Chloroprocaine

Base Information

• Chemical Name: Chloroprocaine
• CAS No.: 133-16-4
• Molecular Formula: C13H19ClN2O2
• Molecular Weight: 270.759
• Hs Code.: 2922499990
• UNII: 5YVB0POT2H
• DSSTox Substance ID: DTXSID8022799
• Nikkaji Number: J5.584K
• Wikipedia: Chloroprocaine
• Wikidata: Q2964133
• NCI Thesaurus Code: C72168
• RXCUI: 20859
• Pharos Ligand ID: LHL2NHCUAKMX
• Metabolomics Workbench ID: 43381
• ChEMBL ID: CHEMBL1179047
• Mol file: 133-16-4.mol

Synonyms:2-chloroprocaine;chlor-procaine;chloroprocaine;chloroprocaine hydrochloride;Nesacaine;Nesacaine MPF

Chemical Property of Chloroprocaine

Chemical Property:

• Vapor Pressure: 1.08E-06mmHg at 25°C
• Melting Point: 42°C
• Refractive Index: 1.553
• Boiling Point: 402.632 °C at 760 mmHg
• PKA: 9.14±0.25(Predicted)
• Flash Point: 197.305 °C
• PSA: 55.56000
• Density: 1.17 g/cm³
• LogP: 3.80400
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 270.1135055
• Heavy Atom Count: 18
• Complexity: 259

Purity/Quality:

99%, ^*data from raw suppliers

Chloroprocaine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)CCOC(=O)C1=C(C=C(C=C1)N)Cl
• Recent ClinicalTrials: 1% Chloroprocaine(PF) vs. Bupivacaine Spinals
• Recent EU Clinical Trials: Comparative study of cloroprocaine versus prilocaine intrathecal anestesia in major ambulatory surgery
• Description: Chloroprocaine (N,N′-diethylaminoethyl 4-amino-2-chlorobenzoate) is a very short-acting, amino ester-type local anesthetic used to provide regional anesthesia by infiltration as well as by peripheral and central nerve block, including lumbar and caudal epidural blocks. The presence of a chlorine atom ortho to the carbonyl of the ester function increases its rate of hydrolysis by plasma cholinesterase at least threefold compared to procaine and benzocaine. Thus, chloroprocaine may be used in maternal and neonatal patients with minimal placental passage of chloroprocaine. The lower plasma cholinesterase activity in the maternal epidural space must still have sufficient activity for degrading chloroprocaine and, thus, not allowing it to cross the placenta barrier. Like PABA, the hydrolysis product of chloroprocaine, 4-amino-2-chlorobenzoic acid, also inhibits the action of sulfonamides. Therefore, its use with sulfonamides should be avoided.
• Uses: Chloroprocaine is an ester that is metabolised rapidly by ester hydrolysis, so its duration of action is short and potential for cardiac toxicity relatively low. It can be used as a preservative-free solution for spinal anaesthesia for surgical procedures up to 40 min in duration. Anesthetic (local).
• Biological Functions: Chloroprocaine hydrochloride (Nesacaine) is obtained from addition of a chlorine atom to procaine, which results in a compound of greater potency and less toxicity than procaine itself. This local anesthetic is hydrolyzed very rapidly by cholinesterase and therefore has a short plasma half-life. Because it is broken down rapidly, chloroprocaine is commonly used in obstetrics. It is believed that the small amount that might get to the fetus continues to be rapidly hydrolyzed, so there may be no residual effects on the neonate.
• Clinical Use: Chloroprocaine is used for cutaneous or mucous membraneinfiltration for surgical procedures, epidural anesthesia(without preservatives) and for peripheral conduction block.

Technology Process of Chloroprocaine

There total 2 articles about Chloroprocaine 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:

2-(diethylamino)ethyl 2-chloro-4-nitrobenzoate (10367-96-1) → chloroprocaine (133-16-4)

Guidance literature:

With water; platinum; Hydrogenation;

Reference yield:

→ chloroprocaine (133-16-4)

Guidance literature:

entspr. Nitroverb., N2H4, Raney-Ni;

DOI:10.1007/BF00771816

Reference yield:

chloroprocaine (133-16-4) → Chlorprocain + C9H11ClN2O2

Guidance literature:

With NADPH; In aq. buffer; at 30 ℃; pH=7.3; Enzymatic reaction;

DOI:10.1021/acs.joc.1c01407

upstream raw materials:

2-(diethylamino)ethyl 2-chloro-4-nitrobenzoate