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Home > Encyclopedia > Acetamide

Acetamide

pharmaceutical raw materials
Acetamide structure

Acetamide 

structure

Description

Acetamide is used primarily as a solvent and a plasticizer.


Acetamide appears as colorless crystals with a mousy odor (NTP, 1999). Low toxicity.|Solid|COLOURLESS DELIQUESCENT CRYSTALS.|Colorless crystals


Acetamide appears as colorless crystals with a mousy odor (NTP, 1999). Low toxicity.|Acetamide is a member of the class of acetamides that results from the formal condensation of acetic acid with ammonia. It is a monocarboxylic acid amide, a N-acylammonia and a member of acetamides. It is a tautomer of an acetimidic acid.|Acetamide is used primarily as a solvent and a plasticizer. Workers may be exposed in the plastics and chemical industries. It causes mild skin irritation from acute (short-term) exposure. No information is available on the chronic (long-term), reproductive/developmental, or carcinogenic effects of acetamide in humans. EPA has not classified acetamide for carcinogenicity.

Acetamide Basic Attributes

59.07

59.07

1071207

200-473-5

8XOE1JSO29

0233

25945

3077

DTXSID7020005

Deliquescent hexagonal crystals|Trigonal monoclinic crystals from alcohol and ether

2924199017

Characteristics

43.1

-1.26

White Crystals

1.159 g/cm3 @ Temp: 20 °C

81 °C

222 °C @ Press: 760 Torr

220-222°C

1.4274

H2O: 0.5 g/mL, Hazen ≤50

Store at RT

1 mm Hg ( 65 °C)

Oral-Rat LD50: 7000 mg/kg; Oral-Mouse LD50: 12900 mg/kg

Flammable; burning produces toxic nitrogen oxide gas

Odorless when pure, but frequently has a mousy odor

Pure acetamide has a bitter taste

0.63None

Henry's Law constant = 2.0X10-9 atm-cu m/mole at 25 °C (est)

0.63|pKb = 14.51 at 25 °C

Acetamide may react with azo and diazo compounds to generate toxic gases. May form flammable gases with strong reducing agents. Reacts as a weak base (weaker than water).|Dissolves easily in water, exhibiting amphoteric behavior. It is slow to hydrolyze unless an acid or base is present.|Hydroxyl radical reaction rate constant = 2.1X10-12 cu cm/molec-sec at 25 °C (est)

Deliquescent. Very soluble in water.

Amides and Imides

ACETAMIDE may react with azo and diazo compounds to generate toxic gases. May form flammable gases with strong reducing agents. Reacts as a weak bases (weaker than water). Mixing with dehydrating agents such as P2O5 or SOCl2 generates acetonitrile Burns to give toxic mixed oxides of nitrogen (NOx).

Liquid: -1198.7 kJ/mole; Solid: -1184.6 kJ/mole

56.1 kJ/mole

Critical temperature: 761 deg K (est); critical pressure 6600 kPa (est)

Safety Information

UN 3077 9/PG 3

1

40

36/37

AB4025000

Xn

Warehouse ventilated, low temperature and dry

Stable. Incompatible with strong acids, strong oxidizing agents, strong bases. Deliquescent. Triboluminescent.

P281

H351

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber; Contaminated packaging: Dispose of as unused product.|PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/|For more Disposal Methods (Complete) data for ACETAMIDE (8 total), please visit the HSDB record page.

Incompatible materials: Strong oxidizing agents, strong acids, strong bases, strong reducing agents.|Reacts with strong acids, such as hydrochloric, sulfuric, and nitric; strong oxidizers; strong bases; strong reducing agents; ammonia, isocyanates, phenols, cresols. Contact with water causes slow hydrolyzation to ammonia and acetate salts.

The flash point of this chemical has not been determined, but it is probably combustible. (NTP, 1992)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

|Warning|H351: Suspected of causing cancer [Warning Carcinogenicity]|P201, P202, P281, P308+P313, P405, and P501|H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]|Aggregated GHS information provided by 412 companies from 5 notifications to the ECHA C&L Inventory.|H320: Causes eye irritation [Warning Serious eye damage/eye irritation]|P201, P202, P264, P281, P305+P351+P338, P308+P313, P337+P313, P405, and P501|H316: Causes mild skin irritation [Warning Skin corrosion/irritation]|P201, P202, P264, P281, P305+P351+P338, P308+P313, P332+P313, P337+P313, P405, and P501

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should keep this material in a tightly-closed container under an inert atmosphere, and store it at refrigerated temperatures. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)|Eye/face protection: Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face particle respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).|For more Personal Protective Equipment (PPE) (Complete) data for ACETAMIDE (6 total), please visit the HSDB record page.

