N-Methyl-2-pyrrolidone
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N-Methyl-2-pyrrolidone
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CAS No:
872-50-4
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Formula:
C5H9NO
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Chemical Name:
N-Methyl-2-pyrrolidone
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Synonyms:
2-Pyrrolidinone,1-methyl-;2-Pyrrolidone,1-methyl-;1-Methyl-2-pyrrolidinone;N-Methylpyrrolidinone;1-Methyl-5-pyrrolidinone;NMP;N-Methyl-2-pyrrolidone;N-Methyl-α-pyrrolidinone;N-Methyl-α-pyrrolidone;N-Methyl-γ-butyrolactam;N-Methyl-2-pyrrolidinone;N-Methylpyrrolidone;M-Pyrol;1-Methylazacyclopentan-2-one;1-Methyl-2-pyrrolidone;Pyrol M;N-Methylpyrrolidone;AgsolEx 1;N 0131;Microposit 2001;N-Methyl-2-ketopyrrolidine;N-Methylbutyrolactam;Pharmasolve;SL 1332;NSC 4594;N-Methylpyrrolidine-2-one;M 0418;EKOS 1;NMP 1165;26138-58-9;53774-35-9;57762-46-6
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CAS No:
Description
1-Methyl-2-pyrrolidinone (NMP) has a molecular formula of C5H9NO, and it is a colorless to light yellow transparent liquid with a slight ammonia odor. Its boiling point is 204℃, flash point is 91℃, chroma HaZen≤25, refractive index N20D 1.468-1.471, density is 1.032-1.035. It is miscible in water at any ratio, it is soluble in ethanol, acetone, esters, halogenated hydrocarbons, aromatic hydrocarbons and other organic solvents, and it can completely mix with practically all solvents. It is stron
N-methyl-2-pyrrolidone appears as a clear colorless liquid with a "fishlike" odor. Denser than water. Flash point 199°F. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion.|Liquid|COLOURLESS HYGROSCOPIC LIQUID WITH CHARACTERISTIC ODOUR.|A clear colorless liquid with a fish-like odor.
N-methyl-2-pyrrolidone appears as a clear colorless liquid with a "fishlike" odor. Denser than water. Flash point 199°F. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion.|N-methylpyrrolidin-2-one is a member of the class of pyrrolidine-2-ones that is pyrrolidin-2-one in which the hydrogen attached to the nitrogen is replaced by a methyl group. It has a role as a polar aprotic solvent. It is a N-alkylpyrrolidine, a lactam and a member of pyrrolidin-2-ones.|N Methyl Pyrrolidone is under investigation for the treatment of Multiple Myeloma.
N-Methyl-2-pyrrolidone Basic Attributes
99.13110
99.13
212-828-1
JR9CE63FPM
0513
4594
1993
DTXSID6020856
Clear liquid
2933990090
Characteristics
20.31000
0.17650
N-methyl-2-pyrrolidone appears as a clear colorless liquid with a "fishlike" odor. Denser than water. Flash point 199°F. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion.
1.027 g/cm3 @ Temp: 25 °C
-25 °C
202 °C @ Press: 760 Torr
91ºC
n20/D 1.479
H2O: >=10 g/100 mL at 20 ºC
2-8ºC
0.29 mm Hg ( 20 °C)
3.4 (vs air)
LD50 orally in Rabbit: 3598 mg/kg LD50 dermal Rabbit 8000 mg/kg
vol% in air: 1.3.5
Mild amine odor
pH = 7.7-8
3.20e-09 atm-m3/mole
Dipole moment at 25 °C: 4.09 debye; Dielectric constant at 25 °C: 32.3|Hydroxy radical rate constant = 7.4X10-11 cu cm/molecule-sec at 25 °C
Soluble in water.
Amides and Imides
This amine is a very mild chemical base. It does tend to neutralize acids to form salts plus water. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
655 °F (346 °C)|245 °C
719 kcal/mol
127.3 kcal/Kg
Critical temperature = 451 °C; Critical pressure = 4.78 MPa
Safety Information
UN 1268 3/PG 3
1
R36/38
S41
UY5790000
Xi
Dry. Ventilation along the floor. Separated from strong oxidants, strong acids, strong bases, copper and plastics.
Stable, but decomposes upon exposure to light. Combustible. Incompatible with strong oxidizing agents, strong acids, reducing agents, bases.
