Diisopropylammonium dichloroacetate

Details:

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)

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.

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.

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.

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%.