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HomeProduct name listDiisopropylammonium dichloroacetate

Diisopropylammonium dichloroacetate

  • CAS NO.:660-27-5
  • Empirical Formula: C8H17Cl2NO2
  • Molecular Weight: 230.13208
  • MDL number: MFCD00868288
  • EINECS: 211-538-2
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-12-07 16:20:24
Diisopropylammonium dichloroacetate Structural

What is Diisopropylammonium dichloroacetate?

Description

Diisopropylammonium dichloroacetate is a hepatoprotective drug that improves the energy metabolism of hepatocytes, promotes the regeneration of injured hepatocytes, increases the rate of tissue cell respiration and oxygen respiration, and reduces the accumulation of fat in the liver. It is mainly used clinically for the treatment of fatty liver, intrahepatic cholestasis, and general liver dysfunction. It is also used in the treatment of acute and chronic hepatitis, hepatomegaly, and early cirrhosis.

Chemical properties

White or off-white loose mass or powder, slightly bitter, easily soluble in water, ethanol or chloroform, slightly soluble in ether.

History

In the 1950s, the compound diisopropylammonium dichloroacetate (DIPA) was used in the synthesis of methylated derivatives of a purportedly naturally occurring B vitamin (pangamic acid; dgluconodimethylaminoacetate). Anecdotal clinical reports appeared claimingefficacy in various metabolic and cardiovascular disorders from pharmaceuticalmixtures of pangamic acid and DIPA. In 1970,DCA was identified as themetabolically active moiety of DIPA(Stacpoole & Felts,1970) and it has beenused thereafter almost exclusively as the sodium salt.

The Uses of Diisopropylammonium dichloroacetate

Diisopropylammonium dichloroacetate (DIPA) is known to produce a significant and prolonged hypoglycemic effect in alloxan-diabetic but not in normal rats.
Diisopropylamine 2,2-Dichloroacetate is used in the treatment of antituberculosis drugs-induced liver injury.

Definition

ChEBI: Diisopropylamine dichloroacetate is an organohalogen compound and a carboxylic acid.

Synthesis

Diisopropylammonium dichloroacetate is prepared by the reaction of dichloro-acetic acid and diisopropylamine. The steps are as follows:
1 volume of acetone is mixed with 1.5 volumes of cyclohexane to obtain a mixed solvent; Add 1 mol of diisopropylamine (101.19g, C6H15N, Mr=101.19) into 150ml of mixed solvent, stir evenly, and heat the liquid material to 50°C; slowly add 1mol of dichloroacetic acid (128.94g, C2H2Cl2O2, Mr=128.94) dropwise to the liquid material obtained in step (at a speed of about 10g/min) under heat preservation and stirring conditions,After the feeding is complete, keep warm and continue to stir for 3 hours, then naturally cool to 4-8°C, and then stand at this temperature for 10 hours; Filter the material obtained in step, separate the mother liquor, collect white crystals, and dry at 70° C. to obtain 216.8 g of the diisopropylamine dichloroacetate (C8H17Cl2NO2, Mr=230.13), with a molar yield of 94.2%.
Diisopropylammonium dichloroacetate synthesis

Mode of action

The mechanism of action of diisopropyl dichloroacetate is to enhance the fluidity of hepatocyte membranes by promoting sequential methylation of membrane phospholipids, to increase the activity of Na+-K+-ATPase, which is the main driving force of bile secretion and flow; to promote the functional repair of damaged hepatocytes, to improve the respiratory function and oxygen utilization of tissue cells, to increase the metabolic activity of fatty acids, to accelerate the oxidation of fatty acids, and to create conditions for the recovery of liver function.

Properties of Diisopropylammonium dichloroacetate

Melting point: 119-121°
RTECS  AG6475000
storage temp.  Sealed in dry,Room Temperature
solubility  DMSO (Slightly), Methanol (Slightly)
form  Crystalline Powder
color  White
Merck  14,3197
Stability: Hygroscopic
InChI InChI=1S/C6H15N.C2H2Cl2O2/c1-5(2)7-6(3)4;3-1(4)2(5)6/h5-7H,1-4H3;1H,(H,5,6)
CAS DataBase Reference 660-27-5
EPA Substance Registry System Acetic acid, dichloro-, compd. with N-(1-methylethyl)-2-propanamine (1:1) (660-27-5)

Safety information for Diisopropylammonium dichloroacetate

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.
P501:Dispose of contents/container to..…

Computed Descriptors for Diisopropylammonium dichloroacetate

InChIKey ILKBHIBYKSHTKQ-UHFFFAOYSA-N
SMILES C(O)(=O)C(Cl)Cl.CC(NC(C)C)C

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