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
  • (Prescription only)
Topical, Epidural, Spinal
Pharmacokinetic data
Protein binding 75.6
Identifiers
94-24-6 YesY
136-47-0 (hydrochloride)
C05AD02 D04AB06 N01BA03 S01HA03
PubChem CID 5411
ChemSpider 5218 YesY
UNII 0619F35CGV YesY
KEGG D00551 YesY
ChEBI CHEBI:9468 YesY
ChEMBL CHEMBL698 YesY
PDB ligand ID TE4 (PDBe, RCSB PDB)
Chemical data
Formula C15H24N2O2
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]

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.[2]

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.[3]

A systematic review and meta-analysis of randomised controlled trials 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.[4]

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.[5]

Tetracaine synthesis: Eisleb Otto, Winthrop Chem., U.S. Patent 1,889,645 (1932). NOTE the N-alkyl sidechain is showing 5 carbons instead of 4

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. ^ Appleton's Nursing Manual - "Cocaine"
  3. ^ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014. 
  4. ^ Pywell, A; Xyrichis, A (2014). "Does topical Amethocaine cream increase first-time successful cannulation in children compared with a eutectic mixture of local anaesthetics (EMLA) cream? A systematic review and meta-analysis of randomised controlled trials" 0 (0). Emerg Med J. pp. 1–5. doi:10.1136/emermed-2014-204066. 
  5. ^ Winthrop Chemical Company, Inc. U.S. Patent 1,889,645, 1932.

Further reading[edit]