ContaminantDB: Benzocaine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:20 UTC

Update Date

2026-05-14 16:57:42 UTC

Accession Number

CHEM002342

Identification

Common Name

Benzocaine

Class

Small Molecule

Description

Benzocaine is a surface anesthetic that acts by preventing transmission of impulses along nerve fibers and at nerve endings. Benzocaine is a local anesthetic commonly used as a topical pain reliever. It is the active ingredient in many over-the-counter analgesic ointments. Benzocaine is an ester, a compound made from the organic acid PABA (para-aminobenzoic acid) and ethanol. The process in which this ester is created is known as Fischer esterification.

Contaminant Sources

Cosmetic Chemicals
FooDB Chemicals
HPV EPA Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Anesthetic
Anesthetic, Local
Antipruritic
Drug
Ester
Ether
Food Toxin
Household Toxin
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-Aminobenzoic acid ethyl ester	ChEBI
Amben ethyl ester	ChEBI
Benzocaina	ChEBI
Benzocainum	ChEBI
Ethyl aminobenzoate	ChEBI
Ethyl p-aminobenzoate	ChEBI
Ethyl p-aminophenylcarboxylate	ChEBI
p-(Ethoxycarbonyl)aniline	ChEBI
p-Carbethoxyaniline	ChEBI
p-Ethoxycarboxylic aniline	ChEBI
Parathesin	Kegg
4-Aminobenzoate ethyl ester	Generator
Ethyl aminobenzoic acid	Generator
Ethyl p-aminobenzoic acid	Generator
Ethyl p-aminophenylcarboxylic acid	Generator
(P-(Ethoxycarbonyl)phenylamine	HMDB
4-(Ethoxycarbonyl)aniline	HMDB
4-(Ethoxycarbonyl)phenylamine	HMDB
4-Aminobenzoate	HMDB
4-Aminobenzoic acid	HMDB
4-Carbethoxyaniline	HMDB
Aethoform	HMDB
Americaine	HMDB, MeSH
Anaesthan-syngala	HMDB
Anaesthesin	HMDB, MeSH
Anaesthin	HMDB
Anestezin	HMDB
Anesthesin	HMDB, MeSH
Anesthesine	HMDB
Anesthone	HMDB
Baby anbesol	HMDB
Benzoak	HMDB
Dermoplast	HMDB
Diet ayds	HMDB
Ethoform	HMDB, MeSH
Ethyl 4-aminobenzoate	HMDB
Ethyl 4-aminobenzoic acid	HMDB
Ethyl P-aminobenzenecarboxylate	HMDB
Ethylester kyseliny P-aminobenzoove	HMDB
Hurricaine	HMDB
Identhesin	HMDB
Keloform	HMDB
Norcain	HMDB
Norcaine	HMDB
Ora-jel	HMDB
Orabase-b	HMDB
Orthesin	HMDB
P-Aminobenzoate	HMDB
P-Aminobenzoic acid	HMDB
P-Aminobenzoic acid ethyl ester	HMDB
Parathesine	HMDB
Slim mint gum	HMDB
Solarcaine	HMDB
Solu H	HMDB
Topcaine	HMDB
Benzocaine acetate	MeSH, HMDB
Formate, benzocaine	MeSH, HMDB
Acetate, benzocaine	MeSH, HMDB
Benzocaine formate	MeSH, HMDB
Hydrobromide, benzocaine	MeSH, HMDB
Methanesulfonate, benzocaine	MeSH, HMDB
Bensokain	MeSH, HMDB
Benzocaine hydrochloride	MeSH, HMDB
Benzocaine hydrobromide	MeSH, HMDB
Benzocaine methanesulfonate	MeSH, HMDB
Hydrochloride, benzocaine	MeSH, HMDB

Chemical Formula

C₉H₁₁NO₂

Average Molecular Mass

165.189 g/mol

Monoisotopic Mass

165.079 g/mol

CAS Registry Number

94-09-7

IUPAC Name

ethyl 4-aminobenzoate

Traditional Name

benzocaine

SMILES

CCOC(=O)C1=CC=C(N)C=C1

InChI Identifier

InChI=1S/C9H11NO2/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6H,2,10H2,1H3

InChI Key

BLFLLBZGZJTVJG-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Aminobenzoic acid or derivatives
Benzoate ester
Benzoyl
Aniline or substituted anilines
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Amine
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

substituted aniline (CHEBI:116735 )
benzoate ester (CHEBI:116735 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	92°C
Boiling Point	310°C
Solubility	1310 mg/L (at 30°C)

