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73-78-9

Basic Information
CAS No.: 73-78-9
Name: 2-Diethylamino-2',6'-acetoxylidide hydrochloride
Molecular Structure:
Molecular Structure of 73-78-9 (2-Diethylamino-2',6'-acetoxylidide hydrochloride)
Formula: C14H22N2O.HCl
Molecular Weight: 270.84
Synonyms: 2',6'-Acetoxylidide,2-(diethylamino)-, monohydrochloride (8CI);Acetamide, 2-(diethylamino)-N-(2,6-dimethylphenyl)-,monohydrochloride (9CI);2-(Diethylamino)-2',6'-dimethylacetanilide hydrochloride;Alphacaine;DioCaine;Irtopan;Lidesthesin;Lidocain hydrochloride;Lidocaine monohydrochloride;Lidothesin;Lignavet;Luan;Metaclopromide hydrochloride;Odontalg;Proliferol;Sedagul;Versicane;Xylocaine Astra;Xylocard;Xylotox;Lidocaine HCl .1H2O;
EINECS: 200-803-8
Density:
Melting Point: 80-82 °C
Boiling Point: 350.8 °C at 760 mmHg
Flash Point: 166 °C
Solubility:
Appearance: white crystal powder
Hazard Symbols:
Risk Codes:
Safety:
Transport Information:
PSA: 32.34000
LogP: 3.45870
Synthetic route
137-58-6

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

73-78-9

lidocaine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether100%
With hydrogenchloride; pyrographite In water; 1,2-dichloro-ethane for 0.333333h; pH=3.5; pH-value;88.72%
With hydrogenchloride In water; acetone at 20℃; pH=<= 4;80.6%
109-89-7

diethylamine

79-04-9

chloroacetyl chloride

87-62-7

2,6-dimethylaniline

73-78-9

lidocaine hydrochloride

Conditions
ConditionsYield
Stage #1: chloroacetyl chloride; 2,6-dimethylaniline In 1-methyl-pyrrolidin-2-one; methanol; water at 120℃; for 0.306667h; Flow reactor;
Stage #2: diethylamine With potassium hydroxide In methanol; water at 130℃; under 12751.3 Torr; for 0.295h; Flow reactor;
Stage #3: With hydrogenchloride In methanol; diethyl ether; water
576-26-1

2.6-dimethylphenol

73-78-9

lidocaine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ammonium hydroxide; 2,6-dimethylcyclohexanone; 5%-palladium/activated carbon / 5 h / 180 °C
2: sodium methylate / 0.5 h / 95 °C
3: hydrogenchloride; pyrographite / 1,2-dichloro-ethane; water / 0.33 h / pH 3.5
View Scheme
87-62-7

2,6-dimethylaniline

73-78-9

lidocaine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / acetone / 3 h / 20 °C
2: acetone / 8 h / Reflux
3: hydrogenchloride / water; acetone / 20 °C / pH <= 4
View Scheme
128-44-9

saccharin sodium salt

73-78-9

lidocaine hydrochloride

2-((2,6-dimethylphenyl)amino)-N,N-diethyl-2-oxoethan-1-aminium benzo[d]isothiazol-3-olate 1,1-dioxide

Conditions
ConditionsYield
In acetonitrile at 50℃; for 4h; Sonication;99%
55589-62-3

potassium acesulfame

73-78-9

lidocaine hydrochloride

2-((2,6-dimethylphenyl)amino)-N,N-diethyl-2-oxoethan-1-aminium 6-methyl-1,2,3-oxathiazin-4-olate 2,2-dioxide

