Diisopropylammonium dichloroacetate Chemical Properties

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)

InChIKey

ILKBHIBYKSHTKQ-UHFFFAOYSA-N

SMILES

C(O)(=O)C(Cl)Cl.CC(NC(C)C)C

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

TSCA 

Yes

HS Code 

2921199990

Toxicity

LD50 orally in mice: 1700 mg/kg (Kraushaar)

Diisopropylammonium dichloroacetate Usage And Synthesis

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.

Uses

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%.

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.

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