Tetracaine (ophthalmic)

Tetracaine (ophthalmic)

File:Tetracaine2DCSD.svg
Clinical data
AHFS/Drugs.com	Monograph
MedlinePlus	a682640
Routes of administration	Topical, Epidural, Spinal
ATC code	C05AD02 (WHO) D04AB06 (WHO) N01BA03 (WHO) S01HA03 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding	75.6
Identifiers
IUPAC name 2-(dimethylamino)ethyl 4-(butylamino)benzoate
CAS Number	94-24-6 Y 136-47-0 (hydrochloride)
PubChem CID	5411
ChemSpider	5218 Y
UNII	0619F35CGV
KEGG	D00551 Y
ChEBI	CHEBI:9468 Y
ChEMBL	ChEMBL698 Y
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C15H24N2O2
Molar mass	264.363 g/mol
3D model (JSmol)	Interactive image
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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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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.

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.

Chemistry

Tetracaine is synthesized from 4-butylaminobenzoic acid. The ethyl ester is formed through an acid-catalyzed esterification reaction. Base-catalyzed transesterification is achieved by boiling the ethyl ester of 4-butylaminobenzoic acid with excess 2-dimethylaminoethanol in the presence of a small amount of sodium ethoxide.

Tetracaine synthesis from Winthrop Chem. Co. Patent US1889645, 1932

Further reading

• O. Eisleb, Template:US Patent (1932).