N-Nitrosomorpholine
From Wikipedia, the free encyclopedia
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| Names | |
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| Other names
4-nitrosomorpholine, alpha-acetoxy-N-nitrosomorpholine, nitrosomorpholine, NMOR, 4-nitroso-morpholine, NNM | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.155.913 |
| EC Number |
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| KEGG | |
PubChem CID |
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| UNII | |
| UN number | 2810 3077 |
CompTox Dashboard (EPA) |
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| Properties | |
| C4H8N2O2 | |
| Molar mass | 116.120 g·mol−1 |
| Appearance | Pale yellow powder |
| Melting point | 29 °C (84 °F; 302 K)[1] |
| Boiling point | 435 to 436 °F at 747 mmHg |
| greater than or equal to 100 mg/mL in water at 66 °F | |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
hepatocarcinogen |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N-Nitrosomorpholine (NNM, NMOR) is an organic compound which is known to be a carcinogen and mutagen.
NMOR is a pale yellow sand-like powder below 84°F. [1][2] NMOR is most commonly produced from morpholine, but can also be made by the reaction of dimorpholinomethane in fuming nitric acid.[3] Few reactions using NMOR as a starting material are reported in the organic synthesis literature, but it can be used as a precursor to a nitrogen-centered radical.[4]
Occurrence
NMOR is generally not used intentionally, but is instead created by the nitrosation of morpholine or morpholine derivatives which are used for several industrial purposes.
Rubber
2-(Morpholinothio)benzothiazole is used as an accelerator/stabilizer for vulcanization, or the manufacture of rubber products. It is the precursor to NMOR in the vulcanization process, as it is nitrosated by ambient sources of the nitro group present in the manufacturing process. As such, workers and others exposed to the rubber industry or its byproducts are exposed to higher levels of NMOR than the general population, raising their risk of cancer.[5]
Tobacco products
NMOR is a component of tobacco products. As of 2014, detectable levels of NMOR are present in tobacco products in the United States and China.[6][7] The presence of NMOR and other n-nitrosoamines is not limited to cigarettes, but is found in smokeless tobacco products (snuff tobacco, Snus, etc.) as well.[8] Volatile nitrosamines, including NMOR, are detectable in the urine of tobacco smokers. [9]
Food
Morpholine oleate is used in glazing wax which covers fruit. NMOR can be generated by the nitration of morpholine, causing its presence in waxed fruits.[10][11]Health Canada, the Canadian governmental department of public health, has stated in 2002 that this does not pose a risk to human health.[12]
Consumption of nitrate-rich diets is correlated with levels of salivary and urinary NMOR.[13] The presence of NMOR can also be observed in gastric juices.[14]