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137-58-6

Basic Information
CAS No.: 137-58-6
Name: Lidocaine
Article Data: 34
Cas Database
Molecular Structure:
Molecular Structure of 137-58-6 (Lidocaine)
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: HarmfulXn
Risk Codes: 22
Safety: 22-26-36
Transport Information: N/A
PSA: 32.34000
LogP: 2.65670
Synthetic route
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With dipotassium peroxodisulfate In water at 100℃; for 0.166667h; Microwave irradiation; Green chemistry;95%
3734-33-6

denatonium benzoate

A

137-58-6

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide

B

2-diethylamino-N-(2,6-dimethyl-phenyl)-3-phenyl-propionamide

Conditions
ConditionsYield
at 250℃;
87-62-7

2,6-dimethylaniline

137-58-6

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide

Conditions
ConditionsYield
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

[(2,6-dimethylphenylcarbamoyl)methyl]diethyl-(2-phosphonooxybenzyl)ammonium trifluoroacetate disodium salt

A

90-01-7

salicylic alcohol

B

137-58-6

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide

Conditions
ConditionsYield
With alkaline phosphatase In water at 37℃; for 6h; pH=7.4; Enzyme kinetics; Enzymatic reaction;

[(2,6-dimethylphenylcarbamoyl)methyl]diethyl-(2-phosphonooxybenzyl)ammonium trifluoroacetate disodium salt

137-58-6

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide

Conditions
ConditionsYield
With rat lung homogenate at 37℃; for 3h; Enzyme kinetics;

[(2,6-dimethylphenylcarbamoyl)methyl]diethyl-(4-phosphonooxybenzyl)ammonium trifluoroacetate disodium salt

A

623-05-2

(4-hydroxyphenyl)methanol

B

137-58-6

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With sodium methylate at 95℃; for 0.5h; Concentration; Temperature;
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Chemistry

Molecular Structure:

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:HarmfulXn
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