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 |
|---|---|---|
| Bitter taste receptors on airway smooth muscle bronchodilate by localized calcium signaling and reverse obstruction. | 2010-11 |
|
| Ghrelin is produced in taste cells and ghrelin receptor null mice show reduced taste responsivity to salty (NaCl) and sour (citric acid) tastants. | 2010-09-14 |
|
| Chemoreception regulates chemical access to mouse vomeronasal organ: role of solitary chemosensory cells. | 2010-07-30 |
|
| Responses of single chorda tympani taste fibers of the calf (Bos taurus). | 2010-06 |
|
| Vasoactive intestinal peptide-null mice demonstrate enhanced sweet taste preference, dysglycemia, and reduced taste bud leptin receptor expression. | 2010-05 |
|
| Molecular and cellular designs of insect taste receptor system. | 2010 |
|
| Chemical analysis and risk assessment of diethyl phthalate in alcoholic beverages with special regard to unrecorded alcohol. | 2009-12-02 |
|
| Residual chemosensory capabilities in double P2X2/P2X3 purinergic receptor null mice: intraoral or postingestive detection? | 2009-11 |
|
| A Drosophila gustatory receptor essential for aversive taste and inhibiting male-to-male courtship. | 2009-10-13 |
|
| Discrimination of taste qualities among mouse fungiform taste bud cells. | 2009-09-15 |
|
| Signalling mechanisms in mouse bitter responsive taste cells. | 2009-07-01 |
|
| Delineation of the chemomechanosensory regulation of gastrin secretion using pure rodent G cells. | 2009-07 |
|
| Gustatory responsiveness to six bitter tastants in three species of nonhuman primates. | 2009-05 |
|
| Contribution of the T1r3 taste receptor to the response properties of central gustatory neurons. | 2009-05 |
|
| Bitter-responsive gustatory neurons in the rat parabrachial nucleus. | 2009-03 |
|
| Central Fos expression and conditioned flavor avoidance in rats following intragastric administration of bitter taste receptor ligands. | 2009-03 |
|
| 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 |
|
| Norepinephrine is coreleased with serotonin in mouse taste buds. | 2008-12-03 |
|
| Safety evaluation of topical applications of ethanol on the skin and inside the oral cavity. | 2008-11-13 |
|
| Tonic activity of Galpha-gustducin regulates taste cell responsivity. | 2008-11-12 |
|
| Construction of a taste-blind medaka fish and quantitative assay of its preference-aversion behavior. | 2008-11 |
|
| Constructing quality profiles for taste compounds in rats: a novel paradigm. | 2008-10-20 |
|
| Preferences of 14 rat strains for 17 taste compounds. | 2008-10-20 |
|
| The impact of bittering agents on suicidal ingestions of antifreeze. | 2008-07 |
|
| Nasal solitary chemoreceptor cell responses to bitter and trigeminal stimulants in vitro. | 2008-06 |
|
| The taste transduction channel TRPM5 is a locus for bitter-sweet taste interactions. | 2008-05 |
|
| Intragastric infusion of denatonium conditions flavor aversions and delays gastric emptying in rodents. | 2008-03-18 |
|
| Responses of the ciliates tetrahymena and paramecium to vertebrate odorants and tastants. | 2008-02-07 |
|
| Role of CCK1 and Y2 receptors in activation of hindbrain neurons induced by intragastric administration of bitter taste receptor ligands. | 2008-01 |
|
| Riboflavin-binding protein is a novel bitter inhibitor. | 2008-01 |
|
| 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 |
|
| A non-invasive method for ending thumb- and fingersucking habits. | 2007-10 |
|
| Analysis of axonal regeneration in the central and peripheral nervous systems of the NG2-deficient mouse. | 2007-09-27 |
|
| The neural processing of taste. | 2007-09-18 |
|
| Behavioral genetics and taste. | 2007-09-18 |
|
| Predators' toxin burdens influence their strategic decisions to eat toxic prey. | 2007-09-04 |
|
| Exploratory behaviour in NO-dependent cyclase mutants of Drosophila shows defects in coincident neuronal signalling. | 2007-08-06 |
|
| Broad tuning of the human bitter taste receptor hTAS2R46 to various sesquiterpene lactones, clerodane and labdane diterpenoids, strychnine, and denatonium. | 2007-07-25 |
|
| Characterization of ligands for fish taste receptors. | 2007-05-23 |
|
| Functional characterization of human bitter taste receptors. | 2007-05-01 |
|
| Adverse reactions associated with respirator fit testing of healthcare workers in British Columbia, Canada: a review of compensation claim cases. | 2007 |
|
| Single neurons in the nucleus of the solitary tract respond selectively to bitter taste stimuli. | 2006-11 |
|
| Bitter stimuli induce Ca2+ signaling and CCK release in enteroendocrine STC-1 cells: role of L-type voltage-sensitive Ca2+ channels. | 2006-10 |
|
| Mouse taste cells with G protein-coupled taste receptors lack voltage-gated calcium channels and SNAP-25. | 2006-03-30 |
|
| Trpm5 null mice respond to bitter, sweet, and umami compounds. | 2006-03 |
|
| Differential covariation in taste responsiveness to bitter stimuli in rats. | 2005-11 |
|
| Acute ethanol intoxication after consumption of hairspray. | 2005-11 |
|
| Chemotaxis of the nematode Caenorhabditis elegans toward cycloheximide and quinine hydrochloride. | 2001 |
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 |
|