Denatonium

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
CAS Number	3734-33-6 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1371493 ;
ChemSpider	18392 ;
ECHA InfoCard	100.020.996
EC Number	223-095-2;
PubChem CID	19518;
UNII	M5BA6GAF1O ;
CompTox Dashboard (EPA)	DTXSID8034376 ;
	InChI 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) Key: VWTINHYPRWEBQY-UHFFFAOYSA-N ; 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
Chemical formula	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:
Pictograms
Signal word	Danger
Hazard statements	H302, H315, H318, H332, H412
Precautionary statements	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). verify (what is ?) Infobox references

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.^[1] It was discovered in 1958 during research on local anesthetics by T. & H. Smith of Edinburgh, Scotland, and registered under the trademark Bitrex.^[2]

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,^[3] 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.^[1]

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.

^ ^a ^b 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.
^ "Bitrex(R) — Branded Denatonium Benzoate". Macfarlan Smith. Archived from the original on 2010-08-17. Retrieved 2010-05-09.
^ "Ethanol Denaturants". The Online Distillery Network. 1993-11-22. Archived from the original on 2015-05-10. Retrieved 2007-09-30.

[auto-1] 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.

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