136-47-0 Usage
Chemical Properties
Tetracaine hydrochloride is a white, crystalline powder, odourless; hygroscopic; it has a slightly bitter taste and causes local numbness after being placed on the tongue. Soluble in water, soluble in ethanol (~750 g/l), practically insoluble in ether. even in the absence of light, it is gradually degraded on exposure to a humid atmosphere, the decomposition being faster at higher temperatures.
Originator
Anestesia topica,Miro
Uses
Tetracaine hydrochloride is a local anesthetic used topically in opthalmology.It is a highly effective local anesthetic that reversibly blocks nerve function. It is clinically used for infiltration anesthesia, nerve block anesthesia, epidural anesthesia, etc. Compared with procaine, its local anesthesia effect is remarkable. Tetracaine hydrochloride has been widely used in clinical practice.
Definition
ChEBI: Tetracaine hydrochloride is a benzoate ester. It is a potent local anesthetic of the ester type used for surface and spinal anesthesia.
Application
Tetracaine hydrochloride is also known as ropivacaine hydrochloride, pantocaine, pantocaine and four ropivacaine hydrochloride. It is easily soluble in water and ethanol, but insoluble in ether, benzene. Tetracaine hydrochloride is a local anesthetic with long-acting ester. In addition, procaine is widely used in clinical, but because of its poor permeability and poor narcotic performance, a small tetracaine was found in 1930 found.Tetracaine hydrochloride can be used for topical anesthesia, and 0.05%-0.1% tetracaine hydrochloride can provide long-term and good effect of surface anesthesia. Meanwhile, tetracaine hydrochloride is still widely used in ophthalmic surface anesthesia, which has a long time for surface anesthesia and sensory resistance.
Preparation
Synthesis of tetracaine hydrochloride using 4-Methyl-2-pentanone as starting material: To the reaction kettle, first add 320.0kg of methyl isobutyl ketone, then add 40.0kg (207mol) of 4-Butylaminobenzoic acid and 56.8kg of anhydrous potassium carbonate in turn, heat the oil bath to 116°C for reflux reaction for 4h, stop heating, and react for a while. Cool for 0.5h, then add 38.3kg (266mol) of 2-Dimethylaminoethyl Chloride Hydrochloride, continue to heat to 116°C for reflux reaction for 4h, and cool to below 30°C after the reaction is complete, then add deionized water 127.0 kg stirred for 30min, left standing for 1h, separated the organic layer, dried and concentrated to obtain an oily substance, then added 169.0kg of acetone and stirred, adjusted the pH value with concentrated hydrochloric acid to 3-4, and precipitated a large number of crystals, which continued to crystallize for 12h after freezing. , centrifugal filtration and drying to obtain 53.0kg of white solid which is tetracaine hydrochloride, the yield is 85.07%, and the HPLC purity is 99.34%.
Therapeutic Function
Local anesthetic
General Description
Tetracaine hydrochloride is a local anesthetic drug and an ester derivative of p-amino benzoic acid. It acts by interfering with the entry of sodium ions into nerve cells and is one of the commonly used topical anesthetics.
Biological Activity
tetracaine hcl is a potent local anaesthetic and a channel function allosteric inhibitor.tetracaine hydrochloride is a calcium channel protein inhibitor and blocks voltage-sensitive release of ca2+ from sarcoplasmic reticulum. tetracaine is a potent local
Biochem/physiol Actions
Blocks voltage-sensitive release of Ca2+ from sarcoplasmic reticulum.
Contact allergens
Amethocaine is a local anesthetic used in dental surgery.
It was reported as an agent of contact dermatitis
in dentists or dental nurses and in ophthalmologists
Side effects
Tetracaine hydrochloride is in the ester-type local anesthetic family of medications. It works by blocking the sending of nerve impulses. common side effects include Transient stinging, burning, and conjunctival redness, eye irritation, eye pain, ocular discomfort. Allergic reactions may uncommonly occur. Long term use is generally not recommended as it may slow healing of the eye. It is unclear if use during pregnancy is safe for the baby.
Check Digit Verification of cas no
The CAS Registry Mumber 136-47-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 6 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 136-47:
(5*1)+(4*3)+(3*6)+(2*4)+(1*7)=50
50 % 10 = 0
So 136-47-0 is a valid CAS Registry Number.
