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Record Information
Creation Date2006-10-16 10:59:41 UTC
Update Date2014-09-23 05:26:59 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameBenzocaine
DescriptionBenzocaine 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.
  1. (p-(Ethoxycarbonyl)phenylamine
  2. 4-(Ethoxycarbonyl)aniline
  3. 4-(Ethoxycarbonyl)phenylamine
  4. 4-Aminobenzoate
  5. 4-Aminobenzoic acid
  6. 4-Aminobenzoic acid ethyl ester
  7. 4-Carbethoxyaniline
  8. Aethoform
  9. Amben ethyl ester
  10. Americaine
  11. Anaesthan-syngala
  12. Anaesthesin
  13. Anaesthin
  14. Anestezin
  15. Anesthesin
  16. Anesthesine
  17. Anesthone
  18. Baby Anbesol
  19. Benzoak
  20. Benzocaine
  21. Dermoplast
  22. Diet Ayds
  23. Ethoform
  24. Ethyl 4-aminobenzoate
  25. Ethyl 4-aminobenzoic acid
  26. Ethyl aminobenzoate
  27. Ethyl aminobenzoic acid
  28. Ethyl p-aminobenzenecarboxylate
  29. Ethyl p-aminobenzoate
  30. Ethyl p-aminobenzoic acid
  31. Ethyl p-aminophenylcarboxylate
  32. Ethylester kyseliny p-aminobenzoove
  33. Hurricaine
  34. Identhesin
  35. Keloform
  36. Norcain
  37. Norcaine
  38. Ora-jel
  39. Orabase-B
  40. Orthesin
  41. p-(Ethoxycarbonyl)aniline
  42. p-Aminobenzoate
  43. p-Aminobenzoic acid
  44. p-Aminobenzoic acid ethyl ester
  45. p-Carbethoxyaniline
  46. p-Ethoxycarboxylic aniline
  47. Parathesin
  48. Parathesine
  49. Slim Mint Gum
  50. Solarcaine
  51. Solu H
  52. Topcaine
Chemical FormulaC9H11NO2
Average Molecular Weight165.1891
Monoisotopic Molecular Weight165.078978601
IUPAC Nameethyl 4-aminobenzoate
Traditional Namebenzocaine
CAS Registry Number94-09-7
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
  • Benzoate ester
  • Aminobenzoic acid or derivatives
  • Benzylether
  • Substituted aniline
  • Benzoyl
  • Aniline
  • Primary aromatic amine
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
StatusExpected but not Quantified
  • Drug
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
Experimental Properties
Melting Point92 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.86HANSCH,C ET AL. (1995)
Predicted Properties
Water Solubility2.85 mg/mLALOGPS
pKa (Strongest Basic)2.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.53 m3·mol-1ChemAxon
Polarizability17.46 Å3ChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-6 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-3 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023574
KNApSAcK IDNot Available
Chemspider ID13854242
KEGG Compound IDC07527
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzocaine
NuGOwiki LinkHMDB04992
Metagene LinkHMDB04992
PubChem Compound2337
PDB IDNot Available
ChEBI ID116735
Synthesis ReferenceSalts from naphtholmonosulphonic acids and p-aminobensoic acid ethyl ether. (1904), DE 181324 19040213 CAN 1:9748 AN 1907:9748
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Bong CL, Hilliard J, Seefelder C: Severe methemoglobinemia from topical benzocaine 7.5% (baby orajel) use for teething pain in a toddler. Clin Pediatr (Phila). 2009 Mar;48(2):209-11. doi: 10.1177/0009922808324491. Epub 2008 Oct 3. [18836057 ]
  2. FENTON PF, COWGILL GR, STONE MA, JUSTICE DH: The nutrition of the mouse. VIII. Studies on pantothenic acid, biotin, inositol and paminobenzoic acid. J Nutr. 1950 Oct;42(2):257-69. [14795275 ]


General function:
Involved in ion channel activity
Specific function:
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Its electrophysiological properties vary depending on the type of the associated beta subunits (in vitro). Plays a role in neuropathic pain mechanisms
Gene Name:
Uniprot ID:
Molecular weight: