Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C21H29N2O |
| Molecular Weight | 325.4685 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 1 |
SHOW SMILES / InChI
SMILES
CC[N+](CC)(Cc1ccccc1)CC(=Nc2c(C)cccc2C)O
InChI
InChIKey=ZFQMTVNLDNXRNQ-UHFFFAOYSA-O
InChI=1S/C21H28N2O/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/h7-14H,5-6,15-16H2,1-4H3/p+1
| Molecular Formula | C21H29N2O |
| Molecular Weight | 325.4685 |
| Charge | 1 |
| Count |
|
| Stereochemistry | RACEMIC |
| 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) n = 14 Health Status: healthy Age Group: 27 years (range: 22–33 years) Sex: M+F Population Size: 14 Sources: |
|
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 |
|---|---|---|
| Chemotaxis of the nematode Caenorhabditis elegans toward cycloheximide and quinine hydrochloride. | 2001 |
|
| Taste + odor interactions in compound aversion conditioning. | 2004 Nov |
|
| 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 |
|
| Characterization of bitter taste responses of intestinal STC-1 cells. | 2005 May |
|
| Differential covariation in taste responsiveness to bitter stimuli in rats. | 2005 Nov |
|
| Bitterness suppression with zinc sulfate and na-cyclamate: a model of combined peripheral and central neural approaches to flavor modification. | 2005 Nov |
|
| PLCbeta2-independent behavioral avoidance of prototypical bitter-tasting ligands. | 2005 Sep |
|
| Trpm5 null mice respond to bitter, sweet, and umami compounds. | 2006 Mar |
|
| Mouse taste cells with G protein-coupled taste receptors lack voltage-gated calcium channels and SNAP-25. | 2006 Mar 30 |
|
| Single neurons in the nucleus of the solitary tract respond selectively to bitter taste stimuli. | 2006 Nov |
|
| Bitter stimuli induce Ca2+ signaling and CCK release in enteroendocrine STC-1 cells: role of L-type voltage-sensitive Ca2+ channels. | 2006 Oct |
|
| Exploratory behaviour in NO-dependent cyclase mutants of Drosophila shows defects in coincident neuronal signalling. | 2007 Aug 6 |
|
| Broad tuning of the human bitter taste receptor hTAS2R46 to various sesquiterpene lactones, clerodane and labdane diterpenoids, strychnine, and denatonium. | 2007 Jul 25 |
|
| Functional characterization of human bitter taste receptors. | 2007 May 1 |
|
| Characterization of ligands for fish taste receptors. | 2007 May 23 |
|
| A non-invasive method for ending thumb- and fingersucking habits. | 2007 Oct |
|
| The neural processing of taste. | 2007 Sep 18 |
|
| Behavioral genetics and taste. | 2007 Sep 18 |
|
| Analysis of axonal regeneration in the central and peripheral nervous systems of the NG2-deficient mouse. | 2007 Sep 27 |
|
| Adverse reactions associated with respirator fit testing of healthcare workers in British Columbia, Canada: a review of compensation claim cases. | 2007 Winter |
|
| Bitter taste receptors influence glucose homeostasis. | 2008 |
|
| 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 |
|
| Role of CCK1 and Y2 receptors in activation of hindbrain neurons induced by intragastric administration of bitter taste receptor ligands. | 2008 Jan |
|
| Riboflavin-binding protein is a novel bitter inhibitor. | 2008 Jan |
|
| Responses of the ciliates tetrahymena and paramecium to vertebrate odorants and tastants. | 2008 Jan-Feb |
|
| 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 |
|
| Intragastric infusion of denatonium conditions flavor aversions and delays gastric emptying in rodents. | 2008 Mar 18 |
|
| The taste transduction channel TRPM5 is a locus for bitter-sweet taste interactions. | 2008 May |
|
| Construction of a taste-blind medaka fish and quantitative assay of its preference-aversion behavior. | 2008 Nov |
|
| 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 |
|
| Sweet taste receptor expressed in pancreatic beta-cells activates the calcium and cyclic AMP signaling systems and stimulates insulin secretion. | 2009 |
|
| Gustation in fish: search for prototype of taste perception. | 2009 |
|
| Chemical analysis and risk assessment of diethyl phthalate in alcoholic beverages with special regard to unrecorded alcohol. | 2009 Dec 2 |
|
| Delineation of the chemomechanosensory regulation of gastrin secretion using pure rodent G cells. | 2009 Jul |
|
| Signalling mechanisms in mouse bitter responsive taste cells. | 2009 Jul 1 |
|
| Bitter-responsive gustatory neurons in the rat parabrachial nucleus. | 2009 Mar |
|
| Central Fos expression and conditioned flavor avoidance in rats following intragastric administration of bitter taste receptor ligands. | 2009 Mar |
|
| Gustatory responsiveness to six bitter tastants in three species of nonhuman primates. | 2009 May |
|
| Contribution of the T1r3 taste receptor to the response properties of central gustatory neurons. | 2009 May |
|
| Residual chemosensory capabilities in double P2X2/P2X3 purinergic receptor null mice: intraoral or postingestive detection? | 2009 Nov |
|
| Discrimination of taste qualities among mouse fungiform taste bud cells. | 2009 Sep 15 |
|
| Molecular and cellular designs of insect taste receptor system. | 2010 |
|
| Responses of single chorda tympani taste fibers of the calf (Bos taurus). | 2010 Jun |
|
| Vasoactive intestinal peptide-null mice demonstrate enhanced sweet taste preference, dysglycemia, and reduced taste bud leptin receptor expression. | 2010 May |
|
| 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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 22:53:22 UTC 2021
by
admin
on
Fri Jun 25 22:53:22 UTC 2021
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| Record UNII |
4IK22DF4OU
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C83486
Created by
admin on Fri Jun 25 22:53:22 UTC 2021 , Edited by admin on Fri Jun 25 22:53:22 UTC 2021
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| Code System | Code | Type | Description | ||
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DENATONIUM
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SUB01582MIG
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15488
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1546417
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47324-98-1
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C83659
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4IK22DF4OU
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admin on Fri Jun 25 22:53:22 UTC 2021 , Edited by admin on Fri Jun 25 22:53:22 UTC 2021
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