chemistry

N-Nitrosomorpholine

N-Nitrosomorpholine is a chemistry topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand N-Nitrosomorpholine rather than just read about it. In short: N-Nitrosomorpholine (NNM, NMOR) is an organic compound which is known to be a carcinogen and mutagen. Chemistry NMOR is a pale yellow sand-like powder below 84°F.

Key takeaways

N-Nitrosomorpholine belongs to chemistry; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect N-Nitrosomorpholine to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of N-Nitrosomorpholine from memory before moving on to harder problems.

Reference excerpt

N-Nitrosomorpholine (NNM, NMOR) is an organic compound which is known to be a carcinogen and mutagen.

Chemistry NMOR is a pale yellow sand-like powder below 84°F. NMOR is most commonly produced from morpholine, but can also be made by the reaction of dimorpholinomethane in fuming nitric acid. 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.

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.

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. 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. Volatile nitrosamines, including NMOR, are detectable in the urine of tobacco smokers.

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.Health Canada, the Canadian governmental department of public health, has stated in 2002 that this does not pose a risk to human health. Consumption of nitrate-rich diets is correlated with levels of salivary and urinary NMOR. The presence of NMOR can also be observed in gastric juices.

Other NMOR has been found in several cosmetic products.

Health hazards The mechanisms of carcinogenesis are not completely clear in humans. NMOR and its metabolites may induce DNA damage by directly forming reactive oxygen species or compounds which crosslink DNA. In a rat model in 2013, it was observed that NMOR is hydroxylated, probably by a P450 enzyme, alpha to the N-nitroso moiety. This then decomposes into a diazonium-containing aldehyde which is capable of crosslinking DNA. Endogenous synthesis from morpholine in the digestive system is observed. NMOR can be generated from N-nitrosating species formed by salivary nitrite and stomach acid, potentially leading to more damage in individuals with acid reflux. H. pylori does not induce NMOR formation in vitro, though this has yet to be confirmed in vivo. NMOR is in fact used to generate liver cancer models in rats. Along with N-diethylnitrosamine, it is the gold standard for producing hepatocarcinoma with 100% lung metastasis.

See also Nitrosamine N-Nitrosodiethylamine Hepatotoxicity

References

Illustrations

Worked examples

Example 1 — a first encounter with N-Nitrosomorpholine

Start with the simplest possible case. Write down what N-Nitrosomorpholine claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In chemistry, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to N-Nitrosomorpholine before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about N-Nitrosomorpholine ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of N-Nitrosomorpholine

In research: N-Nitrosomorpholine appears in chemistry research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses N-Nitrosomorpholine in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: N-Nitrosomorpholine is common in secondary-school and first-year university syllabi. It links to neighbouring topics 4-Morpholinyl compounds, Carcinogens, Nitrosamines, so understanding it makes those chapters shorter.
In everyday life: Look for N-Nitrosomorpholine outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

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How to study N-Nitrosomorpholine in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what N-Nitrosomorpholine means in your own words.
Compare your version with the excerpt and mark what you missed.
Work through the three examples above with pen and paper.
Explain N-Nitrosomorpholine out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is N-Nitrosomorpholine in simple terms?

N-Nitrosomorpholine (NNM, NMOR) is an organic compound which is known to be a carcinogen and mutagen. Chemistry NMOR is a pale yellow sand-like powder below 84°F.

Why does N-Nitrosomorpholine matter?

Because it connects several chemistry ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study N-Nitrosomorpholine?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on N-Nitrosomorpholine.