Tetramethylenedisulfotetramine

Tetramethylenedisulfotetramine[1]
Names
IUPAC name
2,6-Dithia-1,3,5,7-tetraaza-tricyclo[3.3.1.13,7]decane 2,2,6,6-tetraoxide
Other names
Tetramine, TETS, DSTA, Dushuqiang, Four-two-four, 424, NSC 172824, Meishuming, Sanbudao
Identifiers
80-12-6 YesY
Abbreviations TETS, DSTA
ChemSpider 57722 YesY
Jmol interactive 3D Image
PubChem 64148
Properties
C4H8N4O4S2
Molar mass 240.26 g/mol
Appearance White powder
Melting point 255 to 260 °C (491 to 500 °F; 528 to 533 K)
0.25 mg/mL
Hazards
Main hazards Poison
Lethal dose or concentration (LD, LC):
0.20 mg/kg (mice)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Tetramethylenedisulfotetramine (TETS) is an organic compound that is used as a rodenticide (rat poison).[2] It is an odorless, tasteless white powder that is slightly soluble in water, DMSO and acetone, and insoluble in methanol and ethanol. It is a sulfamide derivative. When crystallized from acetone, it forms cubic crystals with a melting point of 255–260 °C.

Toxicity and mechanism

TETS is a neurotoxin,[3] causing lethal convulsions.[4] Its effect is similar to picrotoxin, a GABA-A receptor antagonist widely used in research. As one of the most hazardous pesticides, it is 100 times more toxic than potassium cyanide. It might be a more powerful convulsant than the glycine antagonist strychnine. TETS is an non-competitive GABA antagonist and binds irreversibly to neuronal GABA receptors and disables chloride channels, activating neurons. No antidote is known. The lethal dose for humans is 7–10 mg. Poisoning is diagnosed by gas chromatography and the treatment is mainly supportive, with large doses of benzodiazepines and pyridoxine (A form of vitamin B6).[5] It is retained in tissues of poisoned poultry and animals, and can pose severe risk of secondary poisoning.

Continued use in China

Its use worldwide has been banned since 1984, but due to continuing demand and its ease of production,[6][7] it is still readily, although illegally, available in China and can be found in some illegally imported rat poisons. The best known Chinese rodenticide, containing about 6–20% TETS, is Dushuqiang, "very strong rat poison". It has been used for mass poisonings in China: in April 2004, there were 74 casualties after eating scallion-flavored pancakes tainted by their vendor's competitor; and in September 2002, 400 people were poisoned and 38 died from contaminated food.[8][9] In 2002, there was one documented case of accidental poisoning in the US.[5]

References

  1. ↑ Merck Index, 11th Edition, 9158.
  2. ↑ "Basic datasheet for tetramethylene disulfotetramine". Inchem.
  3. ↑ Banks CN , Yang D, Lein PJ, Rogawski MA (2014). "Tetramethylenedisulfotetramine". In P. Wexler. Encyclopedia of Toxicology, 3rd edition. Elsevier Inc., Academic Press. pp. 509–511.
  4. ↑ Zolkowska, D.; Banks, C. N.; Dhir, A.; Inceoglu, B.; Sanborn, J. R.; McCoy, M. R.; Bruun, D. A.; Hammock, B. D.; Lein, P. J.; Rogawski, M. A. (2012). "Characterization of Seizures Induced by Acute and Repeated Exposure to Tetramethylenedisulfotetramine". Journal of Pharmacology and Experimental Therapeutics 341 (2): 435–446. doi:10.1124/jpet.111.190579. PMC 3336809. PMID 22328574.
  5. 1 2 CDC (2003). "Poisoning by an Illegally Imported Chinese Rodenticide Containing Tetramethylenedisulfotetramine - New York City, 2002". JAMA 289 (20): 2640–2642. doi:10.1001/jama.289.20.2640. PMID 12771101.
  6. ↑ Hecht, G.; Henecka, H. (1949). "Über ein hochtoxisches Kondensationsprodukt von Sulfamid und Formaldehyd" [About a Highly Toxic Condensation Product of Sulfamide and Formaldehyde]. Angewandte Chemie (in German) 61 (9): 365–366. doi:10.1002/ange.19490610905.
  7. ↑ US patent 2650186, Hecht, G.; Henecka, H.; Meisenheimer, M., "Rodenticidal compositions", issued 1953-08-25, assigned to Bayer Leverkusen, Germany
  8. ↑ Whitlow, K. S.; Belson, M.; Barrueto, F.; Nelson, L.; Henderson, A. K. (2005). "Tetramethylenedisulfotetramine: Old Agent and New Terror" (pdf). Annals of Emergency Medicine 45 (6): 609–613. doi:10.1016/j.annemergmed.2004.09.009. PMID 15940093.
  9. ↑ Croddy, E. (2004). "Rat Poison and Food Security in the People's Republic of China: Focus on Tetramethylene Disulfotetramine (Tetramine)". Archives of Toxicology 78 (1): 1–6. doi:10.1007/s00204-003-0509-0. PMID 14551672.
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