Denatonium
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| Denatonium benzoate | |
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| Chemical name | N-benzyl-2-(2,6-dimethylphenylamino)- N,N-diethyl-2-oxoethanaminium benzoate |
| Chemical formula | C21H29N2O·C7H5O2 |
| Molecular mass | 446.58 g/mol |
| Melting point | 166-170 °C |
| CAS number | 3734-33-6 |
| SMILES | CC1=CC=CC(C)=C1NC(C[N+] (CC)(CC)CC2=CC=CC=C2)=O. O=C([O-])C3=CC=CC=C3 |
| Missing image Denatonium_chemical_structure.png Chemical structure of Denatonium Missing image Denatonium_benzoate_chemical_structure_part_2.png Chemical structure of benzoate | |
Denatonium, usually available as denatonium benzoate (e.g. under the tradename Bitrex) and as denatonium saccharide, is the bitterest compound known. It was discovered in 1958 during research on local anesthetics. Dilutions of as little as ten parts per million 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 to prevent accidental ingestion. Denatonium is used in denatured alcohol, antifreeze, nail biting preventions, animal repellents, liquid soaps, and shampoos. It is not known to pose any long-term health risks although exposure may be irritating and unpleasant.
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.
Applications
The bitterness of the compound guides most applications of denatonium. Denatonium is used to denature ethanol so that it is not taxed as an alcoholic beverage. One designation in particular, SD-40, indicates that ethanol has been denatured using denatonium. In fact, the common name for this chemical, denatonium alludes to this application.
Denatonium also discourages consumption of harmful alcohols like methyl alcohol and isopropyl alcohol. Denatonium is therefore often used in rubbing alcohol as a non-active ingredient. It's also added to all kinds of harmful liquids including solvents, paints, varnishes, toiletries, and other household products.
Since 1995 when Oregon required that it be added to antifreeze and windshield wiper fluid, the compound has been increasingly found in these substances throughout the world. The addition of denatonium is credited with saving children and animals who might otherwise drink sweet antifreeze or wiper fluid and get ethylene glycol or methanol poisoning respectively.
Other uses include nail polish for preventing nail biting, and as animal repellent (especially for big game like deer).
It should be noted that animals are known to have different sensitivities to the effects of denatonium. It has been used to safeguard rat poisons, so presumably rats are not deterred by it, although there is evidence that a small percentage of rodents do avoid it. Some cats have been known to disturb such baits - it may not be as effective a deterrent for them 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.
External links
- Welcome to Bitrex (http://www.bitrex.com/)
- Denatonium benzoate product description (http://ntapl.com/DB_prod.htm)
- MSDS for users of Denatonium Benzoate (http://www.rcpharmachem.com/rcpharmachem/msds.php?ms=1)