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Details

Stereochemistry ACHIRAL
Molecular Formula C21H29N2O.C7H4NO3S
Molecular Weight 507.644
Optical Activity NONE
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DENATONIUM SACCHARIDE

SMILES

O=C1[N-]S(=O)(=O)C2=CC=CC=C12.CC[N+](CC)(CC(=O)NC3=C(C)C=CC=C3C)CC4=CC=CC=C4

InChI

InChIKey=AOVWCKBXCSVODH-UHFFFAOYSA-N
InChI=1S/C21H28N2O.C7H5NO3S/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;9-7-5-3-1-2-4-6(5)12(10,11)8-7/h7-14H,5-6,15-16H2,1-4H3;1-4H,(H,8,9)

HIDE SMILES / InChI

Molecular Formula C7H5NO3S
Molecular Weight 183.185
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 / 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.

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
Cellular responses of NG108-15 and SK-N-MC lines to sweet and bitter tastants as measured by extracellular acidification rates.
2001 Jan 1
Identification of ligands for two human bitter T2R receptors.
2004 Sep
Diverse bitter stimuli elicit highly similar patterns of Fos-like immunoreactivity in the nucleus of the solitary tract.
2004 Sep
Trpm5 null mice respond to bitter, sweet, and umami compounds.
2006 Mar
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
Gustation in fish: search for prototype of taste perception.
2009
Signalling mechanisms in mouse bitter responsive taste cells.
2009 Jul 1
Bitter-responsive gustatory neurons in the rat parabrachial nucleus.
2009 Mar
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
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 Wed Apr 02 17:55:38 GMT 2025
Edited
by admin
on Wed Apr 02 17:55:38 GMT 2025
Record UNII
G2NT7SMW7M
Record Status Validated (UNII)
Record Version
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Name Type Language
DENATONIUM SACCHARIDE
INCI   VANDF  
INCI  
Official Name English
BENZENEMETHANAMINIUM, N-(2-((2,6-DIMETHYLPHENYL)AMINO)-2-OXOETHYL)-N,N-DIETHYL-, SALT WITH 1,2-BENZISOTHIAZOL-3(2H)-ONE 1,1-DIOXIDE (1:1)
Preferred Name English
DENATONIUM SACCHARINATE
Common Name English
DENATONIUM SACCHARIDE [VANDF]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 129045
Created by admin on Wed Apr 02 17:55:38 GMT 2025 , Edited by admin on Wed Apr 02 17:55:38 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID9034361
Created by admin on Wed Apr 02 17:55:38 GMT 2025 , Edited by admin on Wed Apr 02 17:55:38 GMT 2025
PRIMARY
CAS
90823-38-4
Created by admin on Wed Apr 02 17:55:38 GMT 2025 , Edited by admin on Wed Apr 02 17:55:38 GMT 2025
PRIMARY
MESH
C053525
Created by admin on Wed Apr 02 17:55:38 GMT 2025 , Edited by admin on Wed Apr 02 17:55:38 GMT 2025
PRIMARY
WIKIPEDIA
Denatonium saccharide
Created by admin on Wed Apr 02 17:55:38 GMT 2025 , Edited by admin on Wed Apr 02 17:55:38 GMT 2025
PRIMARY
PUBCHEM
64772
Created by admin on Wed Apr 02 17:55:38 GMT 2025 , Edited by admin on Wed Apr 02 17:55:38 GMT 2025
PRIMARY
FDA UNII
G2NT7SMW7M
Created by admin on Wed Apr 02 17:55:38 GMT 2025 , Edited by admin on Wed Apr 02 17:55:38 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY