N,O-Dimethylhydroxylamine

61.084

61.08

214-255-2

783670HYEO

DTXSID5051577

Liquid

2922199090

21.3

0.11

0.796

97.0 °C

42.3 °C @ Press: 760 Torr

-29℃

1.4152 (estimate)

In water, 1.21X10+5 mg/L at 25 °C (est)

378.97 mmHg

379 mm Hg at 25 °C

Henry's Law constant = 4.86X10-6 atm-cu m/mol at 25 °C (est)

pKa = 4.75 (conjugate acid)

Hydroxyl radical reaction rate constant = 6.43X10-11 cu cm/molec-sec at 25 °C (est)

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.

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

IDENTIFICATION AND USE: N-methoxymethylamine (NDMH) is a liquid. HUMAN STUDIES: NDMH caused inhibition of glucose 6-phosphate dehydrogenase but not of glutathione reductase, severe methemoglobin formation, only little lipid peroxidation and some impairment of NADPH methemoglobin reductase. ANIMAL STUDIES: There are no data available.

N-Methoxymethylamine is a degradation product of the herbicide linuron(1), therefore, it may be present in areas treated with this herbicide(SRC).|Year-long degradation of (14)CH3O-labeled monolinuron in sterile soil, resulted in 9% (14)C conversion into CO2 and of 28% into N,O-dimethylhydroxylamine, whereas in nonsterile soil 58% and 8% (14)C was converted into CO2 and N,O-dimethylhydroxylamine, respectively.|Monolinuron adsorbed to soil was more rapidly degraded than non-adsorbed, forming 4-chloroaniline, N,O-dimethylhydroxylamine and CO2.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 24(SRC), determined from a structure estimation method(2), indicates that N-methoxymethylamine is expected to have very high mobility in soil(SRC). Volatilization of N-methoxymethylamine from moist soil surfaces may occur(SRC) given an estimated Henry's Law constant of 4.9X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). N-Methoxymethylamine is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 379 mm Hg at 25 °C(3). Biodegradation data in soil were not available(SRC, 2018).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 24(SRC), determined from a structure estimation method(2), indicates that N-methoxymethylamine is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 4.9X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 6 and 46 days, respectively(SRC). According to a classification scheme(4), an estimated BCF of 3(SRC), from an estimated log Kow of 0.06(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low. Biodegradation data in water were not available(SRC, 2018).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N-methoxymethylamine, which has a vapor pressure of 379 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase N-methoxymethylamine 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 6 hours(SRC), calculated from its rate constant of 6.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). N-Methoxymethylamine does not contain chromophores that absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of N-methoxymethylamine with photochemically-produced hydroxyl radicals has been estimated as 6.4X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 6 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). N-Methoxymethylamine does not contain chromophores that absorb at wavelengths >290 nm(2) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 3 was calculated in fish for N-methoxymethylamine(SRC), using an estimated log Kow of 0.06(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

Using a structure estimation method based on molecular connectivity indices(1), the Koc of N-methoxymethylamine can be estimated to be 24(SRC). According to a classification scheme(2), this estimated Koc value suggests that N-methoxymethylamine is expected to have very high mobility in soil(SRC).

The Henry's Law constant for N-methoxymethylamine is estimated as 4.9X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that N-methoxymethylamine is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 6 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 46 days(SRC). N-Methoxymethylamine's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). N-Methoxymethylamine is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 379 mm Hg(3).

Occupational exposure to N-methoxymethylamine may occur through inhalation and dermal contact with this compound at workplaces where the herbicide linuron is produced or used. Exposure to N-methoxymethylamine of the general population is unlikely; however, exposure may occur via inhalation of ambient air and dermal contact in areas where the herbicide linuron has been applied. (SRC)

N, O-dimethylhydroxylamine was identified as a degradation product of linuron formed in the presence of extracts of Bacillus sphaericus ATCC 12123 by characterization of its dinitrophenyl derivative.

/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 the 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. /Organic bases/Amines 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 pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 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 patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Cover skin burns with dry sterile dressings after decontamination ... . /Organic bases/Amines and related compounds/|/SRP:/ 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. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias as 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 patient is unresponsive to these measures, vasopressors may be helpful. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen ... . Treat seizures with diazepam (Valuim) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic bases/Amines and related compounds/

/ALTERNATIVE and IN VITRO TESTS/ Hydroxylamine (HYAM, HONH2) and some of its derivatives are known to cause erythrotoxic effects both in vitro and in vivo. Previous studies have shown that the primary in vitro effect of HYAM and O-ethyl hydroxylamine (OEH) is methemoglobin formation, leading to liberation of free radicals which cause lipid peroxidation, enzyme inhibitions and glutathione depletion. By contrast, N-substituted N,O-dimethyl hydroxylamine (NODMH), primarily induces impairment of glucose 6-phosphate dehydrogenase (G6PDH) and glutathione reductase (GR). The oxidative potency of HYAM and the O-derivative was larger than the potency of the N,O-derivative. This seemed to indicate that attachment of an alkyl group to the nitrogen atom of hydroxylamine leads to decreased reactivity. To achieve a better understanding of the structure activity relationship for hydroxylamines three methylated derivatives were tested: N-methyl hydroxylamine (NMH). N-dimethyl hydroxylamine (NDMH) and O-methyl hydroxylamine (OMH). We were also interested in the erythrotoxic potency of OMH which recently entered industrial production. Methemoglobin formation, high release of lipid peroxidation products, inhibition of NADPH methemoglobin reductase and glutathione S-transferase (GST) and depletion of total glutathione (GT) were seen for OMH. The reducing enzymes G6PDH and GR were not impaired by OMH. These findings for OMH are consistent with the proposed mechanism for O-derivatives. Since both the effects caused by OMH and its potency are comparable to those of HYAM and OEH this indicates that possible occupational exposure to this compound may be approached similarly to HYAM and OEH. NMH only inhibited G6PDH and GR activity, which is fully in accord with the proposed mechanism for N-substituted derivatives of HYAM. However, NDMH a double N-substituted compound, caused a strikingly different scheme of reactivity inhibition of G6PDH but not of GR, severe methemoglobin formation, only little lipid peroxidation and some impairment of NADPH methemoglobin reductase. This study confirms that O-derivatives of HYAM are potent hemoglobin oxidators, leading to other oxidative effects. The main effect was confirmed for single N-derivatives as inhibition of the two protective enzymes G6PDH and GR. However, the results for NDMH indicate that this simple classification of O-derivatives and N-derivatives has to be extended for double N-substituted compounds which give a mixture of effects.

N,O-dimethylhydroxylamine

Methanamine, N-methoxy-: INACTIVE

Methyl-substituted hydroxylamine pesticide metabolites such as n-methylmethoxyamine were identified in plant materials by thin layer chromatography.