U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C9H16ClN4
Molecular Weight 215.703
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 1

SHOW SMILES / InChI
Structure of CHLOROALLYL METHENAMINE

SMILES

Cl\C=C/C[N+]12CN3CN(CN(C3)C1)C2

InChI

InChIKey=LDLCEGCJYSDJLX-UPHRSURJSA-N
InChI=1S/C9H16ClN4/c10-2-1-3-14-7-11-4-12(8-14)6-13(5-11)9-14/h1-2H,3-9H2/q+1/b2-1-

HIDE SMILES / InChI

Molecular Formula C9H16ClN4
Molecular Weight 215.703
Charge 1
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Quaternium-15, a preservative, is one of the most used substances and is added to several cosmetics and other industrial products. Quaternium-15 is a mixture of isomers, where the cis-form is the dominant form and where the trans-form is the minor component present as an impurity. Quaternium-15 can be found under a variety of names, most commonly those of the Dow Chemical Company: Dowicil 200 (cis isomer only), Dowicil 75 and Dowicil 100 (both a mix of cis and trans isomers). The isolated cis-compound is used primarily in cosmetic applications, with a maximum permitted concentration in the EU of 0.2%. DOWICIL 200 preservative (cis form) is used primarily as a preservative in a wide variety of personal-care and cosmetic products. It is designed to provide highly effective broad-spectrum antimicrobial activity, especially in water-based formulations. It is used in both leave-on and rinse-off application such as baby-care products, hair-care products, lotions, powders, and creams. The mixed product (cis- and trans-) is used in a wider range of formulations such as: emulsifiable metal-cutting fluids; latex and emulsion paints; liquid floor polishes and floor waxes; glues and adhesives. Recently, the cis-form has been classified as a CMR substance with the classification toxic to reproduction, category 3. This classification only concerns the cis-isomer:

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Inactive ingredient
Dovonex

Approved Use

DOVONEX cream and ointment is used for the topical treatment of psoriasis
PubMed

PubMed

TitleDatePubMed
[Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations].
2004 May
Relationship between formaldehyde and quaternium-15 contact allergy. Influence of strength of patch test reactions.
2010 Oct
Patch testing with formaldehyde 2.0% in parallel with 1.0% by the Swedish contact dermatitis research group.
2014 Jul
Investigation on formaldehyde release from preservatives in cosmetics.
2015 Oct
Evaluation of Functionality and Biological Responses of Mytilus galloprovincialis after Exposure to Quaternium-15 (Methenamine 3-Chloroallylochloride).
2016 Jan 26
Sensitization to Formaldehyde in Northeastern Italy, 1996 to 2012.
2016 Jan-Feb
Cytotoxicity, haemolymphatic parameters, and oxidative stress following exposure to sub-lethal concentrations of quaternium-15 in Mytilus galloprovincialis.
2016 Nov
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
quaternium-15 was exposured for Mytilus galloprovincialis for 18 days at three different concentrations (0.1, 1.0 and 2.0 mg/L). The results demonstrate that at higher concentrations histological damages to M. galloprovincialis gills occur, like melanosis, light exfoliations, increase of mucus production and infiltrative inflammation. In addition digestive gland cells of M. galloprovincialis, were not able to perform the regulation volume decrease (RVD) owing to osmotic stress following the exposure to the preservative.
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:10:22 GMT 2023
Edited
by admin
on Sat Dec 16 10:10:22 GMT 2023
Record UNII
H4IHD3E11G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHLOROALLYL METHENAMINE
Common Name English
1-((2Z)-3-CHLORO-2-PROPEN-1-YL)-3,5,7-TRIAZA-1-AZONIATRICYCLO(3.3.1.13,7)DECANE
Systematic Name English
3,5,7-TRIAZA-1-AZONIATRICYCLO(3.3.1.13,7)DECANE, 1-((2Z)-3-CHLORO-2-PROPEN-1-YL)-
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID1047992
Created by admin on Sat Dec 16 10:10:22 GMT 2023 , Edited by admin on Sat Dec 16 10:10:22 GMT 2023
PRIMARY
CAS
56060-15-2
Created by admin on Sat Dec 16 10:10:22 GMT 2023 , Edited by admin on Sat Dec 16 10:10:22 GMT 2023
PRIMARY
FDA UNII
H4IHD3E11G
Created by admin on Sat Dec 16 10:10:22 GMT 2023 , Edited by admin on Sat Dec 16 10:10:22 GMT 2023
PRIMARY
PUBCHEM
5846454
Created by admin on Sat Dec 16 10:10:22 GMT 2023 , Edited by admin on Sat Dec 16 10:10:22 GMT 2023
PRIMARY