Denatonium benzoate

Benzyldiethyl[(2,6-xylylcarbamoyl)methyl]ammoniumbenzoate (denatonium benzoate [3734-33-6] Bitrex) is an extremely bitter tasting, nonirritating, and nonmutagenic compound that has been widely used in many household products such as detergents, nail poHsh removers, and cleaning agents, to prevent childhood poisoning. It is also used as an alcohol denaturant. 

When used in products not licensed for drinking, ethanol usually occurs in the form of denatured alcohol, or specially denatured alcohol—alcohol that has been rendered unfit for drinking. You will often see SD alcohol mentioned on a label, sometimes followed by a number and letter, such as 40-B. This is the designation given by the U.S. Bureau of Alcohol, Tobacco, and Firearms to the denaturing method used. For example, SD-40 is ethanol denatured by adding tiny amounts of the most bitter-tasting substance known denatonium benzoate. 

Denatonium benzoate is the bitterest-tasting substance known. It gets its name from denatured alcohol—alcohol that has been rendered unfit for drinking—and is often used in the denaturing process. Specially denatured alcohol 40, or SD-40, is ethanol that has been denatured by a tiny amount of denatonium benzoate. Denatonium benzoate is an ester of PABA, and is related to lidocaine, benzocaine, novocaine, and cocaine. 

Pranaityte, B., Daunoravicus, Z., and Padarauskas, A. (2004). Development and validation of a capillary electrophoresis method for the determination of denatonium benzoate in denaturated alcohol formulations. Chromatographia 60(5 — 6), 353 — 357. 

When the counterion is a UV-absorbing compound, two articles describe simultaneous determination of the drug with its counterion. This was done for denatonium benzoate by Assi et al. and ragaglitazar arginine by Jamali and Lehmann. 

Recently, studies were reported measuring the kinetics of stimulation of both cAMP and 3 using a mixing device and rapid quenching, in the millisecond range, in rat olfactory cilia (67). The response to a mixture of < orants peaks within 25 to 50 milliseconds, the time frame expected for receptors, with both cAMP and IP3. Similar measurements of the change in concentration of cAMP or IP3 were also done in the taste cell. Here mice, which were bred as bitter tasters and nontasters , were used as subjects. The bitter stimuli, sucrose octaacetate, strychnine and denatonium benzoate, were shown to increase IP3 levels in a membrane preparation from "taster" mice in the presence of GTP-protein and Ca but not in membranes from "nontaster" mice (68). 

Salicylic acid 17% w/w, alcohol, 26.3% w/w, t-Butyl alcohol, denatonium benzoate, flexible collodion, and propylene glycol dipelargonate. 

Denatonium benzoate Synthetic added to toxic substances Bitter (one of the... 

Note. Two other classes of methylated spirits are recognised in the United Kingdom mineralised methylated spirits and denatured ethanol. Mineralised methylated spirits is ethanol of an appropriate strength, 90 parts by volume mixed with wood naphtha 9.5 parts by volume and crude pyridine 0.5 parts by volume, and to every 2000 litres of this mixture is added 7.5 litres of mineral naphtha (petroleum oil) and 3.0 g of methyl violet. Denatured ethanol is ethanol, of a strength not less than 85% v/v, 98 parts by volume mixed with propanol 2 parts by volume, and to the resulting mixture is added denatonium benzoate 10 pg/ml, or solid quassin 120 pg/ml, or sucrose octa-acetate 4000 pg/ml. 

Rubbing Alcohol U.S.P.) is a mixture of acetone 8 volumes, methyl isobutyl ketone 1.5 volumes, and Alcohol 100 volumes the mixture contains not less than 3550 pg/ml of sucrose octa-acetate, or 14 pg/ml of denatonium benzoate. 

Denatonium Benzoate 467.5 Saccharin Calcium 492.7 Isometheptene Mucate... 

Azacyclonol Betahistine Denatonium Benzoate Mequitazine Stilbazium Iodide... 

Denatonium benzoate is among the most bitter of substances known and is detectable at concentrations of approximately 10 ppb. In pharmaceutical and other industrial applications it is added to some products as a deterrent to accidental ingestion. It is most commonly used at levels of 5-500 ppm. Denatonium benzoate may also be used to replace brucine or quassin as a denaturant for ethanol. 

In pharmaceutical formulations, denatonium benzoate has been used as a flavoring agent in placebo tablets, and in a topical formulation it has been used in an anti-nailbiting preparation. ... 

Denatonium benzoate occurs as an odorless, very bitter tasting, white crystalline powder or granules. 

Denatonium benzoate is incompatible with strong oxidizing agents. 

Denatonium benzoate was first synthesized in the 1950s and is usually prepared by reacting denatonium chloride with benzyl benzoate. 

Denatonium benzoate is generally regarded as a nonirritant and nonmutagenic substance. However, there has been a single report of contact urticaria attributed to denatonium benzoate occurring in a 30-year-old man who developed asthma and pruritus after using an insecticidal spray denatured with denatonium benzoate. ... 

Observe normal precautions appropriate to the circumstances and quantity of material handled. Containers should be kept tightly closed and handled in areas with good ventilation. Eye protection, gloves, and a dust mask are recommended. Denatonium benzoate is moderately toxic by ingestion and when heated to decomposition emits toxic vapors of NO ,. Denatonium benzoate may also cause hypersensitization. 

Denatonium benzoate is used worldwide as a denaturant for alcohol. It is included in the FDA Inactive Ingredients Guide (topical gel and solution). 

Bjorkner B. Contact urticaria and asthma from denatonium benzoate (Bitrex). Contact Dermatitis 1980 6(7) 466-471. 

Sugden K, Mayne TG, Loscombe CR. Determination of denatur-ants in alcoholic toilet preparations 1 denatonium benzoate (Bitrex) by high performance liquid chromatography. Analyst 1978 103(Jun) 653-656. 

Faulkner A, DeMontigny P. High-performance liquid chromatographic determination of denatonium benzoate in ethanol with 5 % polyvinylpyrrolidone. / Chromatogr-A 1995 715(1) 189-194. Henderson MC, Neumann CM, Buhler DR. Analysis of denatonium benzoate in Oregon consumer products by HPLC. Chemo-sphere 1998 36(1) 203-210. 

Several HPLC methods of analysis for denatonium benzoate have been reported. The EINECS number for denatonium... 

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