P201-P305 + P351 + P338-P308 + P313
H315-H319-H335-H360D
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.
Reacts with sulfur or carbon disulfide at high temperatures and pressures.|Attacks aluminum, light metals, rubber and plastics.
Bower DB; Journal of Occupational and Environmental Medicine 39 (5): 393-4 (1997). Stillbirth after exposure to N-methyl-2-pyrrolidone.|Solomon GM et al; Journal of Occupational and Environmental Medicine 38 (7): 705-13 (1996). Stillbirth after occupational exposure to n-methyl-2-pyrrolidone. A case report and review of the literature.|Akesson B; Arbetsmilj"oinstitutet, F"orlagstj"anst 171 (84): 24 (1994). The Nordic Expert Group for Criteria Documentation of Health Risks from Chemicals - N-Methyl-2-pyrrolidone.|Wallen M; Nord 6: 75-89 (1992). Health effects of selected chemicals: methylpyrrilidinone.|Lee KP et al; Fundam Appl Toxicol 9 (2):222-35 (1987). Toxicity of N-methyl-2-pyrrolidone teratogenic subchronic and two-year inhalation study.
Special Hazards of Combustion Products: Toxic oxides of nitrogen may be formed in fire. (USCG, 1999)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 86 °C explosive vapour/air mixtures may be formed.|Teratogens, Flammable - 2nd degree
|Danger|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P261, P264, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|Aggregated GHS information provided by 2736 companies from 65 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H227: Combustible liquid [Warning Flammable liquids]|P201, P202, P210, P260, P261, P264, P270, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P314, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501
Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a 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 store this material in a refrigerator. (NTP, 1992) Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary.
Goggles or face shield; rubber gloves (USCG, 1999)|Protective gloves. Protective clothing. Wear safety spectacles.|This paper describes the temperature dependence of N-methylpyrrolidone (NMP) permeation through gloves used in microelectronics fabrication facilities. One type of butyl-rubber glove, two types of natural-rubber gloves, and a natural rubber/nitrile/neoprene-blend glove were tested at four temperatures from 25-50~ C using the ASTM F739-85 permeation test method. The butyl-rubber gloves showed no breakthrough after four hours of exposure at any temperature. The variations with temperature of measured breakthrough times and steady-state permeation rates for the other gloves were described well by Arrhenius relationships, with breakthrough time values decreasing by factors of 7-10 and steady-state permeation rate values increasing by factors of 4-6 over the temperature range studied. Extrapolation to 70 and 93~ C, the temperatures at which decreasing is often performed, yielded breakthrough time values of <2 min and <0.5 min, respectively, in all cases. With the exception of the butyl-rubber glove, following an initial exposure at 25~ C and air drying overnight, low levels of NMP vapor were detected off-gassing from the inner surfaces of the gloves. Experimental results were then compared to those expected from several permeation models. Estimates of the equilibrium solvent solubility, S, were calculated using a model based on three-dimensional solubility parameters. Estimates of the solvent diffusion coefficient, D, were obtained from correlations with either the solvent kinematic viscosity or the product of the Flory interaction parameter, X, and the solvent molar volume. Combining these values of solvent diffusion coefficient and solvent solubility in Fickian diffusion equations gave modeled breakthrough time estimates that were within 23% of experimental values over the temperature range examined. Modeled steady-state permeation rate values were within 50% (typically within 25%) of experimental values. Another model based on a generalized Arrhenius relationship also provided useful but generally less accurate estimates of the changes in breakthrough time and steady-state permeation rate values with temperature.
Combustible when exposed to heat, open flame, or powerful oxidizers.
Expolsion Prevention: Above 96 °C use a closed system and ventilation.|Above 96 °C explosive vapor/air mixtures may be formed.|Explosive limits , vol% in air: 1.3-9.5
Use water spray, powder, alcohol-resistant foam, carbon dioxide.
Spillage Disposal: Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.
Do not eat, drink, or smoke during work.|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit 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.
The substance is irritating to the eyes and skin.
Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking liquid in sealable containers. Absorb liquid in sand or inert absorbent. Store and dispose of according to local regulations. Wash away remainder with plenty of water.
Dry. Ventilation along the floor. Separated from strong oxidants, strong acids, strong bases, copper and plastics.
