Names | |
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Preferred IUPAC name N1,N3-Bis(2-sulfanylethyl)benzene-1,3-dicarboxamide | |
Other names BDET; BDTH2; BDETH2; N,N′-Bis(2-mercaptoethyl)-1,3-benzenedicarboxamide; N1,N3-bis(2-mercaptoethyl)isophthalamide; NBMI; | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
MeSH | 1,3-benzenediamidoethanethiol |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
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) [1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
BDTH2 (also called BDET and BDETH2; trade names B9, MetX, and OSR#1) is an organosulfur compound that is used as a chelation agent. [2] It is a colourless solid. The molecule consists of two thiol groups and linked via a pair of amide groups. [3]
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 to treat mercury poisoning. [4] This compound is prepared by treating isophthaloyl dichloride with two equiv of cysteamine: [1] [2]
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. [2]
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. [5] The company Covalent Research Technologies had investigated BDTH2 for the removal of mercury from flue gas without success. [4]
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; this enables it to cross lipid membranes, including the blood-brain-barrier, and enter bone marrow. [4] In animal experiments, mercury in brain tissue neither increased nor decreased. There are indications that the BDTH2-mercury-compound moves into adipose tissue. [3] It is unknown how BDTH2 works with methyl-mercury.
BDTH2 appears to bind copper and zinc in vivo weakly. In contrast, DMPS und DMSA bind these ions more strongly. Its affinity is low for other "hard" ions, e.g., Ca2+, Mg2+, Na+, and K+. [3]
Until July 2010, CTI Science sold BDTH2 as a nutritional supplement under the name OSR#1. [6] Since OSR#1 didn't fulfill criteria of a nutritional supplement, its sale was stopped under pressure of the U.S. Food and Drug Administration. [7] In January 2012, BDTH2 was designated by the European Commission as an orphan drug, which guarantees CTI Science ten years of exclusive marketing rights. [8] In April 2012, the FDA designated the compound as an orphan drug. [9]
Like most thiols, BDTH2 binds to mercury salts to form thiolate complexes. In principle, it could be used to remove mercury from water for industrial applications under a wide range of conditions, including the high pH and cyanide of the effluent from gold mining. In industrial use, BDTH2 is easy to make and can be used either as-is or in the form of sodium or potassium salts that are more soluble in water. [1]
BDTH2 binds to mercury with a strong, nonpolar covalent bond within a water-insoluble organic framework. The resulting BDT–Hg precipitate is stable, and leaches mercury only under highly acidic or basic conditions. BDTH2 also binds to other elements, including arsenic, cadmium, copper, lead, and selenium. [1] It is effective and economical for removing small traces of mercury from polluted soil, as the precipitate is inert and can be left in the soil after treatment. [10]
BDTH2 had been marketed under the name OSR#1 as a dietary supplement for treatment of autism. [11] The U.S. Food and Drug Administration determined that BDTH2 is a drug rather than a supplement and issued a warning, [12] [13] resulting in its removal from the market. [14] The main proponent of the compound, Dr. Boyd Haley, was chairman of the department of chemistry where research is also conducted on the utility of this compound for remediation of heavy metal pollution. [1] [11]
A toxic heavy metal is a common but misleading term for a metal noted for its potential toxicity. Not all heavy metals are toxic and some toxic metals are not heavy. Elements often discussed as toxic include cadmium, mercury and lead, all of which appear in the World Health Organization's list of 10 chemicals of major public concern. Other examples include chromium and nickel, thallium, bismuth, arsenic, antimony and tin.
In organic chemistry, a thiol, or thiol derivative, is any organosulfur compound of the form R−SH, where R represents an alkyl or other organic substituent. The −SH functional group itself is referred to as either a thiol group or a sulfhydryl group, or a sulfanyl group. Thiols are the sulfur analogue of alcohols, and the word is a blend of "thio-" with "alcohol".
Chelation is a type of bonding of ions and their molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate ligand and a single central metal atom. These ligands are called chelants, chelators, chelating agents, or sequestering agents. They are usually organic compounds, but this is not a necessity.
