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Chemical substance record

Prilocaine

721-50-6C13H20N2O220.316 g/mol
Organic/Inorganic Small MoleculeChEBI source record

An amino acid amide in which N-propyl-DL-alanine and 2-methylaniline have combined to form the amide bond; used as a local anaesthetic. — ChEBI

Safety references

Safety documents & references

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Identity & molecular properties

Source-linked values
CAS number721-50-6ChEBI ↗
Molecular formulaC13H20N2OChEBI ↗
Molar mass220.316 g/molChEBI ↗
Monoisotopic mass220.15756 DaChEBI ↗
Formal charge0ChEBI ↗
ChEBI identifierCHEBI:8404ChEBI ↗

Cross-source molecular data

PubChem
Molar mass220.31 g/molPubChem ↗
Exact mass220.157563266 DaPubChem ↗
Computed XLogP2.1PubChem ↗
Topological polar surface area (Ų)41.1PubChem ↗
H-bond donors2PubChem ↗
H-bond acceptors2PubChem ↗
Rotatable bonds5PubChem ↗

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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prilocaine
N-(2-methylphenyl)-N(2)-propylalaninamide
MVFGUOIZUNYYSO-UHFFFAOYSA-N
CCCNC(C)C(=O)Nc1ccccc1C
InChI=1S/C13H20N2O/c1-4-9-14-11(3)13(16)15-12-8-6-5-7-10(12)2/h5-8,11,14H,4,9H2,1-3H3,(H,15,16)

Names & synonyms

N-(2-methylphenyl)-N(2)-propylalaninamideprilocainaprilocainum

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

Classification & relationships

ChEBI ontology
amino acid amideChEBI parent class · 22475 ↗monocarboxylic acid amideChEBI parent class · 29347 ↗
organic molecular entity

Roles recorded in ChEBI

analgesicantineoplastic agentanticonvulsantlocal anaesthetic

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
Equivalent amount
0.00453893 mol

Uses 220.316 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 · 13 atoms
70.87%
N
Nitrogen · 2 atoms
12.72%
H
Hydrogen · 20 atoms
9.15%
O
Oxygen · 1 atom
7.26%

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 randomised double-blinded crossover study comparing pain during anaesthetising the eyelids in upper blepharoplasty: First versus second eyelid and lidocaine versus prilocaine. ↗Journal of plastic, reconstructive & aesthetic surgery : JPRAS · 2015 Sep · PMID 26049614
A Case Report of Prilocaine-Induced Methemoglobinemia after Liposuction Procedure. ↗Case reports in emergency medicine · 2015 · PMID 26199764
GB839943 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.
US3160662 · 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
EMBL-EBI ChEBI · CHEBI:8404

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

NCBI PubChem · CID 4906 · 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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