66532-86-3

Basic information

• Product Name: Propacetamol hydrochloride
• Synonyms: 4-acetamidophenyl n,n-diethylaminoacetate monohydrochloride;n,n-diethylglycine 4-(acetylamino)phenyl ester hydrochloride;PROPACETAMOL HCL;PROPACETAMOL HYDROCHLORIDE;4-(Acetylamino)phenylN,N-diethylglycinate,9CI.;(4-acetamidophenyl) 2-(diethylamino)acetate hydrochloride;(4-acetamidophenyl) 2-(diethylamino)ethanoate hydrochloride;2-(diethylamino)acetic acid (4-acetamidophenyl) ester hydrochloride
• CAS NO: 66532-86-3
• Molecular Formula: C14H21ClN2O3
• Molecular Weight: 300.78
• EINECS: 266-391-7
• Mol File: 66532-86-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 228°
• Boiling Point: 434.5 °C at 760 mmHg
• Flash Point: 216.6 °C
• Appearance: /
• Vapor Pressure: 9.46E-08mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Freely soluble in water, slightly soluble in anhydrous ethanol, practically insoluble in acetone.
• CAS DataBase Reference: Propacetamol hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Propacetamol hydrochloride(66532-86-3)
• EPA Substance Registry System: Propacetamol hydrochloride(66532-86-3)

Safety Data

• Hazardous Substances Data: 66532-86-3(Hazardous Substances Data)

Usage

Description

Propacetamol hydrochloride is an injectable prodrug of paracetamol, a widely used analgesic and antipyretic agent. It is designed to provide rapid and effective relief from pain and fever, making it a valuable pharmaceutical compound for symptomatic treatment.

Uses

Used in Pharmaceutical Industry:
Propacetamol hydrochloride is used as an analgesic and antipyretic agent for the symptomatic treatment of pain and fever. It offers rapid relief from various types of pain, including headache, migraine, toothache, and postoperative pain, as well as reducing fever.
Used in Hospital Settings:
In hospital settings, Propacetamol hydrochloride is used as an injectable form of paracetamol, allowing for quick administration and absorption in patients who may have difficulty taking oral medications or require immediate pain relief.
Used in Emergency Medicine:
Propacetamol hydrochloride is used in emergency medicine to provide rapid pain relief and fever reduction in patients experiencing severe pain or high fever, ensuring prompt and effective treatment.
Overall, Propacetamol hydrochloride serves as a versatile and effective pharmaceutical compound, playing a crucial role in the management of pain and fever across various medical applications.

Originator

Hexachimie (UPSA) (France)

InChI:InChI=1/C14H20N2O3.ClH/c1-4-16(5-2)10-14(18)19-13-8-6-12(7-9-13)15-11(3)17;/h6-9H,4-5,10H2,1-3H3,(H,15,17);1H

Upstream product

• 103-90-2 4-acetaminophenol 
• 17321-63-0 4-acetamidophenyl 2-chloroacetate 
• 109-89-7 diethylamine 
• 24376-01-0 N,N-diethylaminoacetic acid hydrochloride 
• 2644-21-5 ethyl N,N-diethylglycinate 

Relevant articles and documents

Acetaminophen prodrug: Microwave-assisted synthesis and in vitro metabolism evaluation by mass spectrometry

Propacetamol is an acetaminophen prodrug of intravenous administration used to control fever and pain of perioperative period in multimodal analgesia therapy. After injection, it is completely converted by plasma esterases into N,N-diethylglycine and acetaminophen, its active metabolite whose mechanism of action is the inhibition of prostaglandin synthesis. Herein, we report an improved protocol for the synthesis of propacetamol hydrochloride that allows the isolation of the active pharmaceutical ingredient (API) with high purity and yield. In addition, the in vitro metabolism of propacetamol in a microssomal reaction was evaluated by ion trap tandem mass spectrometry.

N,N′-Dialkylaminoalkylcarbonyl (DAAC) prodrugs and aminoalkylcarbonyl (AAC) prodrugs of 4-hydroxyacetanilide and naltrexone with improved skin permeation properties

N,N′-Dialkylaminoalkylcarbonyl (DAAC) and aminoalkylcarbonyl (AAC) prodrugs of phenolic drugs acetaminophen (APAP) and naltrexone (NTX) are reported. The effects of incorporation of a basic amine group into the promoiety of an acyl prodrug of a phenolic drug on its skin permeation properties are also presented. DAAC-APAP prodrugs were synthesized via a three-step procedure starting with haloalkylcarbonyl esters which were reacted with five different amines: dimethylamine, diethylamine, dipropylamine, morpholine, and piperidine. The spacing between the amino group and the carbonyl group of the acyl group was 1-3 CH2. After the hydrolysis of the ester, the carboxylic acid product was subsequently coupled with the parent drug via a dicyclohexyl carbodiimide (DCC) mediated coupling to yield the DAAC-APAP-HCl prodrugs in excellent yields. The AAC prodrugs were synthesized using commercially available Boc-protected amino acids using DCC or EDCI as coupling agents. The yields of the prodrugs synthesized using these two different methods have been compared. Half-lives (t1/2) of a few members of the DAAC and AAC series were measured in buffer (pH 6.0, 20 mM). The members evaluated in hydrolysis experiments exhibit a t1/2 range of 15-113 min. Among AAC-APAP prodrugs, the isopropyl group in valinate-APAP-HCl exerted a steric effect that increased the t1/2 value for this prodrug compared to alaninate-APAP-HCl or prolinate-APAP-HCl. The 2-morpholinylacetate-APAP prodrug was able to achieve twice the flux of APAP in in vitro diffusion cell experiments through hairless mouse skin.