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ChemicalBook--->CAS DataBase List--->61413-54-5

61413-54-5

61413-54-5 Structure

61413-54-5 Structure
IdentificationBack Directory
[Name]

ROLIPRAM
[CAS]

61413-54-5
[Synonyms]

ZK-62711
ROLIPRAM
SB 95952
Roliprame
ROLIPRAM 98+%
(R,S)-Rolipram
Rolipram, >=97%
ZK-62711, SB95952, ME-3167
4-(3-(cyclopentyloxy)-4-methoxyphenyl)-2-pyrrolidinon
4-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]-2-PYRROLIDINONE
4-(3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL)PYRROLIDIN-2-ONE
2-Pyrrolidinone, 4-[3-(cyclopentyloxy)-4-methoxyphenyl]-
PYRROLIDIN-2-ONE, 4-(3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL)- (+/-)
4-[3-(Cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidinone, ZK62711
[EINECS(EC#)]

262-771-1
[Molecular Formula]

C16H21NO3
[MDL Number]

MFCD00270906
[MOL File]

61413-54-5.mol
[Molecular Weight]

275.34
Chemical PropertiesBack Directory
[Appearance]

Yellowish solid
[Melting point ]

127-133 °C
[Boiling point ]

418.29°C (rough estimate)
[density ]

1.0677 (rough estimate)
[refractive index ]

1.5500 (estimate)
[storage temp. ]

0-6°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.
Hazard InformationBack Directory
[Chemical Properties]

Yellowish solid
[Uses]

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

antipsychotic
[Uses]

Pharmacological tool for characterization of phosphodiesterase isoenzymes.
[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).
[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.
[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.
[Biochem/physiol Actions]

Cell permeable: yes
[storage]

Store at -20°C
[References]

1) Reeves et al. (1987), 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; Biochem. J., 241 535 2) Nishi et al. (2008), Distinct Roles of PDE4 and PDE10A in the Regulation of cAMP/PKA Signaling in the Striatum; J. Neurosci., 28 10460 3) Christiansen et al. (2011), Combined anti-inflammatory effects of β2-adrenergic agonists and PDE4 inhibitors on astrocytes by upregulation of intracellular cAMP; Neurochem. Int., 59 837
Safety DataBack Directory
[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
Spectrum DetailBack Directory
[Spectrum Detail]

ROLIPRAM(61413-54-5)1HNMR
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