StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
Huagongshe Open Project:[email protected]KI-Anbindung: llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.7.8
  1. Startseite
  2. /Verbindung

N,N-Dimethylnitrosamin

N-Nitrosodimethylamine

HCID 6124
NotizenReaktionen
GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
62-75-9
Standard-SMILES
CN(C)N=O
InChIKey
UMFJAHHVKNCGLG-UHFFFAOYSA-N
Summenformel
C2H6N2O
Durchschnittliche Molmasse
74,08 g/mol
Monoisotopische Masse
74,04801281

Überblick

n-Nitrosodimethylamine is produced by industry only in small amounts for research. At room temperature, it is a yellow liquid with no distinct odor. It was used to make rocket fuel, but this use was stopped after unusually high levels of this chemical were found in air, water, and soil samples collected near a rocket fuel manufacturing plant. It is used in some cosmetic and toiletry products and in cleansers.n-Nitrosodimethylamine is unintentionally formed during various manufacturing processes and in air, water, and soil from reactions involving other chemicals called alkylamines. It is also found in some foods and may be formed in the body.

Namen und Bezeichner

Bevorzugter Name
N-Nitrosodimethylamine
IUPAC
N,N-dimethylnitrous amide
Lokaler Name
N,N-Dimethylnitrosamin
Englischer Name
N-Nitrosodimethylamine
Summenformel
C2H6N2O
Molmasse
74.08

Namen und Synonyme

N-NITROSODIMETHYLAMINE62-75-9DimethylnitrosamineNDMAN,N-dimethylnitrous amideN-Methyl-N-nitrosomethanamineDimethylnitrosoamineNitrosodimethylamineN,N-DimethylnitrosamineDMNAMethanamine, N-methyl-N-nitroso-Dimethylnitrosamin
Weitere Namen anzeigen
DMNn-methyl-n-nitroso-methanaminN56-001NSC 23226
dimethyl(nitroso)amineN-Nitroso-N,N-dimethylamineDimethylamine, N-nitroso-N-NitroaodimethylamineN-Dimethyl-nitrosaminenitrous dimethylamideRCRA waste number P082N-methyl-N-nitroso-methanamine

Datenbank-Bezeichner

CAS
62-75-9
PubChem CID
6124
DTXSID
DTXSID7021029
ChEMBL
CHEMBL117311
ChEBI
CHEBI:35807
UNII
M43H21IO8R
EC Number
200-549-8

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-0,6
Polarare Oberfläche (TPSA)
32,7 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
0
Schwere Atome
5
Formalladung
0
Komplexität
34,6

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 4 Einträge

Hazardous Air Pollutants (HAPs)

Nitrogen Compounds -> Nitrosamines

Carcinogens

Semi-Volatile Organic Compound (SVOC)

SpringerMaterials PropertiesSchoenflies notation
PesticidesPesticide -> EPA IRIS
LogP · 4 Einträge

log Kow = -0.57

-0.57

-0.57

-0.38

OdorFaint, characteristic odor
Density · 6 Einträge

1.0048 at 68 °F (EPA, 1998) - Denser than water; will sink

1.0048 at 20 °C/4 °C

Relative density (water = 1): 1.0

1.005

1.0048 @25 °C

1.005

ViscosityLow
Color/Form · 2 Einträge

Yellow, oily liquid

Yellow liquid

Solubility · 6 Einträge

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P203, P260, P264, P270, P271, P273, P280, P284, P301+P316, P304+P340, P316, P318, P319, P320, P321, P330, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H300 (19.6%): Fatal if swallowed [Danger Acute toxicity, oral]

P203, P260, P264, P270, P271, P273, P280, P284, P301+P316, P304+P340, P316, P318, P319, P320, P321, P330, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: Methanamine, N-methyl-N-nitroso-

Hazard Traits - Carcinogenicity; Hepatotoxicity and Digestive System Toxicity

Regulation (EC) No 257/2010

N-Nitrosodimethylamine: 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.)

Other Safety InformationIMAP assessments - Methanamine, N-methyl-N-nitroso-: Human health tier I assessment
DOT LabelPoison
Fire Hazards · 2 Einträge

When heated to decomposition, it emits toxic fumes of nitrogen oxides. Avoid exposure to ultraviolet light. (EPA, 1998)

Combustible.

