Tetracaine hydrochloride

Base Information

• Chemical Name: Tetracaine hydrochloride
• CAS No.: 136-47-0
• Deprecated CAS: 2706-41-4,41585-83-5,41585-83-5
• Molecular Formula: C15H25ClN2O2
• Molecular Weight: 300.829
• Hs Code.: 29224999
• European Community (EC) Number: 205-248-5
• NSC Number: 757337
• UNII: 5NF5D4OPCI
• DSSTox Substance ID: DTXSID6042448
• Wikidata: Q27262597
• NCI Thesaurus Code: C75104
• RXCUI: 91189
• ChEMBL ID: CHEMBL1255654
• Mol file: 136-47-0.mol

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

Chemical Property of Tetracaine hydrochloride

Chemical Property:

• Appearance/Colour: White or off white crystalline powder
• Vapor Pressure: 2.87E-06mmHg at 25°C
• Melting Point: 149 ºC
• Refractive Index: 1.5200 (estimate)
• Boiling Point: 389.4 ºC at 760 mmHg
• PKA: 8.39(at 25℃)
• Flash Point: 189.3 ºC
• PSA: 41.57000
• Density: 1.1279 (rough estimate)
• LogP: 3.49200
• Storage Temp.: Refrigerator
• Solubility.: alcohol: solublesoluble 40 parts of solvent
• Water Solubility.: Soluble in water at 50mg/ml
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 300.1604557
• Heavy Atom Count: 20
• Complexity: 249

Purity/Quality:

99%, ^*data from raw suppliers

Tetracaine Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-36-43-42/43
• Safety Statements: 26-36/37-45-36/37/39-22-53

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCNC1=CC=C(C=C1)C(=O)OCCN(C)C.Cl
• Recent ClinicalTrials: Postoperative Analgesic Efficacy of Tetracaine Hydrochloride Gel
• Recent EU Clinical Trials: Efficacy and safety assessment of intracameral T2380
• Description: Tetracaine Hydrochloride is a local anesthetic drug composed of amphiphilic molecules of a tertiary amine, exhibiting colloidal properties in aqueous media. ^[1]
• Uses: Tetracaine Hydrochloride is a local anesthetic commonly used for pain control during procedures such as skin laceration repair or ophthalmic surgery. Recent evidence suggests its potential antitumor effects in various cancers, including neuroblastoma, breast cancer, and melanoma. ^[3]
• Mechanism of Action: Role of Tetracaine Hydrochloride as an Organic Counterion: Tetracaine Hydrochloride serves as an organic counterion, enhancing the micellization properties of ionic surfactants such as sodium bis(2-ethylhexyl) sulfosuccinate (AOT) and sodium dodecyl sulfate (SDS) in aqueous media. ^[1]; TCH exhibits colloidal properties in aqueous media and undergoes micellization similar to other surface-active molecules. ^[2]; Tetracaine hydrochloride exerts its effects by downregulating heterogeneous nuclear ribonucleoprotein A1 (hnRNPA1), a protein implicated in tumor development and progression. ^[3]
• History and Development: Tetracaine Hydrochloride (TCH) is an amphiphilic anesthetic drug with a long-acting ester, synthesized in 1928. TCH is initially formulated as tetracaine hydrochloride, and its aqueous dissolution creates a bioactive species (TCH+), which acts by entering the ionic channel of the cell membrane to stop pain sensation along the nerve. ^[2]
• References: [1] Binding behaviour of hydrophobic drug tetracaine hydrochloride used as organic counterion on ionic surfactants (DOI 10.1016/j.molliq.2021.116564); [2] Investigation of an anaesthetic drug (tetracaine hydrochloride) in the presence of ionic fluid and surfactant: Mixed micellization & spectroscopic studies (DOI 10.1016/j.molliq.2022.121057); [3] Tetracaine hydrochloride induces cell cycle arrest in melanoma by downregulating hnRNPA1 (DOI 10.1016/j.taap.2021.115810)

Technology Process of Tetracaine hydrochloride

There total 9 articles about Tetracaine hydrochloride 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%

amethocaine (94-24-6) → tetracaine hydrochloride (136-47-0,41585-83-5)

Guidance literature:

With hydrogenchloride; In water; ethyl acetate;

Reference yield: 85.0%

2-(N,N-dimethylamino)ethanol (108-01-0) + ethyl 4-(N-butylamino)benzoate (94-32-6) → tetracaine hydrochloride (136-47-0,41585-83-5)

Guidance literature:

With hydrogenchloride; sodium methylate; In water; at 130 ℃; for 8h;

DOI:10.1002/cctc.201600635

Reference yield: 83.0%

2-(N,N-dimethylamino)ethanol (108-01-0) + N-(n-butyl)-4-methoxycarbonylaniline (71839-12-8) → tetracaine hydrochloride (136-47-0,41585-83-5)

Guidance literature:

2-(N,N-dimethylamino)ethanol; N-(n-butyl)-4-methoxycarbonylaniline; With sodium methylate; at 130 ℃; for 8h;

With hydrogenchloride;

DOI:10.1002/adsc.201801447

upstream raw materials:

N-(4-ethoxycarbonylphenyl)butyramide

2-(N,N-dimethylamino)ethanol

ethyl 4-(N-butylamino)benzoate

4-nitrobenzoic acid 2-(dimethylamino)ethyl ester

Downstream raw materials:

2-(dimethylamino)ethyl 4-(butylamino)-3-chlorobenzoate

2-dimethylaminoethyl 4-(n-butylamino)benzoate α-cyclodextrin

2-dimethylaminoethyl 4-(n-butylamino)benzoate γ-cyclodextrin

2-dimethylaminoethyl 4-(n-butylamino)benzoate β-cyclodextrin

Refernces

• 1、 Pan, Yixiao,Luo, Zhenli,Han, Jiahong,Xu, Xin,Chen, Changjun,Zhao, Haoqiang,Xu, Lijin,Fan, Qinghua,Xiao, Jianliang. "B(C6F5)3-Catalyzed Deoxygenative Reduction of Amides to Amines with Ammonia Borane". . p. 2301 - 2308. Retrieved 2019/01/30.
• 2、 -. "Preparation method of tetracaine hydrochloride". . . Retrieved 2017/04/22.