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Name |
Tetracaine hydrochloride |
EINECS | 205-248-5 |
CAS No. | 136-47-0 | Density | 1.1279 (rough estimate) |
PSA | 41.57000 | LogP | 3.49200 |
Solubility | freely soluble in water, soluble in alcohol and practically insoluble in ether. | Melting Point |
149 ºC |
Formula | C15H25ClN2O2 | Boiling Point | 389.4 ºC at 760 mmHg |
Molecular Weight | 300.829 | Flash Point | 189.3 ºC |
Transport Information | UN 2811 | Appearance | White or off white crystalline powder |
Safety | 26-36/37-45-36/37/39-22-53 | Risk Codes | 25-36-43-42/43 |
Molecular Structure | Hazard Symbols | T | |
Synonyms |
Benzoic acid, p-(butylamino)-, 2-(dimethylamino)ethyl ester, monohydrochloride(8CI);2-(Dimethylamino)ethyl p-(butylamino)benzoate hydrochloride;Amethocainehydrochloride;Amethocaine monohydrochloride;Anethain;Anethaine;Dianguang;Pantocaine;Pantocaine monohydrochloride;Pontocainehydrochloride;p-(Butylamino)benzoic acid 2-(dimethylamino)ethyl ester hydrochloride;Tetracaine Hydrochloride;Tetracaine HCL; |
Article Data | 5 |
Conditions | Yield |
---|---|
With hydrogenchloride In water; ethyl acetate | 94% |
2-(N,N-dimethylamino)ethanol
ethyl 4-(N-butylamino)benzoate
tetracaine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride; sodium methylate In water at 130℃; for 8h; | 85% |
2-(N,N-dimethylamino)ethanol
N-(n-butyl)-4-methoxycarbonylaniline
tetracaine hydrochloride
Conditions | Yield |
---|---|
Stage #1: 2-(N,N-dimethylamino)ethanol; N-(n-butyl)-4-methoxycarbonylaniline With sodium methylate at 130℃; for 8h; Stage #2: With hydrogenchloride | 83% |
2-(N,N-dimethylamino)ethanol
4-amino-benzoic acid
butyraldehyde
tetracaine hydrochloride
Conditions | Yield |
---|---|
Stage #1: 2-(N,N-dimethylamino)ethanol; 4-amino-benzoic acid; butyraldehyde With hydrogen at 40 - 45℃; under 2250.23 Torr; for 3h; Autoclave; Large scale; Stage #2: With dmap In 5,5-dimethyl-1,3-cyclohexadiene for 4h; Reflux; Large scale; Stage #3: With hydrogenchloride In ethanol; tert-butyl methyl ether; water at 45℃; pH=3 - 4; Reagent/catalyst; Temperature; Pressure; Solvent; Large scale; | 75% |
N-(4-ethoxycarbonylphenyl)butyramide
tetracaine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dihydridocarbonyl(1,1,1-tris(diphenylphosphinomethyl)ethane)ruthenium(II) complex; hydrogen; toluene-4-sulfonic acid; boron trifluoride diethyl etherate / tetrahydrofuran / 20 h / 120 °C / 38002.6 Torr / Glovebox; Autoclave; Inert atmosphere 2: sodium methylate; hydrogenchloride / water / 8 h / 130 °C View Scheme |
4-nitrobenzoic acid 2-(dimethylamino)ethyl ester
tetracaine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: iron; acetic acid / 8 h / 30 °C 2: potassium carbonate / N,N-dimethyl-formamide / 5 h / 50 °C 3: hydrogenchloride / ethyl acetate; water View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: dichloromethane / 2 h / 0 °C 2: iron; acetic acid / 8 h / 30 °C 3: potassium carbonate / N,N-dimethyl-formamide / 5 h / 50 °C 4: hydrogenchloride / ethyl acetate; water View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: copper / water; N,N-dimethyl-formamide / 25 h / 130 °C / Autoclave 2.1: sulfuric acid / 5,5-dimethyl-1,3-cyclohexadiene / Reflux 2.2: 20 - 25 °C / pH 3 - 4 View Scheme |
2-(N,N-dimethylamino)ethanol
4-(N-butylamino)benzoic acid
tetracaine hydrochloride
Conditions | Yield |
---|---|
Stage #1: 2-(N,N-dimethylamino)ethanol; 4-(N-butylamino)benzoic acid With sulfuric acid In 5,5-dimethyl-1,3-cyclohexadiene Reflux; Stage #2: With hydrogenchloride In water; isopropyl alcohol at 20 - 25℃; pH=3 - 4; | 22 g |
tetracaine hydrochloride
Conditions | Yield |
---|---|
Stage #1: tetracaine hydrochloride; tetramethylammonium trifluoromethanethiolate In acetonitrile at 20℃; Stage #2: With silver fluoride In acetonitrile at 50℃; for 4h; | 97% |