Fire PotentialCombustible
Health Hazards

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 2 Einträge

The effect of dimethylnitrosamine on functional activities of liver chromatin was studied in mice. After a single dose of dimethylnitrosamine injected i.v. (25 mg/kg body wt, 45 min before sacrifice) liver nuclei were isolated and incubated with micrococcal nuclease (EC 3.1.4.7) to an acid-solubility of 2.5% of total DNA. Chromatin was fractionated into a 1,200 g pellet P1, 102,000 g pellet P2 and supernatant fraction S2. Chromatin-bound RNA polymerase I plus III activity decreased 15% in the P1 and 25% in the P2 fraction. No changes in activity were observed in the S2 fraction. Chromatin-bound RNA polymerase II activity decreased 19% in the P1, 49% in the P2 and 32% in the S2 fraction. Heparin stimulated RNA polymerase II activity decreased 10% in the P1 and 44% in the P2 fraction. Formation of initiation in nuclear lysates with RNA polymerase from Escherichia coli increased after administration of dimethylnitrosamine suggesting an increase in the number of sites available for the start of new RNA chains. The results show that limited digestion of nuclei with endonuclease cleaves chromatin regions which are more affected by dimethylnitrosamine than the total chromatin suggesting a non-random effect of the hepatotoxin on chromatin. Modifications of the DNA template by dimethylnitrosamine is indicated by the change in number of initiation complexes.

... Hamsters are more susceptible than rats to liver cancer by dimethylnitrosamine because of its deficiency in repair of O6-alkylation of guanine in DNA. In rats a single large dose of dimethylnitrosamine induces kidney, but not liver, cancer because of the capability of liver repair enzymes to remove alkylated forms of DNA from the liver.

Biological Half-Life · 2 Einträge

No reports found; [TDR, p. 955]

When administered to rats, mice and rabbits, it is ... metabolized rapidly, with a half-life of approximately 4 hr.

Metabolism/Metabolites · 6 Einträge

Formation of n-nitrosodimethylamine (NDMA) in the stomachs of rats and mice after simultaneous oral administration of (14)C-labeled dimethylamine and potassium nitrite was determined by measuring the methylation of liver DNA. Simultaneous administration of 50 mg ascorbate/kg inhibited the nitrosation by approximately 80%. 50 mg alpha-tocopherol acetate/kg reduced the nitrosation by approximately 50%.

Zugehörige Reaktionen

3
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 259496
HRID 259496als Produktuspto-grants-1977_07
Reaktionsgleichung von HRID 1500343
HRID 1500343als Eduktuspto-grants-2015_12
Reaktionsgleichung von HRID 1722767
HRID 1722767als Eduktuspto-grants-1989_08

Notizen zur Verbindung

Wird geladen…

Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
Nikkaji
J1.928C

greater than or equal to 100 mg/mL at 66 °F (NTP, 1992)

Infinitely soluble in water at 23-25 °C

Soluble in all common organic solvents and in lipids

Very soluble in water, alcohol, ether

Miscible with methylene chloride, vegetable oils

Soluble in ethanol, ethyl ether, and chloroform; soluble in water.

Flash Point · 4 Einträge

142 °F (NTP, 1992)

142 °F

61 °C

142 °F

Boiling Point · 6 Einträge

304 to 307 °F at 760 mmHg (EPA, 1998)

152 °C

151 °C

306 °F

152 °C @760 [mm Hg]

306 °F

DecompositionWhen heated to decomp it emits toxic fumes of /oxides of nitrogen/.

Physikochemische Eigenschaften

Schmelzpunkt
25 °C · <25 °C
Siedepunkt
153 °C774 · 153 °C774 mm Hg(lit.)
Dichte
1.01 g/mL · 1.01 g/mL(lit.)
Dampfdruck
5 mm · 5 mm Hg ( 20 °C)
Brechungsindex
20 · n20/D 1.437(lit.)
Flammpunkt
142 °F · 142 °F
storage temp.
2 · 2-8°C
Löslichkeit
Soluble in solvents (U.S. EPA, 1985), including ethanol and ether (Weast, 1986)
pka
-3.63 · -3.63±0.70(Predicted)
Aggregatzustand
Yellow liquid
Farbe
Colourless to Light Yellow
Wasserlöslichkeit
Miscible (Mirvish et al., 1976)
Merck
13 · 13,6671
Henry's Law Constant
0.143 at · 0.143 at 25 °C (estimated using a solubility of 1,000 g/L)
Dielectric constant
54 · 54.0(20℃)
Stabilität
Stability Stable, but light-sensitive. Combustible. Incompatible with strong oxidizing agents, strong bases, strong reducing agents.
Major Application
cleaning productscosmeticsenvironmentalfood and beveragespersonal care
InChI
1S/C2H6N2O/c1-4(2)3-5/h1-2H3
InChIKey
UMFJAHHVKNCGLG-UHFFFAOYSA-N
SMILES
N(N=O)(C)C
CAS Datenbank
62 · 62-75-9(CAS DataBase Reference)
EPA chemische Informationen
N-Nitrosodimethylamine (62-75-9)
Excerpt from NIOSH Pocket Guide for N-Nitrosodimethylamine:
Hazards Summary · 3 Einträge

n-Nitrosodimethylamine is produced by industry only in small amounts for research. At room temperature, it is a yellow liquid with no distinct odor. It was used to make rocket fuel, but this use was stopped after unusually high levels of this chemical were found in air, water, and soil samples collected near a rocket fuel manufacturing plant. It is used in some cosmetic and toiletry products and in cleansers.n-Nitrosodimethylamine is unintentionally formed during various manufacturing processes and in air, water, and soil from reactions involving other chemicals called alkylamines. It is also found in some foods and may be formed in the body.

