Chemical substance record

Rolipram

61413-54-5C₁₆H₂₁NO₃275.348 g/mol

Organic/Inorganic Small MoleculeChEBI source record

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. — ChEBI

Safety references

Safety documents & references

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Identity & molecular properties

Source-linked values

CAS number	61413-54-5	ChEBI ↗
Molecular formula	C₁₆H₂₁NO₃	ChEBI ↗
Molar mass	275.348 g/mol	ChEBI ↗
Monoisotopic mass	275.15214 Da	ChEBI ↗
Formal charge	0	ChEBI ↗
ChEBI identifier	CHEBI:104872	ChEBI ↗

Cross-source molecular data

PubChem

Molar mass	275.34 g/mol	PubChem ↗
Exact mass	275.15214353 Da	PubChem ↗
Computed XLogP	2.2	PubChem ↗
Topological polar surface area (Å²)	47.6	PubChem ↗
H-bond donors	1	PubChem ↗
H-bond acceptors	3	PubChem ↗
Rotatable bonds	4	PubChem ↗

PubChem computed values are shown separately from the ChEBI record. An exact InChIKey match was used to connect the records. Molecular descriptors do not describe a supplied product’s purity, particle size or performance.

Names & structural identifiers

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Source preferred name

rolipram

IUPAC name

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

InChIKey

HJORMJIFDVBMOB-UHFFFAOYSA-N

SMILES

COc1ccc(C2CNC(=O)C2)cc1OC1CCCC1

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)

Names & synonyms

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

Names are supplied by ChEBI. Trade names and related synonyms may describe a broader product context.

Classification & relationships

ChEBI ontology

pyrrolidin-2-onesChEBI parent class · 74223 ↗

organic heterocyclic compound organic molecular entity

Roles recorded in ChEBI

antidepressantimmunosuppressive agentEC 3.1.4.* (phosphoric diester hydrolase) inhibitor

Database role annotations describe reported biological or chemical roles; they are not product approvals or recommendations for use.

Mass ↔ amount of substance

Calculated from sourced mass

Amount

Input unit

Equivalent amount

0.00363177 mol

Uses 275.348 g/mol from ChEBI. Assumes the substance described by this record; no purity or concentration correction is applied.

Elemental composition

Theoretical mass fractions

C

Carbon · 16 atoms

69.79%

O

Oxygen · 3 atoms

17.43%

H

Hydrogen · 21 atoms

7.69%

N

Nitrogen · 1 atom

5.09%

Calculated theoretical mass fractions from the reported formula and PubChem periodic-table atomic masses. These are not assay or purity results.

Research & patent references

Selected source associations

A selective phosphodiesterase IV inhibitor, rolipram blocks both withdrawal behavioral manifestations, and c-Fos protein expression in morphine dependent mice. ↗Behavioural brain research · 2001 Jan 8 · PMID 11163637

Inhibiting the inflammatory response in joint sepsis. ↗Arthroscopy : the journal of arthroscopic & related surgery : official publication of the Arthroscopy Association of North America and the International Arthroscopy Association · 2001 Mar · PMID 11239354

US4193926 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

US6337325 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

WO2011143607 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

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Sources & record history

Checked 27 Sep 2026

Identity, formula, mass, synonyms & ontologyEMBL-EBI ChEBI · CHEBI:104872

Release 255, 9 September 2026. ChEBI three-star (manually annotated) source entry. View original record ↗ · CC BY 4.0

Additional molecular descriptorsNCBI PubChem · CID 5092 · retrieved 2026-09-27

PubCAS formats source data, connects references and computes explicitly labelled conversions. CAS cross-references are supplied by ChEBI; they do not constitute CAS verification or endorsement.

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