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59-46-1

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Identification

Name
PROCAINE
CAS
59-46-1
Synonyms
4-AMINO-BENZOIC ACID 2-DIETHYLAMINO-ETHYL ESTER
AKOS B006598
ART-CHEM-BB B006598
PROCAINE
2-(Diethylamino)ethyl 4-aminobenzoate
2-(Diethylamino)ethyl p-aminobenzoate
2-(diethylamino)ethylp-aminobenzoate
2-diethylaminoethyl4-aminobenzoate
2-Diethylaminoethylester kyseliny p-aminobenzoove
2-diethylaminoethylesterkyselinyp-aminobenzoove
2-diethylaminoethylp-aminobenzoate
4-Aminobenzoic acid diethylaminoethyl ester
4-amino-benzoicaci2-(diethylamino)ethylester
4-aminobenzoicaciddiethylaminoethylester
Allocaine
Benzoic acid, p-amino-, 2-(diethylamino)ethyl ester
Benzoicacid,4-amino-2-(diethylamino)ethylester
beta-(Diethylamino)ethyl 4-aminobenzoate
beta-(Diethylamino)ethyl p-aminobenzoate
beta-(diethylamino)ethylp-aminobenzoate
EINECS(EC#)
200-426-9
Molecular Formula
C13H20N2O2
MDL Number
MFCD00007893
Molecular Weight
236.31
MOL File
59-46-1.mol

Chemical Properties

Melting point 
61°
Boiling point 
378.78°C (rough estimate)
density 
1.0604 (rough estimate)
refractive index 
1.5430 (estimate)
storage temp. 
Keep in dark place,Sealed in dry,Room Temperature
pka
pKa 9.04±0.01(H2O,t=25,I=0.1(NaCl))(Approximate)
Water Solubility 
9.45g/L(30 ºC)
Merck 
14,7757
Contact allergens
Procaine is a local anesthetic with para-amino function. Sensitization mainly concerns the medical, dental, and veterinary professions.
CAS DataBase Reference
59-46-1(CAS DataBase Reference)
NIST Chemistry Reference
Benzoic acid, 4-amino-, 2-(diethylamino)ethyl ester(59-46-1)

Hazard Information

Uses
inhibitor of sodium channel
Definition
ChEBI: 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.
Description
Procaine is a local anesthetic with a para-amino function. Sensitization mainly concerns medical, dental and veterinary professions.
Chemical Properties
The 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.
Brand name
Novocain (Hospira).
Biological Functions
Procaine 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 Description
Procaine 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.
Clinical Use
Procaine 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 Methods
Procain 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.]

Safety Data

RIDADR 
3249
RTECS 
DG2100000
HazardClass 
6.1(b)
PackingGroup 
III
Hazardous Substances Data
59-46-1(Hazardous Substances Data)
Toxicity
LD50 in mice (mg/kg): 195 i.p.; 45 i.v. (North, Urbach)

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