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R6520

Sigma-Aldrich

Rolipram

≥98% (HPLC), solid, cAMP-specific phosphodiesterase (PDE4) inhibitor

Synonyme(s) :

4-[3-(Cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidinone, ZK 62711

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About This Item

Formule empirique (notation de Hill):
C16H21NO3
Numéro CAS:
61413-54-5
Poids moléculaire :
275.34
Numéro CE :
262-771-1
Numéro MDL:
MFCD00270906
Code UNSPSC :
41106305
ID de substance PubChem :
24278196
Nomenclature NACRES :
NA.77

product name

Rolipram, solid, ≥98% (HPLC)

Source biologique

synthetic (organic)

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

solid

Couleur

white to off-white

Solubilité

H2O: 0.2 mg/mL
ethanol: 7 mg/mL
DMSO: 7.3 mg/mL

Chaîne SMILES 

COc1ccc(cc1OC2CCCC2)C3CNC(=O)C3

InChI

1S/C16H21NO3/c1-19-14-7-6-11(12-9-16(18)17-10-12)8-15(14)20-13-4-2-3-5-13/h6-8,12-13H,2-5,9-10H2,1H3,(H,17,18)

Clé InChI

HJORMJIFDVBMOB-UHFFFAOYSA-N

Informations sur le gène

human ... LITAF(9516) , PDE3A(5139) , PDE4A(5141) , PDE4B(5142) , PDE4C(5143) , PDE4D(5144) , PDE5A(8654) , PDE7A(5150)
mouse ... Pde4a(18577)
rat ... Adora1(29290) , Pde1b(29691) , Pde2a(81743) , Pde3a(50678) , Pde4a(25638) , Pde4b(24626) , Pde4c(290646) , Pde5a(171115)

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Description générale

Rolipram enhances tissue protection, anatomical repair and functional recovery. It is used to treat asthma, arthritis, Huntington′s disease and multiple sclerosis. Rolipram inhibits injury-induced reductions in cyclic AMP, which is associated with acute central nervous system injury. It functions as an antidepressant, stimulates neurite outgrowth and axonal regeneration in the presence of myelin inhibitors.

Application

Rolipram has been used:
  • to investigate its effects on testicular torsion–detorsion injury(36)
  • to block the effects of phosphodiesterase-4 (PDE4)(37)
  • as a component in chemically induced long-term potentiation (cLTP) induction media(38)

Actions biochimiques/physiologiques

Selective cAMP-specific phosphodiesterase (PDE4) inhibitor.

Caractéristiques et avantages

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Phosphodiesterases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Raehannah J Jamshidi et al.
The Journal of pharmacology and experimental therapeutics, 359(2), 319-328 (2016-10-21)
A single administration of the κ opioid receptor (KOR) antagonist, norbinaltorphimine (norBNI), produces long-term reduction in KOR function in heterologous expression systems and brain that is mediated by activation of c-Jun N-terminal kinase (JNK). In this study, we examined the
Eva Bollen et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 39(11), 2497-2505 (2014-05-13)
Memory consolidation is defined by the stabilization of a memory trace after acquisition, and consists of numerous molecular cascades that mediate synaptic plasticity. Commonly, a distinction is made between an early and a late consolidation phase, in which early refers
Ju-Ing Shao et al.
Journal of the Chinese Medical Association : JCMA, 82(7), 568-575 (2019-07-06)
Meconium aspiration syndrome (MAS) is a major cause of severe respiratory failure in near- and full-term neonates. Alleviating inflammation is key to successfully treating severe MAS. Phosphodiesterase (PDE) inhibitors are known to play a role in airway smooth muscle relaxation
Badar Mahmood et al.
BMC cancer, 16(1), 938-938 (2016-12-09)
Intracellular signaling through cyclic nucleotides, both cyclic AMP and cyclic GMP, is altered in colorectal cancer. Accordingly, it is hypothesized that an underlying mechanism for colorectal neoplasia involves altered function of phosphodiesterases (PDEs), which affects cyclic nucleotide degradation. Here we
CNS Regeneration: Basic Science and Clinical Advances (2011)
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