N-Decyl-N,N-dimethyldecan-1-aminium chloride, also known as Diecyldimethylammonium chloride, or DDAC, is a broad-spectrum biocide that has antimicrobial activity against a variety of pathogens, including both enveloped and non-enveloped viruses, Pseudomonas aeruginosa, Legionella pneumophilia, Staphylococcus aureus, and Escherichia coli[1].

Absorption, Distribution and Excretion
DDAC (40% aqueous in both radiolabled (14C) and nonradiolabled form), used in a definitive pharmacokinetic study to determine absorption, distribution and excretion and was administered orally (single dose), by gavage, to Charles River CD Rats (Crl CD(SD)Br--5/sex/group) in 3 dose regimens: 1) A single low dose (5 mg/kg), 2) a repeated low dose in diet containing 34 ppm "cold" in the feed daily for 14 days, followed by a 5 mg/kg dose of (14C)]-DDCA (9.01 mCi/mmole, and 99% radiochemical purity) or 3) a single high dose of 50 mg/kg. Excretion of radioactivity was shown to occur primarily in the feces (89-99%), some in urine (<2.5%), and an insignificant amount was expired. Highly ionic DDAC is not readily absorbed from the GI tract...

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Metabolism / Metabolites
DDAC (40% aqueous in both radiolabled (14C) and nonradiolabled form), used in a definitive pharmacokinetic study to determine absorption, distribution and excretion and was administered orally (single dose), by gavage, to Charles River CD (Crl CD(SD)Br--5/sex/group) ... . In the addendum the metabolic profile was determined in a 2 step experiment. First, another group of rats (10 male Charles River CD (Crl CD(SD)Br) were treated with (14C)-DDAC at 50 mg/kg in order to obtain enough (14C) residues to use as standards. The (14C) metabolites were characterized by TLC, HPLC and MS. The second part of the experiment involved using the "standard" metabolic profiles to analyze the metabolites from feces samples obtained in the initial study. It was shown that metabolism tends to be sex specific. Females metabolize the parent compound more so than males. Metabolism, which may be microbial in nature, involved the oxidation of the 2 decyl side chains to form hydroxy and hydroxyketo derivatives. Modification of methyl substituents was not evident.

Toxicity Summary
IDENTIFICATION AND USE: Didecyl dimethylammonium chloride is a clear yellow liquid with an ethanolic odor. It is used as an algaecide, bacteriocide, fungicide, fungistat, microbiocide, microbiostat disinfectant, viricide, tuberculocide, molluscide, sanitizer, wood preservative, deodorant, and insecticide. It has been tested for treatment of impetiginized eczema patients in combination with prednicarbate. HUMAN EXPOSURE AND TOXICITY: Nausea, headache, and sore throat are the primary systemic effects that have been reported. The primary dermal effects that have been reported are rash, burning sensation, numbness, and itching. A case report of dermatitis from detergent/disinfectant was described. A 24 year old woman, who had worked in a hospital for 2 years, presented with a 2 month history of dermatitis of the dorsum of the hands and wrists. Patch testing showed she was positive for didecyldimethylammonium chloride and bis-(aminopropyl)-laurylamine which was present in detergents/disinfectants. According to the EPA classification didecyl dimethylammonium chloride is not likely to be carcinogenic to humans. ANIMAL STUDIES: In animals it is a severe eye irritant, severe dermal irritant, but not a sensitizer. It was of moderate acute oral toxicity in rodents, with possible effects on the liver and central nervous system being seen. In rats no adverse oncogenic effects were observed, however, there were treatment-related changes in both sexes in the mesenteric lymph node (blood filled sinuses, hemosiderosis and hystiocytosis) and bile duct hyperplasia at 1500 ppm. There were no developmental effects in rats. In developmental study in rabbits an increased number of dead fetuses/litter and decreased fetal body weight at 10.0 mg/kg was observed. In the Ames test, with or without the microsomal activation (S-9 fraction), didecyl dimethylammonium chloride was not mutagenic to Salmonella typhimurium tester strains. It was not mutagenic in vivo in rats, in Chinese hamster ovary cells, and did not produce unscheduled DNA synthesis. ECOTOXICITY STUDIES: Swimming performance decreased significantly in juvenile rainbow trout. Significant decreases in larval growth and survival were noted at all tested concentrations and in all sturgeon age groups. The larval stage was usually more sensitive than the fry stage. Acute toxicity tests with fertilized eggs were unsuccessful. Developmental stage altered the sensitivity of coho salmon to Bardac 2280, with alevins being approximately twice as sensitive as smolts.

