Tetracaine

Tetracaine

Systematic (IUPAC) name
2-(dimethylamino)ethyl 4-(butylamino)benzoate
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a682640
Legal status	℞ (Prescription only)
Routes of administration	Topical, Epidural, Spinal
Pharmacokinetic data
Protein binding	75.6
Identifiers
CAS Number	94-24-6 Y Template:CAS (hydrochloride)
ATC code	C05AD02 (WHO) D04AB06 N01BA03 S01HA03
PubChem	CID: 5411
ChemSpider	5218 Y
UNII	0619F35CGV Y
KEGG	D00551 Y
ChEBI	CHEBI:9468 Y
ChEMBL	CHEMBL698 Y
PDB ligand ID	TE4 (PDBe, RCSB PDB)
Chemical data
Formula	C15H24N2O2
Molecular mass	264.363 g/mol
SMILES O=C(OCCN(C)C)c1ccc(NCCCC)cc1
InChI 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 Y Key:GKCBAIGFKIBETG-UHFFFAOYSA-N Y
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Tetracaine (INN, also known as amethocaine; trade name Pontocaine. Ametop and Dicaine) is a potent local anesthetic of the ester group. It is mainly used topically in ophthalmology and as an antipruritic, and it has been used in spinal anesthesia.

In biomedical research, tetracaine is used to alter the function of calcium release channels (ryanodine receptors) that control the release of calcium from intracellular stores. Tetracaine is an allosteric blocker of channel function. At low concentrations, tetracaine causes an initial inhibition of spontaneous calcium release events, while at high concentrations, tetracaine blocks release completely.

Tetracaine is the T in Tac, a mixture of 5 to 12 per cent tetracaine, 5‱ (per myriad), a half per mille (0.5‰), or .05 per cent (1 part in 2000) adrenaline, and 4 or 10 per cent cocaine hydrochloride used in ear, nose & throat surgery and in the emergemcy department where numbing of the surface is needed rapidly, especially when children have been injured in the eye, ear, or other sensitive locations.

It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.

A systematic review investigated tetracaine for use in emergency departments, especially for IV cannulation in children, in view of its analgesic and cost-saving properties - however it did not find a statistically significant improvement in first attempt cannulations.

Further reading

• O. Eisleb, U.S. Patent 1,889,645 (1932).