Tetracaine

Base Information

• Chemical Name: Tetracaine
• CAS No.: 94-24-6
• Molecular Formula: C15H24N2O2
• Molecular Weight: 264.368
• Hs Code.: DERIVATION
• European Community (EC) Number: 202-316-6
• UNII: 0619F35CGV
• DSSTox Substance ID: DTXSID1043883
• Nikkaji Number: J3.945D
• Wikipedia: Tetracaine
• Wikidata: Q419608
• NCI Thesaurus Code: C66590
• RXCUI: 10391
• Pharos Ligand ID: JKQRC1DJ7J79
• Metabolomics Workbench ID: 50027
• ChEMBL ID: CHEMBL698
• Mol file: 94-24-6.mol

Synonyms:Amethocaine;Ametop;Dicaine;Hydrochloride, Tetrracaine;Pantocaine;Pontocaine;Tetracaine;Tetracaine Monohydrochloride;Tetrakain;Tetrracaine Hydrochloride

Chemical Property of Tetracaine

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 2.87E-06mmHg at 25°C
• Melting Point: 41.0 to 45.0 °C
• Refractive Index: 1.537
• Boiling Point: 389.4 °C at 760 mmHg
• PKA: pKa 8.33±0.03(H2O t = 20.0 I = 0.10 (KCl)) (Uncertain)
• Flash Point: 189.3 °C
• PSA: 41.57000
• Density: 1.044 g/cm³
• LogP: 2.69000
• Storage Temp.: 2-8°C
• Solubility.: soluble in Methanol
• Water Solubility.: 156mg/L(temperature not stated)
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 264.183778013
• Heavy Atom Count: 19
• Complexity: 249

Purity/Quality:

99% ^*data from raw suppliers

Tetracaine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-40-42/43-43
• Safety Statements: 22-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Canonical SMILES: CCCCNC1=CC=C(C=C1)C(=O)OCCN(C)C
• Recent ClinicalTrials: Comparing Topical Tetracaine Drops to Topical Focal Phenol for Local Anesthesia During Intratympanic Steroid Injection
• Recent EU Clinical Trials: A prospective, observer-masked, randomized clinical trial to investigate and compare the clinical efficacy of chloroprocaine 3% gel and tetracaine 0.5% eye drop as topical anesthetics in phacoemulsification.
• Recent NIPH Clinical Trials: Evaluation on pain relief by applying mixed solution with lidocaine, adrenaline, tetracaine (LAT solution) to lacerated wound
• Uses: Tetracaine is used in assessing the potential for drug-nanoparticle surface interactions to improve drug penetration into the skin. analgesic 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 Tetracaine, also known as amethocaine, is the most potent and lipidsoluble ester local anaesthetic and has significant potential for toxicity if used systemically. It is commonly used as a 4% gel for topical application to decrease the pain from venous puncture or cannulation.
• Description: Tetracaine is a local anesthetic or numbing medicine that is used to numb the throat, eyes, or nose. Normally, the drug is administered before starting a surgery to decrease pain from the procedure. Tetracaine is applied to the eyes 30 minutes before the start of an intravenous and its effects can last up to 15 minutes.
• Biological Functions: Tetracaine hydrochloride (Pontocaine) is an ester of PABA that is an effective topical local anesthetic agent and also is quite commonly used for spinal (subarachnoid) anesthesia. Epinephrine is frequently added to prolong the anesthesia.Tetracaine is considerably more potent and more toxic than procaine and cocaine. It has approximately a 5-minute onset and 2 to 3 hours of action.

Technology Process of Tetracaine

There total 13 articles about Tetracaine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

2-(N,N-dimethylamino)ethanol (108-01-0) + ethyl 4-nitrobenzoate (99-77-4) + butyraldehyde (123-72-8) → amethocaine (94-24-6)

Guidance literature:

With hydrogen; palladium-containing anion exchanger AV-17-8; In ethanol; at 45 ℃; under 760 Torr; Further Variations:; Catalysts; concentrations; Kinetics;

DOI:10.1023/A:1015748808266

Reference yield: 85.0%

2-(dimethylamino)ethyl 4-bromobenzoate + N-butylamine (109-73-9,85404-21-3) → amethocaine (94-24-6)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; nickel(II) bromide dimethoxyethane; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; In dimethyl sulfoxide; at 80 ℃; for 0.166667h; Flow reactor; Sealed tube; Schlenk technique; Inert atmosphere; Irradiation;

DOI:10.1021/acs.joc.9b03107

Reference yield: 82.8%

1-bromo-butane (109-65-9) + Dimethylprocaine (10012-47-2) → amethocaine (94-24-6)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 50 ℃; for 5h;

upstream raw materials:

2-(N,N-dimethylamino)ethanol

4-(N-butylamino)benzoic acid

4-nitrobenzoic acid 2-(dimethylamino)ethyl ester

4-nitro-benzoyl chloride

Downstream raw materials:

4-butylamino-benzoic acid-[2-(dimethyl-oxy-amino)-ethyl ester]

tetracaine hydrochloride

Refernces

• 1、 Park, Boyoung Y.,Pirnot, Michael T.,Buchwald, Stephen L.. "Visible Light-Mediated (Hetero)aryl Amination Using Ni(II) Salts and Photoredox Catalysis in Flow: A Synthesis of Tetracaine". . p. 3234 - 3244. Retrieved 2020/02/04.
• 2、 Strassmaier, Timothy,Kirk, Sarah R.,Banerji, Tapasree,Karpen, Jeffrey W.. "Block of cyclic nucleotide-gated channels by tetracaine derivatives: Role of apolar interactions at two distinct locations". . p. 645 - 649. Retrieved 2008/09/19.