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Tetracaine hydrochloride

CAS No.
136-47-0
Chemical Name:
Tetracaine hydrochloride
Synonyms
TETRACAINE HCL;Dimethylaminoethyl;anacel;tonexol;decicain;anethaine;curtacain;decicaine;menonasal;PANTOCAINE
CBNumber:
CB1373091
Molecular Formula:
C15H25ClN2O2
Molecular Weight:
300.82
MDL Number:
MFCD00038912
MOL File:
136-47-0.mol
MSDS File:
SDS
Last updated:2024-11-19 23:02:33

Tetracaine hydrochloride Properties

Melting point 149°C
Density 1.1279 (rough estimate)
refractive index 1.5200 (estimate)
storage temp. 2-8°C
solubility alcohol: solublesoluble 40 parts of solvent
form Solid
pka 8.39(at 25℃)
color White to Almost white
Water Solubility Soluble in water at 50mg/ml
Merck 14,9188
InChI InChI=1S/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
InChIKey PPWHTZKZQNXVAE-UHFFFAOYSA-N
SMILES C1(C=CC(NCCCC)=CC=1)C(=O)OCCN(C)C.Cl
LogP 3.649 (est)
FDA 21 CFR 310.545
CAS DataBase Reference 136-47-0(CAS DataBase Reference)
FDA UNII 5NF5D4OPCI
EPA Substance Registry System Tetracaine hydrochloride (136-47-0)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H301-H319-H336
Precautionary statements  P261-P264-P270-P271-P301+P310-P305+P351+P338
Hazard Codes  T
Risk Statements  25-36-43-42/43
Safety Statements  26-36/37-45-36/37/39-22-53
RIDADR  2811
WGK Germany  3
RTECS  DG4900000
HazardClass  6.1
PackingGroup  III
HS Code  29224999
Toxicity LD50 i.p. in mice: 70 mg/kg (Dawes); also reported as LD50 in female mice (mg/kg): 13 i.v.; 35 s.c. (Bopp)
NFPA 704
0
2 0

Tetracaine hydrochloride price More Price(28)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PHR1129 Tetracaine hydrochloride Pharmaceutical Secondary Standard; Certified Reference Material 136-47-0 1g $270 2024-03-01 Buy
Sigma-Aldrich 1650006 Tetracaine hydrochloride United States Pharmacopeia (USP) Reference Standard 136-47-0 200mg $436 2024-03-01 Buy
TCI Chemical T1688 Tetracaine Hydrochloride >98.0%(HPLC)(T) 136-47-0 5g $36 2024-03-01 Buy
TCI Chemical T1688 Tetracaine Hydrochloride >98.0%(HPLC)(T) 136-47-0 25g $89 2024-03-01 Buy
Sigma-Aldrich T7508 Tetracaine hydrochloride ≥99% 136-47-0 5g $53.9 2024-03-01 Buy
Product number Packaging Price Buy
PHR1129 1g $270 Buy
1650006 200mg $436 Buy
T1688 5g $36 Buy
T1688 25g $89 Buy
T7508 5g $53.9 Buy

Tetracaine hydrochloride Chemical Properties,Uses,Production

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.

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%.

Definition

ChEBI: Tetracaine hydrochloride is a benzoate ester. It is a potent local anesthetic of the ester type used for surface and spinal anesthesia.

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.

Health effects

Tetracaine hydrochloride (TTC) is a long-lasting local anesthetic commonly used for topical anesthesia, which is water-soluble, has strong penetrability and a good anesthetic effect. However, TTC has a higher cytotoxicity compared with other local anesthetics due to its high permeability. Previous studies have reported that TTC exerts a cytotoxic effect on certain cell types, such as human corneal stromal cells and human corneal epithelial cells, inducing apoptosis and necrosis. Research jave found that large doses of intrathecal TTC increase the concentration of glutamate in cerebrospinal fluid, thereby causing neuronal injury in rabbits. In addition, AMPA receptor activation was revealed to be involved in TTC-induced neurotoxicity in the spinal cord. TTC-induced apoptosis may be triggered through Fas death receptors and mediated by Bcl-2 family proteins, in a mitochondria-dependent pathway. TTC-induced human corneal epithelial (HCEP) cell apoptosis via a death receptor-mediated mitochondrion-dependent pathway. Low concentrations of TTC induced the apoptosis of human T-lymphoma cells, whereas a higher concentration of TTC induced necrosis[1].

Clinical claims and research

Topical administration of Tetracaine Hydrochloride Ophthalmic Solution, USP 0.5% results in localized temporary anesthesia. The maximum effect is achieved within 10–20 seconds after instillation, with efficacy lasting 10–20 minutes. Duration of effect can be extended with repeated dosing.

