Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C21H29N2O.C2H3O2.H2O |
| Molecular Weight | 402.5271 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.CC([O-])=O.CC[N+](CC)(CC(=O)NC1=C(C)C=CC=C1C)CC2=CC=CC=C2
InChI
InChIKey=GNXLNAUMSDPCGP-UHFFFAOYSA-N
InChI=1S/C21H28N2O.C2H4O2.H2O/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;1-2(3)4;/h7-14H,5-6,15-16H2,1-4H3;1H3,(H,3,4);1H2
| Molecular Formula | C21H29N2O |
| Molecular Weight | 325.4678 |
| Charge | 1 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C2H3O2 |
| Molecular Weight | 59.044 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Denatonium, usually available as denatonium benzoate (trade names Bitrex) is the most bitter chemical compound known, with bitterness thresholds of 0.05 ppm for the benzoate and 0.01 ppm for the saccharide. Scientists at Macfarlan Smith, Ltd. of Edinburgh, Scotland discovered Bitrex during research on derivatives of the anesthetic lidocaine. The extremely bitter taste proved effective in reducing ingestion by humans and animals. Denatonium is commonly included in placebo medications used in clinical trials to match the bitter taste of certain medications. Denatonium activates bitter taste receptor, mainly, TAS2R4, TAS2R8, TAS2R10, TAS2R13 on many cell types and plays important roles in chemical release, ciliary beating and smooth muscle relaxation through intracellular Ca(2+)-dependent pathways.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Q9NYW5 Gene ID: 50832.0 Gene Symbol: TAS2R4 Target Organism: Homo sapiens (Human) |
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Target ID: Q9NYV9 Gene ID: 50838.0 Gene Symbol: TAS2R13 Target Organism: Homo sapiens (Human) |
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Target ID: Q9NYW0 Gene ID: 50839.0 Gene Symbol: TAS2R10 Target Organism: Homo sapiens (Human) |
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Target ID: Q9NYW2 Gene ID: 50836.0 Gene Symbol: TAS2R8 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
Doses
| Dose | Population | Adverse events |
|---|---|---|
300 ppm single, ophthalmic Dose: 300 ppm Route: ophthalmic Route: single Dose: 300 ppm Sources: |
healthy, 27 years (range: 22–33 years) Health Status: healthy Age Group: 27 years (range: 22–33 years) Sex: M+F Sources: |
|
1 umol/kg single, intragastric Dose: 1 umol/kg Route: intragastric Route: single Dose: 1 umol/kg Sources: |
healthy, 29 years |
|
1.69 mg/mL single, respiratory Dose: 1.69 mg/mL Route: respiratory Route: single Dose: 1.69 mg/mL Sources: |
healthy, 34 years |
Other AEs: Asthma... |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Asthma | 1 patient | 1.69 mg/mL single, respiratory Dose: 1.69 mg/mL Route: respiratory Route: single Dose: 1.69 mg/mL Sources: |
healthy, 34 years |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Immunocytochemical evidence for co-expression of Type III IP3 receptor with signaling components of bitter taste transduction. | 2001 |
|
| Covariation in individuals' sensitivities to bitter compounds: evidence supporting multiple receptor/transduction mechanisms. | 2001 Jul |
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| Effect of compound sequence on bitterness enhancement. | 2001 May |
|
| Rats fail to discriminate quinine from denatonium: implications for the neural coding of bitter-tasting compounds. | 2002 Mar 1 |
|
| Role of the G-protein subunit alpha-gustducin in taste cell responses to bitter stimuli. | 2003 Oct 29 |
|
| Was it necessary to add Bitrex (denatonium benzoate) to automotive products? | 2004 Jun |
|
| Identification of ligands for two human bitter T2R receptors. | 2004 Sep |
|
| Diverse bitter stimuli elicit highly similar patterns of Fos-like immunoreactivity in the nucleus of the solitary tract. | 2004 Sep |
|
| Umami taste responses are mediated by alpha-transducin and alpha-gustducin. | 2004 Sep 1 |
|
| In vivo imaging of C. elegans ASH neurons: cellular response and adaptation to chemical repellents. | 2005 Jan 12 |
|
| Genomic organization, expression, and function of bitter taste receptors (T2R) in mouse and rat. | 2005 Jul 14 |
|
| G-protein-dependent and -independent pathways in denatonium signal transduction. | 2005 Sep |
|
| Exploratory behaviour in NO-dependent cyclase mutants of Drosophila shows defects in coincident neuronal signalling. | 2007 Aug 6 |
|
| Functional characterization of human bitter taste receptors. | 2007 May 1 |
|
| Adverse reactions associated with respirator fit testing of healthcare workers in British Columbia, Canada: a review of compensation claim cases. | 2007 Winter |
|
| Final report of the safety assessment of Alcohol Denat., including SD Alcohol 3-A, SD Alcohol 30, SD Alcohol 39, SD Alcohol 39-B, SD Alcohol 39-C, SD Alcohol 40, SD Alcohol 40-B, and SD Alcohol 40-C, and the denaturants, Quassin, Brucine Sulfate/Brucine, and Denatonium Benzoate. | 2008 |
|
| Norepinephrine is coreleased with serotonin in mouse taste buds. | 2008 Dec 3 |
|
| The impact of bittering agents on suicidal ingestions of antifreeze. | 2008 Jul |
|
| Nasal solitary chemoreceptor cell responses to bitter and trigeminal stimulants in vitro. | 2008 Jun |
|
| Construction of a taste-blind medaka fish and quantitative assay of its preference-aversion behavior. | 2008 Nov |
|
| Tonic activity of Galpha-gustducin regulates taste cell responsivity. | 2008 Nov 12 |
|
| Safety evaluation of topical applications of ethanol on the skin and inside the oral cavity. | 2008 Nov 13 |
|
| Constructing quality profiles for taste compounds in rats: a novel paradigm. | 2008 Oct 20 |
|
| Preferences of 14 rat strains for 17 taste compounds. | 2008 Oct 20 |
|
| Central Fos expression and conditioned flavor avoidance in rats following intragastric administration of bitter taste receptor ligands. | 2009 Mar |
Patents
Sample Use Guides
1 µmol/kg bodyweight (10mM) was administered as a bolus into the stomach through a nasogastric feeding tube.
Route of Administration:
Other
Denatonium inhibits growth and induces apoptosis of airway epithelial cells. After treatment with 2 mM denatonium for 24 h, the expression of the anti-apoptotic protein Bcl-2 was significantly reduced and the release of cytochrome c and Smac/DIABLO from the mitochondria to the cytoplasm was drastically increased in human bronchial epithelial cell lines 16HBE. To examine whether denatonium induces mitochondrial damage in airway epithelial cells, was used transmission electron microscopy to examine the ultrastructures of human lung cancer cell line A549 treated with 2 mM denatonium. The control cells appeared to have normal mitochondria and mostly homogeneous cytoplasms, while A549 cells treated with denatonium showed large amplitude swelling of mitochondria.
| Substance Class |
Chemical
Created
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admin
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Edited
Wed Apr 02 08:03:49 GMT 2025
by
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Wed Apr 02 08:03:49 GMT 2025
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| Record UNII |
YE84H43CRF
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| Record Status |
Validated (UNII)
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| Record Version |
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Common Name | English | ||
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Preferred Name | English |
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FDA ORPHAN DRUG |
942123
Created by
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YE84H43CRF
Created by
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168429466
Created by
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