2891. Denatonium Benzoate

Nomenclature

CAS number: 3734-33-6
N-[2-[(2,6-Dimethylphenyl)amino]-2-oxoethyl]-N,N-diethylbenzenemethanaminium benzoate; benzyldiethyl[(2,6-xylylcarbamoyl)methyl]ammonium benzoate; lignocaine benzyl benzoate; Bitrex (Macfarlan Smith).
C28H34N2O3; mol wt 446.58.
C 75.31%, H 7.67%, N 6.27%, O 10.75%.

Description and references

Prepn: J. E. Hay, US 3080327 (1963 to T. & H. Smith Ltd.); idem, US 3268575 (1966 to Edinburgh Pharm. Ind.). HPLC determn in rapeseed oil: C. E. Damon, B. C. Pettitt, Jr., J. Chromatogr. 195, 243 (1980). Brief review of substance history and uses: H. A. S. Payne, Chem. Ind. (London) 22, 721-723 (1988).

Chemical structure

Properties

Crystals from isopropyl alcohol + ethyl acetate, mp 166-170°. Among the most bitter substances known to man. Soluble in water, alcohol; sparingly sol in acetone. Practically insol in ether.

Use

Pharmaceutic aid (alcohol denaturant; flavor). Added to toxic substances as a deterrent to accidental ingestion. Can replace brucine or quassin as denaturant for ethyl alcohol.