96-88-8

Usage

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.

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.

InChI:InChI=1S/C15H22N2O/c1-11-7-6-8-12(2)14(11)16-15(18)13-9-4-5-10-17(13)3/h6-8,13H,4-5,9-10H2,1-3H3,(H,16,18)

Upstream product

• 111562-44-8 2-(2,6-dimethyl-phenylcarbamoyl)-1-methyl-pyridinium; iodide 
• 77-78-1 dimethyl sulfate 
• 626-67-5 N-methylcyclohexylamine 
• 40397-98-6 2,5-dimethylphenyl isocyanate 
• 98-98-6 2-Picolinic acid 
• 39627-98-0 2-pyridine-carboxamide-N-(2,6-dimethylphenyl) 
• 50-00-0 formaldehyd 
• 87-62-7 2,6-dimethylaniline 
• 67-56-1 methanol 

Relevant academic research and scientific papers

Synthesis of Mepivacaine and Its Analogues by a Continuous-Flow Tandem Hydrogenation/Reductive Amination Strategy

Herein we report a convenient, fast, and high-yielding method for the generation of the racemic amide anaesthetics mepivacaine, ropivacaine, and bupivacaine. Coupling of α-picolinic acid and 2,6-xylidine under sealed-vessel microwave conditions generates the intermediate amide after a reaction time of only 5 min at 150 °C. Subsequent reaction in a continuous-flow high-pressure hydrogenator (H-Cube ProTM) in the presence of the respective aldehyde directly converts the intermediate to the final amide anaesthetics in a continuous, integrated, multi-step ring-hydrogenation/reductive amination protocol. Merits and limitations of the protocol are discussed.

Radical fixation of functionalized carbon resources: α-sp 3C - H carbamoylation of tertiary amines with aryl isocyanates

A new carbamoylation of tertiary amines is reported. This rare C - H transformation features the direct generation of α-aminoalkyl radicals from tertiary amines, followed by the addition of the resultant nucleophilic radicals to isocyanates, enabling unique access to N,N-dialkylated amino acid derivatives. The authors put forward a mechanistic proposal that is based on the isolation of borinamides produced by capturing nitrogen radical intermediates with Et3B. The present transformation provides a novel one-step process for producing mepivacaine, a clinically important local anesthetic, from readily available materials.

Local anaesthetic salts of chondroitinsulfate compounds

Water-soluble local anaesthetic compounds having sustained effect are prepared by reacting a chondroitin derivative with a basic local anaesthetic compound.