Individuals may be exposed to low levels of N-nitrosodimethylamine in occupational settings, through the ingestion of food that contains it (e.g., cured meat products and smoked fish), and from breathing cigarette smoke. Acute (short-term) exposure to N-nitrosodimethylamine may damage the liver in humans, with symptoms that include nausea, vomiting, headaches, and malaise. Chronic (long-term) exposure of humans toN-nitrosodimethylamine may cause liver damage and low platelet counts. Severe liver damage has been observed in animals. Limited human data are available on the carcinogenic effects of N- nitrosodimethylamine. Animal studies have suggested that chronic ingestion and inhalation of N- nitrosodimethylamine may cause an increase in liver tumors and other types of tumors. EPA has classified N-nitrosodimethylamine as a Group B2, probable human carcinogen.

A animal carcinogen; At least one death and a number of cases of hepatic injury have been reported in workers handling DMNA. [ACGIH] A skin, eye, and respiratory tract irritant; May cause liver injury and jaundice; [ICSC]

Reactive GroupAzo, Diazo, Azido, Hydrazine, and Azide Compounds
EC ClassificationSymbol: T+, N; R: 45-25-26-48/25-51/53; S: 53-45-61; Note: E
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: I
Special Reports · 5 Einträge

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-Nitrosodimethylamine (62-75-9) was first listed in the Second Annual Report on Carcinogens (1981) as reasonably anticipated to be a human carcinogen.[Available from, as of August 3, 2012: http://ntp.niehs.nih.gov/]

TSCA CHIPs present a preliminary assessment of N-nitrosodimethylamine's potential for injury to human health & the environment (available at EPA's TSCA Assistance Office: (202) 554-1404

Eisenbrand G et al; Some recent results on the Chemistry, Formation and Biological Activity of N-nitroso Compounds. Gann Monograph 133-143: (1975)

Longnecker DS; Carcinogenesis in the Pancreas. Archives of Pathology and Lab Medicine 107 (2): 54-8 (1983)

For more Special Reports (Complete) data for N-NITROSODIMETHYLAMINE (10 total), please visit the HSDB record page.

RCRA Requirements · 1 Eintrag

P082; As stipulated in 40 CFR 261.33, when N-nitrosodimethylamine, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use powder, carbon dioxide.

First Aid Measures · 4 Einträge

Fresh air, rest. Refer for medical attention.

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

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

Give a slurry of activated charcoal in water to drink. Refer for medical attention .

First Aid · 2 Einträge

Warning: Nitrosodimethylamine is a suspected human carcinogen, hepatotoxin, and hemorrhagic agent. Caution is advised. Effects may be delayed.

(General first aid procedures)

Safe StorageSeparated from strong oxidants and food and feedstuffs. Cool. Keep in the dark. Well closed.
Fire Fighting Procedures/Fire fighters should wear/ any self-contained breathing apparatus with a full facepiece and operated in a pressure demand or other positive pressure mode.
Storage ConditionsALL BOTTLES OF N-NITROSODIETHYLAMINE SHOULD BE STORED & TRANSPORTED WITHIN UNBREAKABLE OUTER CONTAINER; STORAGE SHOULD BE IN VENTILATED STORAGE CABINET (OR IN HOOD). /N-NITROSODIETHYLAMINE, ALSO APPLICABLE TO OTHER DIALKYLNITROSAMINES/
Cleanup Methods · 5 Einträge

SPILLS OF N-NITROSODIETHYLAMINE CAN BE ABSORBED BY CELITE OR COMMERCIAL SPILL ABSORBANT. AFTER ABSORBANT CONTAINING MAJOR SHARE OF NITROSAMINE HAS BEEN PICKED UP (AVOID DUSTS; DO NOT SWEEP), SURFACE SHOULD BE THOROUGHLY CLEANED WITH STRONG DETERGENT SOLN. IF MAJOR SPILL OCCURS OUTSIDE OF VENTILATED AREA, ROOM SHOULD BE EVACUATED & CLEANUP OPERATION SHOULD BE CARRIED OUT BY PERSONS EQUIPPED WITH SELF-CONTAINED RESPIRATORS. THOSE INVOLVED IN THIS OPERATION SHOULD WEAR RUBBER GLOVES, LAB COATS, & PLASTIC APRONS OR EQUIVALENT PROTECTIVE APPAREL. /N-NITROSODIETHYLAMINE, ALSO APPLICABLE TO OTHER DIALKYLNITROSAMINES/

Nitrosamine residues generated in laboratory research or accidental spills in research laboratories and diluted to concn of 10 mg/l or less are rapidly reduced to innocuous amines, ammonia, or alcohols by aluminum-nickel alloy powder and aqueous alkali. The method is applicable to a variety of media (water, mineral oil, olive oil, dimethylsulfoxide, soln of agar gel) but is not recommended for use with nitrosamines in acetone or dichloromethane because reactions are slow and incomplete. After the reduced reaction mixture is filtered, the liquid is disposed of by pouring it over sufficient absorbent material to convert it to a solid waste for incineration. /Nitrosamines/

After covering the spills with soda ash, mix and spray with water. Scoop into a bucket of water and /let/ it stand for two hr. Neutralize with 6M hydrochloric acid and flush with sufficient water.