This substance is a combustible solid.

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical, or carbon dioxide.|Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.|Use dry chemical, carbon dioxide, water spray, or alcohol foam extinguishers. ... If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position.|The only respirators recommended for firefighting are self-contained breathing apparatuses that have full face-pieces and are operated in a pressure-demand or other positive-pressure mode.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.|Evacuate persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Ventilate area after cleanup is complete. Material is very water soluble and hydrolyzes slowly to ammonia and acetate salts. May be removed from alkaline solutions with adsorbent carbon. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters.|PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains.|Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.|PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/|For more Preventive Measures (Complete) data for ACETAMIDE (14 total), please visit the HSDB record page.

PRECAUTIONS FOR "CARCINOGENS": Procurement ... of unduly large amt ... should be avoided. To avoid spilling, carcinogens should be transported in securely sealed glass bottles or ampoules, which should themselves be placed inside strong screw-cap or snap-top container that will not open when dropped & will resist attack from the carcinogen. Both bottle & the outside container should be appropriately labelled. ... National post offices, railway companies, road haulage companies & airlines have regulations governing transport of hazardous materials. These authorities should be consulted before ... material is shipped. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": When no regulations exist, the following procedure must be adopted. The carcinogen should be enclosed in a securely sealed, watertight container (primary container), which should be enclosed in a second, unbreakable, leakproof container that will withstand chem attack from the carcinogen (secondary container). The space between primary & secondary container should be filled with absorbent material, which would withstand chem attack from the carcinogen & is sufficient to absorb the entire contents of the primary container in the event of breakage or leakage. Each secondary container should then be enclosed in a strong outer box. The space between the secondary container & the outer box should be filled with an appropriate quantity of shock-absorbent material. Sender should use fastest & most secure form of transport & notify recipient of its departure. If parcel is not received when expected, carrier should be informed so that immediate effort can be made to find it. Traffic schedules should be consulted to avoid ... arrival on weekend or holiday ... /Chemical Carcinogens/

Powdered form irritates eyes and respiratory tract.

Personal protection: P2 filter respirator for harmful particles. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Dry. Well closed.

Evaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly when dispersed, especially if powdered.

The substance is irritating to the eyes and skin.

This substance is possibly carcinogenic to humans.

NO open flames.

PREVENT DISPERSION OF DUST! STRICT HYGIENE!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety spectacles.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Acetamide is produced, as an intermediate or a final product, by process units covered under this subpart.|Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Acetamide is included on this list.

Acetamide is used primarily as a solvent and a plasticizer. Workers may be exposed in the plastics and chemical industries. It causes mild skin irritation from acute (short-term) exposure. No information is available on the chronic (long-term), reproductive/developmental, or carcinogenic effects of acetamide in humans. EPA has not classified acetamide for carcinogenicity.

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV.D.3.b).

Acetamide was detected at concentrations of 2.4 and 28.6 ug/L in distillate and residue, respectively, in leachate from a landfill for municipal wastes in Japan(1). Acetamide was detected in condensate and process oil-shale retort water at concentrations of 0.6 mg/L and 23.2 mg/L, respectively(2).

SOURCE DOMINATED: Acetamide has been identified in the air of a water treatment plant in Zurich, Switzerland(1).

Acetamide has been detected in tobacco smoke(1,2).

Toxicity

practically nontoxic

IDENTIFICATION AND USE: Acetamide is a solid. It is used as a solvent and stabilizer, accelerator in the estimation of bilirubin, antidote against monofluoroacetamide poisoning, and humectant for paper. HUMAN EXPOSURE AND TOXICITY: There are no data available. ANIMAL STUDIES: When acetamide was administered at a concentration of 5% in the diet to 99 male rats, with 2 rats returned to a control diet each week, liver tumors were found after treatment for 14-40 weeks in 22/81 rats. Acetamide-treated rats developed neoplastic nodules and hepatocellular carcinomas. The incidence, speed of onset, and frequency of metastases were greater in males than in females. Acetamide had the least toxic effects in regards to teratogenicity and embryotoxicity, compared to its derivatives. Acetamide produced morphological transformation in Syrian hamster embryo cells without metabolic activation. ECOTOXICITY STUDIES: Acetamide exhibited a selective damaging action on Entosiphon sulcatum.

Two groups of 40 male wistar rats were fed diets containing 2.5% acetamide or 2.5% acetamide + 5.6 l-arginine, & 2 groups of 15 males were fed diet containing 5.6% arginine glutamate or a control diet for 1 yr. In 2/8 rats fed acetamide ... hepatomas ... were observed; 7/16 rats fed acetamide for 1 yr and maintained on control diet for further 3 MO developed liver tumors. In contrast, 1/11 rats that received acetamide + arginine glutamate for 1 yr and control diet for 3 MO had hyperplastic liver nodules. No liver tumors occurred in control group nor in rats fed 5.6% arginine glutamate alone.

LD50 Rat oral 7000 mg/kg|LD50 Rat ip 10,300 mg/kg|LD50 Rat sc 10,000 mg/kg|LD50 Rat iv 12,500 mg/kg|For more Non-Human Toxicity Values (Complete) data for ACETAMIDE (9 total), please visit the HSDB record page.

/AQUATIC SPECIES/ ... In rainbow trout, increase in sperm motility parameters (VAP and MOT) were observed in the presence of acetamide, an inhibitor for beta-N-Acetylglucosaminidase (beta-NAGase). In contrast, sperm motility parameters (VCL, VSL, VAP, MOT, and PRG) were reduced on the Siberian sturgeon in the presence of acetamide. The inhibition of the activity of beta-NAGase in rainbow trout spermatozoa was led to a reduction in the number of fertilized eggs from 79% to 40%, whereas in sturgeon no change was observed in fertilization. Moreover, inhibition of beta-NAGase in both spermatozoa and eggs of trout and sturgeon resulted in significant decrease in fertilization rate from 79% to 1% in rainbow trout and from 84% to 12% in Siberian sturgeon. ...|/AQUATIC SPECIES/ The toxicity threshold using the cell multiplication inhibition test was determined for pseudomonas putida (bacteria), scendesmus quadricauda (green algae) and entosiphon sulcatum (protozoa). Test based on principle that dissolved toxic water ingredients will inhibit multiplication of test organisms as compared to culture free from such influence. Acetamide exhibited a selective damaging action on entosiphon sulcatum.

Acetamide has been detected near the center of the Milky Way galaxy(1). On July 30, 2015, acetamide was detected on comet 67/P's surface after the Philae lander touch-downed on the comet(2). Acetamide has been detected in the roots of sugar beets(4).

Acetamide's production and use as a solvent and plasticizer(1), as a solubilizer and in organic synthesis(2) may result in its release to the environment through various waste streams(SRC). Acetamide occurs as in waste piles of a coal shaft as a seasonal compound, appearing only in periods of dry weather. It also occurs in burning waste coal heaps, formed between 50 and 150 °C(3).

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 5(SRC) indicates that acetamide is expected to have very high mobility in soil(SRC). Volatilization of acetamide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.0X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 0.0182 mm Hg(3), and water solubility, 7.05X10+5 mg/L(4). Acetamide is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. A 69% of theoretical BOD in 2 weeks using activated sludge in the Japanese MITI test(5) and a 69% of theoretical degradation in a 10-day window of an OECD 301D Closed Bottle test(3) indicates that biodegradation is an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), a Koc value of 5(2) indicates that acetamide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.0X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 0.0182 mm Hg(3), and water solubility, 7.05X10+5 mg/L(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow of -1.26(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A 69% of theoretical BOD in 2 weeks using activated sludge in the Japanese MITI test(8) and a 69% of theoretical degradation in a 10-day window of an OECD 301D Closed Bottle test(3) indicates that biodegradation is an important environmental fate process in water(SRC). Results of hydrolysis studies indicate the hydrolysis half-life of acetamide at 25 °C and pH 7 is 3,440 to 3,950 years(9,10).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), acetamide, which has a vapor pressure of 0.0182 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase acetamide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 7.6 days(SRC), calculated from its rate constant of 2.1X10-12 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Acetamide does not absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of acetamide with photochemically-produced hydroxyl radicals has been estimated as 2.1X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7.6 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The acid and base rate constants for acetamide were reported to be 0.030 per M-hr and 0.17 per M-hr, respectively, which correspond to a half-life of 3,440 yrs at pH 7(2). The acid and base-catalyzed hydrolysis rate constants for acetamide at 25 °C have also been reported as 8.36X10-6 and 4.71X10-5 per M-sec respectively which correspond to a half-life of 3,950 years at pH 7(3). The rate constant for the reaction of hydroxyl radicals in aqueous solutions at pH 5.5 is 1.9X10+8 L/mol-sec(4); this corresponds to an aquatic half-life of 11.5 years at an aquatic concentration of 1X10-17 hydroxyl radicals per liter(5). Acetamide in aqueous solution does not absorb at wavelengths >290 nm(6) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 3 was calculated in fish for acetamide(SRC), using a log Kow of -1.26(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

