Denatonium
- Benzyldiethyl (2,6- xylylcarbamoyl ) - methylammoniumbenzoat
- Bitrex ®
- Aversion ®
White, odorless powder
Fixed
163-170 ° C
45 g · L-1 in water (at 20 ° C)
Attention
584 mg · kg -1 ( LD50, rat, oral)
Template: Infobox chemical / molecular formula search available
Denatonium, available as denatonium benzoate or Denatoniumsaccharinat, is the bitterest known substance ( bittern ). Was discovered in 1958 by the Scottish chemist denatonium JR Smith in the search for drugs for local anesthesia.
Structure and Properties
Denatonium is a quaternary ammonium compound and a derivative of the local anesthetic lidocaine with an additional benzyl group on the amine nitrogen. As benzoic acid anion or saccharin is often used.
Solution concentrations of 10 ppm have an intolerable for human bitter taste. The salts of denatonium are usually colorless and odorless, but are usually offered only as solutions on the market.
Synthesis
The synthesis of lidocaine by reaction with benzyl bromide and subsequent precipitation with benzoic acid.
Applications
The bitter taste of Denatoniumbenzoats is crucial for its applications. It is used to denature ethanol so that the alcohol is no longer suitable for human consumption. This allows an exemption from the tax on spirits reach. Other alcohols are also treated with denatonium to prevent personal injury resulting from accidental or deliberate enjoyment, the intake of methanol can otherwise lead to blindness, for example.
Denatonium is used to prevent accidental swallowing of harmful liquids by small children. To find denatonium in solvents, detergents, shampoos, soaps, and in nail polish against the chewing fingernails use.
About long-term health risks are no findings.
Denatonium works on animals other than humans. So can be assumed that the rats Bittern in the usual concentrations hardly notice. Therefore, rat poison for security can also be treated with denatonium and protects humans and other animals from accidental ingestion of the poison. However, there are also cats that were observed as they ate the poison bait. For them, a genetic defect is suspected, the basis of which they also were not able to perceive the bitter substance.