Nitroguanidin

Nitrogen Compounds -> Other Nitrogen Compounds

Flammable agents - 4th degree

Needles, prisms from water /alpha 1-Nitroguanidine/

Long, thin, flat, flexible lustrous needles (alpha); small, thin elongated plates (beta)

Slightly soluble in ethanol; insoluble in ethyl ether; very soluble in alkali

Slightly soluble in methanol (less than 0.5%), alcohol; practically insoluble in ether; soluble in concentrated acids from which it is precipitated by water; soluble in cold solution of alkalies (not of carbonates) with slow decomposition /alpha/

Beta form appears to be more soluble in water than alpha form

In water, 4.40X10+3 mg/L at 25 °C

Decomposes immediately on melting to form ammonia, water vapor, and solid products. The gases from the decomposition of nitroguanidine are far less erplosive than gases from other similar explosives.

When heated to decomposition it emits highly toxic fumes of /nitroxides/.

It decomposes at 480 °F and emits toxic oxides of nitrogen. /Nitroguanidine, dry/

Nitroguanidine is shipped as a slurry or wet mass of pale yellow crystals. If it should dry out it can explode due to shock, heat, flame, or friction. The primary hazard is blast where the entire load can explode instantaneously and not from flying projectiles and fragments. Under prolonged exposure to fire or heat they can explode.

Nitroguanidine, [dry] appears as a yellow solid in the form of crystalline needles. Decomposes at 480 °F and emits toxic oxides of nitrogen. May explode under exposure to intense heat or fire. Primary hazard is blast of explosion, not flying projectiles or fragments.

Liquid

Exists as two isomers, needles and plates; [Hawley] Yellow solid; Shipped as a slurry or wet mass; [CAMEO] White powder; [Aldrich MSDS]

Decomposition at 225-250 °C (depending on speed of heating) giving off ammonia fumes /alpha/

Heat of formation = -92.4 kJ/mol

When heated to decomposition it emits toxic fumes of NOx.

Danger

H201 (93.9%): (Deleted) Explosive; mass explosion hazard [Danger Explosives]

P210, P230, P240, P250, P280, P370+P380, P372, P373, P401, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 163 reports by companies from 5 notifications to the ECHA C&L Inventory.

Danger

H201: (Deleted) Explosive; mass explosion hazard [Danger Explosives]

Chemical: Guanidine, nitro-

Guanidine, N-nitro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Guanidine, N-nitro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 09-09-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/13550

Guanidine, nitro-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Flammable Solid

Explosive 1.1D

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

· Flammable/combustible material.

· Flammable/combustible material.

A very dangerous fire hazard when exposed to heat, flame, or by chemical reaction with oxidizers.

Under exposure to intense heat or if involved in fire they may detonate. /Nitroguanidine, dry/

Dry it is easily ignited and burns very vigorously ... The wet material will also burn.

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

· Some are toxic and may be fatal if inhaled, ingested or absorbed through skin. Specifically, Dinitrophenol, wetted (UN1320); Dinitrophenolates, wetted (UN1321), Sodium dinitro-o-cresolate, wetted (UN1348); and Barium azide, wetted (UN1571) are known to be toxic.

· Some are toxic and may be fatal if inhaled, ingested or absorbed through skin. Specifically, Dinitrophenol, wetted (UN1320); Dinitrophenolates, wetted (UN1321), Sodium dinitro-o-cresolate, wetted (UN1348); and Barium azide, wetted (UN1571) are known to be toxic.

May explode when shocked or heated. [Hawley] No adverse effects in histopathology, fertility, development, or offspring observed in three-generation feeding study of rats; [HSDB] May explode from shock, heat, or friction if dry; [CAMEO] Not teratogenic at maternally toxic doses; [REPROTOX] Causes cyanosis in oral lethal-dose studies of rats, mice, and guinea pigs; [RTECS] An irritant; [Aldrich MSDS]

1336 113

1336 113

Amines, Phosphines, and Pyridines

Amines, Phosphines, and Pyridines

BURROWS D, DACRE JC; TOXICITY TO AQUATIC ORGANISMS AND CHEMISTRY OF NINE SELECTED WATERBORN POLLUTANTS FROM MUNITIONS MANUFACTURE. LITERATURE EVALUATION; US NTIS AD-A REP(ISS 010660) 96 (1975). TOXICITY TO AQUATIC ORGANISMS & RELATED CHEMISTRY OF 9 MILITARY RELEVANT COMPD WAS EVALUATED & REVIEWED. BASED ON AVAIL TOXICITY DATA, RECOMMENDATIONS WERE MADE FOR FURTHER INVESTIGATIONS TO BE CONDUCTED ON 7 OF THE SELECTED COMPD INCL NITROGUANIDINE.

Strong Oxidizing Agent

Explosive

Nitroalkanes, such as NITROGUANIDINE, range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. Nitroalkanes are milder oxidizing agents, but still react violently with reducing agents at higher temperature and pressures. Nitroalkanes react with inorganic bases to form explosive salts. The presence of metal oxides increases the thermal sensitivity of nitroalkanes. Nitroalkanes with more than one nitro group are generally explosive. Nitroalkanes are insoluble in water. Flammable/combustible material. May be ignited by heat, sparks or flames. DRIED OUT material may explode if exposed to heat, flame, friction or shock; Treat as an explosive. Mercury and silver complex salts of nitroguanidine are very impact sensitive.

Nitroalkanes, such as NITROGUANIDINE, range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. Nitroalkanes are milder oxidizing agents, but still react violently with reducing agents at higher temperature and pressures. Nitroalkanes react with inorganic bases to form explosive salts. The presence of metal oxides increases the thermal sensitivity of nitroalkanes. Nitroalkanes with more than one nitro group are generally explosive. Nitroalkanes are insoluble in water. Flammable/combustible material. May be ignited by heat, sparks or flames. DRIED OUT material may explode if exposed to heat, flame, friction or shock; Treat as an explosive. Mercury and silver complex salts of nitroguanidine are very impact sensitive.

/GUIDE 113: FLAMMABLE SOLIDS - TOXIC (WET/DESENSITIZED EXPLOSIVE)/ Fire or Explosion: Flammable/combustible material. May be ignited by heat, sparks or flames. DRIED OUT material may explode if exposed to heat, flame, friction or shock; treat as an explosive (GUIDE 112). Keep material wet with water or treat as an explosive (Guide 112). Runoff to sewer may create fire or explosion hazard. /Nitroguanidine (Picrite), wetted with not less than 20% water; Nitroguanidine, wetted with not less than 20% water; Picrite, wetted/

/GUIDE 113: FLAMMABLE SOLIDS - TOXIC (WET/DESENSITIZED EXPLOSIVE)/ Health: Some are toxic and may be fatal if inhaled, swallowed or absorbed through skin. Contact may cause burns to skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may cause pollution. /Nitroguanidine (Picrite), wetted with not less than 20% water; Nitroguanidine, wetted with not less than 20% water; Picrite, wetted/

/GUIDE 113: FLAMMABLE SOLIDS - TOXIC (WET/DESENSITIZED EXPLOSIVE)/ Public Safety: CALL Emergency Response Telephone Number. ... Isolate spill or leak area immediately for at least 100 meters (330 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Ventilate closed spaces before entering. /Nitroguanidine (Picrite), wetted with not less than 20% water; Nitroguanidine, wetted with not less than 20% water; Picrite, wetted/

/GUIDE 113: FLAMMABLE SOLIDS - TOXIC (WET/DESENSITIZED EXPLOSIVE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Nitroguanidine (Picrite), wetted with not less than 20% water; Nitroguanidine, wetted with not less than 20% water; Picrite, wetted/

For more DOT Emergency Guidelines (Complete) data for 1-Nitroguanidine (8 total), please visit the HSDB record page.

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

General First Aid:

General First Aid:

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear positive pressure self-contained breathing apparatus (SCBA).

If material on fire or involved in fire: Dangerously explosive. Do not fight fires in a cargo of explosives. Evacuate area and let burn. /Nitroguanidine, dry/

Evacuation: If the material is on fire or involved in fire consider evacuation of one (1) mile radius. /Nitroguanidine, dry/

If material on fire or involved in fire: Dangerously explosive. Flood with water. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. /Nitroguanidine, wetted/

Evacuation: If fire becomes uncontrollable - consider evacuation of one (1) mile radius. /Nitroguanidine, wetted/

Wear positive pressure self-contained breathing apparatus when fighting fires involving this material.

Keep container tightly closed in a dry and well-ventilated place. Store in cool place. Keep in a dry place. Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.

Use personal protective equipment. Avoid dust formation. Avoid breathing dust. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations. Keep in suitable, closed containers for disposal.

PROCESS PARAMETERS HAVE BEEN DEVELOPED WHICH PERMIT PURIFICATION OF WASTEWATERS CONTAINING DISSOLVED EXPLOSIVES BY TREATING THE WASTEWATER WITH SURFACTANT OF THE QUATERNARY AMINE TYPE AT PH OF APPROX 11.5. NITROGUANIDINE IS UNAFFECTED BY THE SURFACTANT TREATMENT, BUT CAN BE DESTROYED BY CONTACT WITH ION EXCHANGE RESIN. A METHOD OF ANALYSIS IS DESCRIBED.

STUDIES WERE CONDUCTED TO DETERMINE DECOMP RATE OF NITROGUANIDINE BY USE OF SODIUM SULFIDE & SODIUM HYDROXIDE. SODIUM HYDROXIDE WAS USED TO ADJUST PH ABOVE 11.0 & TO INCR SULFIDE REACTION RATE. THESE STUDIES SHOWED THAT NITROGUANIDINE CANNOT BE EFFECTIVELY DECOMPOSED WITH SODIUM HYDROXIDE ALONE; HOWEVER, IT WAS EFFECTIVE IN COMBINATION WITH SODIUM SULFIDE & THE NITROGUANIDINE DECOMPOSITION RATE WAS A FUNCTION OF THE SULFIDE CONCN ADDED. ALTHOUGH SUCCESSFUL, USE OF RELATIVELY LARGE AMT OF SULFIDE IS UNDESIRABLE.

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

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.

Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Observe all federal, state, and local environmental regulations. Contact a licensed professional waste disposal service to dispose of this material.

NITROGUANIDINE REMOVED FROM WASTEWATERS & SOLID WASTE PROPELLANTS & EXPLOSIVES FROM MFR OF MILITARY WEAPONS WAS DISPOSED OF IN SEVERAL DIFFERENT WAYS.

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep spilled material wet. Wet spilled material before picking it up. Do not attempt to sweep up dry material. /Nitroguanidine, dry/

Personnel protection: Avoid breathing dusts, and fumes from burning material ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Nitroguanidine, dry/

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Keep spilled material wet. Do not attempt to sweep up dry material. /Nitroguanidine, wetted/

Personnel protection: Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Nitroguanidine, wetted/