Predicted Properties

Property	Value	Source
Water Solubility	2.85 g/L	ALOGPS
logP	2.2	ALOGPS
logP	1.5	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Basic)	2.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.53 m³·mol⁻¹	ChemAxon
Polarizability	17.46 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-00dl-0980000000-9bd6d020be04ce49bd3e	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-4900000000-9341302295e361a20bfd	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0109-9400000000-8e31c925b871e0f0299e	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0109-9400000000-c755b4e5336a2867357e	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01b9-1900000000-a811093acfd0672fece6	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-014i-0900000000-49302e8e4fd5158a36da	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-5900000000-dcd2847110af7c87bf18	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dl-0980000000-9bd6d020be04ce49bd3e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-3900000000-8d1e571ebb0276875b64	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00kr-0900000000-b54aebb77e7a69ada07c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014i-5900000000-ce90658bd0fc66df820d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-03xu-9100000000-5179b7804d2c59e71aa4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-00di-4900000000-9341302295e361a20bfd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7) , Positive	splash10-0109-9400000000-8e31c925b871e0f0299e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6D) , Positive	splash10-0109-9400000000-c755b4e5336a2867357e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positive	splash10-01b9-1900000000-57d39b512bc5bdbb4987	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - CI-B (HITACHI M-60) , Positive	splash10-014i-0900000000-49302e8e4fd5158a36da	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-DX-300) , Positive	splash10-00di-5900000000-dcd2847110af7c87bf18	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-014i-0900000000-a0f10abbe67842c2c958	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00du-5900000000-43a89461a4d9cc5d1409	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00dl-9600000000-049e2653cbbf24aaf010	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-002f-9100000000-6fbc7720b326773643af	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-00ou-9000000000-d7f7622c3a270c5ffcbb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-000i-5900100000-72ac4bcb64db0d25261e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-0900000000-e061a0f4172b47a8bd22	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00du-5900000000-54757e57c91d3eaa1976	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00dl-9600000000-049e2653cbbf24aaf010	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-002f-9100000000-e16fc2db7a632fc6f4da	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-0900000000-4479c2a548f4aa1aa697	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00xr-0900000000-45723c7ad554a9d56bd1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9300000000-fab7bee6cbcfbc918d9c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1900000000-477a27b8617485132384	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03xr-3900000000-df3eaaf30a4e906fb038	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9400000000-e9f4c1de93ac2ce072b4	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00xr-6900000000-0594451f3b181ab3c883	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Topical; oral

Mechanism of Toxicity

Benzocaine binds to sodium channels and reversibly stabilizes the neuronal membrane which decreases its permeability to sodium ions. Depolarization of the neuronal membrane is inhibited thereby blocking the initiation and conduction of nerve impulses.

Metabolism

Hepatic (to a lesser extent) and plasma via hydrolysis by cholinesterase. Excretion trhough urine (as metabolites) (5)

Toxicity Values

LD50: 3040 mg/kg (Oral, Rat) (1)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Local anesthetic commonly used as a topical pain reliever. Benzocaine is used as a key ingredient in numerous pharmecuticals: Phenazone, an anti-inflammatory; some glycerol-based ear medications for use in removing excess wax as well as relieving ear conditions such as Otitis Media and swimmers ear; some previous diet products such as Ayds; some condoms designed to prevent premature ejaculation. Benzocaine acts to desensitize the penis, and theoretically allows an erection to be maintained. [Wikipedia]

Minimum Risk Level

Not Available

Health Effects

Allergic reactions occur with ester local anaesthetics (like benzocaine) because of the PABA structure. Benzocaine also is a well-known cause of methemoglobinemia. [Wikipedia]. Methemoglobinemia has been reported with benzocaine in oral overdose. (5)

Symptoms

Not Available

Treatment

Treatment is primarily symptomatic and supportive; termination of anesthesia by pneumatic tourniquet inflation should be attempted when the agent is administered by infiltration or regional injection. Methemoglobinemia may be treated with methylene blue, 1-2 mg/kg I.V. infused over several minutes. Seizures commonly respond to diazepam, while hypotension responds to I.V. fluids and Trendelenburg positioning. Bradyarrhythmias (when the heart rate is <60) can be treated with I.V., I.M., or SubQ atropine 15 mcg/kg. With the development of metabolic acidosis, I.V. sodium bicarbonate 0.5-2 mEq/kg and ventilatory assistance should be instituted. (5)

Concentrations

Not Available

External Links

DrugBank ID

DB01086

HMDB ID

HMDB0004992

FooDB ID

FDB023574

Phenol Explorer ID

Not Available

KNApSAcK ID