Procaine

Base Information

• Chemical Name: Procaine
• CAS No.: 59-46-1
• Deprecated CAS: 91484-72-9
• Molecular Formula: C13H20N2O2
• Molecular Weight: 236.314
• Hs Code.: 2922499100
• European Community (EC) Number: 200-426-9
• NSC Number: 169497
• UNII: 4Z8Y51M438
• DSSTox Substance ID: DTXSID7045021
• Nikkaji Number: J4.603E
• Wikipedia: Procaine
• Wikidata: Q423741
• NCI Thesaurus Code: C61906
• RXCUI: 8701
• Pharos Ligand ID: TYZHRBWYXR2Y
• Metabolomics Workbench ID: 43028
• ChEMBL ID: CHEMBL569
• Mol file: 59-46-1.mol

Synonyms:Benzoicacid, p-amino-, 2-(diethylamino)ethyl ester (8CI);2-(Diethylamino)ethylp-aminobenzoate;2-Diethylaminoethyl 4-aminobenzoate;4-Aminobenzoic acid2-(diethylamino)ethyl ester;4-Aminobenzoic acid diethylaminoethyl ester;Diethylaminoethyl p-aminobenzoate;Duracaine;Nissocaine;PfizerpenAS;Procain;Procaine base;SP 01;Spinocaine;Vitamin H3;p-Aminobenzoic acid 2-diethylaminoethyl ester;b-(Diethylamino)ethyl p-aminobenzoate;b-Diethylaminoethyl4-aminobenzoate;

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Chemical Property of Procaine

Chemical Property:

• Vapor Pressure: 8.84E-06mmHg at 25°C
• Melting Point: 61oC
• Refractive Index: 1.542
• Boiling Point: 373.6 °C at 760 mmHg
• PKA: pKa 9.04±0.01(H2O,t=25,I=0.1(NaCl))(Approximate)
• Flash Point: 179.8 °C
• PSA: 55.56000
• Density: 1.077 g/cm³
• LogP: 2.34860
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 9.45g/L(30 oC)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 236.152477885
• Heavy Atom Count: 17
• Complexity: 222

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Canonical SMILES: CCN(CC)CCOC(=O)C1=CC=C(C=C1)N
• Recent ClinicalTrials: A Randomized Controlled Trial of SP-01 (Granisetron Transdermal Delivery System) in Chemotherapy-induced Nausea and Vomiting
• Recent EU Clinical Trials: Selective local anesthesia versus a combined medication injection with corticosteroids in degenerartive spine
• Description: Procaine is a local anesthetic with a para-amino function. Sensitization mainly concerns medical, dental and veterinary professions.
• Uses: Procaine (Novocain) is mainly used in dental or medical procedures requiring infiltration anesthesia, peripheral block, or spinal block. inhibitor of sodium channel Procaine is a sodium channel blocker and inhibitor of a variety of processes.
• 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.

Technology Process of Procaine

There total 24 articles about Procaine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

ethyl 4-nitrobenzoate (99-77-4) + 2-(Diethylamino)ethanol (100-37-8) → Procaine (59-46-1,91484-72-9)

Guidance literature:

With hydrogen; palladium-containing anion exchanger AV-17-8; In ethanol; at 45 ℃; under 760 Torr;

DOI:10.1023/A:1014762419378

Reference yield: 63.0%

2-diethylaminoethyl 4-bromobenzoate (38973-67-0) → Procaine (59-46-1,91484-72-9)

Guidance literature:

With copper (II)-fluoride; sodium azide; ethanolamine; In N,N-dimethyl acetamide; at 95 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.tet.2011.12.058

Reference yield: 58.0%

2-(Diethylamino)ethanol (100-37-8) + 4-methoxycarbonyl aniline (619-45-4) → Procaine (59-46-1,91484-72-9)

Guidance literature:

With tetraethylammonium perchlorate; In acetonitrile; at 23 ℃;

upstream raw materials:

2-(diethylamino)ethyl 4-nitrobenzoate

2-chloro-N,N-diethylethylamine hydrochloride

4-amino-benzoic acid

2-(Diethylamino)ethanol

Downstream raw materials:

4-benzoylamino-benzoic acid 2-diethylamino-ethyl ester

4-[2-(2-Chloro-phenoxy)-acetylamino]-benzoic acid 2-diethylamino-ethyl ester

4-(p-Chlorphenoxyacetylamino)-benzoesaeurediethylaminoethylester

4-<2-(p-Chlorphenoxy)-2-methylpropionylamino>-benzoesaeurediethylaminoethylester

Refernces

• 1、 Aepuru, Radhamanohar,Bustamante, Tatiana M.,Campos, Cristian H.,Leal-Villarroel, Edgardo,Mangalaraja, Ramalinga Viswanathan,Shanmugaraj, Krishnamoorthy,Torres, Cecilia C.,Vinoth, Victor. "Catalytic production of anilines by nitro-compounds hydrogenation over highly recyclable platinum nanoparticles supported on halloysite nanotubes". . . Retrieved 2021/07/28.
• 2、 Gholinejad, Mohammad,Oftadeh, Erfan,Shojafar, Mohammad,Sansano, José M.,Lipshutz, Bruce H.. "Synergistic Effects of ppm Levels of Palladium on Natural Clinochlore for Reduction of Nitroarenes". . p. 4240 - 4248. Retrieved 2019/09/06.