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Rasagiline mesylate

Product Name
Rasagiline mesylate
CAS No.
161735-79-1
Chemical Name
Rasagiline mesylate
Synonyms
Azilect;RASAGILINE MESILATE;RASAGILINE GLUCURONIDE;CS-289;Agilect;TVP-101;TV 1012;TVP-1012;Unii-lh8C2ji290;RASAGILINE MESYLATE
CBNumber
CB7501001
Molecular Formula
C13H17NO3S
Formula Weight
267.34398
MOL File
161735-79-1.mol
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Rasagiline mesylate Property

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.
InChI
InChI=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
InChIKey
JDBJJCWRXSVHOQ-ZLBVLXFENA-N
SMILES
C12C=CC=CC=1CC[C@H]2NCC#C.S(C)(O)(=O)=O |&1:8,r|
CAS DataBase Reference
161735-79-1(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn
Risk Statements 
22
Safety Statements 
24/25
WGK Germany 
3
HS Code 
29214990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0124
Product name
Rasagiline mesylate
Purity
≥98% (HPLC)
Packaging
10mg
Price
$107
Updated
2024/03/01
Sigma-Aldrich
Product number
SML0124
Product name
Rasagiline mesylate
Purity
≥98% (HPLC)
Packaging
50mg
Price
$431
Updated
2024/03/01
TCI Chemical
Product number
R0213
Product name
Rasagiline Mesylate
Packaging
250MG
Price
$84
Updated
2024/03/01
TCI Chemical
Product number
R0213
Product name
Rasagiline Mesylate
Packaging
5G
Price
$684
Updated
2024/03/01
TCI Chemical
Product number
R0213
Product name
Rasagiline Mesylate
Packaging
1G
Price
$228
Updated
2024/03/01
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Rasagiline mesylate Chemical Properties,Usage,Production

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.

Chemical Properties

White to Off-White Crystalline Solid

Uses

A selective irreversible MAO-B inhibitor. Antiparkinsonian

Uses

Rasagiline Mesylate is a new MAO-B inhibitor for the treatment of idiopathic Parkinson's disease.

Uses

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).

brand name

Azilect (Teva).

General Description

Rasagiline 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 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.

Mechanism of action

The specific mechanism of action of Rasagiline mesylate is unknown. One of these mechanisms is thought to be related to its MAO-B inhibitory activity, which leads to elevated extracellular dopamine levels in the striatum. It irreversibly blocks dopamine metabolism, thereby increasing dopamine levels, which can be beneficial for symptoms in Parkinson's disease patients.

Side effects

Rasagiline mesylate has been shown to be effective, safe and well tolerated as monotherapy in early Parkinson's disease. The most common are infection, headache, dizziness, weakness, anorexia and vomiting. In rare patients, it may cause new malignancies (melanoma and squamous cell carcinoma of the skin).

Synthesis

1-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.

storage

room temperature (desiccate)

References

1) 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 materials

Preparation Products

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View Lastest Price from Rasagiline mesylate manufacturers

BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
Product
Rasagiline Mesylate 161735-79-1
Price
US $0.00/g
Min. Order
1g
Purity
More Than 99%
Supply Ability
100kg/Month
Release date
2024-09-25
Zhuozhou Wenxi import and Export Co., Ltd
Product
Rasagiline mesylate 161735-79-1
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-10
Zhuozhou Wenxi import and Export Co., Ltd
Product
Rasagiline mesylate 161735-79-1
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-08

161735-79-1, Rasagiline mesylateRelated Search:

Trifluoromethanesulfonic acid OXADIARGYL PESTANAL Methanesulfonic acid Phentolamine mesilate ILOPERIDONE Pazufloxacin mesilate :(S)-2-Methyl-3-(2-propynyl)-4-oxocyclopent-2-enyl-(lR)-cis,trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate Pefloxacin mesylate Imatinib Propiolic Acid rich-d-t-Prallethrin Rasagiline Rasagiline Propargyl alcohol 1-Aminoindan Propyne methanesulfonate Rasagiline mesylate

  • (1R)-2,3-Dihydro-N-2-propynyl-1H-inden-1-amine methanesulfonate
  • CS-289
  • R-(+)-Rasagiline mesylate
  • 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
  • Azilect
  • TVP-101
  • RASAGILINE MESYLATE
  • (r)-n-2-propynyl-1-indanamine methanesulfonate
  • Rasagiline nesylate
  • RASAGILINE MESILATE
  • TVP-1012
  • (R)-2,3-Dihydro-N-2-propynyl-1-indenaMine Mesylate
  • TV 1012
  • (R)-N-(Prop-2-yn-1-yl)-2,3-dihydro-1H-inden-1-aMine Methanesulfonate
  • RASAGILINE GLUCURONIDE
  • (1R)-2,3-dihydro-N-2-propyn-1-yl-1H-inden-1-amine,methanesulfonate (1:1)
  • (1R)-2,3-Dihydro-N-2-propynl-1H-inden-1-amine methanesulfonate
  • N-Propargyl-1(R)-aminoindan methanesulfonate
  • 1H-Inden-1-amine, 2,3-dihydro-N-2-propynyl-, (R)-, methanesulfonate
  • Rasagiline methanesulfonate
  • Unii-lh8C2ji290
  • 1H-Inden-1-amine, 2,3-dihydro-N-2-propyn-1-yl-, (1R)-, methanesulfonate (1:1)
  • (R)-N-(2-Propyn-1-yl)-1-indanamine Methanesulfonate
  • (R)-N-Propargyl-1-indanamine Methanesulfonate
  • Rasagiline mesylate USP/EP/BP
  • Rasagiline Mesylate(pure)
  • Rasagiline MesylateQ: What is Rasagiline Mesylate Q: What is the CAS Number of Rasagiline Mesylate Q: What is the storage condition of Rasagiline Mesylate Q: What are the applications of Rasagiline Mesylate
  • (1R)-N-prop-2-ynylindan-1-amine
  • Resagiline mesylate
  • Rasagiline mesylate, MAO-B inhibitor
  • 161735-79-1
  • 136235-79-1
  • 161735-79-5
  • C12H13NCH4O3S
  • Chiral
  • Chiral Reagents
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Rasagiline
  • Signalling
  • APIs
  • 161735-79-1