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Sodium nitrite
Not to be confused with sodium nitrate, sodium nitride,
or nitratine.
“E250” redirects here. For the mobile phone, see
Samsung SGH-E250.
Sodium nitrite is the inorganic compound with the
chemical formula NaNO2. It is a white to slightly yellow-
ish crystalline powder that is very soluble in water and
is hygroscopic. It is a useful precursor to a variety of
organic compounds, such as pharmaceuticals, dyes, and
pesticides, but it is probably best known as a food addi-
tive to prevent botulism.
It is on the World Health Organization’s List of Essential
Medicines, the most important medications needed in a
basic health system.[2]
1 Uses
1.1 Industrial chemistry
The main use of sodium nitrite is for the industrial pro-
duction of organonitrogen compounds. It is a reagent for
conversion of amines into diazo compounds, which are
key precursors to many dyes, such as diazo dyes. Nitroso
compounds are produced from nitrites. These are used in
the rubber industry.[3]
Other applications include uses in photography. It may
also be used as an electrolyte in electrochemical grinding
manufacturing processes, typically diluted to about 10%
concentration in water. It is used in a variety of metallur-
gical applications, for phosphatizing and detinning.
Sodium nitrite is an effective corrosion inhibitor and is
used as an additive in industrial greases,[4]
as an aqueous
solution in closed loop cooling systems, and in a molten
state as a heat transfer medium.[5]
1.2 Medicine
Main article: Sodium nitrite (medical use)
Sodium nitrite is used together with sodium thiosulfate to
treat cyanide poisoning.[6]
It is in the section "antidotes and other substances used
in poisonings" of the World Health Organization’s List
of Essential Medicines, the most important medications
needed in a basic health system.[2]
1.3 Food additive
In the early 1900s, irregular curing was commonplace.
This led to further research surrounding the use of sodium
nitrite as an additive in food, standardizing the amount
present in foods to minimize the amount needed while
maximizing its food additive role.[7]
Through this re-
search, sodium nitrite has been found to inhibit growth
of disease-causing microorganisms; give taste and color
to the meat; and inhibit lipid oxidation that leads to
rancidity.[7]
The ability of sodium nitrite to address the
above-mentioned issues has led to production of meat
with improved food safety, extended storage life and im-
proving desirable color/taste.[7]
It has the E number E250.
Potassium nitrite (E249) is used in the same way. It is
approved for usage in the EU,[8][9]
USA[10]
and Australia
and New Zealand.[11]
1.3.1 Inhibition of microbial growth
Sodium nitrite is well known for its role in inhibiting
the growth of Clostridium botulinum spores in refriger-
ated meats.[12]
The mechanism for this activity results
from the inhibition of iron-sulfur clusters essential to en-
ergy metabolism of Clostridium botulinum.[12]
However,
sodium nitrite has had varying degrees of effectiveness
for controlling growth of other spoilage or disease caus-
ing microorganisms.[7]
Even though the inhibitory mech-
anisms for sodium nitrite are not well known, its effec-
tiveness depends on several factors including residual ni-
trite level, pH, salt concentration, reductants present and
iron content.[13]
Furthermore, the type of bacteria also
affects sodium nitrites effectiveness.[13]
It is generally
agreed upon that sodium nitrite is not considered effec-
tive for controlling gram-negative enteric pathogens such
as Salmonella and Escherichia coli.[13]
1.3.2 Taste and color
The appearance and taste of meat is an important com-
ponent of consumer acceptance.[7]
Sodium nitrite is re-
sponsible for the desirable red color (or shaded pink)
of meat.[7]
Very little nitrite is needed to induce this
change.[7]
It has been reported that as little as 2 to 14
parts per million (ppm) is needed to induce this desirable
color change.[13]
However, to extend the lifespan of this
1
2 2 TOXICITY
color change, significantly higher levels are needed.[13]
The mechanism responsible for this color change is the
formation of nitrosylating agents by nitrite, which has
the ability to transfer nitric oxide that subsequently re-
acts with myoglobin to produce the cured meat color.[13]
The unique taste associated with cured meat is also af-
fected by the addition of sodium nitrite.[7]
However, the
mechanism underlying this change in taste is still not fully
understood.[13]
1.3.3 Inhibition of lipid oxidation
Sodium nitrite is also able to effectively delay the de-
velopment of oxidative rancidity.[13]
Lipid oxidation is
considered to be a major reason for the deterioration
of quality of meat products (rancidity and unappetiz-
ing flavors).[13]
Sodium nitrite acts as an antioxidant in
a mechanism similar to the one responsible for the col-
oring affect.[13]
Nitrite reacts with heme proteins and
metal ions, neutralizing free radicals by nitric oxide (one
of its byproducts).[13]
Neutralization of these free radi-
cals terminates the cycle of lipid oxidation that leads to
rancidity.[13]
2 Toxicity
While this chemical will prevent the growth of bacteria,
it can be toxic in high amounts for animals and humans.