InChI:InChI=1/C15H24N2O2.ClH/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;1H
136-47-0Relevant articles and documents
Preparation method of tetracaine hydrochloride
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Paragraph 0026-0035, (2019/06/05)
The invention discloses a preparation method of tetracaine hydrochloride. The preparation method of the tetracaine hydrochloride comprises the steps of a first step reaction of p-aminobenzoic acid andN-butyraldehyde, a second step reaction of a first step reaction product and N,N-dimethyl ethanolamine of and a salt forming reaction of the third step, wherein the first step reaction is carried outin the presence of N,N-dimethyl ethanolamine, a system after the first reaction directly performs the second reaction without concentration. The N,N-dimethyl ethanolamine is adopted to replace alcohol solvent in the aldehyde-amine reaction, solvent switching before a second esterification reaction is eliminated, and the possibility of generating impurities due to incomplete removal of the alcoholsolvent is eliminated, so that the content of a final product is effectively improved.
B(C6F5)3-Catalyzed Deoxygenative Reduction of Amides to Amines with Ammonia Borane
Pan, Yixiao,Luo, Zhenli,Han, Jiahong,Xu, Xin,Chen, Changjun,Zhao, Haoqiang,Xu, Lijin,Fan, Qinghua,Xiao, Jianliang
, p. 2301 - 2308 (2019/01/30)
The first B(C6F5)3-catalyzed deoxygenative reduction of amides into the corresponding amines with readily accessible and stable ammonia borane (AB) as a reducing agent under mild reaction conditions is reported. This metal-free protocol provides facile access to a wide range of structurally diverse amine products in good to excellent yields, and various functional groups including those that are reduction-sensitive were well tolerated. This new method is also applicable to chiral amide substrates without erosion of the enantiomeric purity. The role of BF3 ? OEt2 co-catalyst in this reaction is to activate the amide carbonyl group via the in situ formation of an amide-boron adduct. (Figure presented.).
Method for preparing tetracaine hydrochloride
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Paragraph 0039; 0040; 0042; 0043, (2019/01/21)
The invention discloses a method for preparing tetracaine hydrochloride. The method comprises the following steps: (1) preparing 4-n-butyl aminobenzoic acid, namely adding a solvent, 4-halogen-benzoicacid, n-butylamine and copper catalyst into a high pressure reactor to obtain the 4-n-butyl aminobenzoic acid; (2) preparing tetracaine, namely adding the 4-n-butyl aminobenzoic acid prepared in thestep (1), N,N-dimethylethanolamine, concentrated sulfuric acid and a solvent into a reaction bottle, heating, refluxing and diverting to obtain the tetracaine; and (3) preparing tetracaine hydrochloride, namely reacting the tetracaine prepared in the step (2) with concentrated hydrochloric acid in a solvent at a certain temperature to obtain the tetracaine hydrochloride. The method has the advantages that 1, the copper catalyst has smaller toxicity, is low in price and easily available while the copper catalyst is much safer, and the cost for raw materials and operation can be greatly reduced;2, the raw materials are easily available, the reaction has few steps, the intermediate reacting process can be easily controlled, few byproduct is generated, and large-scale production is easy to implement; and 3, the product has high purity and high total yield.
Preparation method of tetracaine hydrochloride
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Paragraph 0015, (2017/04/22)
The invention relates to the technical field of preparation method of tetracaine hydrochloride. The preparation method comprises the preparation steps: carrying out a reaction of p-nitrobenzoyl chloride (2) and 2-dimethylamino-1-ethanol (3) to generate p-nitrobenzoic acid-2-dimethylamino ethyl (4), reducing the compound (3) to obtain p-aminobenzoic acid-2-dimethylamino ethyl (4), generating pontocaine (7) from a compound (5) and 1-bromobutane (6) under alkaline conditions, and finally carrying out a reaction of the pontocaine (7) with HCl to generate tetracaine hydrochloride (1).
Boron Lewis Acid Promoted Ruthenium-Catalyzed Hydrogenation of Amides: An Efficient Approach to Secondary Amines
Yuan, Ming-Lei,Xie, Jian-Hua,Zhou, Qi-Lin
, p. 3036 - 3040 (2016/10/11)
The hydrogenation of amides to amines has been developed by using the catalyst [Ru(H)2(CO)(Triphos)] (Triphos=1,1,1-tri(diphenylphosphinomethyl)ethane) and catalytic boron Lewis acids such as B(C6F5)3 or BF3?Et2O as additives. The reaction provides an efficient method for the preparation of secondary amines from amides in good yields with high selectivity.