Decontamination of lab wastes using triethyloxonium salts /was described/. This method specifies a procedure for the decontamination of lab wastes either dissolved in or extractable by dichloromethane. This method has been ... studied using triethyloxonium tetrafluoroborate for the treatment of solutions of N-nitrosodimethylamine ... in dichloromethane ... .

For more Cleanup Methods (Complete) data for N-NITROSODIMETHYLAMINE (7 total), please visit the HSDB record page.

Nonfire Spill Response · 1 Eintrag

Avoid inhalation and skin contact. Spills can be absorbed by celite or commercial spill absorbent. After absorbent containing major share of nitrosamine has been picked-up (avoid dusts; do not sweep), surface should be thoroughly cleaned with strong detergent solution. If major spill occurs outside of ventilated area, room should be evacuated and cleanup operation should be carried out by persons equipped with self-contained breathing apparatus. (EPA, 1998)

Disposal Methods · 5 Einträge

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number P082, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

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.

A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.

The following wastewater treatment technology has been investigated for dimethylnitrosamine: Concentration process: Activated carbon.

For more Disposal Methods (Complete) data for N-NITROSODIMETHYLAMINE (13 total), please visit the HSDB record page.

Spillage Disposal · 1 Eintrag

Evacuate danger area! Personal protection: chemical protection suit including self-contained breathing apparatus. 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.

Preventive Measures · 5 Einträge

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.

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.

The worker should immediately wash the skin when it becomes contaminated.

The worker should wash daily at the end of each work shift, and prior to eating, drinking, smoking, etc.

For more Preventive Measures (Complete) data for N-NITROSODIMETHYLAMINE (16 total), please visit the HSDB record page.

Isolation and EvacuationExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Toxikologische Informationen

Toxicological InformationCDC-ATSDR Toxicological Profile
Body Burden · 1 Eintrag

More N-nitrosodimethylamine was detected in human blood immediately after ingestion of a meal containing spinach, bacon, tomato, bread and beer than was present before(1). In 175 samples of human milk collected from 16 nursing women, 76.5% of the samples contained less than 0.2 ppb N-nitrosodimethylamine (minimum level of reliable measurement)(2). In 54 human milk samples from 54 healthy nursing women, trace amounts of N-nitrosodimethylamine (below detection limit of 0.5 ug/L) were detected in the milk of 10 mothers and two other samples contained levels of 1.1 and 1.2 ug/L(3).

Cancer Sites · 2 Einträge

Hepatic

[in animals; lung, kidney, liver & nasal cavity tumors]

Interactions · 5 Einträge

Resveratrol, a phytoalexin found in grapes and red wines, has been reported to exhibit a wide range of pharmacological properties. In this study, we investigated the protective effect of resveratrol on hepatic injury induced by dimethylnitrosamine (DMN) in rats. Oral administration of resveratrol (20 mg/kg daily for 4 weeks) remarkably prevented the DMN-induced loss in body and liver weight, and inhibited the elevation of serum alanine transaminase, aspartate transaminase, alkaline phosphatase and bilirubin levels. Resveratrol also increased serum albumin and hepatic glutathione levels and reduced the hepatic level of malondialdehyde due to its antioxidant effect. Furthermore, DMN-induced elevation of hydroxyproline content was reduced in the resveratrol treated rats, the result of which was consistent with the reduction in type I collagen mRNA expression and the histological analysis of liver tissue stained with Sirius red. The reduction in hepatic stellate cell activation, as assessed by alpha-smooth muscle actin staining, and the reduction in transforming growth factor-beta1 mRNA expression were associated with resveratrol treatment. In conclusion, resveratrol exhibited in vivo hepatoprotective and antifibrogenic effects against DMN-induced liver injury, suggesting that resveratrol may be useful in the prevention of the development of hepatic fibrosis.

To study the effect of chronic alcohol consumption on tumor development due to dimethylnitrosamine (DMN) administration, female Sprague-Dawley rats were pair-fed for 3 weeks a nutritionally adequate liquid diet containing either ethanol (36% of total calories) or isocalorically substituted carbohydrates as control diet. Thereafter, the animals were maintained on laboratory chow and tap water ad libitum for another 2 weeks and received 1.5 mg DMN i.p. per day for the first 5 days. This 5-week cycle was repeated three more times. Chronic treatment with an alcohol-containing diet was shown to significantly improve the mean survival time of DMN-treated rats compared with identically treated animals fed the control diet, but the total number of tumors observed under these experimental conditions and the target organ remained virtually unchanged.

