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T7383

Sigma-Aldrich

Tetracaine

≥98% (TLC)

Synonym(s):

4-(Butylamino)benzoic acid 2-(dimethylamino)ethyl ester

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About This Item

Empirical Formula (Hill Notation):
C15H24N2O2
CAS Number:
Molecular Weight:
264.36
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.32

biological source

synthetic (organic)

Assay

≥98% (TLC)

form

powder

technique(s)

toxicology assay: suitable

storage temp.

2-8°C

SMILES string

CCCCNc1ccc(cc1)C(=O)OCCN(C)C

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

InChI key

GKCBAIGFKIBETG-UHFFFAOYSA-N

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General description

Tetracaine belongs to the amino-ester class and has a pKa of 8.46.

Application

Tetracaine can be used as a research tool for studying E-C coupling in both skeletal as well as cardiac muscle. The product is a local anaesthetic drug used for studying the impact of numerous drugs on Tumour-necrosis-factor (TNF)-mediated cytotoxicity as well as TNF-induced arachidonic acid release.
Tetracaine has been used as an anesthetic and to lower the glucose synthesis in upper small intestinal infusions. It has also been used to inhibit ryanodine receptors (RyRs) in rats.
Topical ophthalmic anesthetic; used for spinal anesthesia

Biochem/physiol Actions

Tetracaine also refers as 4-(Butylamino)benzoic acid 2-(dimethylamino)ethyl ester interfere with calcium movement in muscle and non-muscle cells and can inhibit potassium-induced as well as caffeine-induced shortening of outer hair cells (OHC′s). But, the product can′t inhibit electrically-induced shortening of OHC′s.The product can also stimulate caspase activation and inhibits pro-survival signalling pathways which in turn induce human renal cell apoptosis.
Tetracaine blocks intracellular sodium channels. It mediates phosphorylation of eukaryotic initiation factor 2 (eIF2 α) via translational inhibition of P-body formation.
Blocks voltage-sensitive release of Ca2+ from sarcoplasmic reticulum.

Preparation Note

250 mg of tetracaine dissolves in 5 ml of EtOH to yield a clear, colorless solution. The product is also soluble in chloroform and ether at a ratio of 1:2 and in ethanol at 1:5. It is very slightly soluble in water.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral - Carc. 2 - Skin Sens. 1

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3


Certificates of Analysis (COA)

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Tetracaine, a local anesthetic, preferentially induces translational inhibition with processing body formation rather than phosphorylation of eIF2alpha in yeast
Araki T, et al.
Current Genetics, 61(1), 43-53 (2015)
Insect morphogenetic hormones and developmental mechanisms in the nematode, Nematospiroides dubius.
R D Dennis
Comparative biochemistry and physiology. A, Comparative physiology, 53(1), 53-56 (1976-01-01)
Pharmacological considerations for Regional Anesthesia
Principles and Practice of Opthalmic Anesthesia (2018)
S Györke et al.
The Journal of physiology, 500 ( Pt 2), 297-309 (1997-04-15)
1. Confocal microfluorometry was used to study the effects of tetracaine on spontaneous Ca2+ release from the sarcoplasmic reticulum (SR) in isolated rat ventricular myocytes. 2. At low concentrations (0.25-1.25 mM), tetracaine caused an initial inhibition of spontaneous release events
H Thomas Lee et al.
American journal of nephrology, 23(3), 129-139 (2003-02-15)
Renal cell apoptosis contributes significantly to the pathogenesis of acute renal failure. Local anesthetics induce apoptosis in neuronal and lymphocytic cell lines. We examined the effects of chronic (48 h) local anesthetic treatment (lidocaine, bupivacaine and tetracaine) on human proximal

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