(S)-2,3-DIHYDRO-N-METHYL-N-2-PROPYNYL-1H-INDEN-1-AMINE
(S)-2,3-DIHYDRO-N-METHYL-N-2-PROPYNYL-1H-INDEN-1-AMINE Basic information
- Product Name:
- (S)-2,3-DIHYDRO-N-METHYL-N-2-PROPYNYL-1H-INDEN-1-AMINE
- Synonyms:
-
- (S)-2,3-DIHYDRO-N-METHYL-N-2-PROPYNYL-1H-INDEN-1-AMINE
- (S)-N-(2-Propynyl)-2,3-dihydroinden-1-aMine
- S-(-)-N-Propargyl-1-aminoindan
- S-PAI
- (S)-Rasagiline
- TV 1022
- TVP 1022
- (S)-N-(prop-2-yn-1-yl)-2,3-dihydro-1H-inden-1-amine
- CAS:
- 185517-74-2
- MF:
- C12H13N
- MW:
- 171.24
- Mol File:
- 185517-74-2.mol
(S)-2,3-DIHYDRO-N-METHYL-N-2-PROPYNYL-1H-INDEN-1-AMINE Chemical Properties
- Boiling point:
- 305.5±30.0 °C(Predicted)
- Density
- 1.05±0.1 g/cm3(Predicted)
- storage temp.
- 2-8°C
- solubility
- DMSO: ≥15mg/mL
- form
- powder
- pka
- 6.95±0.20(Predicted)
- color
- Light yellow to yellow
(S)-2,3-DIHYDRO-N-METHYL-N-2-PROPYNYL-1H-INDEN-1-AMINE Usage And Synthesis
Uses
(S)-Rasagiline (TVP1022) is the relatively inactive S-enantiomer form of Rasagiline. Rasagiline is a highly potent selective irreversible MAO inhibitor with IC50s of 4.43 nM and 412 nM for rat brain MAO B and A activity, respectively[1]. (S)-Rasagiline is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
Biological Activity
TVP1022, the S-isomer of rasagiline, an anti-Parkinson drug, appears to have the same neuroprotective activity as the R-isomer, but is 1000-fold less active as an MAO-B inhibitor. TVP1022, a neuroprotective and cytoprotective molecule, is also cardioprotective in r at models. Its activity is believed to involve stabilization of mitochondrial membrane potential, induction of Bcl-2 and activation of the PKC signalling pathway, enhancing the phosphorylation of protein kinase C and glycogen synthase kinase-3β.
References
[1] M B Youdim, et al. Rasagiline [N-propargyl-1R(+)-aminoindan], a selective and potent inhibitor of mitochondrial monoamine oxidase B. Br J Pharmacol. 2001 Jan;132(2):500-6. DOI:10.1038/sj.bjp.0703826
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