Administration of aminoacetonitrile to rats reduced metabolism of NDMA, induction of hepatic dna damage and acute toxicity. ... Pretreatment of rats with pregneolone-16alpha-carbonitrile ... decreased ... toxicity of NDMA. ... Acute toxicity of NDMA in rats and mice and n-7-methylation of guanine in liver DNA were reduced by simultaneous administration of disulfiram.

Dose-related suppression of the 3H-thymidine incorporation into liver DNA of rats after a single injection of dimethylnitrosamine by copper pretreatment was observed. The 3H-thymidine incorporation was not decreased by cadmium pretreatment. On the other hand, the 3H-thymidine incorporation into liver DNA of partially hepatectomized rats was decreased by both copper and cadmium pretreatments. Thymidine kinase activity in the liver of rats treated with dimethylnitrosamine was also decreased by copper pretreatment, but the enzyme activity was not decreased by cadmium pretreatment. Copper accumulation in the liver of copper-administered rats was predominantly in the nuclear fraction, followed by the soluble fraction. Cadmium accumulation in the liver of cadmium-administered rats was predominantly in the soluble fraction, followed by the nuclear fraction. Copper accumulation in the nuclear fraction may suppress the induction of thymidine kinase in the liver of rats by dimethylnitrosamine.

For more Interactions (Complete) data for N-NITROSODIMETHYLAMINE (15 total), please visit the HSDB record page.

Target Organs · 2 Einträge

Cancer, Developmental (effects while organs are developing), Hematological (Blood Forming), Hepatic (Liver)

Liver, kidneys,lungs

Health Effects · 1 Eintrag

NDMA is very harmful to the liver of animals and humans. Moreover, although there are no reports of NDMA causing cancer in humans, it is reasonable to expect that exposure to NDMA by eating, drinking, or breathing could also cause cancer in humans. (L1207)

Ecotoxicity Values · 5 Einträge

LD50; Species: Oncorhynchus mykiss (Rainbow trout) ip 1770 mg/kg for 10 days

LD50; Species: Austropotamobius pallipes (Crayfish) male, adult; iv 2250 mg/kg

EC50; Species: Anabaena flosaquae (Blue-Green Algae) 10000 cells; Conditions: freshwater, static, 24 °C; Concentration: 5100 ug/L for 96 hr; Effect: growth, general

EC50; Species: Pseudokirchneriella subcapitata (Green Algae) 10000 cells; Conditions: freshwater, static, 24 °C; Concentration: 4000 ug/L for 96 hr; Effect: growth, general

For more Ecotoxicity Values (Complete) data for N-NITROSODIMETHYLAMINE (12 total), please visit the HSDB record page.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a recommended classification scheme(1), observed Koc values of 68-118(2) indicate that N-nitrosodimethylamine is expected to have high mobility in soil(SRC). Low adsorption to soils and ready leaching have been observed in other studies(3,4). Volatilization of N-nitrosodimethylamine from moist soil surfaces may be an important fate process(SRC) given a Henry's Law constant of 1.08X10-6 atm-cu m/mole at 20 °C(5). Under laboratory conditions, greater than 70% of N-nitrosodimethylamine applied to the surface of a moist, warm soil (12% moisture content, 22 °C) volatilized in 10 hours(6). The potential for volatilization of N-nitrosodimethylamine from dry soil surfaces may exist(SRC) based on a measured vapor pressure of 2.7 mm Hg at 20 °C(5). A half-life of about three weeks was reported for N-nitrosodimethylamine in aerobic soil under laboratory conditions; the primary removal processes were volatilization and biodegradation(6). 17% of the added N-nitrosodimethylamine (132 ug/g soil) was lost from sandy loam soil after 10 days incubation at 30 °C; no further loss was noted during the next 30 days incubation(7). However, when the organic matter content was increased from 2.16% to 17.5%, over 60% of the added N-nitrosodimethylamine was lost by day 15 of the incubation period(7). At 21 °C, observed half-lives in ground cover soil, turfgrass soil and tree soil were 4.1, 5.6 and 22.5 days respectively(8). The rates and extent of N-nitrosodimethylamine biodegradation in natural environments, including surface waters, sludges and soils have been observed to be highly variable(9).