5.01 L/kg|An experimental Koc of 5 has been reported for acetamide(1). According to a classification scheme(2), this Koc value suggests that acetamide is expected to have very high mobility in soil.

The Henry's Law constant for acetamide is estimated as 2.0X10-9 atm-cu m/mole(SRC) derived from its vapor pressure, 0.018 mm Hg(1), and water solubility, 7.05E10+5 mg/L(2). This Henry's Law constant indicates that acetamide is expected to be essentially nonvolatile from water surfaces(3). Acetamide's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Acetamide is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. Evaporation of acetamide at 20 °C is reported to be negligible(4).

Over-oxidized wine can contain acetamide.

NIOSH (NOES Survey 1981-1983) has statistically estimated that 2,074 workers (1,148 of these are female) are potentially exposed to acetamide in the US(1). Occupational exposure to acetamide may occur through inhalation and dermal contact with this compound at workplaces where acetamide is produced or used(SRC). Monitoring and use data indicate that the general population may be exposed to acetamide via inhalation of tobacco smoke(2), ingestion of over-oxidized wine(3) and dermal contact with consumer products containing acetamide(SRC).

Drug Information

/EXPL THER/ /The study objective was/ to observe the effect of fluoroacetamide on cardiomyocytes of rat and the antidotal effect of acetamide. Four groups of SD rats were treated with various dosages of fluoroacetamid (p.o.) and 2 groups of them were treated with acetamide (i.p.). The changes of cardiomyocytes and serum AST, LDH, CK, CK-MB and HBDH were measured at different intervals after poisoning. In the group treated with fluoroacetamid 8 mg/kg. bw, serum AST[(589.58 +/- 821.72) U/L], CK[(916.78 +/- 343.55) U/L], HBDH[(504.47 +/- 148.88) U/L] raised obviously compared with control[(187.70 +/- 46.87), (755.65 +/- 498.90), (347.25 +/- 228.40) U/L respectively] (p<0.01), and the pathological findings such as degeneration, liquefactive necrosis and filtration of inflammatory cells in cardiac muscles were observed 24 hours later, while all the male dead within 3 days. In the group treated with fluoroacetamid 4 mg/kg. bw, serum LDH and HBDH rose significantly compared with control (p<0.01) 5 day later. On the day of 10, myocardial enzymes restored in all experiment groups with some interstitial fibroblastic proliferation. The pathological changes were reduced in the group treated with acetamide synchronously (100 mg/kg. bw). Acute intoxication of fluoroacetamide could damage cardiomyocytes while acetamide could reduce the injury of them, but the injury was reversible. ...|/EXPL THER/ /The study objective was/ to investigate the effects of acetamide at different doses on the expression of inhibitory amino acids (gamma-aminobutyric acid, GABA) and excitatory amino acid (glutamate, Glu) in the cerebral cortex of rats with acute tetramine (TET) poisoning. Eighty Sprague-Dawley rats (SPF) were randomly divided into five groups, with 16 rats in each group: saline control group, dimethyl sulfoxide (DMSO) control group, TET exposure group, high-dose (2.8 g/kg/d) acetamide treatment group, and super-high-dose (5.6 g/kg/d) acetamide treatment group. Rats in the exposure group and treatment groups were exposed to TET by intragastric administration after fasting, and were then intramuscularly injected with saline or different doses of acetamide in the following 5 days. The cortex of the temporal lobe was collected at 3 hr, 12 hr, 48 hr, or 7 d after treatment. The expression levels of GABA and Glu in the cortex of the temporal lobe were determined by average optical density (OD) values in immunohistochemistry. ... The OD value of GABA in TET exposure group started to increase at 12 hr after treatment, reached the peak at 48 hr, and decreased to the normal level at 7 d. In the high-dose acetamide treatment group, the increase in OD at 12 hr was not so significant as that in the TET exposure group, OD value decreased to the normal level at 48 hr and was lower than that in the exposure group, and the changes were more like those in the control groups. In the super-high-dose acetamide treatment group, OD value began to increase significantly at 3 hr and was significantly higher than that in the TET exposure group (p<0.01), it reached the peak at 12 hr, and was restored to the normal value at 48 hr. ... The OD value of Glu in TET exposure group at 3 hr after treatment was significantly lower than those in the two control groups, it increased gradually from 12 hr to 48 hr, and recovered to the normal level at the 7th d. The changes in the high-dose acetamide treatment group were similar to those in the TET exposure group, but became more like those in the control groups after 48 hr; the OD value in super-high-dose acetamide treatment group was significantly higher than that in the TET exposure group at 3 hr after treatment (p<0.01), while no significant difference was found at 12 hr; it was significantly lower than those of all other groups at 48 hr and 7 d (p<0.01). Treatment with high dose of acetamide has some curative effect on TET poisoning-induced central nervous lesion, while the effect of super-high-dose acetamide on expression of neurotransmitters is too complex to evaluate.

