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Merck

R6520

Rolipram

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

Synonyme(s) :

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

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A propos de cet article

Formule empirique (notation de Hill) :
C16H21NO3
Numéro CAS:
61413-54-5
Poids moléculaire :
275.34
NACRES:
NA.77
PubChem Substance ID:
24278196
UNSPSC Code:
41106305
EC Number:
262-771-1
MDL number:
MFCD00270906
Assay:
≥98% (HPLC)
Form:
solid
Quality level:
100

Principaux documents

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Nom du produit

Rolipram, solid, ≥98% (HPLC)

InChI key

HJORMJIFDVBMOB-UHFFFAOYSA-N

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)

SMILES string

COc1ccc(cc1OC2CCCC2)C3CNC(=O)C3

biological source

synthetic (organic)

assay

≥98% (HPLC)

form

solid

color

white to off-white

solubility

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

Quality Level

100

Gene Information

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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Catégories apparentées

General description

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)

Biochem/physiol Actions

Selective cAMP-specific phosphodiesterase (PDE4) inhibitor.

Features and Benefits

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.

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
0000523460
0000523460
0000523459
0000523459
0000504207

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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
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
Euan Parnell et al.
Scientific reports, 7(1), 294-294 (2017-03-24)
Screening of a carefully selected library of 5,195 small molecules identified 34 hit compounds that interact with the regulatory cyclic nucleotide-binding domain (CNB) of the cAMP sensor, EPAC1. Two of these hits (I942 and I178) were selected for their robust
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