| Identification | More | [Name]
Tetracaine hydrochloride | [CAS]
136-47-0 | [Synonyms]
2-(DIMETHYLAMINO)ETHYL 4-(N-BUTYLAMINO)BENZOATE HYDROCHLORIDE
2-DIMETHYLAMINOETHYL ESTER OFP-BUTYLAMINOBENZOIC ACID HYDROCHLORIDE
4-(BUTYLAMINO)BENZOIC ACID 2-(DIMETHYLAMINO)ETHYL ESTER
4-[BUTYLAMINO]BENZOIC ACID-2-[DIMETHYLAMINO]ETHYL ESTER HYDROCHLORIDE
4-BUTYLAMINOBENZOIC ACID DIMETHYLAMINOETHYL ESTER HCL
4-BUTYLAMINOBENZOIC ACID DIMETHYLAMINOETHYL ESTER HYDROCHLORIDE
4-(N-BUTYLAMINO)BENZOIC ACID 2-(DIMETHYLAMINO)ETHYL ESTER HYDROCHLORIDE
AMETHOCAINE HYDROCHLORIDE
INTERCAIN HYDROCHLORIDE
L AND OCAIN HYDROCHLORIDE
MEETHOBALM HYDROCHLORIDE
PANTOCAINE
PONTOCAINE HYDROCHLORIDE
REXOCAINE HYDROCHLORIDE
TETRACAINE HCL
TETRACAINE HYDROCHLORIDE
2-(dimethylamino)ethylp-(butylamino)benzoatehydrochloride
2-dimethylaminoethanol4-n-butylaminobenzoatehydrochloride
anacel
anethaine | [EINECS(EC#)]
205-248-5 | [Molecular Formula]
C15H25ClN2O2 | [MDL Number]
MFCD00038912 | [Molecular Weight]
300.82 | [MOL File]
136-47-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
149°C | [density ]
1.1279 (rough estimate) | [refractive index ]
1.5200 (estimate) | [storage temp. ]
Refrigerator | [solubility ]
alcohol: solublesoluble 40 parts of solvent | [form ]
neat | [pka]
8.39(at 25℃) | [color ]
White to Almost white | [Water Solubility ]
Soluble in water at 50mg/ml | [Merck ]
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 | [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 | [InChIKey]
PPWHTZKZQNXVAE-UHFFFAOYSA-N | [SMILES]
C1(C=CC(NCCCC)=CC=1)C(=O)OCCN(C)C.Cl | [LogP]
3.649 (est) | [CAS DataBase Reference]
136-47-0(CAS DataBase Reference) | [EPA Substance Registry System]
136-47-0(EPA Substance) |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Uses]
A local anesthetic used topically in opthalmology. | [Uses]
anesthetic (local) | [Originator]
Anestesia topica,Miro | [Application]
Tetracaine hydrochloride(136-47-0) 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.
| [Definition]
ChEBI: Tetracaine hydrochloride is a benzoate ester. It is a potent local anesthetic of the ester type used for surface and spinal anesthesia. | [Preparation]
synthesis of tetracaine hydrochloride: To the reaction kettle, first add 320.0kg of methyl isobutyl ketone, then add 40.0kg (207mol) of p-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%. | [Manufacturing Process]
4-Butylaminobenzoic acid is produced by boiling an aqueous solution of the
sodium salt of 4-aminobenzoic acid with n-butyl-bromide. It forms a colorless
crystalline powder melting at 153-154°C.
Equimolecular quantities of 4-butylaminobenzoic acid and the hydrochloride of
β-dimethylaminoethanol are suspended in 10 times their joint weight of
toluene. The mixture is saturated with hydrochloric acid gas and heated in an
oil bath at about 150°C while a current of hydrochloric acid, gas is slowly
passed through the mixture so that toluene slowly distils. Along with toluene
the water produced by the esterification distils. After heating for about 10
hours the mixture is cooled and water is added until the salt is dissolved. The
layer of toluene is separated and the ester base precipitated from the aqueous
solution by means of a solution of sodium carbonate. By dissolving the base in
ether, drying the ether solution separated over potassium carbonate and
adding alcoholic hydrochloric acid, to the solution until it is neutral to litmus,
the monohydrochloride is obtained in the form of a colorless crystalline
powder which, when recrystallized from alcohol, melts at 147-148°C.
The 4-butylaminobenzoic acid β-di-methylaminoethylester monohydrochloride
is a colorless crystalline powder, which is easily soluble in water. The solution
may be sterilized by boiling without decomposition having to be feared. The
base can be precipitated from the aqueous solution of the salt; it is at first in
the form of an oil but soon solidifies, forms colorless crystals and melts at
43°C. The picrate melts at 120°C. When treated with oxalic acid, the base forms a neutral oxalate which is easily soluble in water and an acid oxalate
which is very difficultly soluble in cold water.
In practice it is usually used as hydrochloride salt. | [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.
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards. | [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. | [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]. | [storage]
Store at -20°C,unstable in solution, ready to use. | [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. |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
R25:Toxic if swallowed.
R36:Irritating to the eyes.
R43:May cause sensitization by skin contact.
R42/43:May cause sensitization by inhalation and skin contact . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust .
S53:Avoid exposure-obtain special instruction before use . | [RIDADR ]
2811 | [WGK Germany ]
3 | [RTECS ]
DG4900000 | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29224900 | [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) |
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