Conditions
ConditionsYield
In acetonitrile at 50℃; for 4h; Sonication;98%
73-78-9

lidocaine hydrochloride

sodium vanillate

lidocaine vanillate

Conditions
ConditionsYield
In methanol; water at 50℃; for 4h;97%

sodium mono-glycyrrhizinate

73-78-9

lidocaine hydrochloride

lidocaine mono-glycyrrhizinate

Conditions
ConditionsYield
In methanol; water at 50℃; for 4h;96%
73-78-9

lidocaine hydrochloride

32845-42-4

1-ethyl-2-methyl-3-(2,6-dimethylphenyl)imidazolidin-4-one

Conditions
ConditionsYield
With glucose dehydrogenase; D-glucose; cytochrome P450BM3 R47L/Y51F/A191T/N239H/I259V/A276T/A330W/L353I mutant; oxygen; β-nicotinamide adenine dinucleotide phosphate sodium salt In ethanol at 25℃; for 2h; pH=8.5; Enzymatic reaction;95%
Multi-step reaction with 2 steps
1: 55 percent / H2O2, imidazole / chloromanganese(III) / CH2Cl2; acetonitrile
2: 80 percent / CH2Cl2; acetonitrile / 3 h / 20 °C
View Scheme

Cs(1+)*C36H83B10S(1-)

73-78-9

lidocaine hydrochloride

C36H83B10S(1-)*C14H22N2O*H(1+)

Conditions
ConditionsYield
In dichloromethane; water for 2h; Sonication;95%
124-38-9

carbon dioxide

73-78-9

lidocaine hydrochloride

lidocainium hydrocarbonate

Conditions
ConditionsYield
With sodium hydrogencarbonate In water at -4 - 0℃; under 760.051 Torr;93%
54-21-7

sodium salicylate

73-78-9

lidocaine hydrochloride

lidocaine monosalicylic acid salt

Conditions
ConditionsYield
In water; acetone at 20℃;87%
In water; acetone at 20℃;87%
In water; acetone at 20℃; Product distribution / selectivity;54%
73-78-9

lidocaine hydrochloride

7728-40-7

N-(2,6-dimethylphenyl)-2-ethylaminoacetamide

Conditions
ConditionsYield
With glucose dehydrogenase; D-glucose; cytochrome P450BM3 R47L/Y51F/F81W/F87V/E267V/I401P mutant; β-nicotinamide adenine dinucleotide phosphate sodium salt In ethanol at 25℃; for 2h; pH=8.5; Enzymatic reaction;85%
With 1H-imidazole; dihydrogen peroxide; chloro(meso-tetrakis(2,6-dichlorophenyl)porphyrinato)manganese(III) In dichloromethane; acetonitrile55%
73-78-9

lidocaine hydrochloride

50-78-2

aspirin

1220976-13-5

lidocainium acetylsalicylate

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone at 0℃;83%
73-78-9

lidocaine hydrochloride

31121-93-4

sodium 2-(4-isobutylphenyl)propionate

1158170-79-6

lidocainium ibuprofenate

Conditions
ConditionsYield
In water at 20℃; for 4h;75.7%
333-20-0

potassium thioacyanate

6018-89-9

nickel(II) acetate tetrahydrate

73-78-9

lidocaine hydrochloride

[Ni(lidocaine)2(thiocyanate)2]

Conditions
ConditionsYield
With triethylamine In methanol; water at 20℃; for 4h; pH=7;72.5%
6018-89-9

nickel(II) acetate tetrahydrate

1934-75-4

sodium dicyanamide

73-78-9

lidocaine hydrochloride

[Ni(lidocaine)2(dicyanamide)2]

Conditions
ConditionsYield
With triethylamine In methanol; water at 20℃; for 4h; pH=7;68%
333-20-0

potassium thioacyanate

6147-53-1

cobalt(II) diacetate tetrahydrate

73-78-9

lidocaine hydrochloride

[Co(lidocaine)2(thiocyanate)2]

Conditions
ConditionsYield
With triethylamine In methanol; water at 20℃; for 4h; pH=7;65.6%
6147-53-1

cobalt(II) diacetate tetrahydrate

1934-75-4

sodium dicyanamide

73-78-9

lidocaine hydrochloride

[Co(lidocaine)2(dicyanamide)2]

