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Nitrosamine
 
 
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Nitrosamines are chemical compound
Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
s of the chemical structure
Chemical structure

A Chemical structure includes molecular geometry, electronic structure and crystal structure of a chemical compound. Molecular geometry refers to the spatial arrangement of atoms in a molecule and the chemical bonds that hold the atoms together....
 R1N(-R2)-N=O, some of which are carcinogenic
Cancer

Cancer is a class of diseases in which a group of cell display uncontrolled growth , invasion , and sometimes metastasis . These three malignant properties of cancers differentiate them from benign tumors, which are self-limited, do not invade or metastasize....
.

Occurrences
Food
Nitrosamines are produced from nitrite
Nitrite

The nitrite ion is NO2-. The anion is bent, being isoelectronic with ozone. More generally, a nitrite compound is either a Salt or an ester of nitrous acid....
s and secondary amine
Amine

Amines are organic compounds and functional groups that contain a base nitrogen atom with a lone pair. Amines are derivative s of ammonia, wherein one or more hydrogen atoms are replaced by organic substituents such as alkyl and aryl groups....
s, which often occur in the form of protein
Protein

Proteins are organic compounds made of amino acids arranged in a linear chain and joined together by peptide bonds between the carboxyl and amino groups of adjacent amino acid Residue ....
s. Their formation can occur only under certain conditions, including strongly acid
Acid

An acid is traditionally considered any chemical compound that, when dissolved in water, gives a solution with a hydrogen ion Activity greater than in pure water, i.e....
ic conditions such as that of the human stomach
Stomach

In most mammals, the stomach is a hollow muscular organ of the gastrointestinal tract involved in the second phase of digestion, following mastication....
. High temperatures, as in frying, can also enhance the formation of nitrosamines.






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Encyclopedia


Nitrosamines are chemical compound
Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
s of the chemical structure
Chemical structure

A Chemical structure includes molecular geometry, electronic structure and crystal structure of a chemical compound. Molecular geometry refers to the spatial arrangement of atoms in a molecule and the chemical bonds that hold the atoms together....
 R1N(-R2)-N=O, some of which are carcinogenic
Cancer

Cancer is a class of diseases in which a group of cell display uncontrolled growth , invasion , and sometimes metastasis . These three malignant properties of cancers differentiate them from benign tumors, which are self-limited, do not invade or metastasize....
.

Usages


  • Most Rubber products
  • Pesticides
  • Certain cosmetics


Occurrences


Food


Nitrosamines are produced from nitrite
Nitrite

The nitrite ion is NO2-. The anion is bent, being isoelectronic with ozone. More generally, a nitrite compound is either a Salt or an ester of nitrous acid....
s and secondary amine
Amine

Amines are organic compounds and functional groups that contain a base nitrogen atom with a lone pair. Amines are derivative s of ammonia, wherein one or more hydrogen atoms are replaced by organic substituents such as alkyl and aryl groups....
s, which often occur in the form of protein
Protein

Proteins are organic compounds made of amino acids arranged in a linear chain and joined together by peptide bonds between the carboxyl and amino groups of adjacent amino acid Residue ....
s. Their formation can occur only under certain conditions, including strongly acid
Acid

An acid is traditionally considered any chemical compound that, when dissolved in water, gives a solution with a hydrogen ion Activity greater than in pure water, i.e....
ic conditions such as that of the human stomach
Stomach

In most mammals, the stomach is a hollow muscular organ of the gastrointestinal tract involved in the second phase of digestion, following mastication....
. High temperatures, as in frying, can also enhance the formation of nitrosamines. These cooking styles may be responsible for thousands of cases of colon cancer per year across the world.

Under acidic conditions the nitrite forms nitrous acid
Nitrous acid

Nitrous acid is a weak and monobasic acid known only in solution and in the form of nitrite salts.Nitrous acid is used to make diazo from amines; this occurs by nucleophilic attack of the amine onto the nitrite, reprotonation by the surrounding solvent, and double-elimination of water....
 (HNO2), which is protonated and splits into the nitrosonium
Nitrosonium

The nitrosonium ion is NO+, the nitrogen atom is bonded to an oxygen atom with a bond order of 3, the overall diatomic species bearing a positive charge....
 cation N=O+ and water: H2NO2+ = H2O + NO+. The nitrosonium cation then reacts with an amine to produce nitrosamine.