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

Immediate precautionary measure

Immediate precautionary measure

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 12(SRC), determined from a log Kow of -0.89(2) and a regression-derived equation(3), indicates that 1-nitroguanidine is expected to have very high mobility in soil(SRC). Volatilization of 1-nitroguanidine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.45X10-16 atm-cu m/mole derived from its vapor pressure, 1.43X10-11 mm Hg(4), and water solubility, 4.4X10+3 mg/L(5). 1-Nitroguanidine is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Utilizing the Japanese MITI test, less than 14% of the theoretical BOD was reached in 4 weeks(5), indicating that biodegradation is not an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 21(SRC), determined from a log Kow of -0.89(2) and a regression-derived equation(3), indicates that 1-nitroguanidine is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon a Henry's Law constant of 4.45X10-16 atm-cu m/mole(SRC), derived from its vapor pressure, 1.43X10-11 mm Hg(5), and water solubility, 4.40X10+3 mg/L(6). According to a classification scheme(7), an estimated BCF of 3.2(SRC), from its log Kow(2) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). The aquatic fate of 1-nitroguanidine is dominated by photolysis, with half-lives at 40 deg N latitude ranging from 0.6 days in summer to 2.3 days in winter(9). Utilizing the Japanese MITI test, less than 14% of the theoretical BOD was reached in 4 weeks(10), indicating that biodegradation is not an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-nitroguanidine, which has a vapor pressure of 1.43X10-11 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase 1-nitroguanidine will be removed from the atmosphere by wet or dry deposition. 1-Nitroguanidine absorbs light at wavelengths of approximately 260 nm and greater(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Nitroguanidine

Developmental

1 x 10 ^-1 mg/kg-day

The Koc of 1-nitroguanidine is estimated as 21(SRC), using a log Kow of -0.89(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1-nitroguanidine is expected to have very high mobility in soil. A sorption partition coefficient of <0.1 was calculated using sediments characterized by high surface areas(4).

AEROBIC: 1-Nitroguanidine is not susceptible to aerobic biodegradation in activated sludge, and was stable under sterile reducing conditions(1,2). No decomposition occurred under aerobic conditions in either batch or continuous cultures(2). After acclimation, nitroguanidine co-metabolizes to form nitrosoguanidine(2). 1-Nitroguanidine, present at 100 mg/L, reached less than 14% of its theoretical BOD after 4 weeks in an activated sludge inoculum at 30 mg/L in the Japanese MITI test(3).

ANAEROBIC: 1-Nitroguanidine biodegrades anaerobically after acclimation of an anaerobic sewage sludge. No decomposition occurred in cultures without a nutrient broth(1). In an anaerobic continous culture test, no nitroguanidine was present in the culture vessel after 7 days. After acclimation 1-nitroguanidine is cometabolically reduced to form nitrosoguanidine(1).

An estimated BCF of 3.2 was calculated in fish for 1-nitroguanidine(SRC), using a log Kow of -0.89(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).

The Henry's Law constant for 1-nitroguanidine is estimated as 4.45X10-16 atm-cu m/mole(SRC) derived from its vapor pressure, 1.43X10-11 mm Hg(1), and water solubility, 4.40X10+3 mg/L(2). This Henry's Law constant indicates that 1-nitroguanidine is expected to be essentially nonvolatile from water surfaces(3). 1-Nitroguanidine is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ The 90-day subchronic oral toxicity of nitroguanidine was evaluated in male and female Sprague-Dawley rats. Nitroguanidine was administered in the diet at dose levels of 0, 100, 316, and 1000 mg/kg/day for 90 days. There were 15 animals/sex/dose. The addition of nitroguanidine to the diet consistently reduced food consumption and caused significant (p<=0.05) increases in water consumption. Significantly (p<=0.05) reduced weight gains were observed in the female high-dose group for 5 of the 13 weeks of the study period. No other clinical signs attributable to the test compound were observed during the study. Blood samples taken at necropsy for hematological and serum chemistry analyses exhibited no significant abnormalities that could be attributed to nitroguanidine dosing. Microscopic examination of tissues from the control and 1000 mg/kg/day dose group animals revealed no lesions attributable to the administration of nitroguanidine. The female 1000 mg/kg/day group had a significantly (p<=0.05) increased brain-to- body weight ratio compared with that of the controls at terminal sacrifice. Based on a significant decrease in the rate of growth of female rats at 1000 mg/kg/day on weeks 5, 6, 8, 9 and 12, the NOAEL is 316 mg/kg/day.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ The 90-day subchronic oral toxicity of nitroguanidine was evaluated in male and female ICR mice. There were 15 animals/sex/ dose. Nitroguanidine was administered in the diet at dose levels of 0, 100, 316, and 1000 mg/kg/day for 90 days. The addition of nitroguanidine to the diet had no effect on food consumption or weight gains, but there was a significant dose- response increase in water consumption. Several serum chemistry parameters did exhibit statistically significant (p<=0.05) alterations from the control values, but these changes were isolated occurrences with no consistent dose- related trends being noted. With the exception of the brain-to-body weight ratio in the high-dose males at interim sacrifice, organ weights and their respective ratios were not significantly affected by dosing. Microscopic examination of tissues from the control and 1000 mg/kg/day dose group animals revealed no lesions attributable to the administration of nitroguanidine. The findings of increased water consumption suggest that nitroguanidine, which is excreted unchanged in the mouse's urine, may be acting as an osmotic diuretic. The finding of increased brain-to-body weight ratios in male mice at 1000 mg/kg/day at interim sacrifice is supportive of a 316 mg/kg/day NOAEL.

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ The potential of nitroguanidine to produce developmental toxicity was evaluated in pregnant Sprague-Dawley rat. Nitroguanidine, suspended in 1% carboxymethylcellulose, was administered at doses of 0, 100, 316, and 1000 mg/kg/day by oral gavage on days 6 through 15 of gestation. Fetuses were delivered by cesarean section on day 20, weighed, examined externally, and processed in either Bouin's solution for visceral examination or alizarin red stain for skeletal examination. Following a generalized failure to thrive, two animals in the 1000 mg/kg/day group were significantly smaller than controls with an increased incidence of retarded ossification of the sternebrae, caudal vertebrae, and pubis. There was no evidence of developmental toxicity of nitroguanidine in rats under conditions of this study. Nitroguanidine produced maternal and fetal toxicity at the 1000 mg/kg/day dose level. The NOEL was 316 mg/kg/day.

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ The potential of nitroguanidine to produce developmental toxicity was evaluated in pregnant New Zealand White rabbits. Nitroguanidine, suspended in 1% carboxymethylcellulose, was administered at doses of 0, 100, 316, and 1000 mg/kg/day by oral gavage on days 6 through 18 of gestation. Fetuses were delivered by Cesarean section on day 29, weighed and examined externally. The soft tissues were examined while the body was being eviscerated for subsequent processing in alizarin red stain for skeletal examination. Ten dams in the 1000-mg/kg/day group died or were terminated in a moribund condition following a generalized failure to thrive. The dams administered nitroguanidine at 1000 mg/kg/day exhibited weight loss and decreased food consumption. There was an increased incidence of resorptions in all dose groups. Fetuses in the 1000 mg/kg/day group were lighter in weight and had an increased incidence of retarded ossification of the sternebrae, olecranon, patellae, and phalanges. There were no dose-related malformations. On the basis of these findings, we concluded that nitroguanidine had no teratogenic potential. There is weak to equivocal evidence for potential developmental toxicity based on percent resorptions in all dose groups.

For more Non-Human Toxicity Excerpts (Complete) data for 1-Nitroguanidine (11 total), please visit the HSDB record page.

CLASSIFICATION: D; not classifiable as to human carcinogenicity. BASIS FOR CLASSIFICATION: Pertinent data regarding carcinogenicity have not been located in the available literature. HUMAN CARCINOGENICITY DATA: None. ANIMAL CARCINOGENICITY DATA: None. /Based on former classification system/

1-Nitroguanidine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). 1-Nitroguanidine absorbs light at wavelengths of approximately 260 nm and greater(2) and therefore may be susceptible to direct photolysis by sunlight(SRC). 1-Nitroguanidine in aqueous solutions was photolyzed by UV light and sunlight to form guanidine nitrite, cyanoguanidine, ammonia, and nitrate(3); 1-nitroguanidine in natural surface water was photolyzed to form nitrite and hydroxyguanidine(4). In surface water, the photolysis half-lives of nitroguanidine at 40 deg N latitude ranged from 0.6 days in summer to 2.3 days in winter(4).

