Benzonatate (CHEM016583)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:37:43 UTC
Update Date2016-11-09 01:15:26 UTC
Accession NumberCHEM016583
Identification
Common NameBenzonatate
ClassSmall Molecule
DescriptionThe ester obtained by formal condensation of 4-butylaminobenzoic acid with nonaethylene glycol monomethyl ether. Structurally related to procaine and benzocaine, it has an anaesthetic effect on the stretch sensors in the lungs, and is used as a non-narcotic cough suppressant.
Contaminant Sources
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-yl p-(butylamino)benzoateChEBI
2-[2-[2-[2-[2-[2-[2-[2-(2-Methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 4-butylaminobenzoateChEBI
3,6,9,12,15,18,21,24,27-Nonaoxaoctacosyl 4-butylaminobenzoateChEBI
4-(Butylamino)benzoic acid 3,6,9,12,15,18,21,24,27-nonaoxaoctacos-1-yl esterChEBI
BenzonatatoChEBI
BenzonatatumChEBI
BenzononatineChEBI
Nonaethyleneglycol monomethyl ether p-N-butylaminobenzoateChEBI
p-Butylaminobenzoic acid omega-O-methylnonaethyleneglycol esterChEBI
Tessalon perlesKegg
2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-yl p-(butylamino)benzoic acidGenerator
2-[2-[2-[2-[2-[2-[2-[2-(2-Methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 4-butylaminobenzoic acidGenerator
3,6,9,12,15,18,21,24,27-Nonaoxaoctacosyl 4-butylaminobenzoic acidGenerator
4-(Butylamino)benzoate 3,6,9,12,15,18,21,24,27-nonaoxaoctacos-1-yl esterGenerator
Nonaethyleneglycol monomethyl ether p-N-butylaminobenzoic acidGenerator
p-Butylaminobenzoate omega-O-methylnonaethyleneglycol esterGenerator
Benzonatic acidGenerator
TessalonHMDB
Chemical FormulaC30H53NO11
Average Molecular Mass603.742 g/mol
Monoisotopic Mass603.362 g/mol
CAS Registry Number104-31-4
IUPAC Name2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl 4-(butylamino)benzoate
Traditional Namebenzonatate
SMILESCCCCNC1=CC=C(C=C1)C(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOC
InChI IdentifierInChI=1S/C30H53NO11/c1-3-4-9-31-29-7-5-28(6-8-29)30(32)42-27-26-41-25-24-40-23-22-39-21-20-38-19-18-37-17-16-36-15-14-35-13-12-34-11-10-33-2/h5-8,31H,3-4,9-27H2,1-2H3
InChI KeyMAFMQEKGGFWBAB-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
Substituents
  • Aminobenzoic acid or derivatives
  • Benzoate ester
  • Benzoyl
  • Aniline or substituted anilines
  • Phenylalkylamine
  • Secondary aliphatic/aromatic amine
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Secondary amine
  • Dialkyl ether
  • Monocarboxylic acid or derivatives
  • Ether
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0016 g/LALOGPS
logP2.09ALOGPS
logP2.35ChemAxon
logS-5.6ALOGPS
pKa (Strongest Basic)3.47ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area121.4 ŲChemAxon
Rotatable Bond Count33ChemAxon
Refractivity161.54 m³·mol⁻¹ChemAxon
Polarizability67.87 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ba-4789430000-3e3f5cdbfca7adf27324Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0nmm-2794000000-e2d12296cd52bc5b6c1bSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-2900000000-3718c62c83080a92ccddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w4i-3922626000-5dc7fe4297607d083b74Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9744340000-9f08af439f9cd3514671Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9665010000-1bf3fbd87ab1a87e011cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6x-0922113000-2d47eaeef80482270092Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0597-2921111000-2cc95d4ee244c9054738Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-4920000000-1c2d9b1acf4ebda28438Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-9321011000-f4806fb7494d3b14849cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9200010000-4fd975b439aea833149fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9600000000-ebbc2bf3aeb5569f4924Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-9731100000-3824f37521f4fc6505b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0btc-9411100000-2057400c582684721e81Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-4910000000-a4a3ebc1f733a1ccfe9dSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00868
HMDB IDHMDB0015006
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBenzonatate
Chemspider ID7413
ChEBI ID3032
PubChem Compound ID7699
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15445814
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19121573
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21673569
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=7223452
5. Cohen V, Jellinek SP, Stansfield L, Truong H, Baseluos C, Marshall JP: Cardiac arrest with residual blindness after overdose of Tessalon(R) (benzonatate) perles. J Emerg Med. 2011 Aug;41(2):166-71. doi: 10.1016/j.jemermed.2009.08.027. Epub 2009 Nov 5.