TETRACAINE (CED0003841)

Record Information
Version1.0
Creation Date2016-06-03 10:22:12 UTC
Update Date2026-08-19 12:37:14 UTC
Accession NumberCHEM042881
Identification
Common NameTETRACAINE
ClassSmall Molecule
Description
TETRACAINE is an organic compound with the formula C15H24N2O2 and an average molecular weight of 264.37 g/mol. TETRACAINE belongs to the benzoic acids and derivatives, a subclass of benzene and substituted derivatives within the organic compounds. It is recorded as being found in or released from 19 sources, including healthcare, pharmaceuticals and veterinary products such as local anesthetics, anesthetics, antipruritics, and vasoprotectives. Other sources include food preservation and the preparation of wine or sparkling wine, as well as household cleaning and consumer products like soap dispensers, perfumes within detergents and soaps, cigar cigarettes, other smoking requisites, and non electric simulated smoking devices. Additionally, it is associated with electrical and electronic equipment, including electric hearing aids, electrically stimulated smoking devices, fixed capacitors and their manufacture, antennas, and conductors or conductive bodies characterised by the conductive materials. The compound is associated with 12 recorded protein targets, acting as a blocker, inhibitor, or modulator of the sodium channel protein type 4 subunit alpha (SCN4A), sodium channel protein type 1 subunit alpha (SCN1A), ryanodine receptor 2 (RYR2), ryanodine receptor 1 (RYR1), and 8 other proteins. Recorded exposure routes for TETRACAINE include oral, nasal, buccal, dental, cutaneous, topical, subcutaneous, parenteral, infiltration, intraspinal, subarachnoid, and ophthalmic.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
2-(Dimethylamino)ethyl p-(butylamino)benzoateChEBI
AmethocaineChEBI
Diaethylaminoaethanol ester der p-butylaminobenzoesaeureChEBI
p-(Butylamino)benzoic acid beta-(dimethylamino)ethyl esterChEBI
p-Butylaminobenzoyl-2-dimethylaminoethanolChEBI
TetracainaChEBI
TetracainumChEBI
2-(Dimethylamino)ethyl p-(butylamino)benzoic acidGenerator
p-(Butylamino)benzoate b-(dimethylamino)ethyl esterGenerator
p-(Butylamino)benzoate beta-(dimethylamino)ethyl esterGenerator
p-(Butylamino)benzoate β-(dimethylamino)ethyl esterGenerator
p-(Butylamino)benzoic acid b-(dimethylamino)ethyl esterGenerator
p-(Butylamino)benzoic acid β-(dimethylamino)ethyl esterGenerator
AmetopMeSH
DicaineMeSH
Hydrochloride, tetrracaineMeSH
PantocaineMeSH
PontocaineMeSH
Tetracaine monohydrochlorideMeSH
TetrakainMeSH
Tetrracaine hydrochlorideMeSH
2-(Dimethylamino)ethyl 4-(butylamino)benzoic acidGenerator
Chemical FormulaC15H24N2O2
Average Molecular Mass264.369 g/mol
Monoisotopic Mass264.184 g/mol
CAS Registry Number94-24-6
IUPAC Name2-(dimethylamino)ethyl 4-(butylamino)benzoate
Traditional Nametetracaine
SMILESCCCCNC1=CC=C(C=C1)C(=O)OCCN(C)C
InChI IdentifierInChI=1S/C15H24N2O2/c1-4-5-10-16-14-8-6-13(7-9-14)15(18)19-12-11-17(2)3/h6-9,16H,4-5,10-12H2,1-3H3
InChI KeyGKCBAIGFKIBETG-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
  • Carboxylic acid ester
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.56 g/LALOGPS
logP3.54ALOGPS
logP2.79ChemAxon
logS-2.7ALOGPS
pKa (Strongest Basic)8.42ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.57 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity80.17 m³·mol⁻¹ChemAxon
Polarizability31.9 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a4i-9410000000-44410ef7c8aa9cf69c00Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0390000000-0435246ac53e48fff280Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0900000000-987e041aca4bd931c37eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-2900000000-8fb0dc9fe24fa06781f9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00fu-8900000000-13f5e95cf7277be78720Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0603-9500000000-43bdd69ad39be196db4dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-2910000000-a6e7d7e502323aaae4e8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0900000000-5675ccb86810d0c19921Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0900000000-f667e0561040fde13a6eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0390000000-0435246ac53e48fff280Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-2910000000-177a9f94ee33c5e3a780Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0900000000-987e041aca4bd931c37eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00fu-8900000000-13f5e95cf7277be78720Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-2900000000-8fb0dc9fe24fa06781f9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0910000000