Succimer Chemical Properties

Melting point:

196-198 °C (dec.)(lit.)

Boiling point:

285.62°C (rough estimate)

Density 

1.439 (estimate)

refractive index 

1.5220 (estimate)

storage temp. 

-20°C

solubility 

DMSO (Sparingly), Methanol (Slightly, Heated)

pka

pK1:2.71;pK2:3.48;pK3:8.89(SH);pK4:10.79(SH) (25°C)

form 

Powder

color 

White to off-white

Water Solubility 

Soluble in water, and ethanol (25 mg/ml, results in colorless to light yellow, clear).

Merck 

14,8865

BRN 

1725150

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents.

InChIKey

ACTRVOBWPAIOHC-XIXRPRMCSA-N

CAS DataBase Reference

304-55-2(CAS DataBase Reference)

EPA Substance Registry System

Butanedioic acid, 2,3-dimercapto-, (2R,3S)-rel- (304-55-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-36-26

WGK Germany 

2

RTECS 

WM7650000

F 

10-23

TSCA 

Yes

HS Code 

29309090

Hazardous Substances Data

304-55-2(Hazardous Substances Data)

Toxicity

LD50 i.p. in mice: >3000 mg/kg (Friedheim, Corvi)

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Succimer Usage And Synthesis

Description

Succimer is a newly available oral chelator of lead and other heavy metals. The compound is indicated for the treatment of lead poisoning in children. Succimer does not bind iron, calcium or magnesium and preferentially binds lead, mercury and arsenic over copper or zinc. The metal-bound succimer is excreted in the urine. The drug may also be effective in adults.

Chemical Properties

white or off-white powder

Originator

Johnson and Johnson (J&J) (U.S.A.)

Uses

chelating agent, antihypertensive

Uses

meso-2,3-Dimercaptosuccinic Acid is used as a chelating agent and masking agent for cadmium in EDTA titration of zinc.

Uses

A water-soluble chelating agent.

Uses

chelating agent, treatment of lead poisoning

Preparation

Isolate the solid complexes of trivalent lanthanide complexes with meso-2,3-Dimercaptosuccinic Acid, furan-2-carboxylic acid, meso-2,3-dimercaptosuccinic acid and sarcosine from the mixture of equimolar solutions of metal nitrates and ligands. Adjust the pH of the mixture to 7 by adding dilute solution of KOH. Reflux the mixture in ethanol (15-20 ml) for 3-4 hours on a steam bath. The clear solution gives a solid mass on cooling, filter through G4 glass crucible and wash several times with the mixture of doubly distilled water and alcohol. Recrystallise it to obtain pure crystal and dry at 60 ?? -70 ??C [1].

Definition

ChEBI: A sulfur-containing carboxylic acid that is succinic acid bearing two mercapto substituents at positions 2 and 3. A lead chelator used as an antedote to lead poisoning.

brand name

Chemet (Ovation).

Pharmaceutical Applications

Dimercaptosuccinic acid (DMSA) is a modification of BAL containing two thiol groups, which are responsible for the unpleasant smell, and two carboxylic acid groups. DMSA is also known under the name Succimer. It chemical name is meso-2,3-dimercaptosuccinic acid and the chemical formula is HO₂CCH(SH)CH(SH)CO₂H. There are two diastereomeric forms, meso and the chiral DL forms, with the meso isomer being used as chelating agent.
DMSA was developed in the 1960s and replaced BAL and edetate in some countries for the treatment of lead, arsenic and mercury poisoning. Furthermore, the dimethylester modification of DMSA has been successfully used for the treatment of heavy-metal poisoning.

Pharmaceutical Applications

The unlicensed drug Succimer (DMSA, meso-2,3-dimercaptosuccinic acid) may be valuable in the treatment of most forms of heavy-metal poisoning including lead, arsenic and mercury. These and other chelating agents such as unithiol (DMPS, 2,3-dimercapto-1-propanesulfonic acid) and α-lipoic acid (ALA) are also used in alternative medicine, which has led to much criticism and discussion. So far, no medical study has proven the effectiveness of chelation therapy for any clinical application other than heavy-metal poisoning.

Veterinary Drugs and Treatments

In veterinary medicine, succimer may be useful for the oral treatment of lead poisoning in small animals (including birds). Potentially, it also may be of benefit for the treatment of other toxic heavy metals such as arsenic or mercury, but more research must be done before this can be recommended.

Purification Methods

Purify the acid by dissolving it in NaOH and precipitating with dilute HCl, drying and recrystallising from MeOH. IR has at 2544 (SH) and max 1689 (CO2H) cm-1 . The bis-S-acetyl derivative has m 183-185o (from EtOAc or Me2CO), and its Me ester has m 119-120o (from pet ether) [Gerecke et al. Helv Chim Acta 44 957 1961, Owen & Sultanbawa J Chem Soc 3112 1949]. [Beilstein 3 III 1033.]

Succimer(304-55-2)Related Product Information

• 2-Ethylhexyl mercaptoacetate
• Mercaptoacetic acid
• Calcium thioglycolate
• 2,3-Dimercapto-1-propanol
• Succinic acid
• Citric acid
• Mercaptosuccinic acid
• POTASSIUM THIOGLYCOLATE
• 3-Mercaptopropionic acid
• Disodium succinate
• Folic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Ascoric Acid
• 2-Mercaptobutyric acid
• 2,3-Butanedithiol
• DMSA
• 2-Mercaptoethanol
• Succimer