Product Name

  • Name

    Tetracaine hydrochloride

  • EINECS 205-248-5
  • CAS No. 136-47-0
  • Article Data5
  • CAS DataBase
  • Density 1.1279 (rough estimate)
  • 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 Molecular Structure of 136-47-0 (Tetracaine hydrochloride)
  • Hazard Symbols ToxicT
  • 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;
  • PSA 41.57000
  • LogP 3.49200

Synthetic route

amethocaine
94-24-6

amethocaine

tetracaine hydrochloride
136-47-0

tetracaine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water; ethyl acetate94%
2-(N,N-dimethylamino)ethanol
108-01-0

2-(N,N-dimethylamino)ethanol

ethyl 4-(N-butylamino)benzoate
94-32-6

ethyl 4-(N-butylamino)benzoate

tetracaine hydrochloride
136-47-0

tetracaine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; sodium methylate In water at 130℃; for 8h;85%
2-(N,N-dimethylamino)ethanol
108-01-0

2-(N,N-dimethylamino)ethanol

N-(n-butyl)-4-methoxycarbonylaniline
71839-12-8

N-(n-butyl)-4-methoxycarbonylaniline

tetracaine hydrochloride
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%
2-(N,N-dimethylamino)ethanol
108-01-0

2-(N,N-dimethylamino)ethanol

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

butyraldehyde
123-72-8

butyraldehyde

tetracaine hydrochloride
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%
...Expand
N-(4-ethoxycarbonylphenyl)butyramide
71134-92-4

N-(4-ethoxycarbonylphenyl)butyramide

tetracaine hydrochloride
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
4-nitrobenzoic acid 2-(dimethylamino)ethyl ester
38152-22-6

4-nitrobenzoic acid 2-(dimethylamino)ethyl ester

tetracaine hydrochloride
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
4-nitro-benzoyl chloride
122-04-3

4-nitro-benzoyl chloride

tetracaine hydrochloride
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
4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

tetracaine hydrochloride
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
2-(N,N-dimethylamino)ethanol
108-01-0

2-(N,N-dimethylamino)ethanol

4-(N-butylamino)benzoic acid
4740-24-3

4-(N-butylamino)benzoic acid

tetracaine hydrochloride
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
tetracaine hydrochloride
136-47-0

tetracaine hydrochloride

tetramethylammonium trifluoromethanethiolate

tetramethylammonium trifluoromethanethiolate

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

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%
tetracaine hydrochloride
136-47-0

tetracaine hydrochloride

2-(dimethylamino)ethyl 4-(butylamino)-3-chlorobenzoate
1344028-77-8

2-(dimethylamino)ethyl 4-(butylamino)-3-chlorobenzoate

Conditions
ConditionsYield
With N-chloro-succinimide In acetonitrile for 24h; Reflux;75%
With N-chloro-succinimide In acetonitrile for 24h; Reflux;75%
tetracaine hydrochloride
136-47-0

tetracaine hydrochloride

A

2-(N,N-dimethylamino)ethanol
108-01-0

2-(N,N-dimethylamino)ethanol

B

4-(N-butylamino)benzoic acid
4740-24-3

4-(N-butylamino)benzoic acid

Conditions
ConditionsYield
With water Thermodynamic data; Rate constant; var. pH-values;
tetracaine hydrochloride
136-47-0

tetracaine hydrochloride

β‐cyclodextrin
7585-39-9

β‐cyclodextrin

2-dimethylaminoethyl 4-(n-butylamino)benzoate β-cyclodextrin
150398-16-6

2-dimethylaminoethyl 4-(n-butylamino)benzoate β-cyclodextrin

Conditions
ConditionsYield
aq. buffer;
tetracaine hydrochloride
136-47-0

tetracaine hydrochloride

cyclomaltooctaose
17465-86-0

cyclomaltooctaose

2-dimethylaminoethyl 4-(n-butylamino)benzoate γ-cyclodextrin
150398-18-8

2-dimethylaminoethyl 4-(n-butylamino)benzoate γ-cyclodextrin

Conditions
ConditionsYield
aq. buffer;
tetracaine hydrochloride
136-47-0

tetracaine hydrochloride

alpha cyclodextrin
10016-20-3

alpha cyclodextrin

2-dimethylaminoethyl 4-(n-butylamino)benzoate α-cyclodextrin
150398-13-3

2-dimethylaminoethyl 4-(n-butylamino)benzoate α-cyclodextrin

Conditions
ConditionsYield
aq. buffer;
bovine β-lactoglobulin isoform A

bovine β-lactoglobulin isoform A

tetracaine hydrochloride
136-47-0

tetracaine hydrochloride

1:1 complex of bovine β-lactoglobulin isoform A and tetracaine hydrochloride

1:1 complex of bovine β-lactoglobulin isoform A and tetracaine hydrochloride

Conditions
ConditionsYield
at 25℃; pH=7.5;

Tetracaine hydrochloride Chemical Properties

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 Uses

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

Tetracaine hydrochloride 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.

Tetracaine hydrochloride Consensus Reports

EPA Genetic Toxicology Program.

Tetracaine hydrochloride 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.

Tetracaine hydrochloride 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.

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