Picrite

A Commercial Grade

5000

A Commercial Grade

400

Explosive chemical that can be released at a facility.

The metabolism and disposition of nitroguanidine (NG), a component of military propellants and munitions, were examined in the rat. Radiolabeled nitroguanidine ((14C)NG) was administered orally at doses of 20 and 200 mg/kg and intravenously at a dose of 20 mg/kg. Regardless of the route of administration, the radiolabel was recovered quantitatively in the urine of all animals within 48 hr after dosing. Chromatographic analysis of the urine indicated that the (14C)NG was excreted unchanged; no radiolabel was found in the expired air, feces, or tissues of the treated animals. No sex differences were seen in the disposition of NG. The kinetics of (14C)NG in the blood of the dosed animals was followed. The elimination half-life of NG was on the order of 2 hr. The bioavailability of orally administered NG was 100%; the kinetics of NG in the blood was not dose dependent. Examination of tissues 1 hr after an oral dose of NG showed that NG was evenly distributed throughout the body. Nitroguanidine is a chemical of low toxicity (LD50 greater than 5 g/kg); it is quantitatively absorbed from the gastrointestinal tract, distributed throughout the body, and rapidly excreted in the urine.

Urine contained nitroguanidine, a metabolite, resulting from oral admin of 1-methyl-3-nitro-1-nitrosoguanidine to rats.

The nitroguanidine or nitromethylene moiety of the newest major class of insecticides, the neonicotinoids, is important for potency at insect nicotinic receptors and selectivity relative to mammalian receptors. Aldehyde oxidase (AOX) was recently identified as the imidacloprid nitroreductase of mammalian liver, producing both nitrosoguanidine and aminoguanidine metabolites. /This/ study considers the ability of AOX, partially purified from rabbit liver, to reduce five commercial nitroguanidine (i.e., imidacloprid, thiamethoxam, clothianidin, and dinotefuran) and nitromethylene (i.e., nitenpyram) neonicotinoid insecticides and three derivatives thereof (i.e., the N-methyl and nitromethylene analogues of imidacloprid and desmethylthiamethoxam). LC/MS/MS was used to demonstrate that AOX reduces nitroguanidines to both nitroso- and aminoguanidines, while nitromethylenes are reduced only to the corresponding nitroso metabolites. Additionally, nitrosonitenpyram was found to spontaneously dehydrate to form a 2-cyanoamidine metabolite, mimicking a predominant photoreaction. The substrate specificity of AOX was characterized as follows: Neonicotinoids with a tertiary nitrogen (N-methylimidacloprid and thiamethoxam) are poor substrates; nitroguanidines are metabolized faster than nitromethylenes; and clothianidin is the most rapidly reduced. Kinetic constants were measured for reduction of three nitroguanidines at two concentrations of AOX. At 2 mg protein/mL, only nitroso metabolites were detected, with Km values of 1.03, 2.99, and 2.41 mM and Vmax values of 5.13, 2.54, and 0.98 nmol/min/mg protein measured for clothianidin, imidacloprid, and dinotefuran, respectively. At 5 mg protein/mL, both amino and nitroso metabolites were detected. However, with each nitroguanidine, the formation of nitroso metabolites did not saturate at substrate levels up to 4 mM, whereas amino metabolite formation exhibited Km values of 0.052, 0.16, and 0.084 mM with corresponding Vmax values of 0.80, 1.24, and 0.79 nmol/min/mg protein for clothianidin, imidacloprid, and dinotefuran, respectively. These in vitro observations show large structural differences in the rates of AOX-catalyzed reduction and help to interpret the extensive studies on in vivo metabolism of neonicotinoid insecticides.

