Grundinformationen
- Standard-SMILES
CCCCCCCCCCCCCCCC[n+]1ccccc1.[Br-]- InChIKey
DVBJBNKEBPCGSY-UHFFFAOYSA-M- Summenformel
- C21H38N.Br
- Durchschnittliche Molmasse
- 384,4 g/mol
Überblick
Cetylpyridinium bromide is a pyridinium salt that has N-hexadecylpyridinium as the cation and bromide as the anion. It has a role as a surfactant, an antiseptic drug and an EC 2.7.11.18 (myosin-light-chain kinase) inhibitor. It is a bromide salt and a pyridinium salt.
Namen und Bezeichner
- Bevorzugter Name
- Cetylpyridinium Bromide
- IUPAC
- 1-hexadecylpyridin-1-ium bromide
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
140-72-7- PubChem CID
- 8816
- DTXSID
DTXSID3033307- ChEMBL
CHEMBL334255- ChEBI
CHEBI:77052- UNII
- O77BKZ14DE
- EC Number
- 205-428-3
Eigenschaften
Berechnete Struktureigenschaften
- Polarare Oberfläche (TPSA)
- 3,9 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 1
- Frei drehbare Bindungen
- 15
- Schwere Atome
- 23
- Formalladung
- 0
- Komplexität
- 208
Experimentelle und physikochemische Eigenschaften
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H302 (96.1%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P261, P264, P264+P265, P270, P271, P273, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 51 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
Chemical: Pyridinium, 1-hexadecyl-, bromide
Cetylpyridinium bromide: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Topical use during pregnancy unlikely to cause teratogenic effects; [ToxPlanet: TERIS] Causes changes in leukocyte count, dermatitis, and effects on true cholinesterase in 21-day intermittent dermal studies of rats; [RTECS] A severe irritant that may cause eye injury; Harmful by ingestion; Highly toxic by inhalation; Chloride salt: Not a skin sensitizer in guinea pigs; LC50 (rat) = 90 mg/m3/4hr; [Acros Organics MSDS] See Cetylpyridinium chloride.
FIFRA Requirements
As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Cetylpyridinium bromide is found on List C. Case No: 3013; Pesticide type: insecticide, fungicide, rodenticide, antimicrobial; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Cetylpyridinium bromide; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."
Sicherheit und Schutzausrüstung
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Toxikologische Informationen
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 240(SRC), determined from a log Kow of 1.83(2) and a regression-derived equation(3), indicates that cetylpyridinium bromide is expected to have moderate mobility in soil(SRC). However, quaternary ammonium compounds are known to sorb strongly, and rapidly in well-mixed systems, to a wide variety of materials (such as sewage sludge, sediment, clay)(5) and the mobility of cetylpyridinium bromide in soil may be considerably less than estimated. Volatilization of cetylpyridinium bromide from moist soil surfaces is not expected as this compound is a salt(SRC). Cetylpyridinium bromide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.3X10-7 mm Hg(SRC), determined from a fragment constant method(4). Cetylpyridinium bromide is expected to biodegrade rapidly in the environment(SRC) based on studies using sewage(5,6); rates of biodegradation increased with acclimation of the microbial population(5,6).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 240(SRC), determined from an measured log Kow of 1.83(2) and a regression-derived equation(3), indicates that cetylpyridinium bromide is not expected to adsorb to suspended solids and sediment(SRC). However, quaternary ammonium compounds are known to sorb strongly, and rapidly in well-mixed systems, to a wide variety of materials (such as sewage sludge, sediment, clay)(7); therefore, cetylpyridinium bromide should be strongly adsorbed to suspended solids and sediment in water. This compound is expected to exist in the dissociated form in the environment and therefore volatilization from water surfaces will not be an important fate process(SRC). According to a classification scheme(4), BCF values of 21, 22, and 13, measured for clams, fathead minnows, and tadpoles, respectively(5), suggest the potential for bioconcentration in aquatic organisms is low(SRC). Cetylpyridinium bromide is expected to biodegrade rapidly in the environment(SRC) based on studies using sewage(7,8); rates of biodegradation increased with acclimation of the microbial population(7,8).
ATMOSPHERIC FATE: Cetylpyridinium bromide will exist as the ion in the environment and, thus, will be present solely in the particulate phase in the atmosphere. Particulate-phase cetylpyridinium bromide may be removed from the air by wet and dry deposition.(SRC)
Soil Adsorption/Mobility
Kd values for cetylpyridinium bromide on Sherman Island sediment and bentonite clay were 80 and 33,400, respectively(1). The Koc of cetylpyridinium bromide is estimated as 240(SRC), using a measured log Kow of 1.83(2) and a regression-derived equation(3). According to a classification scheme(4), this estimated Koc value suggests that cetylpyridinium bromide is expected to have moderate mobility in soil. However, quaternary ammonium compounds are known to sorb strongly, and rapidly in well-mixed systems, to a wide variety of materials (such as sewage sludge, sediment, clay)(5) and the mobility of cetylpyridinium bromide in soil may be considerably less than estimated(SRC).
Environmental Biodegradation
Biodegradation: at 18 mg/l (inoculum = sew.) lag period = 6 days; after 17 days complete degradation.
AEROBIC: Concentrations of up to 25 mg/l cetylpyridinium bromide were readily removed by model trickling filters acclimated to this compound; sorption was not a major process of removal as shown by extraction of slime layers(1). Cetylpyridinium bromide at 6 mg/l in the influent was not detected in effluent samples in model activated sludge systems(3). Cetylpyridinium bromide was completely degraded in 17 days in sewage(2). Another study shows 100% biodegradation in 3 days with this reduced to 2 days using the acclimated sewage in a second pass(2). Mean cetylpyridinium (counterion unspecified) removal of 96.0 and 77.2%, respectively, was observed at an activated sludge and a trickling filter wastewater treatment plant in England; in the Heidelsheim plant in Germany, 95% removal was reported(4).
Environmental Bioconcentration
Whole body BCF values of 21, 22, and 13, were measured for clams, fathead minnows, and tadpoles, respectively, under flow-through conditions over a 7-day period(1). According to a classification scheme(2), these BCF values suggest the potential for bioconcentration in aquatic organisms is low(SRC).
Volatilization from Water/Soil
Cetylpyridinium bromide is expected to exist in the dissociated form in the environment and, therefore, volatilization from water surfaces or moist soil surfaces will not be an important fate process. Cetylpyridinium bromide is not expected to volatilize from dry soil surfaces as it exists as an ion in the environment and ions do not volatilize. (SRC)
Environmental Abiotic Degradation
Cetylpyridinium bromide is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(1). Pyridine has a weak absorption band that extends into the environmental UV spectrum(2), which suggests that direct photolysis is not likely to be an important fate process for cetylpyridinium bromide(SRC).
Probable Routes of Human Exposure
Occupational exposure to cetylpyridinium bromide may occur through inhalation and dermal contact with this compound at workplaces where cetylpyridinium bromide is produced or used. The general population may be exposed to cetylpyridinium bromide via its use in consumer products, such as deodorants. (SRC)
Environmental Fate/Exposure Summary
Cetylpyridinium bromide's production and use as a topical antiseptic/disinfectant, deodorant, laboratory reagent, and surfactant may result in its release to the environment through various waste streams. If released to air, cetylpyridinium bromide will exist in the particulate phase in the ambient atmosphere as an ion. Particulate-phase cetylpyridinium bromide will be removed from the atmosphere by wet and dry deposition. If released to soil, cetylpyridinium bromide is expected to have moderate mobility based upon an estimated Koc of 240. However, quaternary ammonium compounds are known to sorb strongly, and rapidly in well-mixed systems, to a wide variety of materials (such as sewage sludge, sediment, clay) and the mobility of cetylpyridinium bromide in soil may be considerably less than the estimated value. Volatilization from moist soil surfaces is not expected to be an important fate process as this compound is expected to exist in the environment in the dissociated form. Cetylpyridinium bromide will not volatilize from dry soil surfaces based upon its vapor pressure. Cetylpyridinium bromide is expected to biodegrade rapidly in aerobic soil and water environments based on studies using sewage; rates of biodegradation increased with acclimation of the microbial population. If released into water, cetylpyridinium bromide is not expected to adsorb to suspended solids and sediment based upon the estimated Koc; however, it is a quaternary ammonium compounds and based on this is expected to adsorb strongly to suspended solids and sediment in the water. Volatilization from water surfaces will not be an important fate process as this compound is expected to exist in the dissociated form in the environment. BCF values of 21, 22, and 13, measured for clams, fathead minnows, and tadpoles, respectively suggests that bioconcentration in aquatic organisms is low. Hydrolysis of cetylpyridinium bromide is not expected due to the lack of hydrolyzable functional groups. Occupational exposure to cetylpyridinium bromide may occur through inhalation and dermal contact with this compound at workplaces where cetylpyridinium bromide is produced or used. The general population will most likely be exposed to cetylpyridinium bromide via dermal contact with consumer products containing cetylpyridinium bromide. (SRC)
Antidote and Emergency Treatment
/SRP:/ Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/
/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
Regulatorische Informationen
FIFRA Requirements
As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Cetylpyridinium bromide is found on List C. Case No: 3013; Pesticide type: insecticide, fungicide, rodenticide, antimicrobial; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Cetylpyridinium bromide; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological Classification
Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects.
Purifying or cleansing agents, usually salts of long-chain aliphatic bases or acids, that exert cleansing (oil-dissolving) and antimicrobial effects through a surface action that depends on possessing both hydrophilic and hydrophobic properties.
Verwendung und Herstellung
Uses
Used in mouthwashes, lozenges, and as a topical disinfectant; [TERIS] Used as a germicide, deodorant, laboratory reagent, surfactant, and topical antiseptic/disinfectant; [HSDB]
All active germicide/disinfectant/mildewcide pesticide product registrations cancelled in 1989 in the US; [NPIRS]
Using Disinfectants or Biocides [Category: Clean]
For Cetylpyridium bromide (USEPA/OPP Pesticide Code: 069118) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./
The active ingredient is no longer contained in any registered pesticide products ... "cancelled."
Germicide, deodorant, laboratory reagent, surfactant
Zugehörige Reaktionen
Verknüpfte Notizen
Wird geladen…