Chemical substance record

Bupivacaine

38396-39-3C₁₈H₂₈N₂O288.435 g/mol

Organic/Inorganic Small MoleculeChEBI source record

A racemate composed of equimolar amounts of dextrobupivacaine and levobupivacaine. Used (in the form of its hydrochloride hydrate) as a local anaesthetic. — ChEBI

Safety references

Safety documents & references

Supplier matching matters

Find the safety document for your specific supplier, product number and grade.

Find a product-specific SDS

Search SDS PDFs Sigma-Aldrich Thermo Fisher

Safety guides and government classification records are not a manufacturer’s SDS. Match supplier, product number, concentration, physical form, region and revision before using a document.

Identity & molecular properties

Source-linked values

CAS number	38396-39-3	ChEBI ↗
Molecular formula	C₁₈H₂₈N₂O	ChEBI ↗
Molar mass	288.435 g/mol	ChEBI ↗
Monoisotopic mass	288.22016 Da	ChEBI ↗
Formal charge	0	ChEBI ↗
ChEBI identifier	CHEBI:3215	ChEBI ↗

Names & structural identifiers

Copy any identifier

Source preferred name

bupivacaine

IUPAC name

rac-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide

Names & synonyms

bupivacainabupivacainumrac-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide

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

Classification & relationships

ChEBI ontology

racemateChEBI parent class · 60911 ↗

Roles recorded in ChEBI

antidepressantanalgesicantineoplastic agentlocal anaestheticEC 3.1.1.8 (cholinesterase) inhibitoradrenergic antagonistanti-arrhythmia drugantitussiveantispasmodic druggastrointestinal drug

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

0.00346699 mol

Uses 288.435 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 · 18 atoms

74.96%

H

Hydrogen · 28 atoms

9.79%

N

Nitrogen · 2 atoms

9.71%

O

Oxygen · 1 atom

5.55%

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

Epidural pain relief in labour: potencies of levobupivacaine and racemic bupivacaine. ↗British journal of anaesthesia · 1998 Dec · PMID 10211016

Effects of levobupivacaine, bupivacaine, and ropivacaine on tail-flick response and motor function in rats following epidural or intrathecal administration. ↗Regional anesthesia and pain medicine · 1999 Sep-Oct · PMID 10499757

US2955111 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

Search PubMed Google Scholar

Sources & record history

Checked 27 Sep 2026

Identity, formula, mass, synonyms & ontologyEMBL-EBI ChEBI · CHEBI:3215

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

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.

How this record was assembled Suggest a correction