A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
The substance is irritating to the eyes and respiratory tract. The substance is mildly irritating to the skin. Exposure to very high concentrations could cause lowering of consciousness.
Repeated or prolonged contact with skin may cause dermatitis. Animal tests show that this substance possibly causes toxic effects upon human reproduction.
NO open flames. Above 86 °C use a closed system and ventilation.
PREVENT GENERATION OF MISTS!
Use local exhaust or ventilation.
Protective gloves. Protective clothing.
Wear safety goggles.
| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.| 0 - Materials that in themselves are normally stable, even under fire conditions.
1-Methyl-2-pyrrolidinone was detected in 1 of 46 US industrial effluent samples(1). 1-Methyl-2-pyrrolidone is present in shale oil retort water(2,3). 1-Methyl-2-pyrrolidinone was found in shale retort water at a concentration of 3 mg/L(2). Retort Water Treatment Cell analysis showed an influent concentration of 2.8 and effluent concentrations of not detected, 1.4, 3.3, and 10.1 mg/L at 1, 3, 5 and 7 weeks of treatment cell operation, respectively, suggesting a desorption from solids over time(3). The compound was detected at concentrations of 66.3 and 33.7 ug/L in wastewaters from a petrochemical plant sampled in January and March 1997, respectively; it was not detected in a July 1996 sample. 1-Methyl-2-pyrroldinone was detected at concentrations of 0.2 and 3.9 ug/L in leachate from an industrial landfill sampled in December 1996 and March 1997, respectively; locations not specified; limit of detection was 0.2 ug/L(4). 1-Methyl-2-pyrrolidinone was detected at 68.9 ug/L in leachate from a municipal waste landfill in Japan(5).|1-Methyl-2-pyrrolidinone was detected in the raw effluent from a textile finishing plant, North Carolina, concentration not provided(1). The compound was detected in spraybooth scrubber automotive painting operation at a concentration of 300 mg/L of boothwater, 1.51X10-8 ar partial pressure, atm in air; the compound was applied in spray at 7700 kg/annum(2).
INDOOR AIR: 1-Methyl-2-pyrrolidinone was detected at 142 ug/cu m (waterborne system) from furniture that had been coated in a wood preservative mixture(1).
1-Methyl-2-pyrrolidone concentrations in a lot-parked car interior were reported as 59.4 (day 1) and 49.2 (day 3), with a mean of 54.3 ug/cu m; the concentration was 72.7 ug/cu m on day 7, which experienced temperatures of 40 °C; air was sampled after 6 hours of heating. Sampling was conducted in August 2006, using a direct sampling method(1). Average emissions from ten PVC cushion vinyl floor coverings were 66 and 33 ug/sq m-hr at 3 and 28 days, respectively(2).
Toxicity
The ability of N-methylpyrrolidone and polar lipids to increase the percutaneous delivery of metronidazole was investigated across full thickness human nonoccluded skin in vitro. Fatty acids and ethyl alcohol were also tested and were effected in penetration enhancement in propylene glycol vehicles; N-methylpyrrolidone increased metronidazole penetration from isopropyl myristate vehicles but not from propylene glycol. N-methylpyrrolidone premeated skin readily when applied in the neat state or in a mixture with isopropyl myristate. Results indicated that variations in barrier permeability to metronidazole were associated with the rate of N-methylpyrrolidone permeating the skin.|The effect of a penetration enhancer, N-methylpyrrolidone (N-methyl-2-pyrrolidone) or isopropyl myristate, on the in vitro permeability of gonadorelin (luteinizing hormone-releasing hormone; LHRH) through porcine epidermis was investigated. The permeability coefficient of gonadorelin significantly increased through penetration enhancer treated epidermis in comparison to the control. It was concluded that both penetration enhancers can enhance the percutaneous absorption of peptides such as gonadorelin.|Laurocapram (Azone; 1-dodecylazacycloheptan-2-one; I), N-methylpyrrolidone (N-methyl-2-pyrrolidone; II) and dodecyl-L-pyroglutamate (III) were studied in permeation cells in vitro, for their ability to improve the absorption of insulin (IV) and FD&C Blue No. 1 (brilliant blue FCF; V) through skin; the compounds were formulated into a 40% solution of propylene glycol in increasing concentrations. ... The permeation of V was improved in the presence of II, with concentrations of II ranging from 6.0 to 20.0% exhibiting the same efficacy. In experiments with IV, the optimum efficacy of II was found at a concentration close to 10.0%, with a decline in efficacy in higher and lower concentrations. ...
LD50 Rat oral 3914 mg/kg|LD50 Rat oral 4.2 ml/kg|LD50 Mouse oral 7725 mg/kg|LD50 Rabbit dermal 8000 mg/kg|For more Non-Human Toxicity Values (Complete) data for 1-METHYL-2-PYRROLIDINONE (13 total), please visit the HSDB record page.
1-Methyl-2-pyrrolidone's production and use as a solvent and chemical intermediate(1) may result in its release to the environment through various waste streams.
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4.3(SRC), determined from a log Kow of -0.38(2) and a regression-derived equation(3), indicates that 1-methyl-2-pyrrolidone is expected to have very high mobility in soil(SRC). Volatilization of 1-methyl-2-pyrrolidone from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 3.20X10-9 atm-cu m/mole(4). 1-Methyl-2-pyrrolidone is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.345 mm Hg at 25 °C(5). Utilizing the Japanese MITI test, 73% of the Theoretical BOD was reached in 4 weeks(6) indicating that biodegradation is an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4.6(SRC), determined from a log Kow of -0.38(2) and a regression-derived equation(3), indicates that 1-methyl-2-pyrrolidone 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 3.20X10-9 atm-cu m/mole(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Utilizing the Japanese MITI test, 73% of the Theoretical BOD was reached in 4 weeks(7) indicating that biodegradation is 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-methyl-2-pyrrolidone, which has a vapor pressure of 0.345 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1-methyl-2-pyrrolidone 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 5.2 hrs(SRC), calculated from its rate constant of 7.40X10-11 cu cm/molecule-sec at 25 °C(3). 1-Methyl-2-pyrrolidone does not absorb light 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 1-methyl-2-pyrrolidone with photochemically-produced hydroxyl radicals is estimated as 7.4X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 5.2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 1-Methyl-2-pyrrolidone is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 1-Methyl-2-pyrrolidone does not absorb light at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC). 1-Methyl-2-pyrrolidinone was listed as a member of Reactivity Class II in a five tiered system used to classify reactivity towards ozone, indicating low reactivity in this reaction(4). In a similar classification scheme developed to aid in controlling the release of solvents in Los Angeles County, CA, it was listed in Reactivity Class 2 in a three tiered system indicating intermediate reactivity(5).
An estimated BCF of 3 was calculated in fish for 1-methyl-2-pyrrolidone(SRC), using a log Kow of -0.38(1). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
The Koc of 1-methyl-2-pyrrolidone is estimated as 5(SRC), using a log Kow of -0.38(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1-methyl-2-pyrrolidone is expected to have very high mobility in soil. 1-Methyl-2-pyrrolidinone had Rf values of 0.74, 0.65, 0.67, and 1.0 in silt, loam, clay and sand, respectively, in laboratory soil thin layer chromatography (TLC) experiments(4) which is consistent with significant mobility in soil(SRC).
The Henry's Law constant for 1-methyl-2-pyrrolidone is 3.20X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 1-methyl-2-pyrrolidone is expected to be essentially nonvolatile from water surfaces(2). 1-Methyl-2-pyrrolidone's Henry's Law constant indicates that volatilization from moist soil surfaces may not occur(SRC). 1-Methyl-2-pyrrolidone is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.345 mm Hg(3).
DRINKING WATER: 1-Methyl-2-pyrrolidinone has been qualitatively detected in US drinking water supplies(1).
1-Methyl-2-pyrrolidinone has been detected as a volatile flavor component of roasted filberts(1).
According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of 1-methyl-2-pyrrolidone is 1000 or greater; the data may be greatly underestimated(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 85,169 workers (23,478 of these were female) were potentially exposed to 1-methyl-2-pyrrolidone in the US(1). Occupational exposure to 1-methyl-2-pyrrolidone may occur through inhalation and dermal contact with this compound at workplaces where 1-methyl-2-pyrrolidone is produced or used. Monitoring data indicate that the general population may be exposed to 1-methyl-2-pyrrolidone via inhalation and dermal contact of water in areas of industrial applications and, to a lesser extent via ingestion of certain foods(SRC).
Drug Information
An agent that causes the production of physical defects in the developing embryo. (See all compounds classified as Teratogens.)