AQUATIC FATE: Based on a recommended classification scheme(1), observed Koc values of 68-118(2) indicate that N-nitrosodimethylamine is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected to occur(3) based upon a Henry's Law constant of 1.08X10-6 atm-cu m/mole at 20 °C(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 29 days and 215 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from a measured log Kow of -0.57(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A photodegradation half-life of 79 hours was measured in distilled water following exposure to fluorescent light through a Pyrex filter(8). The direct photolysis rate constant for N-nitrosodimethylamine in aqueous solution exposed to irradiation representing Southern California midsummer, midday sun was observed to be 0.040/min with a half-life of 16 minutes(9). Hydrolysis is probably not an important removal process since the N-nitrosodimethylamine concentration in lake water essentially did not change after 3.5 months incubation at 30 °C in the dark(10). No biodegradation of N-nitrosodimethylamine was observed in lake water samples during an observation period of 3.5 months(11). Static and continuous biodegradation tests on N-nitrosodimethylamine using seed from an activated sludge plant and feed that contained a nutrient solution based on yeast extract resulted in 47 to 72% degradation of the N-nitrosodimethylamine in 7 days(12). The rates and extent of N-nitrosodimethylamine biodegradation in natural environments, including surface waters, sludges and soils have been observed to be highly variable(13). N-Nitrosodimethylamine disappeared rapidly from aqueous solution due to evaporation and photolysis, with acidic solutions giving a somewhat higher removal than basic solutions or water, half-life of 0.8 hours versus 0.9 and 1.6 hours, respectively(14).

Food Survey Values · 3 Einträge

N-Nitrosodimethylamine has been found to be present in a variety of foods (included smoked, dried or salted fish, ... salami, frankfurters, and cured meats) in the 1 to 100 ug/kg range, but more usually in the 1 to 10 ug/kg range.

N-Nitrosodimethylamine concns in foods were: 0.02 ppb in sukiyaki broth(1); not detected to 7.7 ppb in beer(2); 2.7 ppb (avg) and 68 ppb (max) in draft and bottle beers(3); 7.7 ppb (avg) in lager beer(4); 5 ppb in ale(4); 2.8 ppb (avg) in malt lager(4); 150 ug/kg in barley malt(5); 22 to 118 ppb in commercially malted barley(6); 2.7 ppb (avg) in fried bacon(7); 2.6 ppb in cooked bacon(7); 0.26 to 0.93 ppb in edible oils(8); 0.3 ppb in margarine(9); traces in cheeses(10); 1.2 ppb in whole wheat biscuits(11); 0.8 ppb in flour(11); 0.8 ppb in dried peas(11); 0.4 ppb in malt vinegar(11); and 1.0 ug/kg in infant formula(5). N-Nitrosodimethylamine was detected in samples of smoked and unsmoked bacon at concns ranging from <2.0 to 8.0 ug/kg(12). N-Nitrosodimethylamine was detected in the following canned luncheon meats produced in Italy at the following median concns, ppb: beef with jelly, 0.35; ground beef and pork, 8.7; and turkey, 0.94(13). It was detected in the following cured meats produced in Italy at median concns of, ppb: prosciutto, 0.54; bologna, 4.76; salami, 5.35; rolled bacon, 0.59; coppa, 3.29 to 6.23; and bresaola, 24.70(13). Concns of N-nitrosodimethylamine in Italian beer were not detected to 0.71 ppb in light beer and not detected to 0.42 ppb in dark beer; imported light and dark beer contained 0.07 to 0.19 ppb and 0.15 and 0.36 ppb N-nitrosodimethylamine, respectively(13). N-Nitrosodimethylamine has been detected in the following Italian cheeses, ug/kg: grana padano, 0.35; gorgonzola, 0.84; processed cheese, 0.40; processed cheese with added polyphosphates, 0.38; edam, 0.73; and gouda, 0.39(14). Canadian beer analyzed in 1988-1989 had a mean concentration of only 0.10 ug/L; imported beer averaged 0.71 ug/L in 1991-1992 and 0.15 ug/L in 1994(15). [

Examination of over 100 apple brandies has shown that N-nitrosodimethylamine was present in the majority of samples at an average concentration of 0.5 ug/kg; maximum concentration 10 ug/kg(1). It was also found in a number of ciders, cognacs, Armagnac, rums, and whiskeys; average levels ranged from 0.1 to 0.4 ug/kg with a maximum concentration of 1.6 ug/kg(1).

Adverse EffectsOccupational hepatotoxin - Primary hepatotoxins: the toxic effect to the liver is the principal adverse effect of the chemical.
Exposure Routes · 3 Einträge

The substance can be absorbed into the body by inhalation and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

Oral (L1207) ; inhalation (L1207) ; dermal (L1207)

Milk Concentrations · 1 Eintrag

ENVIRONMENTAL: N-Nitrosodimethylamine concentrations in milk were: 3.559 ppb (average) in nonfat dry milk(1), 0.10 ppb (average) in whole milk(2), 0.09 ppb (average) in low fat milk(2), 0.10 ppb (average) in skim milk(2), 0.32 ppb avg in evaporated milk(2), 0.58 ppb (avearge) in sweetened condensed milk(2), 1.69 ppb (average) and 4.5 ppb in nonfat dried milk(2,3), 1.8 ppb in dried buttermilk(3), and 0.3 ug/kg skim milk powder(4). In 175 samples of human milk collected from 16 nursing women, 76.5% of the samples contained less than 0.2 ppb N-nitrosodimethylamine (minimum level of reliable measurement)(5). In 54 human milk samples from 54 healthy nursing women, trace amounts of N-nitrosodimethylamine (below detection limit of 0.5 ug/L) were detected in the milk of 10 mothers and two other samples contained levels of 1.1 and 1.2 ug/L(6).

Regulatorische Informationen

RCRA Requirements · 1 Eintrag

P082; As stipulated in 40 CFR 261.33, when N-nitrosodimethylamine, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).

Atmospheric Standards · 1 Eintrag

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. N-Nitrosodimethylamine is included on this list.

CERCLA Reportable Quantities · 2 Einträge

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Nitrosodimethylamine is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 1,000 lbs.

Clean Water Act Requirements · 2 Einträge

Toxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations. /Nitrosamines/

The levels for N-nitrosodimethylamine through ingestion of contaminated water and contaminated aquatic organisms ... which may result in incremental increase of cancer risk over the lifetime are estimated at 1X10-5, 1X10-6, and 1X10-7. The corresponding criteria are 14 ng/L, 1.4 ng/L, and 0.14 ng/L, respectively. For consumption of aquatic organisms only, excluding consumption of water, the levels are 160,000 ng/L, 16,000 ng/L, and 1,600 ng/L, respectively. /Nitrosamines/

State Drinking Water Guidelines · 3 Einträge

(CA) CALIFORNIA 0.01ug/l

(FL) FLORIDA 7.5 ug/l

(MA) MASSACHUSETTS 0.01 ug/L

Sicherheitsdaten

wgk
3
tsca
TSCA listed
ridadr
UN 3382 6.1/PG 1
RTECS-Nr.
IQ0525000
risk_code
45-25-26-48/25-51/53-39/23/24/25-23/24/25-11
Toxizität
LD50 i.p. in rats: 34 mg/kg (Heath)
hazard_code
T+,N,T,F
safety_code
53-45-61-36/37-16
hazard_class
6.1(b)
packing_group
III
Speicherklasse
3 - Flammable liquids
Giftige Stoffe Daten
62-75-9(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralCarc. 1BFlam. Liq. 2STOT SE 1

A method for quantitative estimation of the formation of N-nitrosodimethylamine (NDMA) in mice was developed. When 0.25 umole of aminopyrine and 0.25-2.0 umole of sodium nitrite were simultaneously administration orally to mice, the amt of NDMA formed in 20 min was 8.2-60.3 nmol. These values are equal to approximately 30-200 ug/kg of body wt which are nearly daily doses expected to cause carcinogenic effect in mice or rats.

Available evidence suggests that NDMA requires metabolic activation to exert its toxic and carcinogenic effects. Rate of metabolism ... in vivo has been exam by measuring rate of loss of NDMA from blood and exhalation of (14)CO2 following administration of (14)C-NDMA. In rats ... 30 mg/kg administration by ip injection is metabolized within 6 hr. Rate of metab of NDMA in vitro ... Measured by use of slices of liver and other organs ... from rats, hamsters, monkeys, trout, goldfish and various amphibians. ... Oxidative N-demethylation to form formaldehyde has been demonstrated with liver microsomes from rats, mice and hamsters. Microsomal oxidn has been suggested to result in unstable N-nitroso-n-methyl-n-hydroxymethylamine, which decomp to yield methylating species and formaldehyde. ...

... In the metabolism ... one of the intermediary products is diazomethane.

For more Metabolism/Metabolites (Complete) data for N-NITROSODIMETHYLAMINE (16 total), please visit the HSDB record page.

N-Nitrosodimethylamine has known human metabolites that include N-Nitroso-N-methyl-N-hydroxymethylamine, N-Nitrosomethylamine, and acetyl-(dimethylamino)-oxoazanium.

Absorption, Distribution and Excretion · 5 Einträge

In order to elicit the characteristic toxicities, DMNA has required activation to a proximate mutagenic and carcinogenic metabolite. DMNA has undergone oxidative demethylation as catalyzed by rodent and human hepatic microsomes; this reaction has given rise to reactive intermediates. Alkylation of guanine (to 7-methylguanlic acid) and of cytosine (to 3-methylcytosine) has been thought to underlie the biochemical basis of DMNA-induced carcinogenesis. Methylation of the messenger ribonucleic acid (mRNA) in DMNA poisoning inhibited transIation. Although 7- methylguanylic acid has served as a normal nucleotide for RNA polymerase activity, the incorporation of 3-methylcytosine reduced efficiency. The alkylation of DNA by the reactive metabolites of DMNA resulted in a change in base sequence and deletion of one or more base pairs, changes indicative of the genotoxic mechanism of DMNA-induced carcinogenesis.

