96-88-8

Basic information

• Product Name: N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide
• Synonyms: Polocaine;1-Methyl-2',6'-pipecoloxylidide;2',6'-Pipecoloxylidide, 1-methyl- (6CI, 8CI);2-Piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-methyl- (9CI);Carbocain;Carbocaine;DL-Mepivacaine;Mepicaine
• CAS NO: 96-88-8
• Molecular Formula: C₁₅H₂₂N₂O
• Molecular Weight: 246.34798
• EINECS: 202-543-0
• Product Categories: research chemical
• Mol File: 96-88-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 150-151°
• Boiling Point: 389.35°C (rough estimate)
• Flash Point: 185.47 °C
• Appearance: /
• Density: 0.9978 (rough estimate)
• Refractive Index: 1.6280 (estimate)
• PKA: 14.85±0.70(Predicted)
• Water Solubility: 2.217g/L(25 oC)
• CAS DataBase Reference: N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide(96-88-8)
• EPA Substance Registry System: N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide(96-88-8)

Safety Data

• Hazardous Substances Data: 96-88-8(Hazardous Substances Data)

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

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

Relevant articles and documents

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.

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.