Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C21H29N2O.C2H3O2 |
| Molecular Weight | 384.5118 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC([O-])=O.CC[N+](CC)(CC(=O)NC1=C(C)C=CC=C1C)CC2=CC=CC=C2
InChI
InChIKey=MRXPBBXBHPUCQZ-UHFFFAOYSA-N
InChI=1S/C21H28N2O.C2H4O2/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)
| 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 |
| Molecular Formula | C21H29N2O |
| Molecular Weight | 325.4678 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| 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) |
|||
Target ID: Q9NYV9 Gene ID: 50838.0 Gene Symbol: TAS2R13 Target Organism: Homo sapiens (Human) |
|||
Target ID: Q9NYW0 Gene ID: 50839.0 Gene Symbol: TAS2R10 Target Organism: Homo sapiens (Human) |
|||
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) Health Status: healthy Age Group: 27 years (range: 22–33 years) Sex: M+F Sources: |
|
1 umol/kg single, intragastric Dose: 1 umol/kg Route: intragastric Route: single Dose: 1 umol/kg Sources: |
healthy, 29 years |
|
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 |
|---|---|---|
| Soa genotype selectively affects mouse gustatory neural responses to sucrose octaacetate. | 2001 Apr 27 |
|
| Partial rescue of taste responses of alpha-gustducin null mice by transgenic expression of alpha-transducin. | 2002 Oct |
|
| A psychophysical investigation of binary bitter-compound interactions. | 2003 May |
|
| Role of the G-protein subunit alpha-gustducin in taste cell responses to bitter stimuli. | 2003 Oct 29 |
|
| Saccharin stimulates the "deterrent" cell in the blowfly: behavioral and electrophysiological evidence. | 2004 Feb |
|
| The distinctiveness of ionic and nonionic bitter stimuli. | 2004 Jan |
|
| Was it necessary to add Bitrex (denatonium benzoate) to automotive products? | 2004 Jun |
|
| Diverse bitter stimuli elicit highly similar patterns of Fos-like immunoreactivity in the nucleus of the solitary tract. | 2004 Sep |
|
| 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 |
|
| 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 |
|
| Predators' toxin burdens influence their strategic decisions to eat toxic prey. | 2007 Sep 4 |
|
| Riboflavin-binding protein is a novel bitter inhibitor. | 2008 Jan |
|
| Construction of a taste-blind medaka fish and quantitative assay of its preference-aversion behavior. | 2008 Nov |
|
| Constructing quality profiles for taste compounds in rats: a novel paradigm. | 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 |
|
| 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 |
|
| A Drosophila gustatory receptor essential for aversive taste and inhibiting male-to-male courtship. | 2009 Oct 13 |
|
| Discrimination of taste qualities among mouse fungiform taste bud cells. | 2009 Sep 15 |
|
| Vasoactive intestinal peptide-null mice demonstrate enhanced sweet taste preference, dysglycemia, and reduced taste bud leptin receptor expression. | 2010 May |
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
Wed Apr 02 09:14:58 GMT 2025
by
admin
on
Wed Apr 02 09:14:58 GMT 2025
|
| Record UNII |
8QG4DAT7RW
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Preferred Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
118353494
Created by
admin on Wed Apr 02 09:14:58 GMT 2025 , Edited by admin on Wed Apr 02 09:14:58 GMT 2025
|
PRIMARY | |||
|
8QG4DAT7RW
Created by
admin on Wed Apr 02 09:14:58 GMT 2025 , Edited by admin on Wed Apr 02 09:14:58 GMT 2025
|
PRIMARY | |||
|
1995890-04-4
Created by
admin on Wed Apr 02 09:14:58 GMT 2025 , Edited by admin on Wed Apr 02 09:14:58 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
PARENT -> SALT/SOLVATE |
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
ACTIVE MOIETY |
|