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| CAS No.: | 136-47-0 |
|---|---|
| Name: | Tetracaine hydrochloride |
| Molecular Structure: | |
|
|
|
| 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: |
 T
|
| 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 |
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| Conditions | Yield |
|---|---|
| With hydrogenchloride In water; ethyl acetate | 94% |
- 108-01-0
2-(N,N-dimethylamino)ethanol
- 94-32-6
ethyl 4-(N-butylamino)benzoate
- 136-47-0
tetracaine hydrochloride
| Conditions | Yield |
|---|---|
| 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 | 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% |
- 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 | 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% |
- 71134-92-4
N-(4-ethoxycarbonylphenyl)butyramide
- 136-47-0
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 |
- 38152-22-6
4-nitrobenzoic acid 2-(dimethylamino)ethyl ester
- 136-47-0
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 |
- 108-01-0
2-(N,N-dimethylamino)ethanol
- 4740-24-3
4-(N-butylamino)benzoic acid
- 136-47-0
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 |
- 136-47-0
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% |
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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:
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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: 
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.
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.