Tetracaine Hydrochloride
Basic information
- CAS
136-47-0- Standard SMILES
CCCCNc1ccc(C(=O)OCCN(C)C)cc1.Cl- InChIKey
PPWHTZKZQNXVAE-UHFFFAOYSA-N- Molecular formula
- C15H25ClN2O2
- Average molar mass
- 300.82 g/mol
- Monoisotopic mass
- 300.1604557
Overview
Tetracaine hydrochloride is a benzoate ester.
Names & identifiers
- Preferred name
- Tetracaine Hydrochloride
- IUPAC
- 2-(dimethylamino)ethyl 4-(butylamino)benzoate;hydrochloride
- English name
- Tetracaine hydrochloride
- Molecular formula
- C15H25ClN2O2
- Molecular weight
- 300.82
Names & synonyms
Tetracaine hydrochloride136-47-0Tetracaine HClButethanolCurtacainMenonasalPantocaineAnethaineDicainumAmethocaine hydrochlorideTetocaineTetraca
Show more names
DimethylaminoethylTetracaine hydrochloridanaceltonexoldecicaindecicaine
DTXSID60424485NF5D4OPCINSC-757337Pontocaine HydrochlorideTetracaini hydrochloridumBenzoic acid, 4-(butylamino)-, 2-(dimethylamino)ethyl ester, monohydrochlorideDTXCID4022448KOVANAZE COMPONENT TETRACAINE HYDROCHLORIDE
Database identifiers
- CAS
136-47-0、53762-93-9- PubChem CID
- 8695
- DTXSID
DTXSID6042448- ChEMBL
CHEMBL1255654- ChEBI
CHEBI:9469- UNII
- 5NF5D4OPCI
- EC Number
- 205-248-5
Properties
Computed structural properties
- Topological polar surface area
- 41.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 9
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 249
Experimental & physicochemical properties
Solubility>45.1 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Animal DrugsFDA approved animal drugs -> Active ingredient
Collision Cross Section172.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 149 °C · 149°C
- Density
- 1.1279 · 1.1279 (rough estimate)
- refractive index
- 1.52 · 1.5200 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- 40 parts · alcohol: solublesoluble 40 parts of solvent
- pka
- 8.39 · 8.39(at 25℃)
- form
- Solid
- color
- White to Almost white
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (98.2%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P264, P264+P265, P270, P272, P280, P301+P316, P302+P352, P305+P351+P338, P321, P330, P333+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 113 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationTetracaine hydrochloride: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Benzoic acid, 4-(butylamino)-, 2-(dimethylamino)ethyl ester, monohydrochloride: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 3 (98.2%)
Safety data
- wgk
- 3
- rtecs
- DG4900000
- ridadr
- 2811
- 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)
- risk_code
- 25-36-43-42/43
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T
- safety_code
- 26-36/37-45-36/37/39-22-53
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
TETRACAINE HCL
Ester Local Anesthetic [EPC]; Esters [CS]; Local Anesthesia [PE]
TETRACAINE HYDROCHLORIDE
Local Anesthesia [PE]; Esters [CS]; Ester Local Anesthetic [EPC]
MeSH Pharmacological Classification
Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate.
Applications
UsesTetracaine 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.
General DescriptionTetracaine 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.
Preparation methods
PreparationSynthesis 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%.
Related reactions
2 records
Compound notes
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