Conditions
ConditionsYield
With triethylamine In methanol; water at 20℃; for 4h; pH=7;62%
73-78-9

lidocaine hydrochloride

N-(2,6-Dimethyl-phenyl)-2-[(E)-ethylimino]-acetamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 55 percent / H2O2, imidazole / chloromanganese(III) / CH2Cl2; acetonitrile
2: 80 percent / iodosylbenzene, imidazole / chloroiron(III) / CH2Cl2; acetonitrile / 3 h / 20 °C
View Scheme
73-78-9

lidocaine hydrochloride

1-(2,6-dimethylphenyl)-3,5-dihydroxypyrrolidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 55 percent / H2O2, imidazole / chloromanganese(III) / CH2Cl2; acetonitrile
2: 1.) iodosylbenzene, imidazole / 1.) chloroiron(III) / 1.) CH2Cl2, CH3CN, 20 deg C, 3 h, 2.) RT, 3 h
View Scheme
73-78-9

lidocaine hydrochloride

2-(N-ethylacetamido)2',6'-dimethylacetanilide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 55 percent / H2O2, imidazole / chloromanganese(III) / CH2Cl2; acetonitrile
2: 86 percent / CH2Cl2 / 2 h / 20 °C
View Scheme
73-78-9

lidocaine hydrochloride

3-(2,6-dimethylphenyl)-1-ethyl-α-hydroxy-2',6'-dimethyl-4-oxoimidazolidine-2-propanilide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 55 percent / H2O2, imidazole / chloromanganese(III) / CH2Cl2; acetonitrile
2: 18 percent / iodosylbenzene, imidazole / chloroiron(III) / CH2Cl2; acetonitrile / 3 h / 20 °C
View Scheme
73-78-9

lidocaine hydrochloride

577-11-7

sodium docusate

lidocainium docusate

Conditions
ConditionsYield
In methanol for 2h;
In ethanol; dichloromethane at 50℃; Inert atmosphere;

dihydrogen hexachloroplatinate

73-78-9

lidocaine hydrochloride

lignocaine hydrochloride platinum complex

Conditions
ConditionsYield
In ethanol ligand added to soln. of Pt-compound; heated at 60-80°C for ca. 30 min;; filtration; washing (EtOH then ether); drying (vacuum); recrystn. (EtOH) by slow cooling and evapn.;
73-78-9

lidocaine hydrochloride

79-10-7

acrylic acid

3C3H4O2*ClH*C14H22N2O

Conditions
ConditionsYield
at 80℃;
73-78-9

lidocaine hydrochloride

A

7728-40-7

N-(2,6-dimethylphenyl)-2-ethylaminoacetamide

B

32845-42-4

1-ethyl-2-methyl-3-(2,6-dimethylphenyl)imidazolidin-4-one

Conditions
ConditionsYield
With glucose dehydrogenase; D-glucose; cytochrome P450BM3 R47L/Y51F/F87V/E267V/I401P mutant; β-nicotinamide adenine dinucleotide phosphate sodium salt In ethanol at 25℃; for 2h; pH=8.5; Enzymatic reaction;

C62H68N16O24S4(4-)*4Na(1+)

73-78-9

lidocaine hydrochloride

C14H22N2O*ClH*C62H68N16O24S4(4-)*4Na(1+)

Conditions
ConditionsYield
In aq. phosphate buffer pH=7.4; UV-irradiation;
73-78-9

lidocaine hydrochloride

C14H22N2O(18)O

Conditions
ConditionsYield
With hydrogen (18)O-peroxide In water for 0.0166667h;
73-78-9

lidocaine hydrochloride

2903-45-9

lidocaine N-oxide

Conditions
ConditionsYield
With dihydrogen peroxide In water for 0.0166667h;
Downstream Products
7728-40-7
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Chemistry

