Chemical substance record

Cyclobenzaprine

303-53-7C₂₀H₂₁N275.395 g/mol

Organic/Inorganic Small MoleculeChEBI source record

5-Methylidene-5H-dibenzo[a,d]cycloheptene in which one of the hydrogens of the methylidene group is substituted by a 2-(dimethylamino)ethyl group. A centrally acting skeletal muscle relaxant, it is used as its hydrochloride salt in the symptomatic treatment of painful muscle spasm. — ChEBI

Safety references

Safety documents & references

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Identity & molecular properties

Source-linked values

CAS number	303-53-7	ChEBI ↗
Molecular formula	C₂₀H₂₁N	ChEBI ↗
Molar mass	275.395 g/mol	ChEBI ↗
Monoisotopic mass	275.1674 Da	ChEBI ↗
Formal charge	0	ChEBI ↗
ChEBI identifier	CHEBI:3996	ChEBI ↗

Cross-source molecular data

PubChem

Molar mass	275.4 g/mol	PubChem ↗
Exact mass	275.167399674 Da	PubChem ↗
Computed XLogP	5.2	PubChem ↗
Topological polar surface area (Å²)	3.2	PubChem ↗
H-bond donors	0	PubChem ↗
H-bond acceptors	1	PubChem ↗
Rotatable bonds	3	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

cyclobenzaprine

IUPAC name

3-(5H-dibenzo[a,d][7]annulen-5-ylidene)-N,N-dimethylpropan-1-amine

InChIKey

JURKNVYFZMSNLP-UHFFFAOYSA-N

SMILES

CN(C)CCC=C1c2ccccc2C=Cc2ccccc21

InChI

InChI=1S/C20H21N/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-14H,7,15H2,1-2H3

Names & synonyms

3-(5H-dibenzo[a,d][7]annulen-5-ylidene)-N,N-dimethylpropan-1-amine3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethylpropan-1-amineciclobenzaprinacyclobenzaprinum

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

Classification & relationships

ChEBI ontology

carbotricyclic compoundChEBI parent class · 38032 ↗

organic molecular entity

Roles recorded in ChEBI

antidepressanttranquilizing druganalgesicmuscle relaxanthepatoprotective agent

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

0.00363115 mol

Uses 275.395 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 · 20 atoms

87.23%

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

High-throughput screening of drug-brain tissue binding and in silico prediction for assessment of central nervous system drug delivery. ↗Journal of medicinal chemistry · 2007 Sep 20 · PMID 17725338

Identification of new functional inhibitors of acid sphingomyelinase using a structure-property-activity relation model. ↗Journal of medicinal chemistry · 2008 Jan 24 · PMID 18027916

GB858187 · 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:3996

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

Additional molecular descriptorsNCBI PubChem · CID 2895 · 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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