Denatonium

Denatonium, usually available as denatonium benzoate (under trade names such as Denatrol, BITTERANT-b, BITTER+PLUS, Bitrex, Bitrix, and 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 T.& H. Smith of Edinburgh, Scotland, and registered under the trademark Bitrex.

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
EC Number
  • 223-095-2
PubChem CID
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) Y
    Key: VWTINHYPRWEBQY-UHFFFAOYSA-N Y
  • 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
SMILES
  • [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:
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)
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 YN ?)
Infobox references

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, preventive nail biting preparations, respirator mask fit-testing, animal repellents, liquid soaps, shampoos, and Nintendo Switch game cards to prevent accidental swallowing or choking by children. It is not known to pose any long-term health risks.

The name denatonium reflects the substance's primary use as a denaturant and its chemical nature as a cation, hence -onium as a Neo-Latin suffix.

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