References

[1] Ran Zhang. “Tetracaine hydrochloride induces macrophage pyroptosis through caspase?1/11?GSDMD signaling pathways.” Experimental and therapeutic medicine 26 3 (2023): 428.

94-24-6
136-47-0
Synthesis of Tetracaine hydrochloride from Tetracaine

Tetracaine hydrochloride Preparation Products And Raw materials

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View Lastest Price from Tetracaine hydrochloride manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Tetracaine hydrochloride pictures 2024-11-25 Tetracaine hydrochloride
136-47-0
US $1.00 / kg 0.10000000kg 99% 200KG Jinan Million Pharmaceutical Co., Ltd
 Tetracaine HCl  pictures 2024-11-22 Tetracaine HCl
136-47-0
US $150.00 / kg 1kg 99% 20ton Hebei Zhuanglai Chemical Trading Co.,Ltd
Tetracaine hydrochloride pictures 2024-11-22 Tetracaine hydrochloride
136-47-0
US $0.00 / Kg/Drum 1KG 98%-101%; CP 500KGS WUHAN FORTUNA CHEMICAL CO., LTD
  •  Tetracaine HCl  pictures
  • Tetracaine HCl
    136-47-0
  • US $150.00 / kg
  • 99%
  • Hebei Zhuanglai Chemical Trading Co.,Ltd
L AND OCAIN HYDROCHLORIDE INTERCAIN HYDROCHLORIDE MEETHOBALM HYDROCHLORIDE 4-(N-BUTYLAMINO)BENZOIC ACID 2-(DIMETHYLAMINO)ETHYL ESTER HYDROCHLORIDE 4-[BUTYLAMINO]BENZOIC ACID-2-[DIMETHYLAMINO]ETHYL ESTER HYDROCHLORIDE 4-BUTYLAMINOBENZOIC ACID DIMETHYLAMINOETHYL ESTER HCL 4-BUTYLAMINOBENZOIC ACID DIMETHYLAMINOETHYL ESTER HYDROCHLORIDE AMETHOCAINE HYDROCHLORIDE PONTOCAINE HYDROCHLORIDE PANTOCAINE REXOCAINE HYDROCHLORIDE TETRACAINE HYDROCHLORIDE 2-(dimethylamino)ethylp-(butylamino)benzoatehydrochloride 2-dimethylaminoethanol4-n-butylaminobenzoatehydrochloride anacel anethaine benzoicacid,4-(butylamino)-,2-(dimethylamino)ethylester,monohydrochloride benzoicacid,p-(butylamino)-,2-(dimethylamino)ethylester,monohydrochloride butethanol 2-(DIMETHYLAMINO)ETHYL 4-(N-BUTYLAMINO)BENZOATE HYDROCHLORIDE 2-DIMETHYLAMINOETHYL ESTER OFP-BUTYLAMINOBENZOIC ACID HYDROCHLORIDE butylocaine curtacain decicain decicaine dicainehydrochloride dikainhydrochloride dimethylaminoethyl-p-n-butylaminobenzoatehydrochloride gingicainm menonasal p-(butylamino)benzoicacid,2-(dimethylamino)ethylester,hydrochloride pantocainehydrochloride p-butylaminobenzoyl-2-dimethylaminoethanolhydrochloride steriletetracainehydrochloride tetracainehydrochlorideusp tonexol Tertracaine HCL TETRACAINE HYDROCHLORIDE LOCAL ANESTHETI C Tetracaine HCl,USP p-[Butylamino] benzoic acid 2-(Dimethylamino)ethyl 4-(Butylamino)benzoate Hydrochloride Tetracaine hydrochlorid Tetracaine Hydrochloride (200 mg) Tetracaine hydrochlo Tetracaine HCL API 50G/100G/1KG 4-(Butylamino)benzoic Acid 2-(Dimethylamino)ethyl Ester Hydrochloride 2-(Dimethylamino)ethyl 4-(Butylamino)benzoate Hydrochloride AMethocalne 4-(butylamino)-Benzoic acid, 2-(dimethylamino)ethyl ester, monohydrochloride 2-(Dimethylamino)ethyl 4-butylaminobenzoate monohydrochloride Pantocaine hydrochloride
4-(butylamino)-benzoic acid 2-(dimethylamino)ethyl ester, hydrochloride (1:1) Amethocalne HCl Tetracaine hydrochloride 2-Dimethylaminoethyl 4-n-butylaminobenzoate hydrochloride BENZOIC ACID,4-BUTYLAMINO,2-DIMETHYLAMINOETHYL ESTER PANTOCAIN BASE Diaethylaminoaethanol ester der p-butylaminobenzoesaeure [German] 2-Dimethylaminoethylester kyseliny p-butylaminobenzoove [Czech] Tetricaine HCL