N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide Chemical Properties

Melting point:

150-151°

Boiling point:

389.35°C (rough estimate)

Density 

0.9978 (rough estimate)

refractive index 

1.6280 (estimate)

storage temp. 

Store at -20°C

solubility 

DMF: 30 mg/ml; DMSO: 25 mg/ml; Ethanol: 30 mg/ml; Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml

form 

A crystalline solid

pka

14.85±0.70(Predicted)

Water Solubility 

2.217g/L(25 ºC)

EPA Substance Registry System

2-Piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-methyl- (96-88-8)

N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide Usage And Synthesis

Originator

Carboraine,Winthrop,US,1960

Uses

Mepivacaine can be used in biological study of 2-adamantanamine produces prolonged spinal block in rats.

Uses

Anesthetic (local).

Definition

ChEBI: A piperidinecarboxamide in which N-methylpipecolic acid and 2,6-dimethylaniline have combined to form the amide bond. It is used as a local amide-type anaesthetic.

Manufacturing Process

Ethyl magnesium bromide is prepared in the usual way by reacting 185 parts by weight of ethyl bromide in 800 parts of anhydrous ether with 37 parts by weight of magnesium turnings. Under vigorous stirring 121 parts of 2,6- dimethyl aniline are added at a rate depending on the vigor of the gas evaporation. When the evolution of gas has ceased, 85 parts by weight of Nmethylpipecolic acid ethyl ester are added to the 2,6-dimethyl aniline magnesium bromide slurry. The mixture is refluxed for ? hour with continued stirring, after which it is cooled down. Dilute hydrochloric acid is added carefully in order to dissolve and hydrolyze the magnesium compound formed.
The pH is adjusted to 5.5 and the water phase separated and extracted with additional ether in order to remove the surplus dimethyl aniline. After addition of an excess of ammonia to the solution, the reaction product, Nmethylpipecolic acid 2,6-dimethyl anilide, is recovered by extraction with isoamyl alcohol. The isoamyl alcohol solution is evaporated to dryness, the product dissolved in dilute hydrochloric acid, treated with charcoal and reprecipitated with NaOH. N-methylpipecolic acid 2,6-dimethyl anilide is obtained in crystalline form.

brand name

Arestocaine Hydrochloride (Solvay Pharmaceuticals); Carbocaine (Hospira); Isocaine Hydrochloride(Novocol); Polocaine (AstraZeneca); Polocaine (Dentsply); Scandonest (Deproco).

Therapeutic Function

Local anesthetic

Safety Profile

Poison by intravenous route. Moderately toxic by subcutaneous route. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.

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