Rasagiline mesylate

Base Information

• Chemical Name: Rasagiline mesylate
• CAS No.: 161735-79-1
• Molecular Formula: C12H13N^.CH4O3S
• Molecular Weight: 267.349
• Hs Code.: 29214990
• European Community (EC) Number: 694-423-3
• UNII: LH8C2JI290
• DSSTox Substance ID: DTXSID8047848
• Wikidata: Q27282989
• NCI Thesaurus Code: C66511
• RXCUI: 577300
• Pharos Ligand ID: L2PY466DVAZJ
• ChEMBL ID: CHEMBL1201142
• Mol file: 161735-79-1.mol

Synonyms:2,3-dihydro-N-2-propynyl-1H-inden-1-amine-(1R)-hydrochloride;AGN 1135;AGN-1135;Azilect;N-2-propynyl-1-indanamine;N-propargyl-1-aminoindan mesylate;rasagiline;rasagiline hydrochloride;TVP 101;TVP 1022;TVP-101;TVP-1022;TVP1022

Chemical Property of Rasagiline mesylate

Chemical Property:

• Appearance/Colour: white to off-white crystalline solid
• Vapor Pressure: 0.000816mmHg at 25°C
• Melting Point: 155-158 °C
• Boiling Point: 305.5 °C at 760 mmHg
• Flash Point: 146.8 °C
• PSA: 74.78000
• Density: 1.05 g/cm3
• LogP: 2.87240
• Storage Temp.: -20°C Freezer
• Solubility.: H2O: ≥20mg/mL
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 267.09291458
• Heavy Atom Count: 18
• Complexity: 305

Purity/Quality:

99.0% ^*data from raw suppliers

Rasagiline mesylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CS(=O)(=O)O.C#CCNC1CCC2=CC=CC=C12
• Isomeric SMILES: CS(=O)(=O)O.C#CCN[C@@H]1CCC2=CC=CC=C12
• Recent ClinicalTrials: A Phase 3 Study of TVP-1012 (1 mg) in Early Parkinson's Disease Patients
• Recent EU Clinical Trials: A Phase 3, Twelve-week, Multi-Center, Multinational, Randomized, Double-Blind, Double-Dummy, Parallel Group Study to Determine the Efficacy, Safety and Tolerability of P2B001 Once Daily Compared to its Individual Components in Subjects With Early Parkinson’s Disease and to a Calibration Arm of Pramipexole ER.
• Description: Rasagiline mesylate is a potent and selective irreversible monoamine oxidase B (MAO-B) inhibitor launched in 2005 in Israel by Teva as monotherapy in patients with early Parkinson's disease and as adjuvant treatment in moderate-toadvanced disease. Lundbeck will market the drug throughout Europe. Rasagiline is in phase II clinical trials at Teva and Eisai for the treatment of Alzheimer's type dementia.
• Uses: A selective irreversible MAO-B inhibitor. Antiparkinsonian Rasagiline Mesylate is a new MAO-B inhibitor for the treatment of idiopathic Parkinson's disease. Rasagiline is a selective irreversible MAO-B inhibitor. Rasagiline is an Antiparkinsonian agent.
• Indications: Rasagiline mesylate is a novel, potent, second-generation, selective, irreversible MAO-B inhibitor that blocks the breakdown of dopamine. It is approved for the treatment of PD. Indications for use of once-daily rasagiline are as a monotherapy in early PD and as an adjunct to levodopa in moderate to advanced disease. Rasagiline significantly improves symptoms during initial monotherapy in patients with early PD and as an adjunct treatment to levodopa in moderate-to-advanced patients. Rasagiline is well tolerated up to doses as high as 20 mg/day. Evidence for neuroprotective effect of rasagiline is as follows (Jain 2010c): Structure activity studies have shown that the neuroprotective activity is associated with the propargyl moiety of rasagiline, which protects mitochondrial viability. Experimental evidence supports rasagiline's neuroprotective efficacy, showing that neuronal survival is related to the anti-apoptotic properties of its propargyl moiety. Aminoindan metabolite of rasagiline has been shown to have neuroprotective properties (Bar-Am et al. 2010).

Technology Process of Rasagiline mesylate

There total 32 articles about Rasagiline mesylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

methanesulfonic acid (75-75-2,98527-29-8) + rasagiline (136236-51-6,185517-74-2) → rasagiline mesylate (161735-79-1)

Guidance literature:

In isopropyl alcohol; for 1h; Reflux;

DOI:10.1016/j.apcata.2014.12.015

Reference yield: 92.6%

methanesulfonic acid (75-75-2,98527-29-8) + (1R)-N-(prop-2-ynyl)-2,3-dihydro-1H-inden-1-amine hemihydrate → rasagiline mesylate (161735-79-1)

Guidance literature:

(1R)-N-(prop-2-ynyl)-2,3-dihydro-1H-inden-1-amine hemihydrate; With potassium carbonate; In water; pH=Ca. 10; Large scale;

methanesulfonic acid; In isopropyl alcohol; at 20 ℃; for 1.5h; Large scale;

Reference yield: 89.0%

methanesulfonic acid (75-75-2,98527-29-8) + (1R)-N-prop-2-ynyl-2,3-dihydro-1H-inden-1-amine L-(+)-tartrate → rasagiline mesylate (161735-79-1)

Guidance literature:

(1R)-N-prop-2-ynyl-2,3-dihydro-1H-inden-1-amine L-(+)-tartrate; With sodium hydrogencarbonate; In water; ethyl acetate; at 20 - 25 ℃; Inert atmosphere;

methanesulfonic acid; In isopropyl alcohol; Reflux;

upstream raw materials:

methanesulfonic acid

rasagiline

N-(2,3 dibromopropyl)-1-aminoindan

2,3-dihydro-1H-inden-1-amine

Downstream raw materials:

rasagiline

Refernces

• 1、 -. "Preparation method of rasagiline mesylate and intermediate thereof". Paragraph 0073-0079; 0080-0085. . Retrieved 2019/01/21.
• 2、 -. "PROCESS FOR THE PREPARATION OF ENATIOMERICALLY PURE 1-AMINOINDAN". Page/Page column 27. . Retrieved 2015/06/03.