59-46-1

Usage

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.]

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

Upstream product

• 869-24-9 2-chloro-N,N-diethylethylamine hydrochloride 
• 150-13-0 4-amino-benzoic acid 
• 100-37-8 2-(Diethylamino)ethanol 
• 3535-22-6 4-amino-benzoic acid-(2-chloro-ethyl ester) 
• 109-89-7 diethylamine 
• 94-09-7 p-aminoethylbenzoate 
• 619-45-4 4-methoxycarbonyl aniline 
• 99-77-4 ethyl 4-nitrobenzoate 
• 38973-67-0 2-diethylaminoethyl 4-bromobenzoate 
• 122-04-3 4-nitro-benzoyl chloride 
• 13733-21-6 (4-nitro-benzoyl)-carbamic acid ethyl ester 
• 100-35-6 2-(diethylamino)ethyl chloride 
• 13456-39-8 2-(diethylamino)ethyl 4-nitrobenzoate 
• 62-23-7 4-nitro-benzoic acid 

Downstream Products

• 70204-58-9 4-benzoylamino-benzoic acid 2-diethylamino-ethyl ester 
• 63014-02-8 4-(N'-phenyl-ureido)-benzoic acid-(2-diethylamino-ethyl ester) 
• 59440-80-1 4-(N'-phenyl-thioureido)-benzoic acid-(2-diethylamino-ethyl ester) 
• 3772-42-7 4-butylamino-benzoic acid-(2-diethylamino-ethyl ester) 
• 6062-23-3 2-(diethylaminoethyl) 4-acetylaminobenzoate 
• 69018-96-8 4-(2-chloro-acetylamino)-benzoic acid 2-diethylamino-ethyl ester 
• 106843-26-9 4-trans-cinnamoylamino-benzoic acid-(2-diethylamino-ethyl ester) 
• 62276-02-2 4-(2,4-dinitro-anilino)-benzoic acid methyl ester 
• 40950-04-7 4-(2,4-dinitro-anilino)-benzoic acid ethyl ester 
• 112552-43-9 4-cyclohexanecarbonylamino-benzoic acid-(2-diethylamino-ethyl ester); hydrochloride 
• 103329-98-2 4,4'-oxalyldiamino-di-benzoic acid bis-(2-diethylamino-ethyl ester) 

Relevant academic research and scientific papers

Catalytic production of anilines by nitro-compounds hydrogenation over highly recyclable platinum nanoparticles supported on halloysite nanotubes

Pt-nanoparticles supported on halloysite-nanotubes (HNTs) were selectively deposited onto the inner (Pt(IN)/HNT) or outer (Pt(OUT)/HNT) surface of the support to evaluate their operational stability on the cleaner and efficient hydrogenation of nitro compounds to produce their corresponding anilines. The formation of Pt0-aggregates on the inner or outer surfaces was observed, with mean particles sizes of 2.4–2.9 nm. The catalysts were evaluated using ethanol as solvent and nitrobenzene as a model substrate at a temperature of 298 K, under 1 bar of H2 pressure. The Pt(IN)/HNT catalyst showed better catalytic performance than Pt(OUT)/HNT, which was mainly attributed to the confinement effect of the Pt-nanoparticles inside the HNTs. However, the operational stability showed that Pt(OUT)/HNT retained its catalytic performance after 15 cycles, while the Pt(IN)/HNT catalyst suffered deactivation after the 5th cycle. The best catalytic system showed a moderate-to-high efficiency in the efficient hydrogenation of 7 nitro compounds used to produce their corresponding anilines, which are important pharmaceutical building blocks.

ANTIBIOTIC AMMONIUM COMPOUNDS AND METHODS FOR THE TREATMENT OF BACTERIAL INFECTIONS

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.

Synergistic Effects of ppm Levels of Palladium on Natural Clinochlore for Reduction of Nitroarenes

Augmenting the modified naturally occurring clay clinochlore with ppm amounts of palladium leads to a new and very effective reagent for the reduction of numerous aromatic nitro species. When palladium nanoparticles are supported on pyridyltriazole-modified clinochlore, iron within clinochlore acts synergistically with palladium to catalyze the reduction of a wide variety of nitroarenes at room temperature in aqueous media. Based on E-factor calculations, the catalyst system is found to be in line with green chemistry standards and can be recycled up to five times.

Metal-Free Aerobic Oxidation of Nitro-Substituted Alkylarenes to Carboxylic Acids or Benzyl Alcohols Promoted by NaOH

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.

