Bitrex

Denatonium benzoate

Names
IUPAC name phenylmethyl-[2- [(2,6-dimethylphenyl)amino]- 2-oxoethyl]-diethylammonium benzoate
Identifiers
CAS Number	3734-33-6 Y
3D model (Jmol)	Interactive image
ChemSpider	18392 Y
ECHA InfoCard	100.020.996
PubChem CID	19518
UNII	M5BA6GAF1O Y
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) 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(Nc1c(cccc1C)C)C[N+](Cc2ccccc2)(CC)CC.[O-]C(=O)c1ccccc1
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
R-phrases	R22 R36 R37 R38
S-phrases	S26 S36
NFPA 704	1 1 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

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

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, nail biting preventions, respirator mask fit-testing, animal repellents, liquid soaps, and shampoos. It is not known to pose any long-term health risks.

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. Other similar compounds are procaine and benzocaine.