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PROCAINE Basic information
  • Product Name:PROCAINE
  • CAS:59-46-1
  • MF:C13H20N2O2
  • MW:236.31
  • EINECS:200-426-9
  • Mol File:59-46-1.mol
PROCAINE Chemical Properties
Safety Information
  • RIDADR 3249
  • RTECS DG2100000
  • HazardClass 6.1(b)
  • PackingGroup III
  • Hazardous Substances Data59-46-1(Hazardous Substances Data)
  • ToxicityLD50 in mice (mg/kg): 195 i.p.; 45 i.v. (North, Urbach)
PROCAINE Usage And Synthesis
  • DescriptionProcaine is a local anesthetic with a para-amino function. Sensitization mainly concerns medical, dental and veterinary professions.
  • Chemical PropertiesThe hydrochloride salt of 2-(diethylamino) ethyl p-aminobenzoate (C13H21ClN2O2 or N2C6H4COOCH2CH2NH(C2H5)2HCl) is generally referred to as procaine. Although the PABA ester is insoluble in water, the hydrochloride salt is very soluble in water.
  • UsesProcaine (Novocain) is mainly used in dental or medical procedures requiring infiltration anesthesia, peripheral block, or spinal block.
  • Usesinhibitor of sodium channel
  • DefinitionChEBI: A benzoate ester, formally the result of esterification of 4-aminobenzoic acid with 2-diethylaminoethanol but formed experimentally by reaction of ethyl 4-aminobenzoate with 2-diethylaminoethanol.
  • brand nameNovocain (Hospira).
  • Biological FunctionsProcaine hydrochloride (Novocain) is readily hydrolyzed by plasma cholinesterase, although hepatic metabolism also occurs. It is not effective topically but is employed for infiltration, nerve block, and spinal anesthesia. It has a relatively slow onset and short (1 hour) duration of action. All concentrations can be combined with epinephrine. It is available in dental cartridges with phenylephrine as the vasoconstrictor.
  • General DescriptionProcaine was synthesized in 1904 to address the chemical instabilityof cocaine and the local irritation it produced. The pKa of procaine is 8.9; it has low lipid solubility and the estergroup is unstable in basic solutions. Procaine is available inconcentrations ranging from 0.25% to 10% with pHs adjustedto 5.5 to 6.0 for chemical stability. Procaine is also includedin some formulations of penicillin G to decrease the pain ofintramuscular injection.
  • Contact allergensProcaine is a local anesthetic with para-amino function. Sensitization mainly concerns the medical, dental, and veterinary professions.
  • Clinical UseProcaine is very quickly metabolizedin the plasma by cholinesterases and in the liver via ester hydrolysisby a pseudocholinesterase. The in vitroelimination half-life is approximately 60 seconds. Any conditionthat decreases the cholinesterase concentration may increaseexposure to procaine and potential toxicity. Decreasedenzyme activity can be found with genetic deficiency, liverdisease, malignancy, malnutrition, renal failure, burns, thirdtrimester of pregnancy, and following cardiopulmonary bypasssurgery. Ester hydrolysis produces PABA, the compoundresponsible for the allergic reactions common to theester anesthetics. Procaine is not used topically because of itsinability to pass through lipid membranes and finds use as aninfiltration agent for cutaneous or mucous membranes, forshort procedures. Procaine is also used for peripheral nerveblock and as an epidural agent to diagnose pain syndromes.
  • Purification MethodsProcain crystallises as the dihydrate from aqueous EtOH and as the anhydrous material from pet ether or diethyl ether. The latter is hygroscopic. [Beilstein 14 IV 1138.]
PROCAINE Preparation Products And Raw materials
PROCAINE(59-46-1)Related Product Information
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