BDTH2

BDTH₂
Names


IUPAC name N,N′-bis(2-mercaptoethyl)isophthalamide
Other names BDET; BDTH₂; BDETH₂; N,N′-Bis(2-mercaptoethyl)-1,3-benzenedicarboxamide; N1,N3-bis(2-mercaptoethyl)isophthalamide; NBMI;
Identifiers
CAS Number	351994-94-0^Y
3D model (Jmol)	Interactive image Interactive image
ChemSpider	19238563^Y
MeSH	1,3-benzenediamidoethanethiol
PubChem CID	16043475
InChI InChI=1S/C12H16N2O2S2/c15-11(13-4-6-17)9-2-1-3-10(8-9)12(16)14-5-7-18/h1-3,8,17-18H,4-7H2,(H,13,15)(H,14,16)^Y Key: JUTBAVRYDAKVGQ-UHFFFAOYSA-N^Y InChI=1/C12H16N2O2S2/c15-11(13-4-6-17)9-2-1-3-10(8-9)12(16)14-5-7-18/h1-3,8,17-18H,4-7H2,(H,13,15)(H,14,16) Key: JUTBAVRYDAKVGQ-UHFFFAOYAW
SMILES O=C(NCCS)C1=CC(C(NCCS)=O)=CC=C1 O=C(NCCS)c1cccc(c1)C(=O)NCCS
Properties
Chemical formula	C₁₂H₁₆N₂O₂S₂
Molar mass	284.39 g·mol⁻¹
Density	1.23 g/mL
Melting point	132 to 135 °C (270 to 275 °F; 405 to 408 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is ^YN ?)
Infobox references

BDTH₂ (also called BDET and BDETH₂; trade names B9, MetX and OSR#1) is an organosulfur compound that is used as a chelation agent. It is a colourless solid. The molecule consists of two thiol groups and linked via a pair of amide groups.

The compound was reported in about 1994 after a search for chelating agents selective for mercury. It was licensed in 2006 to CTI Science with the long-term goal of using BDTH₂ in mercury poisoning. This compound is prepared by treating isophthaloyl dichloride with two equiv of cysteamine:

BDTH₂ can be used to chelate heavy metals like lead, cadmium, copper, manganese, zinc, iron, and mercury from ground water, coal tailings, gold ore, waste water of battery-recycling plants, and contaminated soil.

BDTH₂ appears to bind mercury more strongly than do other chelators. The mercury-BDT complex does not break down even at high pH and in the presence of cyanides, as in waste water of gold mines. The particular stability of the mercury bond can be attributed to the linear position of the two thiols. The company Covalent Research Technologies had investigated BDTH₂ for the removal of mercury from flue gas without success.

Animal experiments with inorganic mercury showed, that BDTH₂ effectively binds mercury in the body, and the resulting mercury derivative is excreted in the feces. Experimental animals showed no signs of poisoning. It is unclear, how the BDTH₂-mercury-chelate behaves in the long term. BDTH₂ is lipophilic, as opposed to DMPS and DMSA and thus can cross lipid membranes including the blood-brain-barrier and enters the bone marrow. In animal experiments, the amount of mercury in brain tissue was not increased, but also not decreased(can anyone provide a reference for the material/data/research from which this conclusion was drawn?). However, there are indications that the BDTH₂-mercury-compound moves into adipose tissue. It is unknown, how BDTH₂ works with methyl-mercury.

...
Wikipedia