Sodium nitrite’s LD50 in rats is 180 mg/kg and its human
LDLₒ is 71 mg/kg, meaning a 65 kg person would likely
have to consume at least 4.6 g to result in death.[14]
To
prevent toxicity, sodium nitrite (blended with salt) sold
as a food additive is dyed bright pink to avoid mistak-
ing it for plain salt or sugar. Nitrites are not naturally
occurring in vegetables in significant quantities.[15]
How-
ever, nitrates are found in commercially available veg-
etables and a study in an intensive agricultural area in
northern Portugal found residual nitrate levels in 34 veg-
etable samples, including different varieties of cabbage,
lettuce, spinach, parsley and turnips ranged between 54
and 2440 mg/kg, e.g. curly kale (302.0 mg/kg) and green
cauliflower (64 mg/kg).[16][17]
Boiling vegetables lowers
nitrate but not nitrite.[16]
Fresh meat contains 0.4–0.5
mg/kg nitrite and 4–7 mg/kg of nitrate (10–30 mg/kg ni-
trate in cured meats).[15]
The presence of nitrite in animal
tissue is a consequence of metabolism of nitric oxide, an
important neurotransmitter.[18]
Nitric oxide can be cre-
ated de novo from nitric oxide synthase utilizing arginine
or from ingested nitrate or nitrite.[19]
2.1 Humane toxin for feral hog/wild boar
control
Because of sodium nitrite’s high level of toxicity to swine
(Sus scrofa) it is now being developed in Australia to con-
trol feral pigs and wild boar.[20][21]
The sodium nitrite in-
duces methemoglobinemia in swine, i.e., it reduces the
amount of oxygen that is released from hemoglobin, so
the animal will feel faint and pass out, and then die in a hu-
mane manner after first being rendered unconscious.[22]
The Texas Parks and Wildlife Department operates a re-
search facility at Kerr Wildlife Management Area, where
they examine feral pig feeding preferences and bait tac-
tics to administer sodium nitrite.[23]
2.2 Nitrosamines
A principal concern about sodium nitrite is the formation
of carcinogenic nitrosamines in meats containing sodium
nitrite when meat is charred or overcooked. Such car-
cinogenic nitrosamines can also be formed from the re-
action of nitrite with secondary amines under acidic con-
ditions (such as occurs in the human stomach) as well as
during the curing process used to preserve meats. Di-
etary sources of nitrosamines include US cured meats
preserved with sodium nitrite as well as the dried salted
fish eaten in Japan. In the 1920s, a significant change in
US meat curing practices resulted in a 69% decrease in
average nitrite content. This event preceded the begin-
ning of a dramatic decline in gastric cancer mortality.[24]
About 1970, it was found that ascorbic acid (vitamin C),
an antioxidant, inhibits nitrosamine formation.[25]
Con-
sequently, the addition of at least 550 ppm of ascor-
bic acid is required in meats manufactured in the United
States. Manufacturers sometimes instead use erythorbic
acid, a cheaper but equally effective isomer of ascor-
bic acid. Additionally, manufacturers may include α-
tocopherol (vitamin E) to further inhibit nitrosamine pro-
duction. α-Tocopherol, ascorbic acid, and erythorbic
acid all inhibit nitrosamine production by their oxidation-
reduction properties. Ascorbic acid, for example, forms
dehydroascorbic acid when oxidized, which when in
the presence of nitrosonium, a potent nitrosating agent
