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Substance Name: Benzocaine [USP:INN:BAN]
RN: 94-09-7
UNII: U3RSY48JW5
InChIKey: BLFLLBZGZJTVJG-UHFFFAOYSA-N

Note

  • A surface anesthetic that acts by preventing transmission of impulses along nerve fibers and at nerve endings.

Molecular Formula

  • C9-H11-N-O2

Molecular Weight

  • 165.191
 

Classification Codes

  • Agricultural Chemical
  • Anesthetic (Topical)
  • Anesthetics
  • Anesthetics, Local
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Human Data
  • Peripheral Nervous System Agents
  • Sensory System Agents
  • Skin / Eye Irritant

Names and Synonyms

Name of Substance

  • Anestezin
  • Benzocaine [USP:INN:BAN]
  • Benzoic acid, 4-amino-, ethyl ester
  • Ethyl 4-aminobenzoate
  • Ethyl PABA

MeSH Heading

  • Benzocaine

Synonyms

  • 4-(Ethoxycarbonyl)aniline
  • 4-14-00-01129 (Beilstein Handbook Reference)
  • 4-Aminobenzoic acid, ethyl ester
  • 4-Carbethoxyaniline
  • Aethylium paraminobenzoicum
  • AI3-02081
  • Amben ethyl ester
  • Americaine
  • Anaesthan-syngala
  • Anaesthesin
  • Anaesthesinum
  • Anaesthin
  • Anestezin
  • Anestezin [Russian]
  • Anesthesin
  • Anesthesine
  • Anesthone
  • Baby Anbesol
  • Benzocaina
  • Benzocaina [INN-Spanish]
  • Benzocaine
  • Benzocainum
  • Benzocainum [INN-Latin]
  • BRN 0638434
  • Caswell No. 430A
  • Chloraseptic
  • Dermoplast
  • EINECS 202-303-5
  • EPA Pesticide Chemical Code 097001
  • Ethoform
  • Ethoforme
  • Ethyl 4-aminobenzoate
  • Ethyl aminobenzoate
  • Ethyl aminobenzoate (VAN)
  • Ethyl p-aminobenzoate
  • Ethyl p-aminophenylcarboxylate
  • Ethylester kyseliny p-aminobenzoove
  • Ethylester kyseliny p-aminobenzoove [Czech]
  • Ethylis aminobenzoas
  • Finafta
  • HSDB 7225
  • Hurricaine
  • Identhesin
  • Keloform
  • Norcain
  • Norcaine
  • Norcainum
  • NSC 41531
  • Ora-jel
  • Orthesin
  • Otocain
  • p-(Ethoxycarbonyl)aniline
  • p-Aminobenzoic acid ethyl ester
  • p-Carbethoxyaniline
  • p-Ethoxycarboxylic aniline
  • Parathesin
  • Parathesine
  • Solarcaine
  • Solu H
  • Topcaine
  • UNII-U3RSY48JW5

Systematic Names

  • Benzocaine
  • Benzoic acid, 4-amino-, ethyl ester
  • Benzoic acid, p-amino-, ethyl ester

Superlist Names

  • Benzocaine
  • Ethyl p-aminobenzoate

Mixture Names

  • Anbesol
  • Auralgan
  • Cough-X
  • Dermoplast
  • Outgro
  • Vagisil

Registry Numbers

CAS Registry Number

  • 94-09-7

FDA UNII

  • U3RSY48JW5

Other Registry Numbers

  • 1865741-16-7
  • 71123-91-6

Related Registry Number

  • 23239-88-5 (hydrochloride)

System Generated Number

  • 0000094097

Structure Descriptors

InChI

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

InChIKey

BLFLLBZGZJTVJG-UHFFFAOYSA-N

Smiles

c1cc(C(OCC)=O)ccc1N

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 56mg/kg (56mg/kg)   Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972.
infant TDLo rectal 12mg/kg (12mg/kg) BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN New England Journal of Medicine. Vol. 263, Pg. 454, 1960.
mouse LD50 intraperitoneal 216mg/kg (216mg/kg)   Journal of Medicinal Chemistry. Vol. 17, Pg. 900, 1974.
mouse LD50 oral 2500mg/kg (2500mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Toksikologicheskii Vestnik. Vol. (2), Pg. 34, 1996.
rabbit LDLo oral 1150mg/kg (1150mg/kg)   Drugs in Japan Vol. 6, Pg. 33, 1982.
rat LD50 oral 3042mg/kg (3042mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Toksikologicheskii Vestnik. Vol. (2), Pg. 34, 1996.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 92 deg C   EXP
Boiling Point 310 deg C   EXP
pKa Dissociation Constant 2.508 (none) 25 EXP
log P (octanol-water) 1.86 (none)   EXP
Water Solubility 1310 mg/L 30 EXP
Henry's Law Constant 1.63E-08 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.65E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.