(1R)-N-(prop-2-yn-1-yl)-2,3-dihydro-1H-inden-1-amine; methanesulfonic acid

• ChemBase ID: 153295
• Molecular Formular: C13H17NO3S
• Molecular Mass: 267.34398
• Monoisotopic Mass: 267.09291441
• SMILES: CS(=O)(=O)O.C#CCN[C@@H]1CCc2c1cccc2
• Canonical SMILES: CS(=O)(=O)O.C#CCN[C@@H]1CCc2c1cccc2
• InChI: InChI=1S/C12H13N.CH4O3S/c1-2-9-13-12-8-7-10-5-3-4-6-11(10)12;1-5(2,3)4/h1,3-6,12-13H,7-9H2;1H3,(H,2,3,4)/t12-;/m1./s1
• InChIKey: JDBJJCWRXSVHOQ-UTONKHPSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R)-N-(prop-2-yn-1-yl)-2,3-dihydro-1H-inden-1-amine; methanesulfonic acid
• IUPAC Traditional name: methanesulfonic acid; rasagiline
• Synonyms: (1R)-N-(prop-2-yn-1-yl)-2,3-dihydro-1H-inden-1-amine; methanesulfonic acid; (1R)-2,3-Dihydro-N-2-propyn-1-yl-1H-inden-1-amine Mesylate; (R)-2,3-Dihydro-N-2-propynyl-1-indenamine Mesylate; Agilect; Azilect; Rasagiline Mesylate; (1R)-2,3-Dihydro-N-2-propynl-1H-inden-1-amine methanesulfonate; N-Propargyl-1(R)-aminoindan methanesulfonate; TVP-1012; Rasagiline mesylate

Database IDs

• CAS Number: 161735-79-1
• MDL Number: MFCD08460604
• PubChem SID: 162247434
• PubChem CID: 3052775

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -0.6091183
• LogD (pH = 7.4): 0.9995979
• Log P: 2.303902
• Molar Refractivity: 54.467 cm^3
• Polarizability: 21.04538 Å^3
• Polar Surface Area: 12.03 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; H2O: ≥20 mg/mL; Methanol; Water
• Apperance: White to Off-White Solid; white to tan powder
• Melting Point: 150-152°C
• Optical Rotation: [α]/D +15 to +28°, c = 0.6 mg/mL in H2O
• Hydrophobicity(logP): 2.524

Safety Information

• Storage Condition: -20°C Freezer; desiccated
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC); 95%
• Empirical Formula (Hill Notation): C12H13N · CH4O3S

DETAILS

Sigma Aldrich - SML0124

Biochem/physiol Actions
Rasagiline mesylate is an irreversible inhibitor of monoamine oxidase selective for MAO type B over type A by a factor of fourteen. It has anti-apoptotic and neuroprotectant activity and has been used as a treatment for Parkinson′s disease.

Toronto Research Chemicals - R126000

Rasagiline is a selective irreversible MAO-B inhibitor. Rasagiline is an Antiparkinsonian agent.

REFERENCES

• Rabey, J.M., et al.: Clin. Neuropharmacol., 23, 324 (2000)
• Glezer, S., et al.: Eur. J. Pharmacol., 472, 173 (2000)
• Youdim, M.B.H., et al.: Biochem. Pharmacol., 66, 1635 (2000)
• Chen, J.J., et al.: J. Clin. Pharmacol., 45, 878 (2000)