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Procaine

CAS No.
59-46-1
Chemical Name:
Procaine
Synonyms
P;Novocaine;Novocain;2-(Diethylamino)ethyl 4-aminobenzoate;Procine;Procain;Procaine powder;Procaine hydrochlori;4-amino-benzoicaci2-(diethylamino)ethylester;Jenacain
CBNumber:
CB9296712
Molecular Formula:
C13H20N2O2
Molecular Weight:
236.31
MDL Number:
MFCD00007893
MOL File:
59-46-1.mol
MSDS File:
SDS
Last updated:2024-03-11 22:19:25

Procaine 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)
EWG's Food Scores 1
FDA UNII 4Z8Y51M438
ATC code C05AD05,N01BA02,N01BA52,S01HA05
NIST Chemistry Reference Benzoic acid, 4-amino-, 2-(diethylamino)ethyl ester(59-46-1)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H413
Precautionary statements  P501-P273-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
RIDADR  3249
RTECS  DG2100000
HS Code  2922.49.3700
HazardClass  6.1(b)
PackingGroup  III
Toxicity LD50 in mice (mg/kg): 195 i.p.; 45 i.v. (North, Urbach)
NFPA 704
0
2 0

Procaine price More Price(30)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TCI Chemical P1961 Procaine >98.0%(HPLC)(T) 59-46-1 5g $49 2024-03-01 Buy
TCI Chemical P1961 Procaine >98.0%(HPLC)(T) 59-46-1 25g $147 2024-03-01 Buy
TRC P755203 Procaine 59-46-1 50g $140 2021-12-16 Buy
American Custom Chemicals Corporation API0007241 PROCAINE 95.00% 59-46-1 10G $1129.59 2021-12-16 Buy
American Custom Chemicals Corporation API0007241 PROCAINE 95.00% 59-46-1 100G $2705.01 2021-12-16 Buy
Product number Packaging Price Buy
P1961 5g $49 Buy
P1961 25g $147 Buy
P755203 50g $140 Buy
API0007241 10G $1129.59 Buy
API0007241 100G $2705.01 Buy

Procaine Chemical Properties,Uses,Production

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.]

13456-39-8
59-46-1
Synthesis of Procaine from 2-diethylaminoethyl 4-nitrobenzoate
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View Lastest Price from Procaine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Procaine Novocaine pictures 2024-03-19 Procaine Novocaine
59-46-1
US $0.00-0.00 / kg 1kg 99% 500 Wuhan Haorong Biotechnology Co.,Ltd
PROCAINE pictures 2024-03-19 PROCAINE
59-46-1
US $1.60-0.10 / g 10g 99% 300tons Hebei Dangtong Import and export Co LTD
PROCAINE pictures 2024-03-18 PROCAINE
59-46-1
US $0.00 / kg 1kg 0.99 10T Shandong Hanjiang Chemical Co., Ltd
  • PROCAINE pictures
  • PROCAINE
    59-46-1
  • US $1.60-0.10 / g
  • 99%
  • Hebei Dangtong Import and export Co LTD
  • PROCAINE pictures
  • PROCAINE
    59-46-1
  • US $0.00 / kg
  • 0.99
  • Shandong Hanjiang Chemical Co., Ltd
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-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 beta-diethylaminoethyl4-aminobenzoate Diethylaminoethyl p-aminobenzoate diethylaminoethylp-aminobenzoate Duracaine Gerovital Gerovital H-3 Jenacain Jenacaine Neocaine Nissocaine Norocaine p-Aminobenzoic acid, 2-(diethylamino)ethyl ester p-amino-benzoicaci2-(diethylamino)ethylester p-aminobenzoicacid2-diethylaminoethylester p-Aminobenzoyldiethylaminoethanol procaine,base 4-Aminobenzoic Acid 2-(Diethylamino)ethyl Ester 2-(Diethylamino)ethyl 4-Aminobenzoate PROCAINE, NOVOCAINE Procaine, >=98.5% Procaine (base and/or unspecified salts) 4-Aminobenzoic acid 2-(diethylamino)ethyl Scurocaine Spinocaine Vitamin H3 vitaminh3 PROCAINE 4-AMINO-BENZOIC ACID 2-DIETHYLAMINO-ETHYL ESTER AKOS B006598 ART-CHEM-BB B006598 PROCAINE HCL, PHARMA GRADE 2-(DIETHYLAMINO)ETHYLPARA-AMINOBENZOICACID PARA-AMINOBENZOICACIDDIETHYLAMINOETHYLESTER PROCAINE(Cas number:59-46-1) Procaine Powder CAS 59-46-1 Procaine kf-wang(at)kf-chem.com procaine base/procaine hcl Procaine> Procaine Lidocaine Tetracaine PROCAINE/CARBOMER 940 Procaine powder on sale procaine on sale Procaine Wickr jane8886 Procaine for pain killer PROCAINE USP/EP/BP 99% Purity Procaine