It is absorbed from gastrointestinal tract and lung ... Skin absorption is slow. When administered to rats, mice, and rabbits, it is distributed uniformly in tissue ... Although the liver is main organ concerned with its metabolism and is site of selective toxicity, dimethylnitrosamine does not concentrate there. Only a small percentage is excreted unchanged in rat urine after oral and iv doses of 50 to 100 mg/kg. A large proportion ... Appears in the expired air as ... Carbon dioxide (approx 60% in 24 hr).

N-nitrosodimethylamine (NDMA) reached equal max concn in the maternal and fetal blood and tissues within 5-15 min and 30-60 min, respectively, after an iv injection of 50 mg/kg into mice and rats on days 21-23 of pregnancy. The subsequent exponential decr in NDMA was more rapid in mice than in rats. Increasing the NDMA level in maternal blood by increased doses, linearly increased the fetal blood NDMA to a peak of 120 mug/mL in mice and 220 ug/mL in rats, whereas the level of NDMA in maternal blood continued to increase as doses were increased to 300 mg/kg.

N-Nitrosodimethylamine (DMN) was shown to be assimilated by the roots and translocated to the tops of lettuce and spinach plants.

The acute toxicities of dimethylnitrosamine and diethylnitrosamine were evaluated in adult male crayfish. Toxicokinetic studies of (14)C dimethylnitrosamine and (14)C diethylnitrosamine in Austropotamobius pallipes (crayfish), administered by iv injection, show high concns of (14)C in abdominal muscle and hepatopancreas. Excretion is greater with dimethylnitrosamine, and retention in tissues, especially the hepatopancreas, is greater with diethylnitrosamine.

Cellular LocationsCytoplasm

Verwendung und Herstellung

Uses · 6 Einträge

N-Nitrosodimethylamine is primarily used as a research chemical. N-Nitrosodimethylamine has been used as an antioxidant, as an additive for lubricants, and as a softener of copolymers. N-Nitrosodimethylamine was formerly used in the production of rocket fuels.

Used as an intermediate in the production of 1,1-dimethylhydrazine; DMNA contaminates common organic amines and may occur as a byproduct of industrial processes; [ACGIH]

Regulated as a carcinogen: See 29CFR1910.1003 (Code of Federal Regulation).

Solvent, rubber accelerator.

NDMA has been used as an intermediate in the manufacture of 1,1-dimethylhydrazine, which is a component of rocket propellants. In the workplace, it also has been encountered as a contaminant of common organic amines or as a reaction by-product. Exposures have been possible in cancer research laboratories where the material may be excreted unchanged by laboratory animals.

Industrial solvent, antioxidant; solvent in fiber and plastics industry; in lubricants, condensers to increase dielectric constant; has been used as nematocide; softener for copolymers. /Former uses/

U.S. Production · 2 Einträge

(1977) NOT PRODUCED COMMERCIALLY IN USA

(1982) NOT PRODUCED COMMERCIALLY IN USA

Methods of Manufacturing · 3 Einträge

It can be prepared by addition of acetic acid and sodium nitrite to dimethylamine.

Industrial preparation: GB 772331 (1957 to Olin Mathieson) ... Campbell, US 2981752 (1961 to C.S.C); Datin, Elliott, US 3136821 (1964 to Allied Chem).

REACTION OF NITROUS ACID WITH DIMETHYLAMINE

Formulations/PreparationsISOPAC
Household ProductsCosmetics product ingredient: N-Nitrosodimethylamine (NDMA)
Use ClassificationChemical Classes -> Nitrosamines/ethers/alcohols
General Manufacturing Information · 2 Einträge

Methanamine, N-methyl-N-nitroso-: ACTIVE

Formed by the interaction of nitrite with dimethylamine and by the action of nitrate-reducing bacteria.

Anwendungen · 1 Eintrag

VerwendenN-Nitrosodimethylamine is a highly toxic semi-volatile organic compound and a suspected human carcinogen. It induces liver tumors in rats after chronic exposure to low doses (1,2). Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA). Environmental contaminants; Food contaminants.NDMA and NDEA were found as an impurity in generic versions of valsartan, losartan and irbesartan.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

DimethylammoniumchloridDimethylammoniumnitratHexamethylphosphorsaeuretriamid

Nachgelagerte Produkte

N-Methylmethanamin, gasförmig1,1-Dimethyl-2-methylenehydrazineN-Nitroso-methyl-ethylaminedimethylnitramine1,3-OxazolidineN-MethylformamidButandial

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N-nitrosodimethylamine, which has a measured vapor pressure of 2.7 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase N-nitrosodimethylamine 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 6.3 days(SRC), calculated from its measured rate constant of 2.53X10-12 cu cm/molecule-sec at 25 °C(3). N-Nitrosodimthylamine is susceptible to direct photolysis in sunlight(SRC) due to its strong absorption of UV light above 290 nm(4,5). The direct photolysis half-life in aqueous solution was observed to be 16 minutes using Southern California midday irradiation levels(5).