Male Sprague-Dawley rats were given a single ip injection (45 mg/kg) of radiolabeled 1-methyl-2-pyrrolidone. Plasma levels of radioactivity and cmpd were monitored for six hr and the results suggested a rapid distribution phase which was followed by a slow elimination phase. The major amount of label was excreted in the urine within 12 hr and accounted for approximately 75% of the labelled dose. ...|This study evaluated the toxicokinetics of N-((14)C)methylpyrrolidone (((14)C)NMP) after intravenous administration (0.1, 1, 10, 100, and 500 mg/kg, in saline solution) or topical application (20 and 40 uL/sq cm; 10 sq cm, neat) in haired male Sprague-Dawley rats. Whatever the dose, unchanged NMP was intensively distributed into the body with a volume of distribution of 69% of body weight. After this phase, unchanged NMP declined almost linearly with time for 3 to 4 hr after administration and then followed a mono-exponential function (t1/2 = 0.8 hr) for the three lowest doses. The maximal plasma level of 5-hydroxy-N-methylpyrrolidone (5-HNMP), the main metabolite, was reached 4 to 6 hr later for the three lowest doses and 8 to 24 hr later for the highest doses. These findings indicate that the elimination of NMP is governed by a saturable metabolism process. The Michaelis-Menten parameters estimated from plasma levels of unchanged NMP were 2 mM and 3.8 mg/hr, respectively. Between 4 and 10% of the administered doses were excreted in the urine as unchanged NMP. Urinary clearance of NMP (0.03 to 0.07 mL/min) indicates intensive tubular reabsorption. 5-HNMP was the main urinary metabolite and accounted for 42 to 55% of the administered doses. Its maximal urinary excretion occurred between 4 and 6 hr after administration of the three lowest doses and between 8 and 24 hr for the two highest doses. Urinary clearance (0.9 to 1.3 mL/min) was compatible with renal elimination by simple glomerular filtration.|Metabolism studies were performed using (14)C and tritium labeled N-methyl-2-pyrrolidinone in the rat. Male Sprague-Dawley rats were injected with labeled or unlabeled N-methyl-2-pyrrolidinone at 45 mg/kg body weight. Urine, feces, expired air, and bile were collected at various times between drug administration and sacrifice. For pharmacokinetic studies, serial blood samples were analyzed at times between 30 minutes and 6 hours post injection. HPLC of plasma N-methyl-2-pyrrlidinone indicated a rapid distribution phase followed by a slow elimination phase with a half life of approximately 7 hours for the (14)C and 10 hours for the tritium isotope. Urinary excretion accounted for approx 70% of the total dose within 12 hours, and a 2:1 ratio in the administered dose was maintained in the urine. The tissue distribution of the radiolabeled isomers showed similar patterns. The rank order of tissue accumulation from highest to lowest concentration was liver, intestine, testes, stomach, kidneys, lungs, brain, heart, pancreas, and spleen. The bladder, thyroid, and thymus showed minimal N-methyl-2-pyrrolidinone levels.|Six male volunteers were exposed for eight hours on four different days to 0, 10, 25, and 50 mg/cu m N-methyl-2-pyrrolidone. ... N-Methyl-2-pyrrolidone was absorbed through the respiratory tract and readily eliminated from the body, mainly by biotransformation to other compounds. ...|For more Absorption, Distribution and Excretion (Complete) data for 1-METHYL-2-PYRROLIDINONE (8 total), please visit the HSDB record page.
