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Details

Stereochemistry ACHIRAL
Molecular Formula C21H29N2O.C7H4NO3S
Molecular Weight 507.6465
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DENATONIUM SACCHARIDE

SMILES

CC[N+](CC)(Cc1ccccc1)CC(=Nc2c(C)cccc2C)[O-].c1ccc2c(c1)C(=NS2(=O)=O)O

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 183.1859
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C21H29N2O
Molecular Weight 325.4685
Charge 1
Count
Stereochemistry RACEMIC
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)
n = 14
Health Status: healthy
Age Group: 27 years (range: 22–33 years)
Sex: M+F
Population Size: 14
Sources:
1 umol/kg single, intragastric
Dose: 1 umol/kg
Route: intragastric
Route: single
Dose: 1 umol/kg
Sources:
healthy, 29 years
n = 65
Health Status: healthy
Age Group: 29 years
Sex: M+F
Population Size: 65
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
n = 1
Health Status: healthy
Age Group: 34 years
Sex: F
Population Size: 1
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
n = 1
Health Status: healthy
Age Group: 34 years
Sex: F
Population Size: 1
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Chemotaxis of the nematode Caenorhabditis elegans toward cycloheximide and quinine hydrochloride.
2001
Bitter taste transduced by PLC-beta(2)-dependent rise in IP(3) and alpha-gustducin-dependent fall in cyclic nucleotides.
2001 Apr
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
Taste receptor cell responses to the bitter stimulus denatonium involve Ca2+ influx via store-operated channels.
2002 Jun
Partial rescue of taste responses of alpha-gustducin null mice by transgenic expression of alpha-transducin.
2002 Oct
Stimulation of insulin secretion by denatonium, one of the most bitter-tasting substances known.
2003 Feb
A psychophysical investigation of binary bitter-compound interactions.
2003 May
The distinctiveness of ionic and nonionic bitter stimuli.
2004 Jan
Umami taste responses are mediated by alpha-transducin and alpha-gustducin.
2004 Sep 1
Genomic organization, expression, and function of bitter taste receptors (T2R) in mouse and rat.
2005 Jul 14
Inbred mouse strains C57BL/6J and DBA/2J vary in sensitivity to a subset of bitter stimuli.
2005 Jun 20
Haplotypes at the Tas2r locus on distal chromosome 6 vary with quinine taste sensitivity in inbred mice.
2005 Jun 6
G-protein signaling: back to the future.
2005 Mar
Differential covariation in taste responsiveness to bitter stimuli in rats.
2005 Nov
Acute ethanol intoxication after consumption of hairspray.
2005 Nov
Bitterness suppression with zinc sulfate and na-cyclamate: a model of combined peripheral and central neural approaches to flavor modification.
2005 Nov
G-protein-dependent and -independent pathways in denatonium signal transduction.
2005 Sep
PLCbeta2-independent behavioral avoidance of prototypical bitter-tasting ligands.
2005 Sep
Mouse taste cells with G protein-coupled taste receptors lack voltage-gated calcium channels and SNAP-25.
2006 Mar 30
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
Bitter taste receptors influence glucose homeostasis.
2008
Riboflavin-binding protein is a novel bitter inhibitor.
2008 Jan
Nasal solitary chemoreceptor cell responses to bitter and trigeminal stimulants in vitro.
2008 Jun
The taste transduction channel TRPM5 is a locus for bitter-sweet taste interactions.
2008 May
Construction of a taste-blind medaka fish and quantitative assay of its preference-aversion behavior.
2008 Nov
Tonic activity of Galpha-gustducin regulates taste cell responsivity.
2008 Nov 12
Preferences of 14 rat strains for 17 taste compounds.
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
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
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
Chemoreception regulates chemical access to mouse vomeronasal organ: role of solitary chemosensory cells.
2010 Jul 30
Responses of single chorda tympani taste fibers of the calf (Bos taurus).
2010 Jun
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 Sat Jun 26 16:16:17 UTC 2021
Edited
by admin
on Sat Jun 26 16:16:17 UTC 2021
Record UNII
G2NT7SMW7M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DENATONIUM SACCHARIDE
INCI   VANDF  
INCI  
Official Name English
DENATONIUM SACCHARINATE
Common 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)
Common Name English
DENATONIUM SACCHARIDE [INCI]
Common Name English
DENATONIUM SACCHARIDE [VANDF]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 129045
Created by admin on Sat Jun 26 16:16:18 UTC 2021 , Edited by admin on Sat Jun 26 16:16:18 UTC 2021
Code System Code Type Description
EPA CompTox
90823-38-4
Created by admin on Sat Jun 26 16:16:18 UTC 2021 , Edited by admin on Sat Jun 26 16:16:18 UTC 2021
PRIMARY
CAS
90823-38-4
Created by admin on Sat Jun 26 16:16:18 UTC 2021 , Edited by admin on Sat Jun 26 16:16:18 UTC 2021
PRIMARY
MESH
C053525
Created by admin on Sat Jun 26 16:16:18 UTC 2021 , Edited by admin on Sat Jun 26 16:16:18 UTC 2021
PRIMARY
WIKIPEDIA
Denatonium saccharide
Created by admin on Sat Jun 26 16:16:18 UTC 2021 , Edited by admin on Sat Jun 26 16:16:18 UTC 2021
PRIMARY
PUBCHEM
64772
Created by admin on Sat Jun 26 16:16:18 UTC 2021 , Edited by admin on Sat Jun 26 16:16:18 UTC 2021
PRIMARY
FDA UNII
G2NT7SMW7M
Created by admin on Sat Jun 26 16:16:18 UTC 2021 , Edited by admin on Sat Jun 26 16:16:18 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY