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Human Metabolome Database Version 3.5

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Showing metabocard for Benzocaine (HMDB04992)

Record Information
Version 3.5
Creation Date 2006-10-16 04:59:41 -0600
Update Date 2013-02-08 17:13:44 -0700
HMDB ID HMDB04992
Secondary Accession Numbers None
Metabolite Identification
Common Name Benzocaine
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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  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 Formula C9H11NO2
Average Molecular Weight 165.1891
Monoisotopic Molecular Weight 165.078978601
IUPAC Name ethyl 4-aminobenzoate
Traditional IUPAC Name benzocaine
CAS Registry Number 94-09-7
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
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Benzoic Acid and Derivatives
Sub Class Aminobenzoic Acid Derivatives
Other Descriptors
  • Organic Compounds
  • benzoate ester(ChEBI)
Substituents
  • Aniline
  • Benzoyl
  • Carboxylic Acid Ester
Direct Parent Aminobenzoic Acid Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 92 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP 1.86 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
LogP 2.20 ALOGPS
LogP 1.5 ChemAxon
LogS -1.76 ALOGPS
pKa (strongest basic) 2.78 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 52.32 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 47.53 ChemAxon
Polarizability 17.42 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI RMU-7M)
MS/MS Spectrum EI-B (HITACHI RMU-7)
MS/MS Spectrum EI-B (HITACHI RMU-6D)
MS/MS Spectrum EI-B (HITACHI M-60)
MS/MS Spectrum CI-B (HITACHI M-60)
MS/MS Spectrum EI-B (JEOL JMS-DX-300)
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023574
KNApSAcK ID Not Available
Chemspider ID 13854242 Link_out
KEGG Compound ID C07527 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Benzocaine Link_out
NuGOwiki Link HMDB04992 Link_out
Metagene Link HMDB04992 Link_out
METLIN ID 3934 Link_out
PubChem Compound 2337 Link_out
PDB ID Not Available
ChEBI ID 116735 Link_out
References
Synthesis Reference Salts 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 Not Available
Enzymes
Name: Sodium channel protein type 10 subunit alpha
Reactions:
    Gene Name: SCN10A
    Uniprot ID: Q9Y5Y9 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA