141-94-6 Usage
Description
Hexetidine is a mixture of stereoisomers that serves as an antibacterial and antifungal agent. It is a colorless or faint yellow-colored oily liquid with a characteristic amine odor and is soluble in methanol, benzene, and petroleum ether, but insoluble in water. Its effectiveness has been examined in reducing supragingival plaque and gingival inflammation when used as a mouthwash.
Uses
Used in Cosmetic Industry:
Hexetidine is used as a plant-derived composite antimicrobial agent for its antibacterial and antifungal properties, making it suitable for use in the cosmetic industry.
Used in Pharmaceutical Research:
Hexetidine is involved in various studies, including the identification of pure liquid salt forms of aspirin, alkyl-based selective displacers for protein purification via ion exchange chromatography, in vivo application of models for testing drugs against nonreplicating Mycobacterium tuberculosis, nutrient-sensitized screening for drugs that shift the energy metabolism from mitochondrial respiration to glycolysis, inhibition of angiogenesis, and screening antimalarial drugs.
Used as a Fungicide, Bactericide, and Algicide:
Hexetidine is used as a fungicide, bactericide, and algicide for its antimicrobial properties, making it suitable for application in the agricultural and environmental industries.
Used as an Antistatic Agent:
Hexetidine is used as an antistatic agent in the synthetics industry, where its properties help reduce the buildup of static electricity.
Used in Medicine:
Hexetidine is used as an antifungal agent in the medical field, where it can be applied to treat various fungal infections.
Originator
Sterisil,Warner Lambert,US,1956
Production Methods
Hexetidine is prepared by hydrogenation under pressure of 1,3-
bis(2-ethylhexyl)-5-methyl-4-nitrohexahydropyriminine at 100°C
using Raney nickel as a catalyst.
Manufacturing Process
Nitroethane and formaldehyde are first reacted to give 2-methyl-2-nitro-1,3-
propanediol. This is reacted with 2-ethylhexylamine and formaldehyde to give
5-nitro-1,3-bis(2-ethylhexyl)-5-methyl-hexahydropyrimidine.To a hydrogenation apparatus containing 500 ml of methanol and 10 g of
Raney nickel catalyst were continuously added over a period of one hour, 240
g of 5-nitro-1,3-bis(2-ethylhexyl)-5-methylhexahydropyrimidine. During the
one-hour period, the resulting mixture was hydrogenated at approximately
1,000 pounds per square inch utilizing room temperature as the initial
temperature and gradually increasing the temperature to about 70°C. At the
end of the one-hour period, hydrogenation was stopped. The reaction mixture
was first filtered to remove the catalyst and was then distilled at atmospheric
pressure at a temperature of 70°C to remove methanol. 197.5 g of 5-amino-
1,3-bis(2-ethylhexyl)-5-methylhexahydropyrimidine were collected.
Therapeutic Function
Antifungal
Hazard
Combustible.
Pharmaceutical Applications
Hexetidine is used as an antimicrobial preservative in cosmetics and
nonparenteral pharmaceutical formulations. Therapeutically, hexetidine
is mainly used as a 0.1% w/v solution in mouthwash
formulations for the prevention and treatment of minor local
infections, gingivitis, and mouth ulcers.
Safety
Hexetidine is mainly used in mouthwashes as a bactericidal and
fungicidal antiseptic. It is also used as an antimicrobial preservative
and is generally regarded as a relatively nontoxic and nonirritant
material at concentrations up to 0.1% w/v. Allergic contact
dermatitis and altered olfactory and taste perception have
occasionally been reported. Hexetidine is toxic when administered
intravenously.
Solutions of hexetidine in oil at concentrations of 5–10% w/v
cause strong primary irritations without sensitization in humans.
Long-term toxicological studies of up to 0.1% w/w of hexetidine in
food for 1 year do not show any toxic effect. Fetotoxicity,
embryotoxicity, and teratogenicity studies in rats of doses up to
50 mg/kg/day exhibit no sign of toxicity.
LD100 (cat, IV): 5–20 mg/kg
LD50 (dog, oral): 1.60 g/kg
LD50 (mouse, IP): 0.142 g/kg
LD50 (mouse, oral): 1.52 g/kg
LD50 (rat, oral): 0.61–1.43 g/kg
storage
Hexetidine is stable and should be stored in a well-closed container
in a cool, dry place. Brass and copper equipment should not be used
for the handling or storage of hexetidine.
Incompatibilities
Hexetidine is incompatible with strong oxidizing agents. Salts are
formed with mineral and organic acids; strong acids cause opening
of the hexahydropyrimidine ring, releasing formaldehyde.
Regulatory Status
Included in nonparenteral formulations licensed in Europe.
Check Digit Verification of cas no
The CAS Registry Mumber 141-94-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 1 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 141-94:
(5*1)+(4*4)+(3*1)+(2*9)+(1*4)=46
46 % 10 = 6
So 141-94-6 is a valid CAS Registry Number.
InChI:InChI=1/C21H45N3/c1-6-10-12-19(8-3)14-23-16-21(5,22)17-24(18-23)15-20(9-4)13-11-7-2/h19-20H,6-18,22H2,1-5H3
