A PDE4 inhibitor
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Enantiomer(s)
10011132(±)-Rolipram
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(−)-Rolipram

Item No. 31111

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(4R)-4-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidinone
CAS Number
85416-75-7
Synonyms
  • (R)-(–)-Rolipram
  • (R)-Rolipram
Molecular Formula
C16H21NO3
Formula Weight
275.3
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: 25 mg/mlEthanol: 25 mg/ml
SMILES
COC1=CC=C([C@@]2([H])CC(NC2)=O)C=C1OC3CCCC3
InChi Code
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)/t12-/m0/s1
InChi Key
HJORMJIFDVBMOB-LBPRGKRZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

    $41

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    5 mg

    $128

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    10 mg

    $215

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    Cayman Chemical
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    Product Description

    (–)-Rolipram is a phosphodiesterase 4 (PDE4) inhibitor (IC50 = 0.22 µM for the guinea pig eosinophil enzyme) and an enantiomer of (±)-rolipram (Item No. 10011132).1 It enhances isoprenaline-induced cAMP accumulation in isolated guinea pig eosinophils (EC50 = 0.19 µM). (–)-Rolipram (1-1,000 µM) inhibits TNF and INF-γ production in L1402 CD4+ encephalitogenic rat T cells.2 It inhibits ovalbumin-induced contraction of tracheal rings isolated from ovalbumin-sensitized guinea pigs when used at a concentration of 1 µM.3 (–)-Rolipram inhibits ovalbumin-induced bronchoconstriction in guinea pigs (ED50 = 0.25 mg/kg).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Souness, J.E., and Scott, L.C. Stereospecificity of rolipram actions on eosinophil cyclic AMP-specific phosphodiesterase. Biochem. J. 291(Pt 1)(Pt 2), 389-395 (1993).

    2. Sommer, N., Löshmann, P.-A., Northoff, G.H., et al. The antidepressant rolipram suppresses cytokine production and prevents autoimmune encephalomyelitis. Nat. Med. 1(3), 244-248 (1995).

    3. Underwood, D.C., Osborn, R.R., Novak, L.B., et al. Inhibition of antigen-induced bronchoconstriction and eosinophil infiltration in the guinea pig by the cyclic AMP-specific phosphodiesterase inhibitor, rolipram. J. Pharmacol. Exp. Ther. 266(1), 306-313 (1993).