Procaine 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

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

pKa 9.04±0.01(H2O,t=25,I=0.1(NaCl))(Approximate)

color 

White to Off-White

Water Solubility 

9.45g/L(30 ºC)

Merck 

14,7757

Stability:

Hygroscopic

InChI

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

InChIKey

MFDFERRIHVXMIY-UHFFFAOYSA-N

SMILES

C(OCCN(CC)CC)(=O)C1=CC=C(N)C=C1

CAS DataBase Reference

59-46-1(CAS DataBase Reference)

NIST Chemistry Reference

Benzoic acid, 4-amino-, 2-(diethylamino)ethyl ester(59-46-1)

Safety Information

RIDADR 

3249

RTECS 

DG2100000

HS Code 

2922.49.3700

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)

Procaine Usage And Synthesis

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.

Uses

Procaine (Novocain) is mainly used in dental or medical procedures requiring infiltration anesthesia, peripheral block, or spinal block.

Uses

Procaine is a sodium channel blocker and inhibitor of a variety of processes.

Definition

ChEBI:Procaine is 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. It has a role as a local anaesthetic, a central nervous system depressant, a peripheral nervous system drug and a drug allergen. It is a benzoate ester, a substituted aniline and a tertiary amino compound. It is functionally related to a 2-diethylaminoethanol and a 4-aminobenzoic acid. It is a conjugate base of a procaine(1+).

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.

Contact allergens

Procaine is a local anesthetic with para-amino function. Sensitization mainly concerns the medical, dental, and veterinary professions.

Mechanism of action

The fundamental mechanism of analgesia underlying all local anesthetics is the blockade of neurotransmission via inhibition of sodium channels along nerve fibers. Procaine acts mainly by inhibiting sodium influx through voltage gated sodium channels in the neuronal cell membrane of peripheral nerves. When the influx of sodium is interrupted, an action potential cannot arise and signal conduction is thus inhibited.

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.

Side effects

When taken by mouth: It is not known whether procaine is safe when taken by mouth. It can cause some side effects including heartburn, migraines, and a serious condition called systemic lupus erythematosus (SLE). SLE causes a variety of symptoms including joint pain, rashes, lung problems, and many other symptoms.

Synthesis

Experimental steps for synthesis of Procaine: In there-necked flask, add p-nitrobenzoic acid 60g, dimethylbenzene 360g, Diethylaminoethanol 44g, reflux divides water, temperature of reaction 141 ~ 143 ℃, reacts 12 hours; React complete, be cooled to less than 20 ℃, reclaim under reduced pressure dimethylbenzene; Reclaim complete, be cooled to less than 40 DEG C, slowly drip 570g6% dilute hydrochloric acid, after adding, stir 30 minutes, be cooled to 20 ~ 25 ℃, filter, obtain filtrate;Upper step filtrate is added in hydrogenation reaction cauldron, add catalyst Ni powder 15g, with nitrogen replacement 2 times, pass into hydrogen, pressure is 10 standard atmospheric pressures, control temperature of reaction 50 ~ 60 ℃ and carry out hydrogenation, react complete, filter, refined salt 16g is added in filtrate, stirring and dissolving, is cooled to 10 ℃, obtains procaine hydrochloride.

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.]

Procaine(59-46-1)Related Product Information

• 4-Amino-2-chlorobenzoic acid
• Otilonium Bromide Impurity 11
• Otilonium Bromide Impurity 12
• Procaine N-Oxide
• N-ALLYL-2-(CARBOXYMETHOXYL)BENZAMIDE
• 4-Acetamido-2-propoxybenzoic Acid
• PROCAINE AMIDE HYDROCHLORIDE
• BENXYLPENICILLIN PROCAINE SALT,PENICILLIN G PROCAINE SALT,PROCAINE PENICILLIN,Procaine penicilline G hydrate
• PROCAINE HCL USP POWDER,PROCAINE HYDROCHLORIDE VETRANAL,PROCAINE HYDROCHLORIDE,PROCAINE HCL,PROCAINE
• component of Dicurin Procaine
• Procaine penicillin G
• PROCAINE AMIDE HYDROCHLORIDE
• procaine borate
• Penicillin G Procaine/Sodium 3:1
• Procaine penicillin G(fortified)
• Penicillin G procaine/Potassium 3:1
• Penicillin G procaine/Benzathine 4:1
• PENICILLIN G PROCAINE USP(CRM STANDARD)
• Novocaine