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Trimecaine

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Name

Trimecaine

EINECS 210-487-3
CAS No. 616-68-2 Density 1.015 g/cm3
PSA 32.34000 LogP 2.96510
Solubility soluble in water and ethanol Melting Point 44°
Formula C15H24N2O Boiling Point 360.298 °C at 760 mmHg
Molecular Weight 248.368 Flash Point 171.702 °C
Transport Information N/A Appearance white crystalline powder
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 616-68-2 (Trimecaine) Hazard Symbols N/A
Synonyms

Acetanilide,2-(diethylamino)-2',4',6'-trimethyl- (6CI,8CI);2-(Diethylamino)-2',4',6'-trimethylacetanilide;Diethylglycinemesidide;Justecaina;Mesdicain;Mesidicaine;Mesokain;N-(Diethylaminoacetyl)-2,4,6-trimethylaniline;w-Diethylaminoacetylaminomesitylene;N2,N2-Diethyl-N-mesitylglycinamide;

 

Trimecaine Synthetic route

3910-51-8

N-(chloroacetyl)-2,4,6-trimethylaniline

109-89-7

diethylamine

616-68-2

trimecaine

Conditions
ConditionsYield
With benzene
603-71-4

nitromesitylene

616-68-2

trimecaine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aq.-ethanolic sulfuric acid / bei der elektrochemischen Reduktion
2: sodium acetate; aqueous acetic acid
3: benzene
View Scheme
88-05-1

2,4,6-trimethylaniline

616-68-2

trimecaine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium acetate; aqueous acetic acid
2: benzene
View Scheme
616-68-2

trimecaine

106-95-6

allyl bromide

79143-64-9

Allyl-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; bromide

Conditions
ConditionsYield
In acetone at 70 - 90℃; for 9h;94%
616-68-2

trimecaine

74-88-4

methyl iodide

68638-18-6

Diethyl-methyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; iodide

Conditions
ConditionsYield
In acetone at 70 - 90℃; for 6h;94%
616-68-2

trimecaine

100-44-7

benzyl chloride

79143-66-1

Benzyl-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; chloride

Conditions
ConditionsYield
In acetone at 70 - 90℃; for 14h;93%
616-68-2

trimecaine

624-65-7

2-propynyl chloride

79143-65-0

Diethyl-prop-2-ynyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; chloride

Conditions
ConditionsYield
In acetone at 70 - 90℃; for 10h;92%
616-68-2

trimecaine

75-03-6

ethyl iodide

68638-19-7

Triethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; iodide

Conditions
ConditionsYield
In acetone at 70 - 90℃; for 10h;90%
616-68-2

trimecaine

611-17-6

1-bromomethyl-2-chlorobenzene

79154-29-3

(2-Chloro-benzyl)-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; bromide

Conditions
ConditionsYield
In acetone at 70 - 90℃; for 15h;88%
616-68-2

trimecaine

99-73-0

para-bromophenacyl bromide

79143-69-4

[2-(4-Bromo-phenyl)-2-oxo-ethyl]-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; bromide

Conditions
ConditionsYield
In acetone at 70 - 90℃; for 10h;87%

Trimecaine Specification

The (Z)-Capsaicin, with the CAS registry number 616-68-2, is also known as 2-(Diethylamino)-N-mesitylacetamide. Its EINECS number is 210-487-3. This chemical's molecular formula is C15H24N2O and molecular weight is 248.36. What's more, its IUPAC name is 2-Diethylamino-N-(2,4,6-trimethylphenyl)acetamide. Its classification codes are: (1)Anesthetics; (2)Anesthetics, local; (3)Central Nervous System Agents; (4)Central Nervous System Depressants; (5)Drug / Therapeutic Agent; (6)Peripheral Nervous System Agents; (7)Sensory System Agents. This chemical is acetanilide derivative used as a local anesthetic. It is white crystalline powder readily soluble in water and ethanol. It is an active ingredient in products available under trademarks Mesdicain, Mesocain, Mesokain and others.

Physical properties of (Z)-Capsaicin are: (1)ACD/LogP: 2.7; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.48; (4)ACD/LogD (pH 7.4): 2.17; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 19.62; (7)ACD/KOC (pH 5.5): 4.23; (8)ACD/KOC (pH 7.4): 207.32; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 32.34 Å2; (13)Index of Refraction: 1.544; (14)Molar Refractivity: 77.252 cm3; (15)Molar Volume: 244.622 cm3; (16)Polarizability: 30.625×10-24cm3; (17)Surface Tension: 38.36 dyne/cm; (18)Density: 1.015 g/cm3; (19)Flash Point: 171.702 °C; (20)Enthalpy of Vaporization: 60.6 kJ/mol; (21)Boiling Point: 360.298 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(Nc1c(cc(cc1C)C)C)CN(CC)CC
(2)Std. InChI: InChI=1S/C15H24N2O/c1-6-17(7-2)10-14(18)16-15-12(4)8-11(3)9-13(15)5/h8-9H,6-7,10H2,1-5H3,(H,16,18)
(3)Std. InChIKey: GOZBHBFUQHMKQB-UHFFFAOYSA-N

The toxicity data is as follows: 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 129mg/kg (129mg/kg)   Farmakologiya i Toksikologiya Vol. 39, Pg. 426, 1976.
mouse LD50 intraperitoneal 180mg/kg (180mg/kg)   Pharmaceutical Chemistry Journal Vol. 23, Pg. 222, 1989.
mouse LD50 intravenous 187mg/kg (187mg/kg)   Russian Pharmacology and Toxicology Vol. 50, Pg. 112, 1987.
mouse LD50 subcutaneous 295mg/kg (295mg/kg)   Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 48, Pg. 402, 1959.

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