Compounds > Ethyl 2-aminobenzoate
Page last updated: 2024-12-05

Ethyl 2-aminobenzoate

Ethyl 2-aminobenzoate, also known as benzocaine, is a local anesthetic commonly used in over-the-counter pain relievers for topical applications. It is synthesized through the esterification of 2-aminobenzoic acid (anthranilic acid) with ethanol. Benzocaine works by blocking nerve impulses, preventing the transmission of pain signals to the brain. Its primary use is for temporary relief of pain and itching associated with minor skin irritations, burns, sunburn, and insect bites. The compound is also used in some dental products and throat lozenges. Extensive research on benzocaine focuses on its effectiveness, safety, and potential interactions with other medications. Studies investigate its pharmacological properties, mechanisms of action, and potential adverse effects. Benzocaine is widely studied due to its widespread use and its importance in pain management.'

Cross-References

ID SourceID
PubMed CID6877
CHEMBL ID1332922
CHEBI ID173741
SCHEMBL ID34474
SCHEMBL ID20634912

Synonyms (71)

Synonym
1333-08-0
CHEBI:173741
ethyl 2-aminobenzoate
nsc4146
ethyl o-aminobenzoate
o-(ethoxycarbonyl)aniline
2-aminobenzoic acid, ethyl ester
nsc-4146
wln: zr bvo2
anthranilic acid, ethyl ester
ethyl anthranilate
87-25-2
benzoic acid, 2-amino-, ethyl ester
OPREA1_179888
NCGC00091211-01
hsdb 404
2-aminobenzoic acid ethyl ester
fema no. 2421
2-(ethoxycarbonyl)aniline
nsc 4146
brn 0878874
2-carboethoxyaniline
ai3-02377
einecs 201-735-1
ccris 6238
anthranilic acid, ethyl ester (6ci,7ci,8ci)
benzoic acid, o-amino-, ethyl ester
inchi=1/c9h11no2/c1-2-12-9(11)7-5-3-4-6-8(7)10/h3-6h,2,10h2,1h
ethyl 2-aminobenzoate, >=96%, fcc, fg
ethyl 2-aminobenzoate, >=99%
STK386184
MLS002415730
2-amino-benzoic acid ethyl ester
smr001252260
anthranilic acid ethyl ester
A0499
AKOS001276737
A842055
NCGC00091211-02
dtxcid805272
cas-87-25-2
dtxsid6025272 ,
tox21_303197
NCGC00257226-01
tox21_202019
NCGC00259568-01
HMS2268O06
38y050iue4 ,
unii-38y050iue4
FT-0626162
ethyl anthranilate [fcc]
ethyl anthranilate [hsdb]
ethyl anthranilate [fhfi]
BBL027654
SCHEMBL34474
CHEMBL1332922
o-ethoxycarbonylaniline
o-carbethoxyaniline
ethyl-2-aminobenzoate
2-amino benzoic acid ethyl ester
ethyl-o-aminobenzoate
W-104037
37-25-2
F0001-2161
mfcd00007711
H11236
fema 2421
VS-08575
Q27256834
SCHEMBL20634912
CS-0070766
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
benzoate esterEsters of benzoic acid or substituted benzoic acids.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (11)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, HADH2 proteinHomo sapiens (human)Potency35.71680.025120.237639.8107AID886; AID893
Chain B, HADH2 proteinHomo sapiens (human)Potency35.71680.025120.237639.8107AID886; AID893
thioredoxin reductaseRattus norvegicus (Norway rat)Potency28.18380.100020.879379.4328AID588456
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency22.38720.011212.4002100.0000AID1030
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency0.48260.003041.611522,387.1992AID1159555
67.9K proteinVaccinia virusPotency0.44670.00018.4406100.0000AID720579
peroxisome proliferator-activated receptor deltaHomo sapiens (human)Potency25.06240.001024.504861.6448AID588535; AID743215
urokinase-type plasminogen activator precursorMus musculus (house mouse)Potency4.46680.15855.287912.5893AID540303
plasminogen precursorMus musculus (house mouse)Potency4.46680.15855.287912.5893AID540303
urokinase plasminogen activator surface receptor precursorMus musculus (house mouse)Potency4.46680.15855.287912.5893AID540303
gemininHomo sapiens (human)Potency0.65130.004611.374133.4983AID624296
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID1090712Thrips luring activity against male New Zealand Thrips obscuratus (flower thrips) assessed as ratio of thrips in baited traps to unbaited traps during field trapping study2007Journal of agricultural and food chemistry, Jul-25, Volume: 55, Issue:15
4-pyridyl carbonyl and related compounds as thrips lures: effectiveness for onion thrips and new zealand flower thrips in field experiments.
AID1090713Thrips luring activity against female New Zealand Thrips obscuratus (flower thrips) assessed as ratio of thrips in baited traps to unbaited traps during field trapping study2007Journal of agricultural and food chemistry, Jul-25, Volume: 55, Issue:15
4-pyridyl carbonyl and related compounds as thrips lures: effectiveness for onion thrips and new zealand flower thrips in field experiments.
AID1090711Thrips luring activity against female Thrips tabaci (onion thrips) assessed as ratio of thrips in baited traps to unbaited traps during field trapping study2007Journal of agricultural and food chemistry, Jul-25, Volume: 55, Issue:15
4-pyridyl carbonyl and related compounds as thrips lures: effectiveness for onion thrips and new zealand flower thrips in field experiments.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (15.38)29.6817
2010's9 (69.23)24.3611
2020's2 (15.38)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 32.23

