4-[3-(cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one

• ChemBase ID: 60157
• Molecular Formular: C16H21NO3
• Molecular Mass: 275.34284
• Monoisotopic Mass: 275.15214354
• SMILES: c1cc(c(cc1C1CNC(=O)C1)OC1CCCC1)OC
• Canonical SMILES: COc1ccc(cc1OC1CCCC1)C1CNC(=O)C1
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[3-(cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one
• IUPAC Traditional name: rolipram; (S)-rolipram
• Synonyms: (4S)-4-[3-(Cyclopentyloxy)-4-methoxyphenyl]-pyrrolidin-2-one; ZK 62711; SB 95952; ME-3167; Adeo; Rolipram; 4-[3-(Cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidinone; Rolipram

Database IDs

• CAS Number: 61413-54-5
• EC Number: 262-771-1
• MDL Number: MFCD03093861; MFCD00270906
• PubChem SID: 24278196; 162025898
• PubChem CID: 5092

CALCULATED PROPERTIES

• Acid pKa: 14.28277
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.9585267
• LogD (pH = 7.4): 1.9585267
• Log P: 1.9585268
• Molar Refractivity: 76.1641 cm^3
• Polarizability: 29.84816 Å^3
• Polar Surface Area: 47.56 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble7.3 mg/mL; ethanol: soluble7 mg/mL; H2O: soluble0.2 mg/mL
• Apperance: white to off-white solid
• Melting Point: 128-132°C

Safety Information

• Storage Condition: -20°C; 2-8°C
• Storage Warning: IRRITANT
• RTECS: UY5749237
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Target: PDE
• 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)

Product Information

• Purity: ≥98%; ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C16H21NO3

DETAILS

MP Biomedicals - 02159810

Purity: >98%
cAMP-specific phosphodiesterase inhibitor, selective for phosphodiesterase IV.

Selleck Chemicals - S1430

Research Area: Metabolic Disease
Biological Activity:
Rolipram is a PDE4-inhibitor. Like most PDE4-inhibitors, it is an anti-inflammatory drug. Rolipram is being studied as a possible alternative to current antidepressants. Recent studies show that rolipram may have antipsychotic effects. [1]

Sigma Aldrich - R6520

Biochem/physiol Actions
Selective cAMP-specific phosphodiesterase (PDE4) inhibitor.

REFERENCES

• Imanishi, T., et al., Eur. Jour. of Pharmacol. , 321(3) : 273-278, (1997).
• http://en.wikipedia.org/wiki/Rolipram