phenylmethyl-[2- [(2,6-dimethylphenyl)amino]- 2-oxoethyl]-diethylammonium benzoate
3D model (JSmol)
|Melting point||163 to 170 °C (325 to 338 °F; 436 to 443 K)|
|R-phrases (outdated)||R22 R36 R37 R38|
|S-phrases (outdated)||S26 S36|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Denatonium, usually available as denatonium benzoate (under trade names such as BITTERANT-b, BITTER+PLUS, Bitrex or Aversion) and as denatonium saccharide (BITTERANT-s), is the most bitter chemical compound known, with bitterness thresholds of 0.05 ppm for the benzoate and 0.01 ppm for the saccharide. It was discovered in 1958 during research on local anesthetics by MacFarlan Smith of Edinburgh, Scotland, and registered under the trademark Bitrex.
Dilutions of as little as 10 ppm are unbearably bitter to most humans. Denatonium salts are usually colorless and odorless solids but are often traded as solutions. They are used as aversive agents (bitterants) to prevent inappropriate ingestion. Denatonium is used in denatured alcohol, antifreeze, nail biting preventions, respirator mask fit-testing, animal repellents, liquid soaps, and shampoos. It is not known to pose any long-term health risks.
Structure and physical properties
Denatonium is a quaternary ammonium cation. It is a compound of a salt with an inert anion like benzoate or saccharide. The structure of denatonium is related to the local anesthetic lidocaine, differing only by the addition of a benzyl group to the amino nitrogen. Other similar compounds are procaine and benzocaine.
One of the chemical names for the compound is Lidocaine benzylbenzoate, although denatonium only denotes the quaternary ammonium cation species itself, and does not necessitate the benzoate counterion.
Denatonium in humans is recognized by eight distinct bitter taste receptors: TAS2R4, TAS2R8, TAS2R10, TAS2R39, TAS2R43, TAS2R16, TAS2R46, TAS2R47, with TAS2R47 being by far the most sensitive to the compound.
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. The common name for this chemical, denatonium, alludes to this application.
Denatonium is commonly included in placebo medications used in clinical trials to match the bitter taste of certain medications.
Denatonium also discourages consumption of harmful alcohols like methanol, and additives like ethylene glycol. Denatonium is used in rubbing alcohol as an inactive ingredient. It is also added to many kinds of harmful liquids including solvents (such as nail polish remover), paints, varnishes, toiletries and other personal care items, special nail polish for preventing nail biting, and various other household products. It is also added to less hazardous aerosol products (such as gas dusters) to discourage inhalant abuse of the volatile vapors.
In 1995, the U.S. state of Oregon required that denatonium benzoate be added to products containing sweet-tasting ethylene glycol and methanol such as antifreeze 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 mammals as deer). It has been used to safeguard rat poisons from human consumption, as humans are able to detect denatonium at much lower concentrations than rodents. However, some cats have been known to be tempted by them[clarification needed]—it may not be as effective a deterrent for cats as it is for humans, or perhaps some cats are not deterred due to a genetic factor similar to that affecting human perceptions of the taste of phenylthiocarbamide.
The video game company Nintendo uses denatonium benzoate on their physical Game Cards for their hybrid gaming console, the Nintendo Switch. The aversive agent is coated on the game cartridges to deter children from ingesting them.
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- Kwame Opam (1 March 2017). "Yes, Nintendo Switch cartridges taste terrible". theverge.com.