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R6520

Sigma-Aldrich

Rolipram

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

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C16H21NO3
Número de CAS:
61413-54-5
Peso molecular:
275.34
Número CE:
262-771-1
Número MDL:
MFCD00270906
Código UNSPSC:
41106305
ID de la sustancia en PubChem:
24278196
NACRES:
NA.77

Nombre del producto

Rolipram, solid, ≥98% (HPLC)

origen biológico

synthetic (organic)

Nivel de calidad

100

Ensayo

≥98% (HPLC)

Formulario

solid

color

white to off-white

solubilidad

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

cadena 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)

Clave InChI

HJORMJIFDVBMOB-UHFFFAOYSA-N

Información sobre el 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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Descripción general

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.

Aplicación

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)

Acciones bioquímicas o fisiológicas

Selective cAMP-specific phosphodiesterase (PDE4) inhibitor.

Características y beneficios

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.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
0000424554
0000424558
0000424556
0000424558
0000424554

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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
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
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
J Zhu et al.
CNS drug reviews, 7(4), 387-398 (2002-02-07)
Rolipram is a selective inhibitor of phosphodiesterases (PDE) IV, especially of the subtype PDE IVB. These phosphodiesterases are responsible for hydrolysis of the cyclic nucleotides cAMP and cGMP, particularly in nerve and immune cells. Consequences of rolipram-induced elevation of intracellular
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