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Substance Name: Tetracaine [USP:INN:BAN]
RN: 94-24-6
UNII: 0619F35CGV
InChIKey: GKCBAIGFKIBETG-UHFFFAOYSA-N

Note

  • A potent local anesthetic of the ester type used for surface and spinal anesthesia.

Molecular Formula

  • C15-H24-N2-O2

Molecular Weight

  • 264.367
 

Classification Codes

  • Anesthetic (Topical)
  • Anesthetics
  • Anesthetics, Local
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Peripheral Nervous System Agents
  • Sensory System Agents

Names and Synonyms

Name of Substance

  • Tetracaine
  • Tetracaine [USP:INN:BAN]

MeSH Heading

  • Tetracaine

Synonyms

  • 2-(Dimethylamino)ethyl p-(butylamino)benzoate
  • 2-Dimethylaminoethylester kyseliny p-butylaminobenzoove
  • 2-Dimethylaminoethylester kyseliny p-butylaminobenzoove [Czech]
  • 4-14-00-01172 (Beilstein Handbook Reference)
  • Amethocaine
  • Anetain
  • Benzoic acid, 4-(butylamino)-, 2-(dimethylamino)ethyl ester
  • BRN 2216051
  • Contralgin
  • Diaethylaminoaethanol ester der p-butylaminobenzoesaeure
  • Diaethylaminoaethanol ester der p-butylaminobenzoesaeure [German]
  • Dicain
  • Dicaine
  • Dikain
  • Dimethylaminoethyl p-butyl-aminobenzoate
  • EINECS 202-316-6
  • Fissucain
  • Intercain
  • Laudocaine
  • Medicaine
  • Medihaler-Tetracaine
  • Meethobalm
  • Metraspray
  • Mucaesthin
  • Niphanoid
  • p-(Butylamino)benzoic acid, 2-(dimethylamino)ethyl ester
  • p-Butylaminobenzoyl-2-dimethylaminoethanol
  • Pontocaine
  • Rexocaine
  • Tetracaina
  • Tetracaina [INN-Spanish]
  • Tetracaine
  • Tetracainum
  • Tetracainum [INN-Latin]
  • Tetrakain
  • Tetrakain [Czech]
  • UNII-0619F35CGV
  • Uromucaesthin

Systematic Names

  • Benzoic acid, 4-(butylamino)-, 2-(dimethylamino)ethyl ester
  • Benzoic acid, p-(butylamino)-, 2-(dimethylamino)ethyl ester
  • Tetracaine

Mixture Name

  • Synera

Registry Numbers

CAS Registry Number

  • 94-24-6

FDA UNII

  • 0619F35CGV

Related Registry Number

  • 136-47-0 (mono-hydrochloride)

System Generated Number

  • 0000094246

Structure Descriptors

InChI

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

InChIKey

GKCBAIGFKIBETG-UHFFFAOYSA-N

Smiles

c1(C(OCCN(C)C)=O)ccc(NCCCC)cc1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
frog LDLo intraspinal 20mg/kg (20mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 45, Pg. 291, 1932.
frog LDLo parenteral 200mg/kg (200mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

CARDIAC: OTHER CHANGES

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 168, Pg. 447, 1932.
man LDLo parenteral 1mg/kg (1mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Sammlung von Vergiftungsfaellen. Vol. 10, Pg. 5C, 1939.
mouse LD50 intraperitoneal 20mg/kg (20mg/kg)   Russian Pharmacology and Toxicology Vol. 35, Pg. 114, 1972.
mouse LD50 intravenous 6mg/kg (6mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 10, Pg. 291, 1975.
mouse LD50 oral 300mg/kg (300mg/kg)   Helvetica Physiologia et Pharmacologica Acta. Vol. 15, Pg. 55, 1957.
mouse LD50 subcutaneous 41500ug/kg (41.5mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 7, Pg. 215, 1957.
rabbit LD50 intratracheal 6500ug/kg (6.5mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 78, 1976.
rabbit LD50 parenteral 33500ug/kg (33.5mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 78, 1976.
rabbit LDLo intraspinal 4900ug/kg (4.9mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 54, Pg. 137, 1935.
rabbit LDLo intravenous 6mg/kg (6mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 160, Pg. 53, 1931.
rabbit LDLo subcutaneous 20mg/kg (20mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 160, Pg. 53, 1931.
rat LD50 intraperitoneal 33mg/kg (33mg/kg)   Klinische Wochenscrift. Vol. 31, Pg. 97, 1953.
rat LD50 intratracheal 4mg/kg (4mg/kg)   Klinische Wochenscrift. Vol. 31, Pg. 97, 1953.
rat LD50 intravenous 6mg/kg (6mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 539, 1958.

Physical Properties

Physical Property Value Units Temp (deg C) Source
pKa Dissociation Constant 8.2 (none) 25 EXP
log P (octanol-water) 3.51 (none)   EXP
Water Solubility 131 mg/L 25 EST
Vapor Pressure 1.87E-05 mm Hg 25 EST
Henry's Law Constant 4.15E-11 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.08E-10 cm3/molecule-sec 25 EST

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