Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C21H29N2O.C2H3O2.H2O |
| Molecular Weight | 402.5271 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| 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 | 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 | C21H29N2O |
| Molecular Weight | 325.4678 |
| Charge | 1 |
| Count |
|
| Stereochemistry | RACEMIC |
| 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) 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 |
|---|---|---|
| Soa genotype selectively affects mouse gustatory neural responses to sucrose octaacetate. | 2001 Apr 27 |
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| Taste receptor cells that discriminate between bitter stimuli. | 2001 Feb 23 |
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| Stimulation of insulin secretion by denatonium, one of the most bitter-tasting substances known. | 2003 Feb |
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| Comparison of the responses of the chorda tympani and glossopharyngeal nerves to taste stimuli in C57BL/6J mice. | 2003 Mar 4 |
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| A psychophysical investigation of binary bitter-compound interactions. | 2003 May |
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| Taste + odor interactions in compound aversion conditioning. | 2004 Nov |
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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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| Umami taste responses are mediated by alpha-transducin and alpha-gustducin. | 2004 Sep 1 |
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| PLCbeta2-independent behavioral avoidance of prototypical bitter-tasting ligands. | 2005 Sep |
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| Trpm5 null mice respond to bitter, sweet, and umami compounds. | 2006 Mar |
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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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| 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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| Characterization of ligands for fish taste receptors. | 2007 May 23 |
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| A non-invasive method for ending thumb- and fingersucking habits. | 2007 Oct |
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| Analysis of axonal regeneration in the central and peripheral nervous systems of the NG2-deficient mouse. | 2007 Sep 27 |
|
| 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 |
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| Responses of the ciliates tetrahymena and paramecium to vertebrate odorants and tastants. | 2008 Jan-Feb |
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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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| Safety evaluation of topical applications of ethanol on the skin and inside the oral cavity. | 2008 Nov 13 |
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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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| Residual chemosensory capabilities in double P2X2/P2X3 purinergic receptor null mice: intraoral or postingestive detection? | 2009 Nov |
|
| Chemoreception regulates chemical access to mouse vomeronasal organ: role of solitary chemosensory cells. | 2010 Jul 30 |
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
Sat Dec 16 16:35:27 GMT 2023
by
admin
on
Sat Dec 16 16:35:27 GMT 2023
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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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Common Name | English |
| Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
942123
Created by
admin on Sat Dec 16 16:35:27 GMT 2023 , Edited by admin on Sat Dec 16 16:35:27 GMT 2023
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YE84H43CRF
Created by
admin on Sat Dec 16 16:35:27 GMT 2023 , Edited by admin on Sat Dec 16 16:35:27 GMT 2023
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168429466
Created by
admin on Sat Dec 16 16:35:27 GMT 2023 , Edited by admin on Sat Dec 16 16:35:27 GMT 2023
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