N-Nitrososarcosine

118.09 g/mol

118.09

IRC08HI7YX

DTXSID9074309

C44425

Pale-yellow crystals

70 Ų

log Kow = -0.78 (est)

66-67 °C

160 °C @ Press: 0.18 Torr

8.47 M|Soluble in polar organic solvents; miscible with water|In water, 1.0X10+6 mg/L (miscible) at 25 °C (est)

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

2.61X10-3 mm Hg at 25 °C (est)

Henry's Law constant = 3.05X10-10 atm-cu m/mol at 25 °C (est)

pKa = 3.63 (est)

The free acid is unstable in aqueous solution.|Light sensitive, especially to ultra-violet light.|Partially decarboxylates on heating at 180 to 190 °C to form N-nitrosodimethylamine; oxidized by strong oxidants (peracids) to the corresponding nitramine.|Hydroxyl radical reaction rate constant = 8.30X10-12 cu cm/molecule-sec at 25 °C (est)

VQ3150000

The free acid is unstable in aqueous solution; a concentration decrease of more than 10% in 24 hr has been observed.|Light-sensitive, especially to ultraviolet light|Partially decarboxylates on heating at 180-190 °C to form N-nitrosodimethylamine|STABILITY OF N-NITROSO COMPOUNDS. Half-lives of N-nitroso compounds at 100 °C in phosphate buffers: N-nitrososarcosine /from table/ pH 2.2/0.3 days; pH 4.0/1.7 days; pH 5.5/18 days;pH 7.0/25 days; pH 8.5/67 days; pH 11.0/120 days;pH 12.2/120 days

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. 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 soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.|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.|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/|PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/|For more Disposal Methods (Complete) data for N-NITROSOSARCOSINE (7 total), please visit the HSDB record page.

... It is oxidized by strong oxidants (peracids) to the corresponding nitramine

U.S. Department of Health & Human Services/National Toxicology Program; Twelfth Report on Carcinogens (2011). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. N-Nitrososarcosine (13256-22-9) is listed as reasonably anticipated to be a human carcinogen. First listed in the Second Annual Report on Carcinogens (1981).[Available from, as of March 1, 2012: http://ntp.niehs.nih.gov/?objectid=03C9AF75-E1BF-FF40-DBA9EC0928DF8B15]

|Warning|H351: Suspected of causing cancer [Warning Carcinogenicity]|P201, P202, P281, P308+P313, P405, and P501

PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... 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. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/

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/

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.|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/|PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/|For more Preventive Measures (Complete) data for N-NITROSOSARCOSINE (10 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/

The tobacco and mainstream smoke of 20 commercial brands of filter and non-filter cigarettes were analysed for N-nitroso compounds. ... The five major non-volatile nitrosamines present in cigarette tobacco were 4-(N-nitroso-N-methylamino)butyric acid (not detected by 200 ng/cigarette), N-nitrosopipecolic acid (not detected to 670 ng/cigarette), N-nitrososarcosine (22-460 ng/cigarette), 3-(N-nitroso-N-methylamino)propionic acid (110-4990 ng/cigarette) and N-nitrosoproline (580-15000 ng/cigarette). ...|N-Nitrososarcosine has been reported in smoke and tobacco(1). Concentrations of not detected to 2.5 ug/g have been reported in smokeless tobacco(2).

LD50 Mouse ip 184 mg/kg

No evidence has been found that N-nitrososarcosine has been manufactured commercially(1), but its presence in smoked meat, boiled ham, bologna and meatloaf(1) and tobacco smoke(2) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3(SRC), determined from a structure estimation method(2), indicates that N-nitrososarcosine is expected to have very high mobility in soil(SRC). The estimated pKa of N-nitrososarcosine is 3.63(3), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because the compound exists as an anion and ions do not volatilize. N-Nitrososarcosine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.6X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(5). Biodegradation data in soil were not available(SRC, 2012).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3(SRC), determined from a structure estimation method(2), indicates that N-nitrososarcosine is not expected to adsorb to suspended solids and sediment(SRC). An estimated pKa of 3.63(3) indicates N-nitrososarcosine will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(4), an estimated BCF of 3(SRC), from an estimated log Kow of -0.78(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water are not available(SRC, 2012).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N-nitrososarcosine, which has an estimated vapor pressure of 2.6X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase N-nitrososarcosine 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 15 hrs(SRC), calculated from its rate constant of 8.3X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). N-Nitrososarcosine absorbs at wavelengths at 324 nm(4), and therefore may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of N-nitrososarcosine with photochemically-produced hydroxyl radicals has been estimated as 8.3X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 15 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). N-Nitrososarcosine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). The maximum adsorption of N-nitrososarcosine, dissolved in water, in the UV spectrum was determined to be 324 nm, with adsorption reported up to 337 nm(3), suggesting that N-nitrososarcosine may be susceptible to direct photolysis by sunlight(SRC). Upon heating from 180 to 190 °C, N-nitrososarcosine decarboxylates to form n-nitrosodimethylamine; it is also oxidized by peracids to the corresponding nitramine(3).

An estimated BCF of 3 was calculated in fish for N-nitrososarcosine(SRC), using an estimated log Kow of -0.78(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).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of N-nitrososarcosine can be estimated to be 3(SRC). According to a classification scheme(2), this estimated Koc value suggests that N-nitrososarcosine is expected to have very high mobility in soil. The estimated pKa of N-nitrososarcosine is 3.63(3), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).