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index32.23 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.60 (4.65)
Search Engine Demand Index25.55 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (32.23)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
anthranilic acid
anthranilic acid: RN given refers to parent cpd; structure in Negwer, 5th ed, #565. anthranilic acid : An aminobenzoic acid that is benzoic acid having a single amino substituent located at position 2. It is a metabolite produced in L-tryptophan-kynurenine pathway in the central nervous system.		2.2110aminobenzoic acidhuman metabolite;
mouse metabolite
benzaldehyde
[no description available]		2.0310benzaldehydesEC 3.1.1.3 (triacylglycerol lipase) inhibitor;
EC 3.5.5.1 (nitrilase) inhibitor;
flavouring agent;
fragrance;
odorant receptor agonist;
plant metabolite
methyl salicylate
methyl salicylate: used in over-the-counter liniments, ointments, lotions for relief of musculoskeletal aches and pains; has hemolytic effect on human & sheep erythrocytes; RN given refers to parent cpd; structure in Merck Index, 9th ed, #5990. methyl salicylate : A benzoate ester that is the methyl ester of salicylic acid.		2.0310benzoate ester;
methyl ester;
salicylates		flavouring agent;
insect attractant;
metabolite
phenylethyl alcohol
Phenylethyl Alcohol: An antimicrobial, antiseptic, and disinfectant that is used also as an aromatic essence and preservative in pharmaceutics and perfumery.. 2-phenylethanol : A primary alcohol that is ethanol substituted by a phenyl group at position 2.		2.0310benzenes;
primary alcohol		Aspergillus metabolite;
fragrance;
plant growth retardant;
plant metabolite;
Saccharomyces cerevisiae metabolite
chloroform
Chloroform: A commonly used laboratory solvent. It was previously used as an anesthetic, but was banned from use in the U.S. due to its suspected carcinogenicity.. chloroform : A one-carbon compound that is methane in which three of the hydrogens are replaced by chlorines.		2.0310chloromethanes;
one-carbon compound		carcinogenic agent;
central nervous system drug;
inhalation anaesthetic;
non-polar solvent;
refrigerant
salicylaldehyde
o-hydroxybenzaldehyde: structure in first source		2.0310hydroxybenzaldehydenematicide;
plant metabolite
methyl benzoate
methyl benzoate : A benzoate ester obtained by condensation of benzoic acid and methanol.		2.0310benzoate ester;
methyl ester		insect attractant;
metabolite
ethyl benzoate
ethyl benzoate : A benzoate ester obtained by condensation of benzoic acid and ethanol. It is a volatile oil component found in ripe kiwifruit, cranberry juice, and palm kernel oil.		2.0310benzoate ester;
ethyl ester		flavouring agent;
fragrance;
volatile oil component
4-cyanopyridine
4-cyanopyridine: spectroscopic probe for cytochrome P450 BM3		2.0310
ethyl salicylate
ethyl salicylate: causes erythema after topical application as an aerosol; found in blood		2.0310hydroxybenzoic acid
methyl anthranilate
methyl anthranilate : A benzoate ester that is the methyl ester of anthranilic acid.		2.0310benzoate esterflavouring agent;
metabolite
4-acetylpyridine
[no description available]		2.0310
ethyl isonicotinate
ethyl isonicotinate: structure in first source		2.0310
4-anisaldehyde
4-anisaldehyde: RN given refers to cpd with specified locants for methoxy moieties; structure in Merck, 9th ed, #696. p-methoxybenzaldehyde : A member of the class of benzaldehydes consisting of benzaldehyde itself carrying a methoxy substituent at position 4.		2.0310benzaldehydesbacterial metabolite;
human urinary metabolite;
insect repellent;
plant metabolite
ethylnicotinate
[no description available]		2.0310aromatic carboxylic acid;
pyridines
beta-ionone
beta-ionone: stimulator of carotenogenesis; carotenoid inhibitor; intermediate in synthesis of Vit A; RN given refers to cpd without isomeric designation; structure. beta-ionone : An ionone that is but-3-en-2-one substituted by a 2,6,6-trimethylcyclohex-1-en-1-yl group at position 4.		2.0310iononeantioxidant;
fragrance
Jasmone
jasmone: RN refers to (Z)-isomer; structure given in first source		2.0310cyclic ketone
alpha-ionone
alpha-ionone: RN given refers to cpd without isomeric designation; structure		2.0310enone;
ionone;
methyl ketone
MeJA
[no description available]		2.0310Jasmonate derivatives
ConditionIndicatedRelationship StrengthStudiesTrials
Innate Inflammatory Response
[description not available]		02.0510
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.0510
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