Denatonium

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Denatonium benzoate
)
Denatonium benzoate
Skeletal formula of the denatonium cation
Skeletal formula of the benzoate anion
Ball-and-stick models of the both ions in denatonium benzoate
Names
Preferred IUPAC name
N-Benzyl-2-(2,6-dimethylanilino)-N,N-diethyl-2-oxoethan-1-aminium benzoate
Other names
N-Benzyl-2-[(2,6-dimethylphenyl)amino]-N,N-diethyl-2-oxoethan-1-aminium benzoate
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
ECHA InfoCard
 100.020.996 Edit this at Wikidata
EC Number
  • 223-095-2
UNII
  • InChI=1S/C21H28N2O.C7H6O2/c1-5-23(6-2,15-19-13-8-7-9-14-19)16-20(24)22-21-17(3)11-10-12-18(21)4;8-7(9)6-4-2-1-3-5-6/h7-14H,5-6,15-16H2,1-4H3;1-5H,(H,8,9) checkY
    Key: VWTINHYPRWEBQY-UHFFFAOYSA-N checkY
  • InChI=1/C21H28N2O.C7H6O2/c1-5-23(6-2,15-19-13-8-7-9-14-19)16-20(24)22-21-17(3)11-10-12-18(21)4;8-7(9)6-4-2-1-3-5-6/h7-14H,5-6,15-16H2,1-4H3;1-5H,(H,8,9)
    Key: VWTINHYPRWEBQY-UHFFFAOYAY
  • [O-]C(=O)c1ccccc1.Cc2cccc(C)c2NC(=O)C[N+](CC)(CC)Cc3ccccc3
Properties
C28H34N2O3
Molar mass 446.581
Appearance white crystalline
Melting point 163 to 170 °C (325 to 338 °F; 436 to 443 K)
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H315, H318, H332, H412
P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P362, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Denatonium, usually available as denatonium benzoate (under

bitter chemical compound known, with bitterness thresholds of 0.05 ppm for the benzoate and 0.01 ppm for the saccharide.[1]
It was discovered in 1958 during research on
T.& H. Smith of Edinburgh, Scotland, and registered under the trademark Bitrex.[2]

Dilutions of as little as 10 

Nintendo Switch game cards to prevent accidental swallowing or choking by children. It is not known to pose any long-term health risks.[1]

The name denatonium reflects the substance's primary use as a

cation, hence -onium as a Neo-Latin suffix
.

Structure, synthesis, and physical properties

Denatonium is a

anion exchange reaction with sodium benzoate, or first sodium hydroxide to make denatonium hydroxide followed by neutralization with benzoic acid.[4] Other similar compounds are procaine and benzocaine.[5]

Biochemistry

Denatonium in humans is recognized by eight distinct

TAS2R47, being by far the most sensitive[clarification needed] to the compound.[6][7]

Denatonium can act as a bronchodilator by activating bitter taste receptors in the airway smooth muscle.[8]

Applications

The bitterness of the compound guides most applications of denatonium. Denatonium benzoate is used to

SD-40B, indicates that ethanol has been denatured using denatonium benzoate.[citation needed
]

Denatonium is commonly included in

placebos used in clinical trials to mimic the bitter taste of certain medications.[1]

Denatonium also discourages consumption of poisonous

inhalant abuse of the volatile vapors.[citation needed
]

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.[9] In December 2012, U.S. manufacturers voluntarily agreed to add denatonium benzoate to antifreeze sold nationwide.[10]

Animals are known to have different sensitivities to the effects of denatonium. It is used in some animal repellents (especially for such large

rat poisons from human consumption,[11] as humans are able to detect denatonium at much lower concentrations than rodents.[12]

Nintendo Switch game cartridges are coated in denatonium benzoate to prevent young children from consuming them.[13]

See also

References

  1. ^ a b c Final Report Study of Aversive Agents (PDF). Consumer Product Safety Commission United States of America. 18 November 1992. Archived from the original (PDF) on 16 June 2011. Retrieved 15 November 2010.
  2. ^ "Bitrex(R) — Branded Denatonium Benzoate". Macfarlan Smith. Archived from the original on 2010-08-17. Retrieved 2010-05-09.
  3. ^ "Ethanol Denaturants". The Online Distillery Network. 1993-11-22. Archived from the original on 2015-05-10. Retrieved 2007-09-30.
  4. ^
    S2CID 247905372
    .
  5. ^ Holvoet, Jean-Patrick. "Denatonium". Sentinalco. Retrieved 2 October 2015.
  6. PMID 20022913
    .
  7. ^ "BitterDB - Denatonium benzoate". Hebrew University of Jerusalem. Retrieved 11 June 2013.
  8. PMID 20972434
    .
  9. PMID 15171494
    .
  10. ^ "Antifreeze and Engine Coolant Being Bittered Nationwide". Consumer Specialty Products Association. 13 December 2012. Archived from the original on 28 December 2012. Retrieved 30 June 2016.
  11. ^ "Rats - Rat Poison & Rat Bait Stations". Pestcontrolshop.co.uk. Archived from the original on 2011-01-06. Retrieved 2011-01-17.
  12. doi:10.1016/j.physbeh.2003.09.009
  13. ^ Dornbush, Johnathon (2 March 2017). "Nintendo Switch Cartridges Taste Terrible". IGN. Retrieved 15 Sep 2020.
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