Mercury poisoning is a type of metal poisoning due to exposure to mercury. Symptoms depend upon the type, dose, method, and duration of exposure. They may include muscle weakness, poor coordination, numbness in the hands and feet, skin rashes, anxiety, memory problems, trouble speaking, trouble hearing, or trouble seeing. High-level exposure to methylmercury is known as Minamata disease. Methylmercury exposure in children may result in acrodynia in which the skin becomes pink and peels. Long-term complications may include kidney problems and decreased intelligence. The effects of long-term low-dose exposure to methylmercury are unclear.
Environmental remediation is the cleanup of hazardous substances dealing with the removal, treatment and containment of pollution or contaminants from environmental media such as soil, groundwater, sediment. Remediation may be required by regulations before development of land revitalization projects. Developers who agree to voluntary cleanup may be offered incentives under state or municipal programs like New York State's Brownfield Cleanup Program. If remediation is done by removal the waste materials are simply transported off-site for disposal at another location. The waste material can also be contained by physical barriers like slurry walls. The use of slurry walls is well-established in the construction industry. The application of (low) pressure grouting, used to mitigate soil liquefaction risks in San Francisco and other earthquake zones, has achieved mixed results in field tests to create barriers, and site-specific results depend upon many variable conditions that can greatly impact outcomes.
Chelation therapy is a medical procedure that involves the administration of chelating agents to remove heavy metals from the body. Chelation therapy has a long history of use in clinical toxicology and remains in use for some very specific medical treatments, although it is administered under very careful medical supervision due to various inherent risks, including the mobilization of mercury and other metals through the brain and other parts of the body by the use of weak chelating agents that unbind with metals before elimination, exacerbating existing damage. To avoid mobilization, some practitioners of chelation use strong chelators, such as selenium, taken at low doses over a long period of time.
Dimercaprol, also called British anti-Lewisite (BAL), is a medication used to treat acute poisoning by arsenic, mercury, gold, and lead. It may also be used for antimony, thallium, or bismuth poisoning, although the evidence for those uses is not very strong. It is given by injection into a muscle.
Succimer, sold under the brand name Chemet among others, is a medication used to treat lead, mercury, and arsenic poisoning. When radiolabeled with technetium-99m, it is used in many types of diagnostic testing. A full course of Succimer lasts for 19 days of oral administration. A second course should be given when more than two weeks pass after the first course.
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Deferoxamine (DFOA), also known as desferrioxamine and sold under the brand name Desferal, is a medication that binds iron and aluminium. It is specifically used in iron overdose, hemochromatosis either due to multiple blood transfusions or an underlying genetic condition, and aluminium toxicity in people on dialysis. It is used by injection into a muscle, vein, or under the skin.
Dithiothreitol (DTT) is an organosulfur compound with the formula (CH CH2SH)2. A colorless compound, it is classified as a dithiol and a diol. DTT is redox reagent also known as Cleland's reagent, after W. Wallace Cleland. The reagent is commonly used in its racemic form. Its name derives from the four-carbon sugar, threose. DTT has an epimeric ('sister') compound, dithioerythritol (DTE).
Boyd Eugene Haley is an American anti-vaccine activist and retired professor of chemistry at the University of Kentucky.
Metal toxicity or metal poisoning is the toxic effect of certain metals in certain forms and doses on life. Some metals are toxic when they form poisonous soluble compounds. Certain metals have no biological role, i.e. are not essential minerals, or are toxic when in a certain form. In the case of lead, any measurable amount may have negative health effects. There is a popular misconception that only heavy metals can be toxic, but lighter metals such as beryllium and lithium can be toxic too. Not all heavy metals are particularly toxic, and some are essential, such as iron. The definition may also include trace elements when abnormally high doses may be toxic. An option for treatment of metal poisoning may be chelation therapy, a technique involving the administration of chelation agents to remove metals from the body.
Susan Swedo is a researcher in the field of pediatrics and neuropsychiatry. Beginning in 1998, she was Chief of the Pediatrics & Developmental Neuroscience Branch at the US National Institute of Mental Health. In 1994, Swedo was lead author on a paper describing pediatric autoimmune neuropsychiatric disorders associated with streptococcal infections (PANDAS), a controversial hypothesis proposing a link between Group A streptococcal infection in children and some rapid-onset cases of obsessive-compulsive disorder (OCD) or tic disorders such as Tourette syndrome. Swedo retired from the NIH in 2019, and serves on the PANDAS Physician Network.
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