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Denatonium, usually available as denatonium benzoate (under such as Denatrol, BITTERANT-b, BITTER+PLUS, Bitrex, Bitrix, and Aversion) and as denatonium saccharinate ( BITTERANT-s), is the bitterest chemical compound known, with bitterness thresholds of 0.05 ppm for the benzoate and 0.01 ppm for the saccharinate. It was discovered in 1958 during research on by T. & H. Smith of , Scotland, and registered under the trademark Bitrex.

Dilutions of as little as 10 ppm are unbearably bitter to most people. Denatonium salts are usually colorless and odorless solids, but are often traded as solutions. They are used as () to prevent inappropriate ingestion. Denatonium is used in denatured alcohol, , preventive preparations, mask fit-testing, , , , and Nintendo Switch game cards to prevent accidental swallowing or choking by children. It is not known to pose any long-term health risks.

The name denatonium reflects the substance's primary use as a denaturant and its chemical nature as a , hence as a .


Structure, synthesis, and physical properties
Denatonium is a quaternary ammonium cation. It is composed as a salt with any of several , such as or . It can be obtained by the quaternization of , a popular anesthetic, with or a similar reagent. To obtain other salts, like the benzoate, the formed denatonium chloride is subjected to an reaction with , or first to make denatonium hydroxide followed by neutralization with . Other similar compounds are and .


Biochemistry
Denatonium in humans is recognized by eight distinct bitter taste receptors: TAS2R4, TAS2R8, TAS2R10, TAS2R39, TAS2R43, TAS2R16, TAS2R46, and TAS2R47, being by far to the compound.

Denatonium can act as a by activating bitter taste receptors in the airway smooth muscle.


Applications
The bitterness of the compound guides most applications of denatonium. Denatonium benzoate is used to denature ethanol so that it is not treated as an alcoholic beverage with respect to taxation and sales restrictions. One designation in particular, SD-40B, indicates that ethanol has been denatured using denatonium benzoate.

Denatonium is commonly included in used in clinical trials to mimic the bitter taste of certain medications.

Denatonium benzoate is an ingredient in certain and varnishes designed to discourage , as the bitter denatonium serves as an .

Denatonium also discourages consumption of poisonous alcohols such as and additives such as . It is also added to many kinds of harmful liquids, including (such as nail polish remover), , , toiletries and other items, special nail polish for preventing nail biting, and various other household products. It is also added to less hazardous aerosol products (such as ) to discourage of the volatile vapors.

In 1995, the U.S. state of required that denatonium benzoate be added to products containing sweet-tasting ethylene glycol and methanol such as and windshield washer fluid to prevent poisonings of children and animals. In December 2012, U.S. manufacturers voluntarily agreed to add denatonium benzoate to antifreeze sold nationwide.

Animals are known to have different sensitivities to the effects of denatonium. It is used in some animal repellents (especially for such large as ). It has been used to safeguard from human consumption, as humans are able to detect denatonium at much lower concentrations than rodents.Frank ME, Bouverat BP, MacKinnon BI, Hettinger TP. The distinctiveness of ionic and nonionic bitter stimuli. Physiol Behav. 2004 Jan;80(4):421-31.

and Nintendo Switch 2 game cartridges are coated in denatonium benzoate to prevent young children from consuming them.

Lithium , which can cause severe internal injuries if swallowed, are sometimes coated with denatonium benzoate to discourage small children from swallowing them.


See also

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