Tetracaine
Basic information
- CAS
94-24-6- Standard SMILES
CCCCNc1ccc(C(=O)OCCN(C)C)cc1- InChIKey
GKCBAIGFKIBETG-UHFFFAOYSA-N- Molecular formula
- C15H24N2O2
- Average molar mass
- 264.36 g/mol
- Monoisotopic mass
- 264.18377801
Overview
Tetracaine is a benzoate ester in which 4-N-butylbenzoic acid and 2-(dimethylamino)ethanol have combined to form the ester bond; a local ester anaesthetic (ester caine) used for surface and spinal anaesthesia. It has a role as a local anaesthetic. It is a benzoate ester and a tertiary amino compound.
Names & identifiers
- Preferred name
- Tetracaine
- IUPAC
- 2-(dimethylamino)ethyl 4-(butylamino)benzoate
- English name
- Tetracaine
- Molecular formula
- C15H24N2O2
- Molecular weight
- 264.36
Names & synonyms
tetracaine94-24-6Amethocaine2-(Dimethylamino)ethyl 4-(butylamino)benzoateLaudocaineMetrasprayPontocaineAnetainDicaineUromucaesthinContralginFissucain
Show more names
TETRACAINE BASETETRACAINTetracainumDlcalnetetracine
IntercainMedicaineMeethobalmMucaesthinNiphanoidMedihaler-TetracaineTetracainaTetrakain
Database identifiers
- CAS
94-24-6- PubChem CID
- 5411
- DTXSID
DTXSID1043883- ChEMBL
CHEMBL698- ChEBI
CHEBI:9468- UNII
- 0619F35CGV
- EC Number
- 202-316-6
- Nikkaji
- J3.945D
Properties
Computed structural properties
- XLogP
- 3.7
- Topological polar surface area
- 41.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 9
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 249
Experimental & physicochemical properties
Chemical ClassesOther Uses -> Pharmaceuticals
Drugs
Pharmaceuticals
Pharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
LogP3.46
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anesthetics, Local
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Pharmaceuticals
Ophthalmological preparations > Local anaesthetics
Dissociation Constants
8.49
8.5
8.6
Collision Cross Section
164.78 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
173.1 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
173.5 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated]
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (97.7%): Toxic if swallowed [Danger Acute toxicity, oral]
P203, P261, P264, P270, P272, P280, P301+P316, P302+P352, P318, P321, P330, P333+P317, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 43 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Other Safety InformationIMAP assessments - Benzoic acid, 4-(butylamino)-, 2-(dimethylamino)ethyl ester: Environment tier I assessment
Hazards SummaryProcaine allergy used to be a common skin sensitizer for dentists. There exists cross-reactivity between procaine, benzocaine, and tetracaine but not with lidocaine and other amide-type local anesthetics currently used. [Kanerva, p. 434]
Hazard Classes and CategoriesAcute Tox. 3 (97.7%)
Toxicology
Adverse Effects
Skin Sensitizer - An agent that can induce an allergic reaction in the skin.
When dosing based on weight, clinicians should not exceed 1.5 to 3 mg/kg of the patient's actual weight. The toxicity of the drug is affected by the site of administration. Tetracaine undergoes absorption (from fastest to slowest) in the following order: IV > intercostal > caudal > epidural > brachial plexus > subcutaneous. Absorption speed may be mitigated by avoiding areas near a large vascular supply and adding local vasoconstrictors to the solution (epinephrine or phenylephrine).
Chemistry & industry
Pharmacology
ATC Code
S01HA03
N - Nervous system
S - Sensory organs
D - Dermatologicals
C - Cardiovascular system
QD - Dermatologicals
Protein BindingTetracaine is rapidly hydrolyzed in the plasma; therefore, protein binding could not be determined.
Mechanism of ActionTetracaine is an ester-type anesthetic and produces local anesthesia by blocking the sodium ion channels involved in the initiation and conduction of neuronal impulses.
Biological Half-LifeTetracaine is hydrolyzed rapidly in the plasma; therefore, half-life has not been determined.
Metabolism/MetabolitesTetracaine is rapidly hydrolyzed by plasma esterases to the following primary metabolites: para-aminobenzoic acid and diethylaminoethanol. The activity of both metabolites is unspecified.
FDA Pharmacological Classification
0619F35CGV
TETRACAINE
Established Pharmacologic Class [EPC] - Ester Local Anesthetic
Chemical Structure [CS] - Esters
Physiologic Effects [PE] - Local Anesthesia
Tetracaine is an Ester Local Anesthetic. The physiologic effect of tetracaine is by means of Local Anesthesia.
MeSH Pharmacological Classification
Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate.
Related reactions
2 records
Compound notes
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