Denatonium: Difference between revisions

| verifiedrevid = 434610104

| ImageFile1=Denatonium chemical structure.svg

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| ImageFile2=Denatonium benzoate chemical structure part 2.svg

| ImageSize2= 100px

| IUPACName=phenylmethyl-[2- [(2,6-dimethylphenyl)amino]- 2-oxoethyl]-diethylammonium benzoate

| OtherNames=

| Section1= {{Chembox Identifiers

| CASNo=3734-33-6

| PubChem=19518

| SMILES = O=C(Nc1c(cccc1C)C)C[N+](Cc2ccccc2)(CC)CC.[O-]C(=O)c1ccccc1

| Section2= {{Chembox Properties

| Formula=C₂₈H₃₄N₂O₃

| MolarMass=446.581

| Appearance=white crystalline

| Density=

| MeltingPt=163-170 °C

| BoilingPt=

| Solubility=

| SolubleOther=

| Section3= {{Chembox Hazards

| MainHazards=

| FlashPt=

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}}

'''Denatonium''', usually available as '''denatonium benzoate''' (under [[trade name]]s such as '''''Bitrex''''' or '''''Aversion''''') and as '''denatonium saccharide''', is the [[Bitter_(taste)#Bitterness|bitterest]] chemical [[Chemical compound|compound]] known; with bitterness thresholds of 0.05 ppm for the benzoate and 0.01 ppm for the saccharide<ref>{{Cite conference | first = | last = | authorlink = | coauthors = | title = Final Report Study of Aversive Agents | booktitle = | pages = | publisher = Consumer Product Safety Commission United States of America | date = 18 November 1992 | location = | url = http://www.cpsc.gov/LIBRARY/FOIA/foia99/os/aversive.pdf | doi = | id = | accessdate = 15 November 2010}}</ref>.

It was discovered in 1958 during research on [[local anesthetic]]s by Macfarlan Smith of [[Edinburgh]], [[Scotland]], and registered under the trademark ''Bitrex''.<ref>{{cite web | title = Bitrex(R) — Branded Denatonium Benzoate | url = http://www.macsmith.com/index.php?page=bitrex | publisher = Macfarlan Smith | accessdate = 2010-05-09}}</ref> Dilutions of as little as 10 [[Parts-per notation#Types of Parts-per notations|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 agent]]s to prevent accidental [[eating|ingestion]]. Denatonium is used in [[denatured alcohol]],<ref>{{cite web | title = Ethanol Denaturants | url = http://www.distill.com/specs/EU2.html | date = 1993-11-22 | publisher = The Online Distillery Network}}</ref> [[antifreeze]], [[nail biting]] preventions, [[respirator]] mask fit-testing, [[animal repellent]]s, [[soap|liquid soaps]], and [[shampoo]]s. It is not known to pose any long-term health risks.<ref>{{Cite conference | first = | last = | authorlink = | coauthors = | title = Final Report Study of Aversive Agents | booktitle = | pages = | publisher = Consumer Product Safety Commission United States of America | date = 18 November 1992 | location = | url = http://www.cpsc.gov/LIBRARY/FOIA/foia99/os/aversive.pdf | doi = | id = | accessdate = 15 November 2010}}</ref>

== Structure and physical properties ==

Denatonium is a [[quaternary ammonium cation]]. It is a compound of a [[salt]] with an [[inert]] [[ion|anion]] like [[benzoate]] or [[saccharide]]. The structure of denatonium is related to the [[local anesthetic]] [[lidocaine]], differing only by the addition of a [[benzyl]] [[Functional group|group]] to the [[amino group|amino]] [[nitrogen]].

The bitterness of the compound guides most applications of denatonium. Denatonium benzoate is used to [[denatured alcohol|denature ethanol]] so that it is not taxed as an [[alcoholic beverage]]. One designation in particular, [[SD alcohol 40-B|SD-40B]], indicates that ethanol has been denatured using denatonium benzoate. The common name for this chemical, ''denat''onium, alludes to this application.

Denatonium also discourages consumption of harmful [[alcohol]]s like [[Methanol|methyl alcohol]], and additives like [[ethylene glycol]]. Denatonium is also used in [[rubbing alcohol]] as an inactive ingredient. It is also added to many kinds of harmful liquids including [[solvent]]s (such as [[nail polish remover]]), [[paint]]s, [[varnish]]es, 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 duster|canned air dusters]]) to discourage [[inhalant abuse]] of the volatile vapors.

Since 1995, when the U.S. State of [[Oregon]] required that denatonium benzoate be added to antifreeze and windshield washer fluid, the compound has been increasingly found in these substances throughout the world. The addition is credited with saving children and animals who might otherwise drink sweet [[antifreeze]] or [[Windshield washer fluid|wiper fluid]] and get [[ethylene glycol]] or [[methanol]] poisoning respectively.

Animals are known to have different sensitivities to the effects of denatonium. It is used in some animal repellents (especially for such large [[mammal]]s as [[deer]]). It has been used to safeguard [[rat poison]]s from human consumption,<ref>{{cite web|url=http://www.pestcontrolshop.co.uk/acatalog/rats.html |title=Rats - Rat Poison & Rat Bait Stations |publisher=Pestcontrolshop.co.uk |date= |accessdate=2011-01-17}}</ref> as humans are able to detect denatonium at much lower concentrations than rodents.<ref>[http://dx.doi.org/doi:10.1016/j.physbeh.2003.09.009 The distinctiveness of ionic and nonionic bitter stimuli]. Frank ME, Bouverat BP, MacKinnon BI, Hettinger TP. ''Physiol Behav''. 2004 Jan;80(4):421-31.</ref> However, some [[cat]]s have been known to be tempted by them — 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 [[genetics|genetic]] factor similar to that affecting human perceptions of the taste of [[phenylthiocarbamide]].{{Fact|date=February 2007}}

{{refs}}

[[Category:Inhalants]]

[[cs:Denatoniumbenzoát]]

[[de:Denatoniumbenzoat]]

[[fa:دناتونیوم]]

[[fr:Benzoate de dénatonium]]

[[nl:Denatoniumbenzoaat]]

[[ja:デナトニウム]]

[[pl:Benzoesan denatonium]]

[[pt:Denatônio]]

[[fi:Denatonium]]

[[sv:Denatoniumbensoat]]

[[zh:苯甲地那铵]]