The aim was to study the metabolic pathway for N-methyl-2-pyrrolidone in humans. Three healthy male volunteers were administered 100 mg N-methyl-2-pyrrolidone orally. All urine was collected during nine consecutive days. The identification and quantification of the metabolites were performed by gas chromatography/mass spectrometry (GC/MS). N-Methyl-2-pyrrolidone, 5-hydroxy-N-methyl-2-pyrrolidone (5-hydroxy-N-methyl-2-pyrrolidone), N-methylsuccinimide, and 2-hydroxy-N-methylsuccinimide were found in urine. The mean excreted fractions for N-methyl-2-pyrrolidone, 5-hydroxy-N-methyl-2-pyrrolidone, N-methylsuccinimide, and 2-hydroxy-N-methylsuccinimide were 0.8%, 44%, 0.4%, and 20%, respectively. There was no conjugation with glucoronic acid or sulfate or either 5-hydroxy-N-methyl-2-pyrrolidone or 2-hydroxy-N-methylsuccinimide. One-third of the orally dosed N-methyl-2-pyrrolidone was not recovered in urine as either N-methyl-2-pyrrolidone, 5-hydroxy-N-methyl-2-pyrrolidone, N-methylsuccinimide, or 2-hydroxy-N-methylsuccinimide. The half-lives for 5-hydroxy-N-methyl-2-pyrrolidone, N-methylsuccinimide, and 2-hydroxy-N-methylsuccinimide in urine were approximately 4, 8, and 17 hr, respectively.|A method for determination of N-methylsuccinimide and 2-hydroxy-N-methylsuccinimide in human urine and of N-methylsuccinimide in human plasma was developed. N-Methylsuccinimide and 2-hydroxy-N-methylsuccinimide are metabolites of the ... organic solvent N-methyl-2-pyrrolidone. ... The method is applicable for analysis of urine and plasma samples from workers exposed to N-methyl-2-pyrrolidone.|This study described the isolation and identification of the major urinary metabolite of N-methylpyrrolidinone in the male Sprague-Dawley-rat following intravenous administration. The rats were injected via the tail vein with either unlabeled N-methylpyrrolidinone or (14)C labeled N-methylpyrrolidinone at 45 mg/kg. Urine was collected during 0 to 12, 12 to 24, and 24 to 48 hours after dosing and analyzed by gas chromatography/mass spectrometry. Thermospray liquid chromatography/mass spectrometry was performed on samples purified using high performance liquid chromatography method. The major metabolite correlated with 5-hydroxy-N-methylpyrrolidinone based on thin layer chromatography and mass spectral comparisons with an authentic sample.
Impurities that may be found within 1-methyl-2-pyrrolidinone are methylamine (.02%) and water (.1%).
Inhalation of hot vapors can irritate nose and throat. Ingestion causes irritation of mouth and stomach. Contact with eyes causes irritation. Repeated and prolonged skin contact produces a mild, transient irritation. (USCG, 1999)
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. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. 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. (NTP, 1992)
Fresh air, rest. Refer for medical attention.
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.
/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 if 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. /Poisons A and B/|/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 needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. 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 IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
/HUMAN EXPOSURE STUDIES/ Six male volunteers were exposed for eight hours on four different days to 0, 10, 25, and 50 mg/cu m N-methyl-2-pyrrolidone. Plasma was collected and urine was sampled during and after the exposure. Changes in nasal volume were measured by acoustic rhinometry and in airway resistance by spirometry. The eight-hour experimental exposure to 10, 25, and 50 mg/cu m did not induce discomfort to eyes or upper airways. Acute changes in nasal volume were not found, and no changes in the spirometric data could be registered. ... N-Methyl-2-pyrrolidone was absorbed through the respiratory tract and readily eliminated from the body, mainly by biotransformation to other compounds. Exposure to 10, 25, or 50 mg/cu m N-methyl-2-pyrrolidone did not cause nose, eye, or airway irritation. Thus, N-methyl-2-pyrrolidone is a mild irritant.|/SIGNS AND SYMPTOMS/ It can cause dermatitis with blistering, edema, and erythema with prolonged or repeated contact.|/SIGNS AND SYMPTOMS/ In the semiconductor industry, headaches and chronic eye irritation were described in some employees exposed to levels as low as 0.7 ppm. Levels of 49 to 83 ppm were found unbearable by the workers.|/SURVEILLANCE/ Several workers in a small electrotechnical company in Norway experienced irritant reaction of the skin after a few days of working with the solvent N-methyl-2-pyrrolidone. ... After 2 days of work with N-methyl-2-pyrrolidone, 10 of the 12 involved workers displayed acute irritant contact dermatitis of the hands. ...|/ALTERNATIVE and IN VITRO TESTS/ The effects of absorption enhancers such as laurocapram (Azone), N-methylpyrrolidone, propylene glycol, and oleic acid on the percutaneous absorption of heparin sodium through excised human skin were investigated. Laurocapram, N-methylpyrrolidone, and propylene glycol promomted heparin flux, while oleic acid did not.
1-methyl-2-pyrrolidinone
The substance can be absorbed into the body by inhalation, through the skin and by ingestion.
Headache.
