Tetracaine

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Tetracaine
Tetracaine2DCSD.svg
Systematic (IUPAC) name
2-(dimethylamino)ethyl 4-(butylamino)benzoate
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a682640
Legal status
  • Rx Only
Routes Topical, Epidural, Spinal
Pharmacokinetic data
Protein binding 75.6
Identifiers
CAS number 94-24-6 YesY
136-47-0 (hydrochloride)
ATC code C05AD02 D04AB06 N01BA03 S01HA03
PubChem CID 5411
ChemSpider 5218 YesY
UNII 0619F35CGV YesY
KEGG D00551 YesY
ChEBI CHEBI:9468 YesY
ChEMBL CHEMBL698 YesY
Chemical data
Formula C15H24N2O2 
Mol. mass 264.363 g/mol
 YesY (what is this?)  (verify)

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.[1]

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.[2]

Synthesis[edit]

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.[3]

Tetracaine synthesis: Eisleb Otto, Winthrop Chem., U.S. Patent 1,889,645 (1932).

References[edit]

  1. ^ Györke, S; Lukyanenko, V et al. (1997). Dual effects of tetracaine on spontaneous sodium release in rat ventricular myocytes 500 (2). J Physiol. pp. 297–309. 
  2. ^ "WHO Model List of EssentialMedicines". World Health Organization. October 2013. Retrieved 22 April 2014. 
  3. ^ Winthrop Chemical Company, Inc. U.S. Patent 1,889,645, 1932.

Further reading[edit]