T3DB: Quaternium-15

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (2)XML

Targets (2)

Record Information

Version

2.0

Creation Date

2009-11-24 01:14:16 UTC

Update Date

2014-12-24 20:26:15 UTC

Accession Number

T3D3628

Identification

Common Name

Quaternium-15

Class

Small Molecule

Description

Quaternium-15 is a quaternary ammonium salt used as a preservative in many cosmetics and industrial substances. It acts as a formaldehyde releaser. It can cause contact dermatitis in sensitive individuals. It's toxicity is also due to it's ability to react and release formaldehyde and nitrosamines, both of which are believed to be carcinogenic. (8, 9)

Compound Type

Amine
Cosmetic Toxin
Household Toxin
Industrial/Workplace Toxin
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
1-(3-Chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloride
1-(3-Chloroallyl)-3,5,7-triazo-1-azoniaadamantane chloride
Chloroallyl methenamine chloride
Cinartc 200
Dowco 184
Dowicide q
Dowicil 100
Dowicil 200
Dowicil 75
Hexamethylenetetramine chloroallyl chloride
Methenamine 3-chloroallylochloride
N-(3-Chloroallyl)hexaminium chloride
Quaternium 15

Chemical Formula

C₉H₁₆Cl₂N₄

Average Molecular Mass

251.156 g/mol

Monoisotopic Mass

250.075 g/mol

CAS Registry Number

4080-31-3

IUPAC Name

1-(3-chloroprop-2-en-1-yl)-1,3,5,7-tetraazatricyclo[3.3.1.1³,⁷]decan-1-ium chloride

Traditional Name

1-(3-chloroprop-2-en-1-yl)-1,3,5,7-tetraazatricyclo[3.3.1.1³,⁷]decan-1-ium chloride

SMILES

[Cl-].ClC=CC[N+]12CN3CN(CN(C3)C1)C2

InChI Identifier

InChI=1S/C9H16ClN4.ClH/c10-2-1-3-14-7-11-4-12(8-14)6-13(5-11)9-14;/h1-2H,3-9H2;1H/q+1;/p-1/b2-1+;

InChI Key

InChIKey=UKHVLWKBNNSRRR-TYYBGVCCSA-M

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 1,3,5-triazinanes. These are triazinanes having three nitrogen ring atoms at the 1-, 3-, and 5- positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Triazinanes

Sub Class

1,3,5-triazinanes

Direct Parent

1,3,5-triazinanes

Alternative Parents

Substituents

1,3,5-triazinane
Tetraalkylammonium salt
Aminal
Vinyl chloride
Azacycle
Vinyl halide
Chloroalkene
Haloalkene
Organic nitrogen compound
Organic salt
Organic chloride salt
Hydrocarbon derivative
Organonitrogen compound
Organochloride
Organohalogen compound
Organopnictogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

quaternary ammonium salt (CHEBI:59607 )
organochlorine compound (CHEBI:59607 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	304 mg/mL at 25°C
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	39.7 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-2.7	ChemAxon
logS	-0.8	ALOGPS
pKa (Strongest Basic)	3.7	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.72 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	66.87 m³·mol⁻¹	ChemAxon
Polarizability	22.05 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0390000000-b38b08aeb969e9ff8719	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0790000000-8e57ee50cfe260ac8b09	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0900000000-afef158b3f0192f3f0c1	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0290000000-25e47eb7f91df97fdac2	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0910000000-b175d86cb0939c89caf0	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-1910000000-fc5ce9f443c864a657ac	2019-02-23	View Spectrum

Toxicity Profile

Route of Exposure

Oral (6) ; inhalation (6) ; dermal (6)

Mechanism of Toxicity

Quaternium-15 is a formaldehyde releaser. It is likely that formaldehyde toxicity occurs when intracellular levels saturate formaldehyde dehydrogenase activity, allowing the unmetabolized intact molecule to exert its effects. Formaldehyde is known to form cross links between protein and DNA and undergo metabolic incorporation into macromolecules (DNA, RNA, and proteins). Quaternium-15 is also a nitrosating agent. Nitrosating agents may decompose and/or react to cause nitrosamine contamination. Nitrosamines are produced from secondary amines and amides in the presence of nitrite ions and are believed to be carcinogenic. Once in the body, nitrosamines are activated by cytochrome P-450 enzymes. They are then believed to induce their carcinogenic effects by forming DNA adducts at the N- and O-atoms. (6, 7, 8, 1, 2, 3, 9)