IUPAC Name: 2-Dimethylaminoethyl 4-(butylamino)benzoate hydrochloride
Synonyms of Tetracaine hydrochloride (CAS NO.136-47-0): Leocaine ; Tetracaine hydrochloride [USAN:JAN] ; Fulvidex (Veterinary) ; 2-(Dimethylamino)ethyl p-(butylamino)benzoate hydrochloride ; Amethocaine monohydrochloride ; EINECS 205-248-5 ; p-Butylaminobenzoyl-2-dimethylaminoethanol hydrochloride ; Benzoic acid, 4-(butylamino)-, 2-(dimethylamino)ethyl ester, monohydrochloride ; Benzoic acid, p-(butylamino)-, 2-(dimethylamino)ethyl ester, monohydrochloride
CAS NO: 136-47-0
Classification Code: Anesthetic [local] ; Drug / Therapeutic Agent ; Mutation data ; Skin / Eye Irritant
Molecular Formula of Tetracaine hydrochloride (CAS NO.136-47-0): C15H25ClN2O2
Molecular Weight: 300.8242
Molecular Structure:
Melting Point: 149°C
H bond acceptors: 4
H bond donors: 1
Freely Rotating Bonds: 9
Polar Surface Area: 32.78 Å2
Flash Point: 189.3 °C
Enthalpy of Vaporization: 63.87 kJ/mol
Boiling Point of Tetracaine hydrochloride (CAS NO.136-47-0): 389.4 °C at 760 mmHg
Vapour Pressure: 2.87E-06 mmHg at 25°C
Tetracaine hydrochloride (CAS NO.136-47-0) is used for spinal anesthesia.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LD50 | intravenous | 4mg/kg (4mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 7, Pg. 739, 1957. | |
guinea pig | LD50 | subcutaneous | 19500ug/kg (19.5mg/kg) | Quarterly Journal of Pharmacy & Pharmacology. Vol. 20, Pg. 380, 1947. | |
mouse | LD50 | intraperitoneal | 23mg/kg (23mg/kg) | Archiv der Pharmazie Vol. 321, Pg. 115, 1988. | |
mouse | LD50 | intravenous | 6400ug/kg (6.4mg/kg) | Drugs in Japan Vol. -, Pg. 815, 1995. | |
mouse | LD50 | oral | 160mg/kg (160mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Oyo Yakuri. Pharmacometrics. Vol. 9, Pg. 413, 1975. |
mouse | LD50 | subcutaneous | 25mg/kg (25mg/kg) | Pharmacology and Toxicology. English translation of FATOAO. Vol. 22, Pg. 138, 1959. | |
rabbit | LD50 | intratracheal | 4400ug/kg (4.4mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Journal of Pharmacology and Experimental Therapeutics. Vol. 132, Pg. 87, 1961. |
rabbit | LD50 | intravenous | 2150ug/kg (2.15mg/kg) | Drugs in Japan Vol. 6, Pg. 490, 1982. | |
rabbit | LD50 | subcutaneous | 15mg/kg (15mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 93, Pg. 388, 1948. | |
rabbit | LDLo | intraspinal | 5mg/kg (5mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 57, Pg. 221, 1936. | |
rat | LD50 | intraperitoneal | 23500ug/kg (23.5mg/kg) | BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Oyo Yakuri. Pharmacometrics. Vol. 9, Pg. 413, 1975. |
rat | LD50 | intravenous | 4500ug/kg (4.5mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Oyo Yakuri. Pharmacometrics. Vol. 9, Pg. 413, 1975. |
rat | LD50 | subcutaneous | 24mg/kg (24mg/kg) | BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Oyo Yakuri. Pharmacometrics. Vol. 9, Pg. 413, 1975. |
EPA Genetic Toxicology Program.
Hazard Codes: T
Risk Statements: 25-36-42/43
R25: Toxic if swallowed.
R36: Irritating to eyes.
R42/43: May cause sensitization by inhalation and skin contact.
Safety Statements: 26-45-36/37/39-22-53
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S22: Do not breathe dust.
S53: Avoid exposure - obtain special instructions before use.
RIDADR: 2811
RTECS: DG4900000
Poison by ingestion, intraperitoneal, intravenous, intraspinal, and subcutaneous routes. An eye irritant. When heated to decomposition it emits very toxic fumes of HCl and NOx. An FDA over-the-counter drug used as a local anesthetic.
Incompatibilities
Iodides, inorganic mercury, silver salts.
Stability
Stable at normal temperatures and pressures.
Decomposition
Carbon monoxide, Carbon dioxide, Nitrogen oxides.
Combustion Products
Fire may produce irritating, corrosive and/or toxic gases.