CAS No.137-58-6,Lidocaine Suppliers

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Basic Information

Molecular Structure:
CAS No.:	137-58-6
Name:	Lidocaine
Article Data:	34

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

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

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

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;

...Expand

: 7409-48-5
(2-diethylaminoethyl)amide

: 87-62-7
2,6-dimethylaniline

: 137-58-6
2-diethylamino-N-(2,6-dimethylphenyl)-acetamide

Conditions

Conditions	Yield
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

Conditions	Yield
at 250℃;

: 87-62-7
2,6-dimethylaniline

: 137-58-6
2-diethylamino-N-(2,6-dimethylphenyl)-acetamide

Conditions

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

: [(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

Conditions	Yield
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

Conditions	Yield
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

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

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

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

Raw Materials

87-62-7

1131-01-7

109-89-7

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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: Harmful 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 NO_x.

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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