Method for preparing aminobenzoic acid or ester thereof

The invention discloses a method for preparing aminobenzoic acid or ester thereof. The method comprises the following steps: S1, sequentially adding nitrobenzoic acid or ester, a solvent and an active nickel catalyst in a reactor; S2, while stirring, introducing hydrogen gas to replace air in a system for 3-4 times, controlling the pressure of the hydrogen gas, and performing a stirring reaction at preset temperature for a scheduled time so as to realize catalytic hydrogenation; S3, performing filtration under reduced pressure, washing filter cakes with a solvent which is the same as the solvent in S1, and collecting the active nickel catalyst; S4, performing reduced-pressure concentration on filtrate obtained in the S3 to obtain a solid namely the product of the aminobenzoic acid or the ester thereof. The method disclosed by the invention can be performed in neutral condition, normal temperature, low pressure or normal pressure, is high in synthetizing yield and low in cost, and has commercial value and environmental protection efficacy; the yield of the obtained product can be 95% or above, and the purity of the product can be 98.5% or above.

One-pot aromatic amination based on carbon-nitrogen coupling reaction between aryl halides and azido compounds

An efficient copper-mediated C-N coupling reaction between various aryl halides and azido compounds to produce the corresponding aromatic primary amines was established. The present amination is apparently involved in both the reduction of an azido functionality to the corresponding primary amino group and its cross-coupling reaction with aryl halides in a one-pot manner. The present amination could be applied to the synthesis of procaine, a local anesthetic drug. A mechanistic study indicated that 2-aminoethanol could work as a major hydrogen donor and the reaction would proceed without the formation of the intermediary aryl azide.

AMMONIUM SALTS AND AMMONIUM SALT/MINERAL SALT CLATHRATE COMPOUNDS FOR USE AS VEHICLE AND EFFECTIVE FORM FOR PHARMACO-MEDICAL APPLICATIONS AND FOR USE AS PHASE TRANSFER AGENTS FOR CHEMICAL APPLICATIONS

The invention relates to ammonium salts and stable storable ammonium salt/mineral salt clathrate compounds (inclusion compounds) having acidic dibasic acid residues such as hydrocarbonate, to methods for producing them and to pharmaco-medical and chemical synthetic applications for said compounds. According to the invention, compounds for pharmaco-medical and chemical synthetic applications are produced which comprise the ammonium salt and ammonium/mineral salt clathrate compounds (inclusion compounds, clusters) having acidic dibasic anionic acid residues of general formula (I) * x mole mineral salt, wherein R1, R2, R3 and R4 = alkyl and substituted alkyl straight-chain or branched, optionally having an alcohol, ether, silylether, ester, amino or amide function, H or aryl-alkyl, whereby aryl is an aromatic or heteroaromatic ring having optionally additional substituents, such as alkyl having 1 to 4 C atoms, OH, NR*2 with R*2= 0, alkyl with alkyl of from 1 to 4 C atoms or H, COOH, COOR, CN, NO2 and the cationic positive N+ optionally is part of an active agent, Y = a dibasic acid residue of an organic dicarboxylic acid or CO3, corresponding to HY- = HCO3 -,and x = 0.5 to 30 represents the number of the mineral salt molecules for clathrate compound formation or 0. In pharmaco-medical applications, the ammonium salt/mineral salt cluster is used as vehicle and active agent for novel forms of application of nitrogen-containing active agent bases. In chemistry, these agents are used in the synthesis of active agents and valuable products, e.g. of cyclic carbonates.

A novel electrochemical method for benzoylation of aminoalcohols with methyl benzoates at room temperature

A novel electrochemical method of benzoylating aminoalcohols 2 by use of methyl benzoates 1 at room temperature was developed. 2-Aminoethanols 2 (n=0, R3=H) and 3-aminopropanols 2 (n=1, R3=H) gave the corresponding benzamides 4, as a result of electrochemical transesterification followed by O,N-acyl migration.In contrast, o- and m-aminobenzylalcohols (7a and 7b) and trans-4-(aminomethyl)cyclohexanemethanol (8a) afforded the corresponding benzoic esters, since their acyl migration is hindered.A local anesthetic, procaine, was prepared by using this electrochemical reaction.A mechanism for electrochemical transesterification, which involves a formation of alcoholate anion by a one-electron reduction of alcohol, is presented.