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| CAS No.: | 137-58-6 |
|---|---|
| Name: | Lidocaine |
| Article Data: | 34 |
| Molecular Structure: | |
|
|
|
| Formula: | C14H22N2O |
| Molecular Weight: | 234.341 |
| Synonyms: | 2',6'-Acetoxylidide,2-(diethylamino)- (8CI);2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide;Antrolin;Cuivasil;Dalcaine;ELA-Max;Esracaine;Isicaine;Jetocaine;Leostesin;Lidocadren;Lidoderm;Linisol;Maricaine;Penles;Remicaine;Solarcaine;Solcain;Xilina;Xycaine;Xyline;Xylocaine;Xylocitin;a-Diethylamino-2,6-acetoxylidide; |
| EINECS: | 205-302-8 |
| Density: | 1.026 g/cm3 |
| Melting Point: | 66-69 °C |
| Boiling Point: | 350.8 °C at 760 mmHg |
| Flash Point: | 166 °C |
| Solubility: | practically insoluble |
| Appearance: | solid |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 22 |
| Safety: | 22-26-36 |
| PSA: | 32.34000 |
| LogP: | 2.65670 |
- 144851-82-1METHYL2-AMINO-3-FLUOROBENZOATE
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- 5156-58-1N-(1-Benzyl-4-pipperidinyl)-N-phenylpropanamide HCl
- 81281-59-67-Benzylideneaminotheophylline
- 50288-62-5threo-Phenyl-2-piperidyl acetamide
- 82993-81-5D-threo-Ritalinic acid hydrochloride
- 47087-37-6Z-D-Glu-OMe
- 73441-42-6METHYL-5-CHLORO-2,2-DIMETHYLVALERATE
- 109-89-7
diethylamine
- 1131-01-7
2-chloro-N-(2,6-dimethylphenyl)acetamide
- 137-58-6
2-diethylamino-N-(2,6-dimethylphenyl)-acetamide
| Conditions | Yield |
|---|---|
| With triethylamine In N,N-dimethyl-formamide at 99℃; under 5171.62 Torr; Temperature; Flow reactor; | 98% |
| at 40℃; for 6h; Temperature; | 97% |
| In hexane at 60℃; Temperature; Reflux; | 91.1% |
- 109-89-7
diethylamine
- 79-04-9
chloroacetyl chloride
- 87-62-7
2,6-dimethylaniline
- 137-58-6
2-diethylamino-N-(2,6-dimethylphenyl)-acetamide
| Conditions | Yield |
|---|---|
| Stage #1: chloroacetyl chloride; 2,6-dimethylaniline In toluene at 80 - 90℃; for 3h; Large scale; Stage #2: With sodium carbonate; potassium iodide In water; toluene for 0.5h; Large scale; Stage #3: diethylamine In water; toluene Solvent; Temperature; Reagent/catalyst; Large scale; | 95.2% |
| With potassium hydroxide In 1-methyl-pyrrolidin-2-one at 120 - 130℃; under 12929 Torr; |
- 7409-48-5
(2-diethylaminoethyl)amide
- 87-62-7
2,6-dimethylaniline
- 137-58-6
2-diethylamino-N-(2,6-dimethylphenyl)-acetamide
| Conditions | Yield |
|---|---|
| With dipotassium peroxodisulfate In water at 100℃; for 0.166667h; Microwave irradiation; Green chemistry; | 95% |
| Conditions | Yield |
|---|---|
| at 250℃; |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: acetic acid; sodium acetate 2: benzene View Scheme | |
| Multi-step reaction with 2 steps 1: triethylamine / chloroform / 0.02 h / Flow reactor 2: triethylamine / N,N-dimethyl-formamide / 0.19 h / 60 °C View Scheme | |
| Multi-step reaction with 2 steps 1: acetic acid; sodium acetate / water / 24 h / Reflux 2: triethylamine / 1,4-dioxane / 120 h / Reflux View Scheme | |
| Multi-step reaction with 2 steps 1: dichloromethane / 105 °C / 12929 Torr / Flow reactor 2: triethylamine / N,N-dimethyl-formamide / 99 °C / 5171.62 Torr / Flow reactor View Scheme | |
| Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 3 h / 20 °C 2: acetone / 8 h / Reflux View Scheme |
| Conditions | Yield |
|---|---|
| With alkaline phosphatase In water at 37℃; for 6h; pH=7.4; Enzyme kinetics; Enzymatic reaction; |
- 137-58-6
2-diethylamino-N-(2,6-dimethylphenyl)-acetamide
| Conditions | Yield |
|---|---|
| With rat lung homogenate at 37℃; for 3h; Enzyme kinetics; |
| Conditions | Yield |
|---|---|
| With alkaline phosphatase In water at 37℃; for 6h; pH=7.4; Enzyme kinetics; Enzymatic reaction; |
- 178421-96-0
C14H22N2O*C56H98O35
A
- 137-58-6
2-diethylamino-N-(2,6-dimethylphenyl)-acetamide
B
- 51166-71-3
heptakis(2,6-di-O-methyl)cyclomaltoheptaose
| Conditions | Yield |
|---|---|
| With pluronic copolymer F290 In water at 25℃; Equilibrium constant; Reagent/catalyst; |
- 30280-35-4
N,N-diethylglycine methyl ester
- 87-62-7
2,6-dimethylaniline
- 137-58-6
2-diethylamino-N-(2,6-dimethylphenyl)-acetamide
| Conditions | Yield |
|---|---|
| With sodium methylate at 95℃; for 0.5h; Concentration; Temperature; |
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- 8001-54-5Quaternary ammonium compounds, alkylbenzyldimethyl, chlorides
- 9003-39-8Povidone
- 10161-34-9Trenbolone acetate
- 402957-28-2Telaprevir
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Chemistry
Molecular Structure:
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Molecular Formula: C14H22N2O
Molecular Weight: 234.3373
IUPAC Name: 2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide
Classification Code: Anesthetic [topical] ; Anesthetics ; Anesthetics, local ; Anti-arrhythmia agents ; Cardiovascular Agents ; Central Nervous System Agents ; Central Nervous System Depressants ; Drug / Therapeutic Agent ; Human Data ; Mutation data ; Peripheral Nervous System Agents ; Reproductive Effect ; Sensory System Agents
Product Categories: Chiral Reagents ; Intermediates & Fine Chemicals ; Pharmaceuticals
EINECS: 205-302-8
Melting Point: 66-69°C
Index of Refraction: 1.547
Molar Refractivity: 72.42 cm3
Molar Volume: 228.3 cm3
Surface Tension: 39.1 dyne/cm
Density: 1.026 g/cm3
Flash Point: 166 °C
Enthalpy of Vaporization: 59.55 kJ/mol
Boiling Point: 350.8 °C at 760 mmHg
Vapour Pressure of Lidocaine (CAS NO.137-58-6) : 4.28E-05 mmHg at 25 °C
Uses
Lidocaine (CAS NO.137-58-6) is an amide local anesthetic widely used in surface anesthesia, infiltration anesthesia, conduction anesthesia and epidural anesthesia.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| child | TDLo | oral | 21mg/kg (21mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Journal of Toxicology, Clinical Toxicology. Vol. 30, Pg. 413, 1992. |
| child | TDLo | oral | 300mg/kg/5D-I (300mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION | Pediatric Emergency Care. Vol. 10, Pg. 344, 1994. |
| guinea pig | LD50 | subcutaneous | 120mg/kg (120mg/kg) | Farmaco, Edizione Scientifica. Vol. 10, Pg. 883, 1955. | |
| guinea pig | LDLo | intravenous | 65mg/kg (65mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 130, Pg. 235, 1961. | |
| human | TDLo | intravenous | 23mg/kg (23mg/kg) | BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Archiv fuer Toxikologie. Vol. 28, Pg. 72, 1971. |
| man | TDLo | intravenous | 1700ug/kg/2M- (1.7mg/kg) | BEHAVIORAL: COMA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION CARDIAC: PULSE RATE | American Journal of Emergency Medicine. Vol. 4, Pg. 143, 1986. |
| man | TDLo | intravenous | 8643ug/kg/4H- (8.643mg/kg) | BEHAVIORAL: TOXIC PSYCHOSIS | Annals of Internal Medicine. Vol. 97, Pg. 149, 1982. |
| mouse | LD50 | intraperitoneal | 102mg/kg (102mg/kg) | PERIPHERAL NERVE AND SENSATION: LOCAL ANESTHETIC BEHAVIORAL: ATAXIA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Journal of Medicinal Chemistry. Vol. 24, Pg. 1059, 1981. |
| mouse | LD50 | intravenous | 20mg/kg (20mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION | Journal of Pharmacology and Experimental Therapeutics. Vol. 123, Pg. 269, 1958. |
| mouse | LD50 | oral | 220mg/kg (220mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: REGIDITY LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION | Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 1275, 1966. |