Metabolism

Formaldehyde may be absorbed following inhalation, oral, or dermal exposure. It is an essential metabolic intermediate in all cells and is produced during the normal metabolism of serine, glycine, methionine, and choline and also by the demethylation of N-, S-, and O-methyl compounds. Exogenous formaldehyde is metabolized to formate by the enzyme formaldehyde dehydrogenase at the initial site of contact. After oxidation of formaldehyde to formate, the carbon atom is further oxidized to carbon dioxide or incorporated into purines, thymidine, and amino acids via tetrahydrofolatedependent one-carbon biosynthetic pathways. Formaldehyde is not stored in the body and is excreted in the urine (primarily as formic acid), incorporated into other cellular molecules, or exhaled as carbon dioxide. Nitrosamines can also enter the body via ingestion, inhalation, or dermal contact. Once in the body, nitrosamines are metabolized by cytochrome P-450 enzymes, which essentially activates them into carcinogens. (6, 1, 2)

Toxicity Values

LD50: 500 mg/kg (Oral, Rat) (4) LD50: 565 mg/kg (Dermal, Rabbit) (4)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

1, carcinogenic to humans (for formaldehyde). (5)

Uses/Sources

Quaternium-15 is used as a preservative in many cosmetics and industrial substances. (9)

Minimum Risk Level

Not Available

Health Effects

Quaternium-15 releases formaldehyde, a known human carcinogen. It may also react to produce nitrosamines, which are believed to be carcinogenic. Quaternium-15 is also an allergen, and can cause contact dermatitis in susceptible individuals. Many of those with an allergy to quaternium-15 are also allergic to formaldehyde. It is the single most often found cause of allergic contact dermatitis of the hands. (6, 8, 9)

Symptoms

Quaternium-15 can cause contact dermatitis in sensitive individuals. (9)

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

PubChem Compound ID

6433396

ChEMBL ID

Not Available

ChemSpider ID

4938552

KEGG ID

Not Available

UniProt ID

Not Available

OMIM ID

ChEBI ID

59607

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Quaternium-15

References

Synthesis Reference

Not Available

MSDS

T3D3628.pdf

General References

Oyama T, Sugio K, Uramoto H, Iwata T, Onitsuka T, Isse T, Nozoe T, Kagawa N, Yasumoto K, Kawamoto T: Increased cytochrome P450 and aryl hydrocarbon receptor in bronchial epithelium of heavy smokers with non-small cell lung carcinoma carries a poor prognosis. Front Biosci. 2007 May 1;12:4497-503. [17485391 ]
Sasaki S, Sata F, Katoh S, Saijo Y, Nakajima S, Washino N, Konishi K, Ban S, Ishizuka M, Kishi R: Adverse birth outcomes associated with maternal smoking and polymorphisms in the N-Nitrosamine-metabolizing enzyme genes NQO1 and CYP2E1. Am J Epidemiol. 2008 Mar 15;167(6):719-26. doi: 10.1093/aje/kwm360. Epub 2008 Jan 23. [18218609 ]
Drablos F, Feyzi E, Aas PA, Vaagbo CB, Kavli B, Bratlie MS, Pena-Diaz J, Otterlei M, Slupphaug G, Krokan HE: Alkylation damage in DNA and RNA--repair mechanisms and medical significance. DNA Repair (Amst). 2004 Nov 2;3(11):1389-407. [15380096 ]
Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
ATSDR - Agency for Toxic Substances and Disease Registry (1999). Toxicological profile for formaldehyde. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
Wikipedia. Nitrosamine. Last Updated 16 November 2009. [Link]
Organic Natural Health (1998). Cancer Causing Toxic Chemical Ingredients in Cosmetic and Skin Care Products. [Link]
Wikipedia. Quaternium-15. Last Updated 4 November 2009. [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

1. RNA

References

ATSDR - Agency for Toxic Substances and Disease Registry (1999). Toxicological profile for formaldehyde. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
Wikipedia. Quaternium-15. Last Updated 4 November 2009. [Link]

2. DNA

General Function:: Used for biological information storage.
Specific Function:: DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:: 2.15 x 10¹² Da

References

Drablos F, Feyzi E, Aas PA, Vaagbo CB, Kavli B, Bratlie MS, Pena-Diaz J, Otterlei M, Slupphaug G, Krokan HE: Alkylation damage in DNA and RNA--repair mechanisms and medical significance. DNA Repair (Amst). 2004 Nov 2;3(11):1389-407. [15380096 ]
ATSDR - Agency for Toxic Substances and Disease Registry (1999). Toxicological profile for formaldehyde. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
Organic Natural Health (1998). Cancer Causing Toxic Chemical Ingredients in Cosmetic and Skin Care Products. [Link]
Wikipedia. Quaternium-15. Last Updated 4 November 2009. [Link]

Quaternium-15 (T3D3628)

Structure for T3D3628: Quaternium-15

Targets

References

References