Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H29N2O.C7H4NO3S |
Molecular Weight | 507.6465 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC[N+](CC)(Cc1ccccc1)CC(=Nc2c(C)cccc2C)[O-].c1ccc2c(c1)C(=NS2(=O)=O)O
InChI
InChIKey=AOVWCKBXCSVODH-UHFFFAOYSA-N
InChI=1S/C21H28N2O.C7H5NO3S/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;9-7-5-3-1-2-4-6(5)12(10,11)8-7/h7-14H,5-6,15-16H2,1-4H3;1-4H,(H,8,9)
Molecular Formula | C7H5NO3S |
Molecular Weight | 183.1859 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20022913 |
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Target ID: Q9NYV9 Gene ID: 50838.0 Gene Symbol: TAS2R13 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20022913 |
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Target ID: Q9NYW0 Gene ID: 50839.0 Gene Symbol: TAS2R10 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20022913 |
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Target ID: Q9NYW2 Gene ID: 50836.0 Gene Symbol: TAS2R8 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20022913 |
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 |
---|---|---|
Chemotaxis of the nematode Caenorhabditis elegans toward cycloheximide and quinine hydrochloride. | 2001 |
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Bitter taste transduced by PLC-beta(2)-dependent rise in IP(3) and alpha-gustducin-dependent fall in cyclic nucleotides. | 2001 Apr |
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Bitter substances suppress afferent responses to an appetitive mixture: evidence for peripheral integration of chemosensory stimuli. | 2001 Dec |
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Taste receptor cells that discriminate between bitter stimuli. | 2001 Feb 23 |
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Taste receptor cell responses to the bitter stimulus denatonium involve Ca2+ influx via store-operated channels. | 2002 Jun |
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Partial rescue of taste responses of alpha-gustducin null mice by transgenic expression of alpha-transducin. | 2002 Oct |
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Stimulation of insulin secretion by denatonium, one of the most bitter-tasting substances known. | 2003 Feb |
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A psychophysical investigation of binary bitter-compound interactions. | 2003 May |
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The distinctiveness of ionic and nonionic bitter stimuli. | 2004 Jan |
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Umami taste responses are mediated by alpha-transducin and alpha-gustducin. | 2004 Sep 1 |
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Genomic organization, expression, and function of bitter taste receptors (T2R) in mouse and rat. | 2005 Jul 14 |
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Inbred mouse strains C57BL/6J and DBA/2J vary in sensitivity to a subset of bitter stimuli. | 2005 Jun 20 |
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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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G-protein signaling: back to the future. | 2005 Mar |
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Differential covariation in taste responsiveness to bitter stimuli in rats. | 2005 Nov |
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Acute ethanol intoxication after consumption of hairspray. | 2005 Nov |
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Bitterness suppression with zinc sulfate and na-cyclamate: a model of combined peripheral and central neural approaches to flavor modification. | 2005 Nov |
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G-protein-dependent and -independent pathways in denatonium signal transduction. | 2005 Sep |
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PLCbeta2-independent behavioral avoidance of prototypical bitter-tasting ligands. | 2005 Sep |
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Mouse taste cells with G protein-coupled taste receptors lack voltage-gated calcium channels and SNAP-25. | 2006 Mar 30 |
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The neural processing of taste. | 2007 Sep 18 |
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Behavioral genetics and 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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Riboflavin-binding protein is a novel bitter inhibitor. | 2008 Jan |
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Nasal solitary chemoreceptor cell responses to bitter and trigeminal stimulants in vitro. | 2008 Jun |
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The taste transduction channel TRPM5 is a locus for bitter-sweet taste interactions. | 2008 May |
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Construction of a taste-blind medaka fish and quantitative assay of its preference-aversion behavior. | 2008 Nov |
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Tonic activity of Galpha-gustducin regulates taste cell responsivity. | 2008 Nov 12 |
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Preferences of 14 rat strains for 17 taste compounds. | 2008 Oct 20 |
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Sweet taste receptor expressed in pancreatic beta-cells activates the calcium and cyclic AMP signaling systems and stimulates insulin secretion. | 2009 |
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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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Signalling mechanisms in mouse bitter responsive taste cells. | 2009 Jul 1 |
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Bitter-responsive gustatory neurons in the rat parabrachial nucleus. | 2009 Mar |
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Gustatory responsiveness to six bitter tastants in three species of nonhuman primates. | 2009 May |
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Contribution of the T1r3 taste receptor to the response properties of central gustatory neurons. | 2009 May |
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Chemoreception regulates chemical access to mouse vomeronasal organ: role of solitary chemosensory cells. | 2010 Jul 30 |
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Responses of single chorda tympani taste fibers of the calf (Bos taurus). | 2010 Jun |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT02759926
1 µmol/kg bodyweight (10mM) was administered as a bolus into the stomach through a nasogastric feeding tube.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25652218
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
Sat Jun 26 16:16:17 UTC 2021
by
admin
on
Sat Jun 26 16:16:17 UTC 2021
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Record UNII |
G2NT7SMW7M
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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EPA PESTICIDE CODE |
129045
Created by
admin on Sat Jun 26 16:16:18 UTC 2021 , Edited by admin on Sat Jun 26 16:16:18 UTC 2021
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90823-38-4
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90823-38-4
Created by
admin on Sat Jun 26 16:16:18 UTC 2021 , Edited by admin on Sat Jun 26 16:16:18 UTC 2021
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C053525
Created by
admin on Sat Jun 26 16:16:18 UTC 2021 , Edited by admin on Sat Jun 26 16:16:18 UTC 2021
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Denatonium saccharide
Created by
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64772
Created by
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G2NT7SMW7M
Created by
admin on Sat Jun 26 16:16:18 UTC 2021 , Edited by admin on Sat Jun 26 16:16:18 UTC 2021
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |