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136-47-0

Basic Information
CAS No.: 136-47-0
Name: Tetracaine hydrochloride
Article Data: 5
Molecular Structure:
Molecular Structure of 136-47-0 (Tetracaine hydrochloride)
Formula: C15H25ClN2O2
Molecular Weight: 300.829
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;
EINECS: 205-248-5
Density: 1.1279 (rough estimate)
Melting Point: 149 ºC
Boiling Point: 389.4 ºC at 760 mmHg
Flash Point: 189.3 ºC
Solubility: freely soluble in water, soluble in alcohol and practically insoluble in ether.
Appearance: White or off white crystalline powder
Hazard Symbols: ToxicT
Risk Codes: 25-36-43-42/43
Safety: 26-36/37-45-36/37/39-22-53
Transport Information: UN 2811
PSA: 41.57000
LogP: 3.49200
Synthetic route
94-24-6

amethocaine

136-47-0

tetracaine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water; ethyl acetate94%
108-01-0

2-(N,N-dimethylamino)ethanol

94-32-6

ethyl 4-(N-butylamino)benzoate

136-47-0

tetracaine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; sodium methylate In water at 130℃; for 8h;85%
108-01-0

2-(N,N-dimethylamino)ethanol

71839-12-8

N-(n-butyl)-4-methoxycarbonylaniline

136-47-0

tetracaine hydrochloride

Conditions
ConditionsYield
Stage #1: 2-(N,N-dimethylamino)ethanol; N-(n-butyl)-4-methoxycarbonylaniline With sodium methylate at 130℃; for 8h;
Stage #2: With hydrogenchloride
83%
108-01-0

2-(N,N-dimethylamino)ethanol

150-13-0

4-amino-benzoic acid

123-72-8

butyraldehyde

136-47-0

tetracaine hydrochloride

Conditions
ConditionsYield
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%
71134-92-4

N-(4-ethoxycarbonylphenyl)butyramide

136-47-0

tetracaine hydrochloride

Conditions
ConditionsYield
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
38152-22-6

4-nitrobenzoic acid 2-(dimethylamino)ethyl ester

136-47-0

tetracaine hydrochloride

Conditions
ConditionsYield
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
122-04-3

4-nitro-benzoyl chloride

136-47-0

tetracaine hydrochloride

Conditions
ConditionsYield
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
586-76-5

4-Bromobenzoic acid

136-47-0

tetracaine hydrochloride

Conditions
ConditionsYield
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
108-01-0

2-(N,N-dimethylamino)ethanol

4740-24-3

4-(N-butylamino)benzoic acid

136-47-0

tetracaine hydrochloride

Conditions
ConditionsYield
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
136-47-0

tetracaine hydrochloride

tetramethylammonium trifluoromethanethiolate

2-(dimethylamino)ethyl 4-(butyl(trifluoromethyl)amino)benzoate

Conditions
ConditionsYield
Stage #1: tetracaine hydrochloride; tetramethylammonium trifluoromethanethiolate In acetonitrile at 20℃;
Stage #2: With silver fluoride In acetonitrile at 50℃; for 4h;
97%
Downstream Products
4740-24-3
108-01-0
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Chemistry

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

Uses

 Tetracaine hydrochloride (CAS NO.136-47-0) is used for spinal anesthesia.

Toxicity Data With Reference

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.

Consensus Reports

EPA Genetic Toxicology Program.

Safety Profile

Hazard Codes: ToxicT
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.

Specification

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.