-c624685ddc6305978e32Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00fu-8900000000-ab562b5fcc5f5c6a4d70Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0910000000-631df0fd7a7f46746624Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-016r-0790000000-7a0686e4023d6a08320aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0603-9500000000-9bcd4ec45b8a7d946ab3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0603-9500000000-43bdd69ad39be196db4dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01b9-7590000000-79cdf8fa4b20ffd244d9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05fr-9410000000-e21d86fb204c6a711827Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ab9-9300000000-dd6c4dcfde5f9b041900Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-3590000000-242f903a843b11683464Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-08mm-5970000000-e8f29f21a99f222fb98bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006x-9500000000-5d93cf36654dd12a934dNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1172.0Log mg/kg[660:2100]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
292VasoprotectivesHealthcare, pharmaceuticals & veterinary productsNot Available
304AntipruriticsHealthcare, pharmaceuticals & veterinary productsNot Available
369AnestheticsHealthcare, pharmaceuticals & veterinary productsNot Available
401Local anestheticsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureCyclic nucleotide-gated channel alpha-1Q00194Bos taurusPredicted (SEA)0.0778492
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)39.781
Amine oxidase [flavin-containing] A structureClick to view 3D structureAmine oxidase [flavin-containing] AP21397HumansPredicted (SEA)17.4382
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)106.186
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)75.358
Sodium channel protein type 5 subunit alpha structureClick to view 3D structureSodium channel protein type 5 subunit alphaQ14524HumansPredicted (SEA)77.8492
Sodium channel protein type 2 subunit alpha structureClick to view 3D structureSodium channel protein type 2 subunit alphaQ99250HumansPredicted (SEA)39.9366
Sodium channel protein type 9 subunit alpha structureClick to view 3D structureSodium channel protein type 9 subunit alphaQ15858HumansPredicted (SEA)125.026
Sodium channel protein type 8 subunit alpha structureClick to view 3D structureSodium channel protein type 8 subunit alphaQ9UQD0HumansPredicted (SEA)94.509
UDP-3-O-acyl-N-acetylglucosamine deacetylase structureClick to view 3D structureUDP-3-O-acyl-N-acetylglucosamine deacetylaseO67648Aquifex aeolicus (strain VF5)Predicted (SEA)20.7079
Apoptotic protease-activating factor 1 structureClick to view 3D structureApoptotic protease-activating factor 1O14727HumansPredicted (SEA)6.69503
Sodium channel protein type 3 subunit alpha structureClick to view 3D structureSodium channel protein type 3 subunit alphaQ9NY46HumansPredicted (SEA)27.9479
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)80.3404
5-hydroxytryptamine receptor 1B structureClick to view 3D structure5-hydroxytryptamine receptor 1BP28222HumansPredicted (SEA)176.562
Sodium channel protein type 7 subunit alpha structureClick to view 3D structureSodium channel protein type 7 subunit alphaQ01118HumansPredicted (SEA)55.1172
Click to view 3D structureProtein RecAP9WHJ3Mycobacterium tuberculosisPredicted (SEA)77.7714
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)175.239
Prothrombin structureClick to view 3D structureProthrombinP00734HumansPredicted (SEA)361.454
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)378.036
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansPredicted (SEA)104.941
Sentrin-specific protease 7 structureClick to view 3D structureSentrin-specific protease 7Q9BQF6HumansPredicted (SEA)120.121
Ubiquitin-conjugating enzyme E2 N structureClick to view 3D structureUbiquitin-conjugating enzyme E2 NP61088HumansPredicted (SEA)2.49118
Click to view 3D structureLiver carboxylesteraseQ29550Sus scrofaPredicted (SEA)4.51525
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)1433.59
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)517.775
Concentrations
Not Available
External Links
DrugBank IDDB09085
HMDB IDHMDB0258868
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTetracaine
Chemspider ID5218
ChEBI ID9468
PubChem Compound IDNot Available
Kegg Compound IDC07526
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=25119673
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=7567006
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=7574001
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=9989796