59-46-1 Usage
Description
Procaine, also known as Novocain, is a local anesthetic with a para-amino function. It was synthesized in 1904 to address the chemical instability of cocaine and the local irritation it produced. Procaine has a pKa of 8.9, low lipid solubility, and an ester group that is unstable in basic solutions. It is available in concentrations ranging from 0.25% to 10% with pHs adjusted to 5.5 to 6.0 for chemical stability. Procaine is also included in some formulations of penicillin G to decrease the pain of intramuscular injection.
Uses
Used in Medical and Dental Procedures:
Procaine is used as an anesthetic agent for procedures requiring infiltration anesthesia, peripheral block, or spinal block in the medical and dental fields. It is particularly useful for its ability to provide local pain relief during these procedures.
Used as a Sodium Channel Inhibitor:
Procaine is used as an inhibitor of sodium channels, functioning as a sodium channel blocker. It inhibits a variety of processes by preventing the flow of sodium ions through the channels, which is essential for the proper functioning of nerve cells.
Used in Pharmaceutical Formulations:
Procaine is used as an additive in some formulations of penicillin G to decrease the pain associated with intramuscular injections. Its local anesthetic properties help to reduce the discomfort experienced by patients during the administration of the antibiotic.
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, which contributes to its effectiveness as a local anesthetic.
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.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 59-46-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 9 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 59-46:
(4*5)+(3*9)+(2*4)+(1*6)=61
61 % 10 = 1
So 59-46-1 is a valid CAS Registry Number.
InChI:InChI=1/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
59-46-1Relevant articles and documents
Development of the method of novocain production
Abdullaev
, p. 556 - 559 (2001)
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ANTIBIOTIC AMMONIUM COMPOUNDS AND METHODS FOR THE TREATMENT OF BACTERIAL INFECTIONS
-
Paragraph 0118, (2020/08/22)
The present disclosure provides ammonium compounds, e.g., compounds according to Formula I as set forth herein, which are useful as antimicrobial agents. Methods for the treatment of bacterial infections and associated conditions, e.g., gastrointestinal conditions, are also described, as well as methods for altering the microbiome of subjects such as humans.
Metal-Free Aerobic Oxidation of Nitro-Substituted Alkylarenes to Carboxylic Acids or Benzyl Alcohols Promoted by NaOH
Fang, Kun,Li, Guijie,She, Yuanbin
supporting information, p. 8092 - 8103 (2018/06/25)
Efficient and selective aerobic oxidation of nitro-substituted alkylarenes to functional compounds is a fundamental process that remains a challenge. Here, we report a metal-free, efficient, and practical approach for the direct and selective aerobic oxidation of nitro-substituted alkylarenes to carboxylic acids or benzyl alcohols. This sustainable system uses O2 as clean oxidant in a cheap and green NaOH/EtOH mixture. The position and type of substituent critically affect the products. In addition, this sustainable protocol enabled gram-scale preparation of carboxylic acid and benzyl alcohol derivatives with high chemoselectivities. Finally, the reactions can be conducted in a pressure reactor, which can conserve oxygen and prevent solvent loss. The approach was conducive to environmental protection and potential industrial application.
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