Nitrosamines are found in many foodstuffs, especially beer
Beer

Beer is the world's oldest and most widely consumed alcoholic beverage and the third most popular drink overall after water and tea. It is produced by the brewing and Fermentation of starches, mainly derived from cereal?the most common of which is malted barley, although wheat, maize , and rice are widely used....
, fish
Fish

A fish is any marine biology vertebrate animal that is typically ectothermic , covered with scale , and equipped with two sets of paired fins and several unpaired fins....
, and fish byproducts, and also in meat
Meat

In modern English usage, meat most often refers to animal biological tissue used as food, mostly skeletal muscle and associated fat, but it may also refer to offal, including livers, skin, brains, bone marrow, kidneys, in some countries lungs, and a variety of other internal organs as well as blood....
 and cheese
Cheese

Cheese is a food consisting of proteins and fat from milk, usually the milk of cattle, Water Buffalo, goats, or sheep's milk. It is produced by Coagulation of the milk protein casein....
 products preserved with nitrite pickling salt. The U.S. government established limits on the amount of nitrites used in meat products in order to decrease cancer risk in the population. There are also rules about adding ascorbic acid
Ascorbic acid

Ascorbic acid is a sugar acid with antioxidant properties. Its appearance is white to light-yellow crystals or powder. It is water-soluble. The L-enantiomer of ascorbic acid is commonly known as vitamin C....
 or related compounds to meat, because they inhibit nitrosamine formation.

Consumer products


Nitrosamines can be found in tobacco
Tobacco

Tobacco is an agricultural product processed from the fresh leaves of plants in the genus Nicotiana. It can be consumed, used as an organic pesticide, and in the form of nicotine tartrate it is used in some medicines....
 smoke and latex
LaTeX

LaTeX is a document markup language and Word processor for the TeX typesetting program. Within the typesetting system, its name is styled as ....
 products. A test of party balloon
Balloon

A balloon is a flexible bag filled with a type of gas, such as helium, hydrogen, nitrous oxide or Earth's atmosphere. Modern balloons can be made from materials such as rubber, latex, polychloroprene, or a nylon fabric, while some early balloons were sometimes made of dried animal urinary bladders....
s and condom
Condom

A condom is a device most commonly used during sexual intercourse. It is put on a man's erect penis and physically blocks ejaculated semen from entering the body of a sexual partner....
s indicated that many of them release small amounts of nitrosamines. However, nitrosamines from condoms are not expected to be of toxicological
Toxicology

Toxicology is the study of the adverse effects of chemicals on living organisms. It is the study of symptoms, mechanisms, treatments and detection of poisoning, especially the poisoning of people....
 significance.

Cancer


Nitrosamines can cause cancer
Cancer

Cancer is a class of diseases in which a group of cell display uncontrolled growth , invasion , and sometimes metastasis . These three malignant properties of cancers differentiate them from benign tumors, which are self-limited, do not invade or metastasize....
s in a wide variety of animal species, a feature that suggests that they may also be carcinogenic in humans. Epidemiological data supports a positive association between nitrite and nitrosamine intake and gastric cancer, between meat and processed meat intake and gastric cancer and oesophageal cancer, but the studies are inconclusive.

Examples of nitrosamines


Tobacco specific


  • N-Nitrosonornicotine
    N-Nitrosonornicotine

    N-Nitrosonornicotine is a nitrosamine found in tobacco that has been classified by the IARC as a List of IARC Group 1 carcinogens.Although no adequate studies of the relationship between exposure to NNN and human cancer have been reported, there is sufficient evidence that NNN causes cancer in experimental animals....
     (NNN)
  • NNK
    NNK

    4-- 1--1-butanone is a nitrosamine present in tobacco that is a potent procarcinogen. It is activated by CYP2A6. It is a biomarker of exposure to cigarette smoke....
  • NNAL
  • NATGRTED
  • NAB
  • Iso-NNAL
  • Iso-NNAC


Other


  • NDEA
  • NDMA


See also


  • Nitroamine
    Nitroamine

    Nitroamines are organic compounds that contain the nitroamino functional group, R2N-NO2. Examples of nitroamines are the explosives HMX, cyclotrimethylene trinitramine, and tetryl....
     (without the 's'), compounds of the formula R2N-NO2.
  • Nitroso
    Nitroso

    Nitroso refers to a functional group in organic chemistry which has the general formula RNO. Nitroso compounds can be prepared by the reduction of nitro compounds or by the oxidation of hydroxylamines....
    , compounds of the formula R-NO


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