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R6520

Sigma-Aldrich

Rolipram

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

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C16H21NO3
CAS Number:
61413-54-5
Molecular Weight:
275.34
EC Number:
262-771-1
MDL number:
MFCD00270906
UNSPSC Code:
41106305
PubChem Substance ID:
24278196
NACRES:
NA.77

product name

Rolipram, solid, ≥98% (HPLC)

biological source

synthetic (organic)

Quality Level

100

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

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)

InChI key

HJORMJIFDVBMOB-UHFFFAOYSA-N

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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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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘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
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
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
View All Related Papers

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