MAY BE ABSORBED! Redness. Pain.
Redness. Pain. Blurred vision.
N-Methyl-2-pyrrolidone Use and Manufacturing
Large-scale production of NMP /N-methyl-2-pyrrolidone/ is predominantly carried out by reacting gamma-butyrolactone with an excess of pure or aqueous methylamine in a high-pressure tube reactor (6-12 MPa). The reaction is exothermic and often run under adiabatic conditions with reactor temperatures in the range of 250-400 °C. The resulting product mixture is decompressed and distilled. The NMP yield is normally more than 97%.|NMP /N-methyl-2-pyrrolidone/ can also be produced by hydrogenation of N-hydroxymethyl-2-pyrrolidone or by reaction of acrylonitrile with methylamine in the presence of a peroxide radical initiator.|... Hydrogenation of N-methylsuccinimide or mixtures of maleic or succinic anhydride and methylamine.|High-pressure synthesis from acetylene and formaldehyde.
It is an excellent solvent, widely used as an extractant for aromatic extraction, lubricating oil refining, acetylene concentration, synthesis gas desulfurization, etc. It is also used for industrial cleaning and other purposes. N-methylpyrrolidone is an excellent extraction solvent. It is widely used as an extractant in the process of aromatics extraction, acetylene concentration, butadiene separation and synthesis gas desulfurization. It is also a solvent in the production of pesticides, engineering plastics, coatings, synthetic fibers, integrated circuits, etc. Industrial detergents, dispersants, dyes, lubricants antifreeze, etc. The product has low toxicity, and the oral LD50 for rats is 7ml/kg. It is widely used in solvents such as high-grade lubricating oil refining, polymer synthesis, insulating materials, pesticides, pigments and cleaning agents. Organic Synthesis. Used in aromatic extraction, purification of acetylene, olefin, and diolefin; used in polymer solvent and polymerization medium, such as engineering plastics such as polyamide, polyimide, polyphenylene sulfide, and aramid fiber
Additive
Adhesives and sealants
100,000,000 - 250,000,000 lb|(1977) PROBABLY GREATER THAN 2.3X10+6 GRAMS|(1979) PROBABLY GREATER THAN 2.3X10+6 GRAMS|Annual production has been estimated at 36-39,000 tons a year (1991 OSHA).|World capacity of NMP is currently estimated at 200,000 - 250,000 t/a.|For more U.S. Production (Complete) data for 1-METHYL-2-PYRROLIDINONE (7 total), please visit the HSDB record page.
Abrasives manufacturing|2-Pyrrolidinone, 1-methyl-: ACTIVE|R - indicates a substance that is the subject of a TSCA section 6 risk management rule.|Due to it's low toxicity and non-halogenated structure, 1-methyl-2-pyrrolidinone is increasingly being used in paint thinners and industrial solvents.
Method: NIOSH 1302, Issue 1; Procedure: gas chromatography with nitrogen phosphorous detector or flame ionization detector; Analyte: N-methyl-2-pyrrolidnone; Matrix: air; Detection Limit: 0.02 ug/sample (nitrogen phosphorous detector), 0.3 ug/sample (flame ionization detector).|Method: OSHA PV2043; Procedure: gas chromatography with a flame ionization detector; Analyte: N-methyl-2-pyrrolidinone; Matrix: air; Detection Limit: 0.1 ppm.|GC DETERMINATION OF N-METHYLPYRROLIDONE AND OTHER SUBSTANCES IN WASTE WATERS.|N-METHYL-2-PYRROLIDONE IS CONCENTRATED BY ADSORPTION ON XAD-2 RESIN FROM AQ SODIUM CHLORIDE SOLUTION & ELUTED WITH METHANOL. IT IS DETERMINED IN METHANOL ELUATE BY GLC. DETERMINED IN WASTE WATER @ PPM LEVEL.
Fire Hazards -> Teratogens, Flammable - 2nd degree|Cosmetics -> Surfactant
Computed Properties
Molecular Weight:99.13
XLogP3:-0.5
Hydrogen Bond Acceptor Count:1
Exact Mass:99.068413911
Monoisotopic Mass:99.068413911
Topological Polar Surface Area:20.3
Heavy Atom Count:7
Complexity:90.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Price Analysis
- Data: 2026-07-31
- Price: 9766.67Yuan/mt
- Change: 0
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