DENATONIUM CHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H29N2O.Cl
Molecular Weight	360.921
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

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 / 0
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

Description
Sources: http://www.marketactives.com/bitrex-bittering-agent/ | https://www.ncbi.nlm.nih.gov/pubmed/20022913

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
Taste receptor type 2 member 4 7 Target ID: Q9NYW5 Gene ID: 50832.0 Gene Symbol: TAS2R4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20022913	Agonist 2678
Taste receptor type 2 member 13 7 Target ID: Q9NYV9 Gene ID: 50838.0 Gene Symbol: TAS2R13 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20022913	Agonist 2678
Taste receptor type 2 member 10 7 Target ID: Q9NYW0 Gene ID: 50839.0 Gene Symbol: TAS2R10 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20022913	Agonist 2678
Taste receptor type 2 member 8 7 Target ID: Q9NYW2 Gene ID: 50836.0 Gene Symbol: TAS2R8 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20022913	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

Doses

Dose	Population	Adverse events
300 ppm single, ophthalmic Dose: 300 ppm Route: ophthalmic Route: single Dose: 300 ppm Sources: https://pubmed.ncbi.nlm.nih.gov/30502985	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: https://pubmed.ncbi.nlm.nih.gov/30502985	Sources: https://pubmed.ncbi.nlm.nih.gov/30502985
1 umol/kg single, intragastric Dose: 1 umol/kg Route: intragastric Route: single Dose: 1 umol/kg Sources: https://pubmed.ncbi.nlm.nih.gov/28148502/	healthy, 29 years n = 65 Health Status: healthy Age Group: 29 years Sex: M+F Population Size: 65 Sources: https://pubmed.ncbi.nlm.nih.gov/28148502/	Sources: https://pubmed.ncbi.nlm.nih.gov/28148502/
1.69 mg/mL single, respiratory Dose: 1.69 mg/mL Route: respiratory Route: single Dose: 1.69 mg/mL Sources: https://pubmed.ncbi.nlm.nih.gov/31124982	healthy, 34 years n = 1 Health Status: healthy Age Group: 34 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/31124982	Other AEs: Asthma... Other AEs: Asthma (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/31124982

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: https://pubmed.ncbi.nlm.nih.gov/31124982	healthy, 34 years n = 1 Health Status: healthy Age Group: 34 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/31124982

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P006MIS
1PlusChem LLC	1P00I7TG
A2B Chem	AD08324
A2B Chem	AI49140
AA Blocks	AA006LZC
AA Blocks	AA00I7A0
ABI Chem	AC1L25ZU
ABI Chem	AC1Q5LWS
AK Scientific	O701
AK Scientific	P665
AbovChem LLC	HY-B1146
Alfa Chemistry	122908-44-5
Alfa Chemistry	222608-06-2
Ambeed	A181673
Ambeed	A618227
AstaTech	F16467
AstaTech	F20409
BLD Pharm	BD123753
BLD Pharm	BD123754
BOC Sciences	122908-44-5
BOC Sciences	1674-99-3
BOC Sciences	222608-06-2
BOC Sciences	3734-33-6
BOC Sciences	90823-38-4
Bide Pharmatech	BD123753
BioSynth	W-106547
BlocksMatrix Scientific	89226
BlocksMatrix Scientific	98530
Bosche Scientific	D2863
Chem Scene	CS-4750
Chem-Impex International	24137
Combi-Blocks	QA-6116
Combi-Blocks	SS-9638
Compound Cloud	15488
Compound Cloud	168900
Hairui	HR103476
Hairui	HR138147
Hairui	HR138408
Hangzhou APIChem Technology	AC-14888
Hangzhou Yuhao Chemical Technology	HL2593
Hangzhou Yuhao Chemical Technology	HL4177
Hangzhou Yuhao Chemical Technology	LQ1874
Heteroz	10286
HongKong Chemhere	90823-38-4
KeyOrganics	AS-15271
KeyOrganics	AS-15511
Lab Network	LN00196762	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00196762
Lab Seeker	SC-13384
Lab Seeker	SC-17476
MedChem Express	HY-B1146
MolPort	MolPort-003-929-793
MolPort	MolPort-009-679-949
Molnova	M14290
MuseChem	M011722
MuseChem	M028211
MuseChem	M119750
MuseChem	R023805
Norris Pharm	NSZB-A221975
Norris Pharm	NSZB-A221976
Oakwood	95403
PI Chemicals	PI-20337
PI Chemicals	PI-20338
Ryan Scientific	Perphenazine
Scientific Exchange	POD_05/0837
Scientific Exchange	POD_09/0054
Sigma Aldrich	1171003
Sigma Aldrich	52487
Sigma Aldrich	52487\|SIAL
Sigma Aldrich	93675\|SIAL
Sigma Aldrich	D5765\|ALDRICH
StruChem	SC-13384
StruChem	SC-17476
TargetMol	T1098
Tetrahedron	TS82315
Tetrahedron	TS83323
TimTec	SBB057812
TimTec	ST51007042
Toronto Research Chemicals	C724810
Toronto Research Chemicals	D231660
Toronto Research Chemicals	D231705
Vesino Industrial Co Ltd	VA10687
W&J PharmaChem	50C151785
ZINC	ZINC000001601437	http://zinc15.docking.org/substances/ZINC000001601437
eMolecules	109860763
eMolecules	313070398
eMolecules	33664792
eMolecules	496852
eMolecules	6886257
eNovation Chemicals	D584553
eNovation Chemicals	D769907
mcule	MCULE-9057328681	https://mcule.com/MCULE-9057328681/