Imidacloprid (IMI) is both oxidatively metabolized by cytochrome P450 enzymes and reduced at the nitroguanidine moiety by a ... cytosolic "neonicotinoid nitroreductase" ... . Two major metabolites are detected on incubation of IMI with rabbit liver cytosol: the nitrosoguanidine (IMI-NO) and the aminoguanidine (IMI-NH2). Three lines of evidence identify the molybdo-flavoenzyme aldehyde oxidase (AOX, EC 1.2.3.1) as the neonicotinoid nitroreductase. First, classical AOX electron donor substrates (benzaldehyde, 2-hydroxypyrimidine, and N-methylnicotinamide) dramatically increase the rate of formation of IMI metabolites. Allopurinol and diquat are also effective electron donors, while NADPH and xanthine are not. Second, AOX inhibitors (potassium cyanide, menadione, and promethazine) inhibit metabolite formation when N-methylnicotinamide is utilized as an electron donor. Without the addition of an electron donor, rabbit liver cytosol reduces IMI only to IMI-NO at a slow rate. This reduction is also inhibited by potassium cyanide, menadione, and promethazine, as well as by additional AOX inhibitors, cimetidine and chlorpromazine. Finally, IMI nitroreduction by AOX is sensitive to an aerobic atmosphere, but to a much lesser extent than cytochrome P450 2D6. Large species differences are observed in the IMI nitroreductive activity of liver cytosol. While rabbit and monkey (Cynomolgus) give the highest levels of total metabolite formation, human, mouse, cow, and rat also metabolize IMI rapidly. In contrast, dog, cat, and chicken liver cytosols do not reduce IMI at appreciable rates. AOX, as a neonicotinoid nitroreductase, may limit the persistence of IMI, and possibly other neonicotinoids, in mammals.

(14)C labeled nitroguanidine was administered to Sprague-Dawley rats intravenously at a dose of 20 mg/kg, by gastric intubation at a dose of 20 mg/kg, and by oral intubation at a dose of 200 mg/kg. Blood samples were collected at times from 5 minutes to 24 hours post dosing, and urine samples were collected at approximately 4, 8, 24, 32, and 48 hours after drug administration. The animals were sacrificed at 48 hours post treatment, and liver, heart, lung, kidney, spleen, brain, testes, ovaries, and muscle were analyzed for (14)C activity. The administered label was rapidly excreted in the urine regardless of the route of dosing. Approximately 50 percent of the label was present in the urine at 4 hours post dosing, and approximately 95 percent was excreted by 24 hours.

Used in explosives as a flashless propellant powder and as a chemical intermediate; [Hawley] Used in explosives and to make pharmaceuticals; [Merck Index]

Used as a component in triple-based propellants, impact-insensitive military ammunition and as a gas generator in automotive airbag applications; used in anticorrosive phosphate coatings

High explosives, especially flashless propellant powder (with nitrocellulose), chemical intermediate.

2023: <50,000 lb

Guanidine, nitro- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5505]

Prepared by the action of concentrated H2SO4 on guanidine nitrate.

Prepared by the nitration of guanidine sulfate with fuming HNO3. Is converted into the alpha-form by dissolving in concentrated H2SO4 and pouring into ice water. /beta-form/

(beta) Nitration of a mixture of guanidine sulfate and ammonium sulfate that results from the hydrolysis of dicyanadiamide by sulfuric acid.

Guanidine nitrate (dehydration)

It is normally mixed with colloided nitrocellulose or ammonium nitrate and paraffin wax.

Exists in two forms; the alpha-form is the usual stable form

Fabricated Metal Product Manufacturing

Guanidine, N-nitro-: ACTIVE

Normally mixed with colloided nitrocellulose or ammonium nitrate and paraffin wax