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R6520

Sigma-Aldrich

Rolipram

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

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C16H21NO3
CAS-Nummer:
61413-54-5
Molekulargewicht:
275.34
EG-Nummer:
262-771-1
MDL-Nummer:
MFCD00270906
UNSPSC-Code:
41106305
PubChem Substanz-ID:
24278196
NACRES:
NA.77

product name

Rolipram, solid, ≥98% (HPLC)

Biologische Quelle

synthetic (organic)

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

solid

Farbe

white to off-white

Löslichkeit

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

SMILES String

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)

InChIKey

HJORMJIFDVBMOB-UHFFFAOYSA-N

Angaben zum Gen

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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Allgemeine Beschreibung

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.

Anwendung

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)

Biochem./physiol. Wirkung

Selective cAMP-specific phosphodiesterase (PDE4) inhibitor.

Leistungsmerkmale und Vorteile

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.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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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
Hao Huang et al.
Acta pharmacologica Sinica, 37(12), 1543-1554 (2016-09-27)
Phosphodiesterase 4 (PDE4) isozymes are involved in different functions, depending on their patterns of distribution in the brain. The PDE4 subtypes are distributed in different inflammatory cells, and appear to be important regulators of inflammatory processes. In this study we
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 Degerman et al.
Acta oto-laryngologica, 137(1), 8-15 (2016-09-30)
The data indicate important roles for phosphodiesterase (PDE) 3, 4, 5, and related cAMP and cGMP pools in the regulation of inner ear fluid homeostasis. Thus, dysfunction of these enzymes might contribute to pathologies of the inner ear. The mechanisms
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