Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C21H29N2O.C7H5O2.H2O |
| Molecular Weight | 464.5964 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.[O-]C(=O)C1=CC=CC=C1.CC[N+](CC)(CC(=O)NC2=C(C)C=CC=C2C)CC3=CC=CC=C3
InChI
InChIKey=YYMVPVZYUYQSJE-UHFFFAOYSA-N
InChI=1S/C21H28N2O.C7H6O2.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;8-7(9)6-4-2-1-3-5-6;/h7-14H,5-6,15-16H2,1-4H3;1-5H,(H,8,9);1H2
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) n = 14 Health Status: healthy Age Group: 27 years (range: 22–33 years) Sex: M+F Population Size: 14 Sources: |
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1 umol/kg single, intragastric Dose: 1 umol/kg Route: intragastric Route: single Dose: 1 umol/kg Sources: |
healthy, 29 years n = 65 Health Status: healthy Age Group: 29 years Sex: M+F Population Size: 65 Sources: |
|
1.69 mg/mL single, respiratory Dose: 1.69 mg/mL Route: respiratory Route: single Dose: 1.69 mg/mL Sources: |
healthy, 34 years n = 1 Health Status: healthy Age Group: 34 years Sex: F Population Size: 1 Sources: |
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 n = 1 Health Status: healthy Age Group: 34 years Sex: F Population Size: 1 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Cellular responses of NG108-15 and SK-N-MC lines to sweet and bitter tastants as measured by extracellular acidification rates. | 2001 Jan 1 |
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| Rats fail to discriminate quinine from denatonium: implications for the neural coding of bitter-tasting compounds. | 2002 Mar 1 |
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| Identification of ligands for two human bitter T2R receptors. | 2004 Sep |
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| Haplotypes at the Tas2r locus on distal chromosome 6 vary with quinine taste sensitivity in inbred mice. | 2005 Jun 6 |
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| Single neurons in the nucleus of the solitary tract respond selectively to bitter taste stimuli. | 2006 Nov |
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| Bitter stimuli induce Ca2+ signaling and CCK release in enteroendocrine STC-1 cells: role of L-type voltage-sensitive Ca2+ channels. | 2006 Oct |
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| Functional characterization of human bitter taste receptors. | 2007 May 1 |
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| The neural processing of taste. | 2007 Sep 18 |
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| Analysis of axonal regeneration in the central and peripheral nervous systems of the NG2-deficient mouse. | 2007 Sep 27 |
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| Bitter taste receptors influence glucose homeostasis. | 2008 |
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| Gustation in fish: search for prototype of taste perception. | 2009 |
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| Delineation of the chemomechanosensory regulation of gastrin secretion using pure rodent G cells. | 2009 Jul |
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| Bitter-responsive gustatory neurons in the rat parabrachial nucleus. | 2009 Mar |
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| Residual chemosensory capabilities in double P2X2/P2X3 purinergic receptor null mice: intraoral or postingestive detection? | 2009 Nov |
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| Bitter taste receptors on airway smooth muscle bronchodilate by localized calcium signaling and reverse obstruction. | 2010 Nov |
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.
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| Classification Tree | Code System | Code | ||
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CFR |
21 CFR 310.536
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NCI_THESAURUS |
C83486
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CHEMBL1738972
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C029408
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C76704
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86398-53-0
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100000083715
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DTXSID50235522
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1313232
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4YK5Z54AT2
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168900
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4YK5Z54AT2
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1171003
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