| mouse | LD50 | subcutaneous | 238mg/kg (238mg/kg) | Journal of Medicinal Chemistry. Vol. 28, Pg. 714, 1985. | |
| rabbit | LDLo | intravenous | 41mg/kg (41mg/kg) | Acta Pharmacologica et Toxicologica. Vol. 31, Pg. 273, 1972. | |
| rat | LD50 | intraperitoneal | 133mg/kg (133mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 243, Pg. 97, 1980. |
| rat | LD50 | intravenous | 18mg/kg (18mg/kg) | United States Patent Document. Vol. #5264432, | |
| rat | LD50 | oral | 317mg/kg (317mg/kg) | Bollettino Chimico Farmaceutico. Vol. 110, Pg. 330, 1971. | |
| rat | LD50 | subcutaneous | 335mg/kg (335mg/kg) | European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 9, Pg. 188, 1974. | |
| rat | LD50 | unreported | 39400ug/kg (39.4mg/kg) | Farmakologiya i Toksikologiya Vol. 54(3), Pg. 32, 1991. | |
| women | TDLo | intraspinal | 1mL/kg (1mL/kg) | BEHAVIORAL: EUPHORIA BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" | Journal of Clinical Pyschopharmacology. Vol. 10, Pg. 442, 1990. |
| women | TDLo | intravenous | 16mg/kg (16mg/kg) | CARDIAC: CHANGE IN RATE LUNGS, THORAX, OR RESPIRATION: DYSPNEA | European Journal of Clinical Pharmacology. Vol. 22, Pg. 129, 1982. |
| women | TDLo | oral | 39mg/kg (39mg/kg) | BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: EXCITEMENT CARDIAC: CHANGE IN RATE | New England Journal of Medicine. Vol. 306, Pg. 381, 1982. |
Consensus Reports
Reported in EPA TSCA Inventory.
Safety Profile
Safety Information of Lidocaine (CAS NO.137-58-6):
Hazard Codes:
Xn
Risk Statements:22
R22:Harmful if swallowed
Safety Statements:22-26-36
S22:Do not breathe dust
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36:Wear suitable protective clothing
RIDADR:3249
WGK Germany:3
RTECS:AN7525000
HazardClass:6.1(b)
PackingGroup:III
Poison by ingestion, intravenous, intraperitoneal, and subcutaneous routes. Human systemic effects: blood pressure lowering, changes in heart rate, coma, convulsions, distorted perceptions, dyspnea, excitement, hallucinations, muscle contraction or spasticity, pulse rate, respiratory depression, toxic psychosis. An experimental teratogen. Other experimental reproductive effects. A local anesthetic. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Specification
First Aid Measures of Lidocaine (CAS NO.137-58-6):
Ingestion:If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Get medical aid immediately.
Inhalation:Get medical aid immediately. Remove from exposure to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Skin:Get medical aid. Flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes.
Eyes:Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Storage of Lidocaine (CAS NO.137-58-6):
Store in a cool, dry place. Keep container closed when not in use.
Synonyms of Lidocaine (CAS NO.137-58-6) are 2',6'-Acetoxylidide, 2-(diethylamino)- ; 2-(Diethylamino)-2',6'-acetoxylidide ; 2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide ; 4-12-00-02538 (Beilstein Handbook Reference) ; Acetamide, 2-(diethylamino)-N-(2,6-dimethylphenyl)- ; Alphacaine ; Anbesol ; Anestacon ; BRN 2215784 ; Cappicaine ; Cito optadren ; Cuivasil ; DentiPatch ; Diethylaminoaceto-2,6-xylidide ; Duncaine ; ; ELA-Max ; Esracaine ; Gravocain ; HSDB 3350 ; Isicaina ; Isicaine ; Jetocaine ; L-Caine ; Leostesin ; Lida-Mantle ; Lidocaina ; Lidocainum ;Maricaine ; Remicaine ; Rucaina ; Solarcaine ; Solcain ; Xilina ; Xilocaina ; Xycaine ; Xylestesin ; Xylocain ; Xylocaine ; Xylocitin ; Xyloneural (free base) ; Xylotox ; alfa-Dietilamino-2,6-dimetilacetanilide ; alfa-Dietilamino-2,6-dimetilacetanilide [Italian] ; alpha-Diethylamino-2,6-dimethylacetanilide
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