Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H29N2O.Cl |
Molecular Weight | 360.921 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Cl-].CC[N+](CC)(CC(=O)NC1=C(C)C=CC=C1C)CC2=CC=CC=C2
InChI
InChIKey=YNQALPDYZRNHNK-UHFFFAOYSA-N
InChI=1S/C21H28N2O.ClH/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;/h7-14H,5-6,15-16H2,1-4H3;1H
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 |
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
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) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20022913 |
|||
Target ID: Q9NYV9 Gene ID: 50838.0 Gene Symbol: TAS2R13 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20022913 |
|||
Target ID: Q9NYW0 Gene ID: 50839.0 Gene Symbol: TAS2R10 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20022913 |
|||
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) 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 |
---|---|---|
Chemotaxis of the nematode Caenorhabditis elegans toward cycloheximide and quinine hydrochloride. | 2001 |
|
Bitter substances suppress afferent responses to an appetitive mixture: evidence for peripheral integration of chemosensory stimuli. | 2001 Dec |
|
Taste receptor cells that discriminate between bitter stimuli. | 2001 Feb 23 |
|
Covariation in individuals' sensitivities to bitter compounds: evidence supporting multiple receptor/transduction mechanisms. | 2001 Jul |
|
Effect of compound sequence on bitterness enhancement. | 2001 May |
|
Diverse bitter stimuli elicit highly similar patterns of Fos-like immunoreactivity in the nucleus of the solitary tract. | 2004 Sep |
|
Haplotypes at the Tas2r locus on distal chromosome 6 vary with quinine taste sensitivity in inbred mice. | 2005 Jun 6 |
|
Mouse taste cells with G protein-coupled taste receptors lack voltage-gated calcium channels and SNAP-25. | 2006 Mar 30 |
|
Exploratory behaviour in NO-dependent cyclase mutants of Drosophila shows defects in coincident neuronal signalling. | 2007 Aug 6 |
|
A non-invasive method for ending thumb- and fingersucking habits. | 2007 Oct |
|
Behavioral genetics and taste. | 2007 Sep 18 |
|
Bitter taste receptors influence glucose homeostasis. | 2008 |
|
Sweet taste receptor expressed in pancreatic beta-cells activates the calcium and cyclic AMP signaling systems and stimulates insulin secretion. | 2009 |
|
Chemical analysis and risk assessment of diethyl phthalate in alcoholic beverages with special regard to unrecorded alcohol. | 2009 Dec 2 |
|
Vasoactive intestinal peptide-null mice demonstrate enhanced sweet taste preference, dysglycemia, and reduced taste bud leptin receptor expression. | 2010 May |
|
Ghrelin is produced in taste cells and ghrelin receptor null mice show reduced taste responsivity to salty (NaCl) and sour (citric acid) tastants. | 2010 Sep 14 |
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
Mon Mar 31 18:52:09 GMT 2025
by
admin
on
Mon Mar 31 18:52:09 GMT 2025
|
Record UNII |
0W5171805N
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
0W5171805N
Created by
admin on Mon Mar 31 18:52:09 GMT 2025 , Edited by admin on Mon Mar 31 18:52:09 GMT 2025
|
PRIMARY | |||
|
C043414
Created by
admin on Mon Mar 31 18:52:09 GMT 2025 , Edited by admin on Mon Mar 31 18:52:09 GMT 2025
|
PRIMARY | |||
|
15487
Created by
admin on Mon Mar 31 18:52:09 GMT 2025 , Edited by admin on Mon Mar 31 18:52:09 GMT 2025
|
PRIMARY | |||
|
DTXSID20937329
Created by
admin on Mon Mar 31 18:52:09 GMT 2025 , Edited by admin on Mon Mar 31 18:52:09 GMT 2025
|
PRIMARY | |||
|
1674-99-3
Created by
admin on Mon Mar 31 18:52:09 GMT 2025 , Edited by admin on Mon Mar 31 18:52:09 GMT 2025
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |