ROLIPRAM Chemical Properties

Melting point:

127-133 °C

Boiling point:

418.29°C (rough estimate)

Density 

1.0677 (rough estimate)

refractive index 

1.5500 (estimate)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

H₂O: 0.2 mg/mL

form 

solid

pka

16.02±0.40(Predicted)

color 

white to off-white

biological source

synthetic (organic)

Water Solubility 

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

Merck 

14,8251

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.

InChI

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)

InChIKey

HJORMJIFDVBMOB-UHFFFAOYSA-N

SMILES

O(C1CCCC1)C1C=C(C2CC(NC2)=O)C=CC=1OC

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-11

Safety Statements 

26-36

RIDADR 

3249

WGK Germany 

3

RTECS 

UY5749237

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29337900

Toxicity

LD50 oral in mouse: > 300mg/kg

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

ROLIPRAM Usage And Synthesis

Description

Rolipram (61413-54-5) is a selective inhibitor of cAMP-specific phosphodiesterase (PDE4), IC50 = 1 μM. Displays beneficial effects in neurodegenerative diseases. Rolipram also displays anti-inflammatory activity and synergizes with forskolin (cat.# 10-2073). Cell permeable.

Chemical Properties

Yellowish solid

Uses

antipsychotic

Uses

A selective, cell permeable inhibitor of cAMP-specific phosphodiesterase (PDE4).

Uses

Pharmacological tool for characterization of phosphodiesterase isoenzymes.

Uses

(±)-Rolipram is a cAMP-specific phosphodiesterase 4 (PDE4) inhibitor.

Definition

ChEBI: Rolipram is a member of the lclass of pyrrolidin-2-ones that is pyrrolidin-2-one bearing a 3-(cyclopentyloxy)-4-methoxyphenyl substituent at the 4-position. It is a type IV-specific phosphodiesterase (PDE4) inhibitor. It has a role as an antidepressant and an EC 3.1.4.* (phosphoric diester hydrolase) inhibitor.

General Description

A cell-permeable, selective inhibitor of cAMP-specific phosphodiesterase (PDE IV; IC₅₀ = 800 nM). A rolipram-insensitive PDE IV subtype is also known to exist. Also inhibits NF-κB and NFAT activation in Jurkat and primary T cells.

Biological Activity

Selective inhibitor of cAMP phosphodiesterase (PDE4) (IC 50 = 2.0 μ M). Discriminates between two conformational states of PDE4 isoenzymes. See separate isomers ((R)-(-)-Rolipram and (S)-(+)-Rolipram).

Biochem/physiol Actions

Cell permeable: yes

storage

Room temperature

References

[1] M L REEVES  P J E  B K Leigh. The identification of a new cyclic nucleotide phosphodiesterase activity in human and guinea-pig cardiac ventricle. Implications for the mechanism of action of selective phosphodiesterase inhibitors.[J]. Biochemical Journal, 1987, 241 2: 535-541. DOI:10.1042/bj2410535
[2] AKINORI NISHI. Distinct roles of PDE4 and PDE10A in the regulation of cAMP/PKA signaling in the striatum.[J]. Journal of Neuroscience, 2008, 28 42: 10460-10471. DOI:10.1523/jneurosci.2518-08.2008
[3] S.H. CHRISTIANSEN . Combined anti-inflammatory effects of β2-adrenergic agonists and PDE4 inhibitors on astrocytes by upregulation of intracellular cAMP[J]. Neurochemistry international, 2011, 59 6: Pages 837-846. DOI:10.1016/j.neuint.2011.08.012

ROLIPRAM(61413-54-5)Related Product Information

• Rolapitant
• Donepezil
• PP242
• Milrinone
• WORTMANNIN
• Vinpocetine
• Cilostazol
• Forskolin
• 2-Pyrrolidinone
• S- (+)-Rolipram
• ROLIPRAM
• (R)-(-)-ROLIPRAM,(S)-(+)-ROLIPRAM,Rolipram (R)-(-)-
• [METHYL-3H]ROLIPRAM
• ROLIPRAM [6-3H]
• S-Desmethyl-Rolipram
• (+)-Desmethyl-Rolipram,R-Desmethyl-Rolipram
• (R,S)-Desmethyl-Rolipram
• (R)-(-)-ROLIPRAM, >98%