The volume of distribution was about 1 mL/g, total body clearance was 0.27 mL/min and renal clearance was 0.19 mL/min. Approximately 64 72% of (14)C acetamide was excreted in the urine, while only 0.5 0.8% appeared in exhaled air during the first 6 hr after dosing. Thus, approximately 30% of the administered dose was not recovered and it was suggested that metabolized acetamide enters the acetate pool.|Less than 0.07% of the recovered urinary radioactivity in rats given 100 or 1000 mg/kg bw (14)C acetamide coeluted upon high performance liquid chromatography with an N-hydroxyacetamide standard and this hydroxamic acid could not be detected after incubation of acetamide with rat liver microsomes and NADPH or in primary cultures of rat hepatocytes. (14)C Acetamide does not bind covalently to proteins in the presence of rat liver microsomes and NADPH or cytosolic fraction, whereas hepatocyte cultures contained non extractable radioactivity. This association was inhibited by cycloheximide to the same extent as (14)C acetate incorporation into cellular proteins.

Acetamide ... was found in small amt in human urine as metabolite of metronidazole.|Metabolism of metronidazole to acetamide was apparently mediated by intestinal flora.|Acetamide is carcinogenic in rats and mice. To clarify the mechanism of carcinogenesis by acetamide, we investigated DNA damage by andacetamide metabolite, acetohydroxamic acid (AHA), using 32P-5'-end-labeled DNA fragments. AHA treated with amidase induced DNA damage in the presence of Cu(II) and displayed a similar DNA cleavage pattern of hydroxylamine. DNA damage was inhibited by both catalase and bathocuproine, suggesting that H2O2 and Cu(I) are involved. Carboxy-PTIO, a specific scavenger of nitric oxide (NO), partially inhibited DNA damage. The amount of 8-oxo-7,8-dihydro-2'-deoxyguanosine (8-oxodG) by amidase-treated AHA was similar to that by hydroxylamine. ESR spectrometry revealed that amidase-treated AHA as well as hydroxylamine generated NO in the presence of Cu(II). From these results, it has been suggested that AHA might be converted into hydroxylamine by amidase. These results suggest that metal-mediated DNA damage mediated by amidase-catalyzed hydroxylamine generation plays an important role in the carcinogenicity of acetamide.

The half life of radioactivity in blood after intravenous dosing of (14)C acetamide to rats averaged 20.6 + or - 0.3 hr after a 10 mg/kg bw dose and 16.1 + or - 1.6 hr after a 50 mg/kg bw dose.

SYMPTOMS: Exposure to this compound may cause irritation to the eyes, skin and mucous membranes. ACUTE/CHRONIC HAZARDS: This chemical may cause skin and eye irritation and corneal damage. (NTP, 1992)|Carcinogens

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)


Fresh air, rest.


Remove contaminated clothes. Rinse skin with plenty of water or shower.