IUPAC Name: 2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide hydrochloride 
Molecular  Formula: C14H23ClN2
Molecular Weight: 270.7982
EINECS: 200-803-8
Melting Point: 80-82°C
Boiling Point: 350.8 °C at 760 mmHg
Flash Point: 166 °C
Freely Rotating Bonds: 5
Polar Surface Area: 23.55 Å2 
Enthalpy of Vaporization: 59.55 kJ/mol
Vapour Pressure: 4.28E-05 mmHg at 25°C
Appearance: white crystal powder
The Cas Register Number  of  2-Diethylamino-2',6'-acetoxylidide hydrochloride is 73-78-9. The chemical synonyms of  2-Diethylamino-2',6'-acetoxylidide hydrochloride (CAS NO.73-78-9) are 2-Diethylamino-n-(2'6'-dimethylphenyl)acetamide HCl ; 2-Diethylamino-n-[2,6-dimethylphenyl]acetamide HCl ; alpha-(Diethylamino)-2',6'-acetoxylidide hydrochloride ; a-(Diethylamino)-2 6-dimethylacetanilide hydrochloride ; Lignocaine hydrochloride ; Lidocaine hydrochloride ; Lidocaine HCl and 2-(diethylamino)-n-(2,6-dimethylphenyl)-acetamidmonohydrochloride . The product Categories are API , Intermediates , Fine Chemicals and Pharmaceuticals . The molecular structure of  2-Diethylamino-2',6'-acetoxylidide hydrochloride (CAS NO.73-78-9) is
.

Uses

 2-Diethylamino-2',6'-acetoxylidide hydrochloride (CAS NO.73-78-9) can be used as a local anesthetics, antiarrhythmic (class IB) drugs, a variety of anesthesia and rapid ventricular arrhythmia.Long-acting, membrane stabilizing agent against ventricular arrhythmia.

Toxicity Data With Reference

1.    

skn-rbt 3% MLD

    AIPTAK    Archives Internationales de Pharmacodynamie et de Therapie. 137 (1962),410.
2.    

eye-rbt 3% MLD

    AIPTAK    Archives Internationales de Pharmacodynamie et de Therapie. 137 (1962),410.
3.    

ivn-cld TDLo:60 mg/kg/1H

    JTCTDW    Journal of Toxicology, Clinical Toxicology. 24 (1986),51.
4.    

ivn-man TDLo:9 mg/kg/4H-C:CVS

    DICPBB    Drug Intelligence and Clinical Pharmacy. 19 (1985),669.
5.    

ivn-man TDLo:7143 µg/kg:BPR

    CHETBF    Chest: The Journal of Circulation, Respiration and Related Systems. 61 (1972),682.
6.    

imp-man TDLo:5714 µg/kg

    CMAJAX    Canadian Medical Association Journal. 137 (1987),219.
7.    

ipr-rat LD50:122 mg/kg

    JPETAB    Journal of Pharmacology and Experimental Therapeutics. 111 (1954),224.
8.    

scu-rat LD50:570 mg/kg

    RPOBAR    Research Progress in Organic Biological and Medicinal Chemistry. 2 (1970),299.
9.    

ivn-rat LD50:21 mg/kg

    RPOBAR    Research Progress in Organic Biological and Medicinal Chemistry. 2 (1970),299.
10.    

orl-mus LD50:220 mg/kg

    RPOBAR &nbs

Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Safety Profile

Poison by ingestion, intraperitoneal, intravenous, subcutaneous, intramuscular, and intratracheal routes. Human systemic effects: somnolence, respiratory depression, low blood pressure, cardiomyopathy including infarction, pulse rate increase. An experimental teratogen. Other experimental reproductive effects. A skin and eye irritant. An anesthetic. When heated to decomposition it emits very toic fumes of NOx and HCl. Its hazard class is 6.1(b).
RIDADR: 3249
HazardClass: 6.1(b)
PackingGroup: III

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