Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H29N2O.C7H4NO3S |
Molecular Weight | 507.644 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O=C1[N-]S(=O)(=O)C2=CC=CC=C12.CC[N+](CC)(CC(=O)NC3=C(C)C=CC=C3C)CC4=CC=CC=C4
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 | 183.185 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C21H29N2O |
Molecular Weight | 325.4678 |
Charge | 1 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
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 |
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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: |
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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 |
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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 |
---|---|---|
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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Identification of ligands for two human bitter T2R receptors. | 2004 Sep |
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Diverse bitter stimuli elicit highly similar patterns of Fos-like immunoreactivity in the nucleus of the solitary tract. | 2004 Sep |
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Trpm5 null mice respond to bitter, sweet, and umami compounds. | 2006 Mar |
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Bitter taste receptors influence glucose homeostasis. | 2008 |
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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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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 |
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
Wed Apr 02 17:55:38 GMT 2025
by
admin
on
Wed Apr 02 17:55:38 GMT 2025
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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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Official Name | English | ||
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Preferred Name | English | ||
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Common Name | English | ||
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Common Name | English |
Classification Tree | Code System | Code | ||
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EPA PESTICIDE CODE |
129045
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DTXSID9034361
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90823-38-4
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C053525
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Denatonium saccharide
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64772
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G2NT7SMW7M
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ACTIVE MOIETY |