Mepivacaine

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Mepivacaine
Mepivacaine.png
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 DB00961
ChemSpider 3922 YesY
UNII B6E06QE59J YesY
KEGG D08181 YesY
ChEBI CHEBI:6759 YesY
ChEMBL CHEMBL1087 YesY
Chemical data
Formula C15H22N2O 
Mol. mass 246.348 g/mol
 YesY (what is this?)  (verify)

Mepivacaine /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]

Synthesis[edit]

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

Mepivacaine synthesis 1:[3][4] E. Thuresson, H. Egner, U.S. Patent 2,799,679 (1957).

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: B.G. Petterson, U.S. Patent 4,110,331 (1977).

A third method also exists:

Mepivacaine synthesis 3:[4]

See also[edit]

References[edit]

  1. ^ Porto GG, Vasconcelos BC, Gomes AC, Albert D (January 2007). "Evaluation of lidocaine and mepivacaine for inferior third molar surgery". Med Oral Patol Oral Cir Bucal 12 (1): E60–4. PMID 17195831. 
  2. ^ Burm AG, Cohen IM, van Kleef JW, Vletter AA, Olieman W, Groen K (January 1997). "Pharmacokinetics of the enantiomers of mepivacaine after intravenous administration of the racemate in volunteers". Anesth. Analg. 84 (1): 85–9. doi:10.1097/00000539-199701000-00016. PMID 8989005. 
  3. ^ af Ekenstam, Bo (1957). "Local Anesthetics I. N-Alkyl Pyrrolidine and N-Alkyl Piperidine Carboxylic Acid Amides.". Acta Chemica Scandinavica 11: 1183–1190. doi:10.3891/acta.chem.scand.11-1183.  edit
  4. ^ a b Rinderknecht, H. (1959). "Neue Lokalanästhetika". Helvetica Chimica Acta 42 (4): 1324–1327. doi:10.1002/hlca.19590420430.  edit

External links[edit]