PubMed

Title	Date	PubMed
Chemotaxis of the nematode Caenorhabditis elegans toward cycloheximide and quinine hydrochloride.	2001	16232999
Differential covariation in taste responsiveness to bitter stimuli in rats.	2005 Nov	16267162
Acute ethanol intoxication after consumption of hairspray.	2005 Nov	16232026
Trpm5 null mice respond to bitter, sweet, and umami compounds.	2006 Mar	16436689
Mouse taste cells with G protein-coupled taste receptors lack voltage-gated calcium channels and SNAP-25.	2006 Mar 30	16573824
Single neurons in the nucleus of the solitary tract respond selectively to bitter taste stimuli.	2006 Nov	16899635
Bitter stimuli induce Ca2+ signaling and CCK release in enteroendocrine STC-1 cells: role of L-type voltage-sensitive Ca2+ channels.	2006 Oct	16707556
Exploratory behaviour in NO-dependent cyclase mutants of Drosophila shows defects in coincident neuronal signalling.	2007 Aug 6	17683617
Broad tuning of the human bitter taste receptor hTAS2R46 to various sesquiterpene lactones, clerodane and labdane diterpenoids, strychnine, and denatonium.	2007 Jul 25	17595105
Functional characterization of human bitter taste receptors.	2007 May 1	17253962
Characterization of ligands for fish taste receptors.	2007 May 23	17522303
A non-invasive method for ending thumb- and fingersucking habits.	2007 Oct	18175885
The neural processing of taste.	2007 Sep 18	17903281
Behavioral genetics and taste.	2007 Sep 18	17903279
Analysis of axonal regeneration in the central and peripheral nervous systems of the NG2-deficient mouse.	2007 Sep 27	17900358
Predators' toxin burdens influence their strategic decisions to eat toxic prey.	2007 Sep 4	17716896
Adverse reactions associated with respirator fit testing of healthcare workers in British Columbia, Canada: a review of compensation claim cases.	2007 Winter	18458024
Bitter taste receptors influence glucose homeostasis.	2008	19092995
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	18569160
Norepinephrine is coreleased with serotonin in mouse taste buds.	2008 Dec 3	19052199
Role of CCK1 and Y2 receptors in activation of hindbrain neurons induced by intragastric administration of bitter taste receptor ligands.	2008 Jan	18003792
Riboflavin-binding protein is a novel bitter inhibitor.	2008 Jan	17846099
Responses of the ciliates tetrahymena and paramecium to vertebrate odorants and tastants.	2008 Jan-Feb	18251800
The impact of bittering agents on suicidal ingestions of antifreeze.	2008 Jul	18584362
Nasal solitary chemoreceptor cell responses to bitter and trigeminal stimulants in vitro.	2008 Jun	18417634
Intragastric infusion of denatonium conditions flavor aversions and delays gastric emptying in rodents.	2008 Mar 18	18174110
The taste transduction channel TRPM5 is a locus for bitter-sweet taste interactions.	2008 May	18070821
Construction of a taste-blind medaka fish and quantitative assay of its preference-aversion behavior.	2008 Nov	18700838
Tonic activity of Galpha-gustducin regulates taste cell responsivity.	2008 Nov 12	18930056
Safety evaluation of topical applications of ethanol on the skin and inside the oral cavity.	2008 Nov 13	19014531
Constructing quality profiles for taste compounds in rats: a novel paradigm.	2008 Oct 20	18664369
Preferences of 14 rat strains for 17 taste compounds.	2008 Oct 20	18639567
Sweet taste receptor expressed in pancreatic beta-cells activates the calcium and cyclic AMP signaling systems and stimulates insulin secretion.	2009	19352508
Gustation in fish: search for prototype of taste perception.	2009	19145412
Chemical analysis and risk assessment of diethyl phthalate in alcoholic beverages with special regard to unrecorded alcohol.	2009 Dec 2	19956573
Delineation of the chemomechanosensory regulation of gastrin secretion using pure rodent G cells.	2009 Jul	19208342
Signalling mechanisms in mouse bitter responsive taste cells.	2009 Jul 1	19562832
Bitter-responsive gustatory neurons in the rat parabrachial nucleus.	2009 Mar	19129294
Central Fos expression and conditioned flavor avoidance in rats following intragastric administration of bitter taste receptor ligands.	2009 Mar	19073908
Gustatory responsiveness to six bitter tastants in three species of nonhuman primates.	2009 May	19399556
Contribution of the T1r3 taste receptor to the response properties of central gustatory neurons.	2009 May	19279151
Residual chemosensory capabilities in double P2X2/P2X3 purinergic receptor null mice: intraoral or postingestive detection?	2009 Nov	19833662
A Drosophila gustatory receptor essential for aversive taste and inhibiting male-to-male courtship.	2009 Oct 13	19765987
Discrimination of taste qualities among mouse fungiform taste bud cells.	2009 Sep 15	19622604
Molecular and cellular designs of insect taste receptor system.	2010	20617187
Chemoreception regulates chemical access to mouse vomeronasal organ: role of solitary chemosensory cells.	2010 Jul 30	20689832
Responses of single chorda tympani taste fibers of the calf (Bos taurus).	2010 Jun	20212013
Vasoactive intestinal peptide-null mice demonstrate enhanced sweet taste preference, dysglycemia, and reduced taste bud leptin receptor expression.	2010 May	20150284
Bitter taste receptors on airway smooth muscle bronchodilate by localized calcium signaling and reverse obstruction.	2010 Nov	20972434
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	20856820

Patents

Sample Use Guides

In Vivo Use Guide

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

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 `Fri Dec 15 17:46:23 GMT 2023` Edited by `admin` on `Fri Dec 15 17:46:23 GMT 2023`
Record UNII	0W5171805N
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DENATONIUM CHLORIDE

Common 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