Procaine

Procaine is a local anesthetic drug of the amino ester group. It is most commonly used in dental procedures to numb the area around a tooth and is also used to reduce the pain of intramuscular injection of penicillin. Owing to the ubiquity of the trade name Novocain or Novocaine, in some regions, procaine is referred to generically as novocaine. It acts mainly as a sodium channel blocker. Today, it is used therapeutically in some countries due to its sympatholytic, anti-inflammatory, perfusion-enhancing, and mood-enhancing effects.

Procaine
Clinical data
AHFS/Drugs.comMonograph
Pregnancy
category
  • AU: B2
Routes of
administration
Parenteral
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
Pharmacokinetic data
BioavailabilityN/A
MetabolismHydrolysis by plasma esterases
Elimination half-life40–84 seconds
ExcretionRenal
Identifiers
  • 2-(diethylamino)ethyl 4-aminobenzoate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.000.388
Chemical and physical data
FormulaC13H20N2O2
Molar mass236.315 g·mol−1
3D model (JSmol)
  • O=C(OCCN(CC)CC)c1ccc(N)cc1
  • InChI=1S/C13H20N2O2/c1-3-15(4-2)9-10-17-13(16)11-5-7-12(14)8-6-11/h5-8H,3-4,9-10,14H2,1-2H3 Y
  • Key:MFDFERRIHVXMIY-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Procaine was first synthesized in 1905, shortly after amylocaine. It was created by the chemist Alfred Einhorn who gave the chemical the trade name Novocaine, from the Latin nov- (meaning "new") and -caine, a common ending for alkaloids used as anesthetics. It was introduced into medical use by surgeon Heinrich Braun.

Prior to the discovery of amylocaine and procaine, cocaine was a commonly used local anesthetic. Einhorn wished his new discovery to be used for amputations, but for this surgeons preferred general anesthesia. Dentists, however, found it very useful.

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