• Solubility: Acetone; DMSO; DMSO: >10 mg/mL
• Apperance: white to off-white solid; White to Off-White Solid
• Melting Point: 177-179°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H25NOS·HCl

DETAILS

Sigma Aldrich - R9281

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.

Toronto Research Chemicals - R700700

It is a non-ergot dopamine agonist drug and is indicated for the treatment of Parkinson’s disease.

REFERENCES

• Loschmann, P., et al.: Eur. J. Pharmacol., 166, 373 (1989)
• Edgar, D., et al.: J. Pharmacol. Exp. Ther., 283, 757 (1989)
• Ferreira, J., et al.: Lancet, 355, 1333 (1989)
• Arnulf, I., et al.: Neurology, 58, 1019 (1989)
• Wisor, J., et al.: Neuroscience, 132,