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 min, occasionally lifting upper and lower lids. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. When this chemical has been swallowed, get medical attention. ... If this chemical has been inhaled, remove from exposure and transfer promptly to a medical facility.|Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention.|Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if necessary. 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 ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) 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. Activated charcoal is not effective ... . Do not attempt to neutralize, because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Early intubation, at the first sign of upper airway obstruction, may be necessary. Positive pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic acids and related compounds/

acetamide

The substance can be absorbed into the body by inhalation of its aerosol.

Redness. Pain.


Redness. Pain.

Acetamide Use and Manufacturing

Methods of Manufacturing

Prepared by fractional distillation of ammonium acetate.|Interaction of ethyl acetate and ammonium hydroxide.|Acetamide can be produced by several methods. Ammonia reacts vigorously with acetyl halides or acetic anhydride to produce acetamide. Alkyl acetates also react with ammonia to yield acetamide. Dehydration of ammonium acetate is the standard procedure for preparation of acetamide. Finally, acetonitrile is hydrolyzed to yield acetamide in the presence of an acid or base catalyst.

Uses

Acetamide is often used as plasticizer and as industrial solvent. molten acetamide is an excellent solvent for many organic and inorganic compounds. Solubilizer. renders sparingly soluble substances more soluble in water by mere addition or by fusion. stabilizer. manufacture of methylamine, denaturing alcohol. In organic syntheses. Acetamide is used as a co-monomer in the production of polymeric materials such as polyvinyl acetamide, a polymeric product used as an absorbent. It can be used for the transamidation of carbxamides in 1,4-dioxane in the absence of a catalyst.

In 1963 ... available in USA as technical grade (99% minimum acetamide and 0.3% maximum free acid) and as chemically pure, odorless grade (99.5-99.9% acetamide and trace of free acid).|Grades: Technical; CP /chemically pure: a grade designation signifying a minimum of impurities, but not 100% purity/ (odorless); intermediate; reagent.

Acetamide: ACTIVE

Method: OSHA 2084; Procedure: gas chromatography with a nitrogen-phosphorous detector; Analyte: acetamide; Matrix: air; Detection Limit: 10 ng/sample.|A sensitive gas chromatographic mass spectrometric (GC-MS) method has been established for the simultaneous determination of acetamide (AA), propanamide (PA), and butyramide (BA) in surface and drinking water based on derivatization with 9-xanthydrol. Deuterated acrylamide was chosen as the internal standard for analyzing the water sample. The derivatization of AA, PA, and BA was performed directly in water and the reaction conditions (10.0-mM 9-xanthydrol, 0.5-M HCl, 20-min reaction time, and ambient temperature) were established. Under these conditions, the detection limit of the analytes was 0.03 ug/L, and the interday relative standard deviation was less than 16% at concentrations of 1.0, 5.0 and 10.0 ug/L. The proposed GC-MS method enables the reliable analysis of trace AA, PA, and BA in environmental water.|A method is described for the simultaneous determination of two short-chained amides, acrylamide and acetamide (classified by the International Agency for Research on Cancer as probable and possible human carcinogens, respectively), in total particulate matter using gas chromatography-on-column injection and mass spectrometric detection. Sample preparation is kept to a minimum, and the proposed analytical procedure proves to be fast, sensitive, and precise. Validation studies show good linearity with a regression coefficient of r2=.000 for both compounds. Quantitation limits are 32 ng/mL for acrylamide and 70 ng/mL for acetamide. In the particulate phase of mainstream smoke from the University of Kentucky Reference Cigarette 2R4F, 2.3 ug/cig acrylamide and 4.7 ug/cig acetamide are found; no acetamide and only .0074 ug/cig acrylamide is found in the gas phase. Possible mechanisms of formation in cigarette smoke are discussed.|Thin layer chromatography analysis of acid amides, including acetamide is mentioned. Amounts down to 10 ug were detectable.

Hazardous Air Pollutants (HAPs)|Health Hazards -> Carcinogens

Flavouring Agent -> FLAVOURING_AGENT;

Computed Properties

Molecular Weight:59.07
XLogP3:-0.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:59.037113783
Monoisotopic Mass:59.037113783
Topological Polar Surface Area:43.1
Heavy Atom Count:4
Complexity:33
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Downstream Products

Drug Function and Efficacy

Extract from the above information

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Registered Holders

  • Shandong Xinhua Pharmaceutical Company Limited

    China China
    Active

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