Trimecaine
IUPAC name 2-diethylamino-N-(2,4,6-trimethylphenyl)acetamide
Other names N2,N2-diethyl-N-mesitylglycinamide
Identifiers
CAS number	616-68-2
PubChem	12028
Jmol-3D images	Image 1
SMILES CCN(CC)CC(=O)NC1=C(C=C(C=C1C)C)C
Properties
Molecular formula	C15H24N2O
Molar mass	248.36 g mol−1
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Trimecaine (systematic name (2,4,6-trimethylphenylcarbamoylmethyl)diethylammonium chloride, chemical formula C₁₅H₂₅ClN₂O) is an organic compound used as a local anesthetic and cardial antiarrhythmic. It is white crystalline powder readily soluble in water and ethanol.^[1] It is an active ingredient in products available under trademarks Mesdicain, Mesocain, Mesokain and others.^[2]

History [link]

Trimecaine is probably a Czech discovery (in light of complex pharmacological and clinical evaluation and practical deployment) although its preparation has been published by Löfgren in 1946.^[2]

Action mechanism, pharmacokinetics [link]

Like other local anesthetics belonging in the amide group trimecaine decreases the cell membrane permeability, causes depolarization and shortens the action potential.^[3] Anesthetic effect starts in 15 minutes and remains 60–90 minutes. Its biological half-life is ca. 90 minutes. 10 % of trimecaine is excreted unchanged (90 % as its metabolites). It passes through the hematoencephalic and placental barriers.^[4]

Indication [link]

Trimecaine has two main application fields. The first one is local anesthesia (topical, infiltrational, topical mucosal and inhalational, spinal and Bier's intravenous). It is used in concentrations 0.4 up to 4 %, in some cases (e.g. in stomatology) in mixtures with adrenaline. The other field is prophylaxis and therapy of ventriculous arrhytmia on myocardial infarction and in cardiosurgery. It is used also for prophylaxis of sympathic reaction during tracheal intubations.^[3][4]

Contraindication [link]

Trimecaine must not be used at hypersensitivity on amide anesthetics, hypervolemia, hypotension, cardial conduction defects, asystole, cardiogenic shock and malignant hyperthermia in anamnesis.^[3][4]

Adverse effects [link]

Rarely allergical reactions may occur (from dermal or mucosal symptoms to anaphylactic shock). At overdosing a toxical reaction arises - excitation, agitation, dishevelment, visual defects, buzzing in ears, muscle thrill to tremor, in more severe cases somnolence, hyporeflexia, breathing defects to apnea, convulsions.^[3][4]

References [link]

1. ^ Trimecaini hydrochloridum - Český lékopis 1997
2. ^ ^{a b} Trimekain
3. ^ ^{a b c d} Antiarytmika (Novák, M.)
4. ^ ^{a b c d} MESOCAIN - Operativa