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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
Structure of DENATONIUM CHLORIDE

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

HIDE SMILES / InChI

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Doses

Doses

DosePopulationAdverse 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
Health Status: healthy
Age Group: 29 years
Sex: M+F
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
Health Status: healthy
Age Group: 34 years
Sex: F
Sources:
Other AEs: Asthma...
Other AEs:
Asthma (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
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
Health Status: healthy
Age Group: 34 years
Sex: F
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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

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 Mon Mar 31 18:52:09 GMT 2025
Edited
by admin
on Mon Mar 31 18:52:09 GMT 2025
Record UNII
0W5171805N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DENATONIUM CHLORIDE [VANDF]
Preferred Name English
DENATONIUM CHLORIDE
VANDF  
Common Name English
BENZENEMETHANAMINIUM, N-(2-((2,6-DIMETHYLPHENYL)AMINO)-2-OXOETHYL)-N,N-DIETHYL-, CHLORIDE (1:1)
Systematic Name English
BENZENEMETHANAMINIUM, N-(2-((2,6-DIMETHYLPHENYL)AMINO)-2-OXOETHYL)-N,N-DIETHYL-, CHLORIDE
Systematic Name English
Code System Code Type Description
FDA UNII
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
MESH
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
PUBCHEM
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
EPA CompTox
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
CAS
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