Rasagiline mesylate

Rasagiline mesylate Basic information
Product Name:Rasagiline mesylate
Synonyms:N-(prop-2-yn-1-yl)-2,3-dihydro-1H-inden-1-amine methanesulfonate;Rasagiline Mesylate/Tartrate/Base;(1R)-2,3-Dihydro-N-2-propyn-1-yl-1H-inden-1-amine Mesylate;(R)-N-2-Propynyl-1-indanamine Mesylate;Agilect;TVP-101;RASAGILINE MESYLATE;(r)-n-2-propynyl-1-indanamine methanesulfonate
CAS:161735-79-1
MF:C13H17NO3S
MW:267.34398
EINECS:694-423-3
Product Categories:Chiral;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Rasagiline;Signalling;APIs;161735-79-1
Mol File:161735-79-1.mol
Rasagiline mesylate Structure
Rasagiline mesylate Chemical Properties
Melting point 155-158°C
storage temp. 2-8°C
solubility H2O: ≥20mg/mL
form powder
color white to tan
optical activity[α]/D +15 to +28°, c = 0.6 mg/mL in H2O
Stability:Stable for 2 years from date of purchase as supplied. Solutions in DMSO, distilled water or ethanol may be stored at -20°C for up to 1 month.
InChIInChI=1/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-;/s3
InChIKeyJDBJJCWRXSVHOQ-ZLBVLXFENA-N
SMILESC12C=CC=CC=1CC[C@H]2NCC#C.S(C)(O)(=O)=O |&1:8,r|
CAS DataBase Reference161735-79-1(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 22
Safety Statements 24/25
WGK Germany 3
HS Code 29214990
MSDS Information
Rasagiline mesylate Usage And Synthesis
DescriptionRasagiline 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.
Chemical PropertiesWhite to Off-White Crystalline Solid
UsesRasagiline is a selective irreversible MAO-B inhibitor. Rasagiline is an Antiparkinsonian agent.
UsesA selective irreversible MAO-B inhibitor. Antiparkinsonian
UsesRasagiline Mesylate is a new MAO-B inhibitor for the treatment of idiopathic Parkinson's disease.
IndicationsRasagiline 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).

Brand nameAzilect (Teva).
General DescriptionRasagiline mesylate, (R)-N-(prop-2-ynyl)-2,3-dihydro-1H-inden-1-amine methanesulfonate(Azilect), belongs to the propargylamine family and is a whiteto off-white powder, soluble in water or ethanol, slightly solublein isopropanol. Rasagiline is rapidly absorbed. Plasmaprotein binding for rasagiline ranges from 88% to 94%, withspecific binding to serum albumin being 61% to 63%. It undergoescomplete biotransformation before excretion, mainlyvia N-dealkylation and hydroxylation, to yield three majormetabolites: 1(R)-aminoindan, 3-hydroxy-N-propargyl-1-aminoindan, and 3-hydroxy-1-aminoindan. Both oxidativepathways are catalyzed by cytochrome P450 (CYP) enzymes,mainly the 1A2 isozyme. Rasagiline and its metabolites undergoglucuronide conjugation with subsequent urinary excretion.Inhibitors of the CYP1A2 may increase plasmaconcentrations of rasagiline up to twofold. Because rasagilineis a selective and irreversible inhibitor of MAO-B, itsduration of action is independent of the drug’s half-life and isinstead determined by the regeneration rate of MAO-B. Thischaracteristic is potentially beneficial in PD, where rasagiline’sprolonged effect may be able to limit the fluctuating responsesthat are characteristic of long-term drug treatmentwith levodopa.
Biochem/physiol ActionsRasagiline 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.
Synthesis1-Indanone (122) was condensed with benzyl amine to give corresponding enamine which was reduced with sodium borohydride in ethanol to give racemic Nbenzyl- 1-inda-namine (123) in 82% yield. The racemic benzylamine 123 was resolved with L-tartaric acid and recrystallized from boiling water to give optical pure Rbenzylamine 124 as a tartarate salt. The recovered S-isomer 125 can be racemized under basic condition to give back as the starting racemic 123. Compound 124 was hydrogenated and basified to give free amine 126 in 72 % yield which was alkylated with propargyl chloride and K2CO3 in hot acetonitrile to yield free resagiline. Finally resagiline mesilate (XVII) was obtained by treating resagiline with methanesulfonic acid in refluxing IPA.

Synthesis_161735-79-1

storageroom temperature (desiccate)
References1) Youdim?et al.?(2001),?Rasagiline [N-propargyl-1R(+)-aminoindan], a selective and potent inhibitor of mitochondrial monoamine oxidase B; Br. J. Pharmacol.,?132?500 2) Cereda?et al.?(2017),?Efficacy of rasagiline and selegiline in Parkinson’s disease: a head-to-head 3-year retrospective case-control study; J. Neurol.,?264?1254 3) Cronin and Grealy (2017),?Neuroprotective and Neuro-restorative Effects of Minocycline and Rasagiline in Zebrafish 6-Hydroxydopamine Model of Parkinson’s Disease; Neuroscience,?367?34 4) Kang?et al.?(2017),?TrkB neurotrophic activities are blocked by α-synuclein, triggering dopaminergic cell death in Parkinson’s disease; Proc. Natl. Acad. Sci. USA,?114?10773 5) Ledreux?et al.?(2016),?BDNF levels are increased by aminoindan and rasagiline in a double lesion model of Parkinson’s disease; Brain Res.,?1631?34
Rasagiline mesylate Preparation Products And Raw materials
Raw materials1-ACETOXYINDAN-->1-INDANOL-->Rasagiline
ILOPERIDONE Rasagiline rich-d-t-Prallethrin 1-Aminoindan Rasagiline Propyne Methanesulfonic acid Propargyl alcohol Pefloxacin mesylate Phentolamine mesilate Pazufloxacin mesilate :(S)-2-Methyl-3-(2-propynyl)-4-oxocyclopent-2-enyl-(lR)-cis,trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate Trifluoromethanesulfonic acid Imatinib OXADIARGYL PESTANAL Rasagiline mesylate methanesulfonate Propiolic Acid

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