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R6520

Rolipram

Name: Rolipram
Brand: SIGMA

≥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

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

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Properties

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)

Description

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.

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Storage Class

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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Certificates of Analysis (COA)

Lot/Batch Number

0000545708

0000541027

0000531320