Prilocaine

Base Information

• Chemical Name: Prilocaine
• CAS No.: 721-50-6
• Molecular Formula: C13H20N2O
• Molecular Weight: 220.315
• Hs Code.: 2924296000
• European Community (EC) Number: 211-957-0
• NSC Number: 40027
• UNII: 046O35D44R
• DSSTox Substance ID: DTXSID7031955
• Nikkaji Number: J6.949C
• Wikipedia: Prilocaine
• Wikidata: Q413598
• NCI Thesaurus Code: C47685
• RXCUI: 8686
• Pharos Ligand ID: XV85L4SVBZ9Q
• Metabolomics Workbench ID: 43051
• ChEMBL ID: CHEMBL1194
• Mol file: 721-50-6.mol

Synonyms:Citanest;Citanest Octapressin;Prilocaine;Prilocaine Hydrochloride;Propitocaine;Xylonest

Chemical Property of Prilocaine

Chemical Property:

• Appearance/Colour: White crystalline powder
• Melting Point: 37-38oC
• Refractive Index: nD20 1.5298
• Boiling Point: 361.6 °C at 760 mmHg
• PKA: pKa 7.32 or 7.89 (Uncertain)
• Flash Point: 134.3 °C
• PSA: 41.13000
• Density: 1.029 g/cm³
• LogP: 2.78550
• Storage Temp.: 2-8°C
• Solubility.: Slightly soluble in water, very soluble in acetone and in ethanol (96 per cent).
• Water Solubility.: 易溶于水和乙醇，略溶于氯仿
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 220.157563266
• Heavy Atom Count: 16
• Complexity: 218

Purity/Quality:

99%, ^*data from raw suppliers

Prilocaine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCNC(C)C(=O)NC1=CC=CC=C1C
• Recent ClinicalTrials: Effect of Intrathecal Morphine on Urinary Bladder Function and Recovery in Patients Having a Cesarean Delivery
• Recent EU Clinical Trials: Comparative study of cloroprocaine versus prilocaine intrathecal anestesia in major ambulatory surgery
• Uses: It is a kind of local anesthetic drug. The product has better efficacy than procaine and the local anesthesia intensity and speed being similar as lidocaine but with longer duration time and less toxicity as well as smaller accumulation effect. It is suitable for epidural anesthesia, conduction anesthesia and infiltration anesthesia. Prilocaine is a local anesthetic of the amino amide type. Prilocaine is often used in dentistry. Prilocaine is also often combined with lidocaine as a preparation for dermal anesthesia (lidocaine/prilocaine or EMLA), for treatment of conditions like paresthesia. In terms of pharmacological parameters, prilocaine is comparable to lidocaine; however, because of a number of toxic manifestations, it is rarely used in medical practice. Citanest and xylonest are well-known synonyms for prilocaine.
• Production method: O-toluidine and α-bromo-propionyl bromide are condensed and further have reaction with propylamine obtain prilocaine.
• Clinical Use: Prilocaine metabolism has beenstudied extensively in animal models, less is known aboutthe human metabolites or the human CYP enzymes involvedin their formation . The metabolism of prilocainein the liver yields o-toluidine, which is a possiblecarcinogen. Many aromatic amines, including o-toluidinehave been shown to be mutagenic, and metabolites of otoluidinehave been shown to form DNA adducts.Metabolites of o-toluidine are also believed to be responsiblefor the methemoglobinemia observed with prilocaineuse. To decrease the potential for methemoglobinemia, strictadherence to the maximum recommended dose should befollowed. Metabolism of prilocaine is extensive with lessthan 5% of a dose excreted unchanged in the urine.

Technology Process of Prilocaine

There total 5 articles about Prilocaine 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%

propylamine (107-10-8,42939-71-9) + 2-chloropropionyl chloride (7623-09-8) + o-toluidine (95-53-4) → prilocaine (721-50-6,14289-31-7)

Guidance literature:

2-chloropropionyl chloride; o-toluidine; With potassium carbonate; In acetone; at 0 - 30 ℃; for 5h;

propylamine; In acetone; at 70 ℃; for 14h;

Reference yield: 90.0%

propylamine (107-10-8,42939-71-9) + N-(2-methylphenyl)-2-chloropropanamide (19281-31-3) → prilocaine (721-50-6,14289-31-7)

Guidance literature:

With potassium carbonate; In acetone; Reflux;

Reference yield:

5-methyl-1-propyl-3-o-tolyl-imidazolidin-4-one; hydrochloride → prilocaine (721-50-6,14289-31-7)

Guidance literature:

In phosphate buffer; acetate buffer; at 60 ℃; pH=2.15 - 7.4; Kinetics;

DOI:10.1016/S0928-0987(03)00198-2

upstream raw materials:

propylamine

N-(2-methylphenyl)-2-chloropropanamide

2-chloropropionyl chloride

o-toluidine

Downstream raw materials:

prilocaine hydrochloride

D(-)-α-Propylamino-2-methyl-propioanilid

L(+)-α-Propylamino-2-methyl-propioanilid

C₄₂H₇₀O₃₅*C₁₃H₂₀N₂O

Refernces

• 1、 -. "A method for preparing prilocaine hydrochloride". Paragraph 0051; 0052. . Retrieved 2017/03/14.