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Toxicity Data
LC50 (rat) = 70 mg/m3

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Interactions
The bactericidal activity of a quaternary ammonium salt, didecyldimethylammonium chloride (DDAC), was depressed by the presence of soap, sodium laurate (NaLA): the minimum lethal concentration (MLC) of DDAC against Staphylococcus aureus was 63 and 250 ug/mL in the absence and presence of 0.01% NaLA, respectively. The neutralizing effect was studied in relation with the mode of action of DDAC. The apparent uptake of DDAC by the cell was not repressed by NaLA's presence when compared to that in its absence. The solution of NaLA showed alkaline pH, but the biocidal activity of DDAC was higher at pH 11 than at pH 7. Although the presence of NaLA had no significant effect on DDAC's action on increasing the turbidity of the cell suspension, the mixture of these reagents alone without cells exhibited some turbidity. From these findings it is deduced that NaLA can form a less active complex with DDAC by both ionic and hydrophobic interactions...

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Non-Human Toxicity Values
LD50 Rat oral 84 mg/kg
LD50 Rat (male) oral 331 mg/kg /65% a.i./ /from table/
LD50 Rat (female) oral 238 mg/kg /65% a.i./ /from table/
LD50 Rat oral 238 mg/kg /80% a.i./
For more Non-Human Toxicity Values (Complete) data for DIDECYL DIMETHYL AMMONIUM CHLORIDE (10 total), please visit the HSDB record page.

[1]. Anderson SE, et al. Evaluation of the irritancy and hypersensitivity potential following topical application of didecyldimethylammonium chloride. J Immunotoxicol. 2016;13(4):557-566.

Didecyldimethylammonium chloride is an organic molecular entity.
See also: Didecyldimonium (has active moiety); BENZALKONIUM CHLORIDE; didecyldimonium chloride (component of); Chlorhexidine gluconate; didecyldimonium chloride (component of) ... View More ...

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Therapeutic Uses
EXPL THER A double blind trial with 2 concentrations of the combination didecyl dimethyl ammonium chloride (Hoe S-2922, Bardac-22) with prednicarbate for the treatment of impetiginized eczema in 30 hospitalized patients is described. The study did not reveal any significant differences in effectiveness, although a trend in favor of the higher concentration was apparent.

C22H48CLN

362.08

361.347

7173-51-5

20256-56-8 (Parent)

23558

Colorless crystals
Clear yellow liquid /commercial aqueous solution/
Solid powder of slight yellowish color at 20 °C

0.95 g/cm3 (20ºC)

>180°C

94-100°C

4.348

0

1

18

24

200

0

[Cl-].[N+](C([H])([H])[H])(C([H])([H])[H])(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]

RUPBZQFQVRMKDG-UHFFFAOYSA-M

InChI=1S/C22H48N.ClH/c1-5-7-9-11-13-15-17-19-21-23(3,4)22-20-18-16-14-12-10-8-6-2;/h5-22H2,1-4H3;1H/q+1;/p-1

didecyl(dimethyl)azanium;chloride

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : 100 mg/mL (276.18 mM)

Solubility in Formulation 1: ≥ 2.5 mg/mL (6.90 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.5 mg/mL (6.90 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (6.90 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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 (Please use freshly prepared in vivo formulations for optimal results.)