An estimated pKa of 3.63(1) indicates N-nitrososarcosine will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process. N-Nitrososarcosine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.6X10-3 mm Hg(SRC), determined from a fragment constant method(2).

... The preliminary survey shows a widespread contamination of N-nitroso compounds in raw foodstuffs from Kashmir. ...Several commonly used raw foodstuffs from a high risk esophageal cancer region in Kashmir (India) were analysed for the presence of N-nitroso compounds. The food items were selected on the basis of their frequent consumption with particular emphasis on the preserved foods (dried, pickled and smoked) and those which are unique to the region. Nine out of 11 food items were found to contain low concentrations of N-nitrosodimethylamine, N-nitrosopyrrolidine, N-nitrososarcosine, N-nitrosoproline and N-nitrosothaizolidine-4-carboxylic acid.|N-Nitrososarcosine has been found in smoked meat at a concentration of 10 ug/kg, boiled ham at a concentration of 2 ug/kg, bologna at concentrations of 2 and 56 ug/kg, and meatloaf at concentrations of 2 and 15 ug/kg(1). The compound was detected in 14 smoked bacon samples with 12 samples at <10 ug/kg, one sample at 84.0 ug/kg, and one sample at 210 ug/kg. Levels in unsmoked bacon did not deviate from those in smoked bacon, with concentrations in the former reported as 7 of 10 samples at <10 ug/kg, one sample at 60.0 ug/kg and one sample at 74.0 ug/kg; the overall mean is 19.0 ug/kg(2).

Monitoring data indicate that the general population may be exposed to N-nitrososarcosine via ingestion of certain meats and use of tobacco products(SRC). N-Nitrososarcosine can be absorbed or consumed from tobacco products(1).

...N-nitrosamino acids (e.g., nitrosoproline (NPRO), nitrosohydroxyproline (NHPRO) and nitrososarcosine (NSAR)) when administered orally to rats, are excreted unchanged almost quantitatively (88-96% of the dose) in the urine and feces. ...

A simple and sensitive method for the quantitative estimation of endogenous N-nitrosation in rats was developed. This approach is based on the findings that N-nitroamino acids (e.g., nitrosoproline (NPRO), nitrosohydroxyproline(NHPRO) and nitrososarcosine (NSAR)) when administered orally to rats, are excreted unchanged almost quantitatively (88-96% of the dose) in the urine and feces. After sequential administration of a nitrosatable amino acid and sodium nitrite, the nitrosamino acid excreted in the urine and feces was analyzed. The amount of nitrosoproline excreted in the urine of rats was proportional to the dose of proline and to the square of the nitrite dose. Co-administration of ascorbic acid and alpha-tocopherol together with the precursors decreased the urinary nitrosoproline whereas thiocyanate increased the yield. After feeding an amino acid precursor and nitrite, the yield of nitrosamino acids, formed in vivo and excreted in the urine increased in the order: nitrosoproline < nitrososarcosine < nitrosohydroxyproline. The same order was seen when the nitrosation rates of the amino acids in vitro were compared. Evidently, N-nitrosation in vivo in rats occurs via a similar mechanism as observed in vitro. Monitoring of N-nitrosamino acids excreted in the urine and feces appears to provide a valuable index for endogenous N-nitrosation. ...

Carcinogens

/SRP:/ 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 as 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. /Nitrates, nitrites, and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Anticipate seizures and treat as 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. Administer activated charcoal ... . /Nitrates, nitrites, and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or is in severe respiratory distress. Monitor cardiac rhythm and treat arrhythmias if necessary. Start IV administration of D5W /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. If unresponsive to these measures, vasopressors may be helpful. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Nitrates, nitrites, and related compounds/

/OTHER TOXICITY INFORMATION/ ... Health hazards ... related to the consumption of water containing large concentrations of nitrate (or nitrite) ... /include/ potential formation of carcinogenic nitrosamines. /Nitrosamines/

N-nitrososarcosine

No evidence has been found that N-nitrososarcosine has been manufactured commercially.|There are three major types of nitroso compounds in smokeless tobacco: (a) nonvolatile TSNA, including 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and N'-nitrosonornicotine (NNN); (b) N-nitrosamino acids, including N-nitrososarcosine (NSAR), 3-(methylnitrosamino)propionic acids (MNPA) and 4-(methylnitrosamino)butyric acids (MNBA); and (c) volatile N-nitrosamines, including N-nitrosodimethylamine (NDMA), N-nitrosopyrrolidine (NPYR), N-nitrosopiperidine (NPIP) and N-nitrosomorpholine (NMOR).|Formed in smoke during the tobacco smoking process

/N-nitrososarcosine was detected/ in meat by Gas Chromatography-Mass Spectrometry with thermal energy analysis.|High-Pressure Liquid Chromatography used to separate nitrosamines such as n-nitrososarcosine which has important environment implications.|Thin layer chromatography procedure was a convenient method for monitoring formation of N-nitrososarcosine.|Nuclear magnetic resonance spectra of N-alkyl-n-(omega-carboxyalkyl)nitrosamines and their esters, and chromatographic separation of the (Z)- and (E)-conformers of the esters.|Gas chromatography & spectroscopy of N-nitroso compounds, including N'-nitrososarcosine.

Health Hazards -> Carcinogens