Mepivacaine


Mepivacaine
Mepivacaine
Systematic (IUPAC) name
(RS)-N-(2,6-dimethylphenyl)- 1-methyl-piperidine-2-carboxamide
Clinical data
AHFS/Drugs.com Consumer Drug Information
MedlinePlus a603026
Pregnancy cat. C, use w/ caution, may cause fetal bradycardia
Legal status  ?
Identifiers
CAS number 96-88-8 YesY
ATC code N01BB03
PubChem CID 4062
DrugBank APRD01094
ChemSpider 3922 YesY
UNII B6E06QE59J YesY
KEGG D08181 YesY
ChEBI CHEBI:6759 N
ChEMBL CHEMBL1087 YesY
Chemical data
Formula C15H22N2O 
Mol. mass 246.348 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Mepivacaine (play /mɛˈpɪvəkn/) is a local anesthetic[1] of the amide type. Mepivacaine has a reasonably rapid onset (more rapid than that of procaine) and medium duration of action (shorter than that of procaine) and is marketed under various trade names including Carbocaine and Polocaine.

Mepivacaine became available in the United States in the 1960s.

Mepivacaine is used in any infiltration and regional anesthesia.

It is supplied as the hydrochloride salt of the racemate.[2]

Chemistry

Two primary methods of synthesis have been suggested. According to the first, mepivacaine is synthesized by reacting the ethyl ester of 1-methylpiperindine-2-carboxylic acid with 2,6-dimethylanilinomagnesium bromide, which is synthesized from 2,6-dimethylaniline and ethylmagnesium bromide.

  • E. Thuresson, H. Egner, U.S. Patent 2,799,679 (1957).
  • B.T. Ekenstam, B. von Egner, G. Petterson, Acta Chem. Scand., 11, 1183 (1957).
  • Rinderknecht, H. (1959). "Neue Lokalan�sthetika". Helvetica Chimica Acta 42 (4): 1324–1327. doi:10.1002/hlca.19590420430.  edit

Mepivacaine synthesis 1.png According to the second method, reacting 2,6-dimethylaniline with the acid chloride of pyridine- carboxylic acid first gives the 2,6-xylidide of α-picolinic acid. Then the aromatic pyridine ring is reduced to piperidine by hydrogen in the presence of a platinum on carbon catalyst. The resulting 2,6-xylidide α-pipecolic acid is methylated to mepivacaine using formaldehyde with simultaneous reduction by hydrogen in the presence of platinum on carbon catalyst.

Mepivacaine synthesis 2.png

References

External links