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CAS RN: 85416-75-7 | Product Number: R0182
(R)-(-)-Rolipram
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Purity: >98.0%(HPLC)
Synonyms:
- (R)-(-)-4-[3-(Cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one
Product Documents:
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| Product Number | R0182 |
Purity / Analysis Method 
|
>98.0%(HPLC) |
| Molecular Formula / Molecular Weight | C__1__6H__2__1NO__3 = 275.35 |
| Physical State (20 deg.C) | Solid |
| Storage Temperature
|
Frozen (<0°C) |
| Condition to Avoid | Heat Sensitive |
| CAS RN | 85416-75-7 |
| Reaxys Registry Number | 5442919 |
| PubChem Substance ID | 354333406 |
| MDL Number | MFCD03093861 |
Specifications
| Appearance | White to Almost white powder to crystal |
| Purity(HPLC) | min. 98.0 area% |
| Optical purity(LC) | min. 98.0 ee% |
| Elemental analysis(Nitrogen) | 4.50 to 5.50 % |
| Melting point | 132.0 to 136.0 °C |
| Specific rotation [a]20/D | -29.0 to -34.0 deg(C=0.5, MeOH) |
| NMR | confirm to structure |
Properties (reference)
| Melting Point | 134 °C |
| Specific Rotation | -32° (C=0.5,MeOH) |
GHS
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Transport Information:
| H.S.code* | 2933.79-000 |
Application
(R)-(-)-Rolipram: The Active Enantiomer of Rolipram, PDE4 Inhibitor
(R)-(-)-Rolipram is the active enantiomer of rolipram [R0110] which is a selective inhibitor of phosphodiesterases 4 (PDE4s). It has been reported that (R)-(-)-rolipram is approximately 3 times more potent than (S)-(+)-rolipram [R0183] against PDE4. In 2015, Kobayashi et al. have been reported a new multistep continuous-flow synthesis of (R)- and (S)-rolipram using only columns packed with heterogeneous catalysts. (The product is for research purpose only.)
References
- Stereospecific binding of the antidepressant rolipram to brain protein structures
- Pharmacokinetics of (+)-rolipram and (-)-rolipram in healthy volunteers
- Stereospecificity of rolipram actions on eosinophil cyclic AMP-specific phosphodiesterase
- Evidence that cyclic AMP phosphodiesterase inhibitors suppress TNFα generation from human monocytes by interacting with a 'low-affinity' phosphodiesterase 4 conformer
- Rolipram and its optical isomers, phosphodiesterase 4 inhibitors, attenuated the scopolamine-induced impairments of learning and memory in rats
- Multistep continuous-flow synthesis of (R)- and (S)-rolipram using heterogeneous catalysts
- Flow “Fine” Synthesis: High Yielding and Selective Organic Synthesis by Flow Methods
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