formed from sodium nitrite, reduces the nitrosonium into
nitric oxide.[26]
The nitrosonium ion formed in acidic ni-
trite solutions is commonly[27][28]
mislabeled nitrous an-
hydride, an unstable nitrogen oxide that cannot exist in
vitro.[29]
Nitrate or nitrite (ingested) under conditions that result
in endogenous nitrosation has been classified as “proba-
bly carcinogenic to humans” by International Agency for
Research on Cancer (IARC).[30][31]
Sodium nitrite consumption has also been linked to the
triggering of migraines in individuals who already suffer
from them.[32]
One study has found a correlation between highly fre-
quent ingestion of meats cured with pink salt and the
COPD form of lung disease. The study’s researchers sug-
gest that the high amount of nitrites in the meats was re-
sponsible; however, the team did not prove the nitrite the-
ory. Additionally, the study does not prove that nitrites or
3
cured meat caused higher rates of COPD, merely a link.
The researchers did adjust for many of COPD’s risk fac-
tors, but they commented they cannot rule out all possible
unmeasurable causes or risks for COPD.[33][34]
3 Mechanism of action
Carcinogenic nitrosamines are formed when amines that
occur naturally in food react with sodium nitrite found in
cured meat products.
R2NH (amines) + NaNO2 (sodium nitrite) → R2N–N=O
(nitrosamine)
In the presence of acid (such as in the stomach) or heat
(such as via cooking), nitrosamines are converted to
diazonium ions.
R2N–N=O (nitrosamine) + (acid or heat) → R–N+
2 (diazonium ion)
Certain nitrosamines such as N-nitrosodimethylamine[35]
and N-nitrosopyrrolidine[36]
form carbocations that react
with biological nucleophiles (such as DNA or an enzyme)
in the cell.
R–N+
2 (diazonium ion) → R+
(carbocation) + N2 (leaving
group) + Nu (biological nucleophiles) → R–Nu
If this nucleophilic substitution reaction occurs at a cru-
cial site in a biomolecule, it can disrupt normal cell func-
tions, leading to cancer or cell death.
4 Production
The salt is prepared by treating sodium hydroxide with
mixtures of nitrogen dioxide and nitric oxide:
2 NaOH + NO2 + NO → 2 NaNO2 + H2O
The conversion is sensitive to the presence of oxygen,
which can lead to varying amounts of sodium nitrate.
In former times, sodium nitrite was prepared by reduction
of sodium nitrate with various metals.[3][37]
5 Chemical reactions
In the laboratory, sodium nitrite can be used to destroy
excess sodium azide.[38][39]
2 NaN3 + 2 NaNO2 + 2 H+
→ 3 N2 + 2 NO + 2 Na+
+
2 H2O
Above 330 °C sodium nitrite decomposes (in air) to
sodium oxide, nitric oxide and nitrogen dioxide.[40]
2 NaNO2 → Na2O + NO + NO2
Sodium nitrite can also be used in the production of
nitrous acid via sulfuric acid. This reaction first yields
nitrous acid and sodium sulfate:
2 NaNO
2 + H
2SO
4 → 2 HNO
2 + Na
2SO
4
The nitrous acid then, under normal conditions, decom-
poses:
2 HNO
2 → NO
2 + NO + H
2O
The nitrogen dioxide of the prior decomposition is then
routed through a condensor or fractional distillation ap-
paratus to react with water and yield nitric acid:
2 NO
2 + H
2O → HNO
3 + HNO
2
6 References
[1] Zumdahl, Steven S. (2009). Chemical Principles (6th ed.).
Houghton Mifflin Company. p. A23. ISBN 0-618-
94690-X.
[2] “WHO Model List of EssentialMedicines” (PDF). World
Health Organization. April 2015. Retrieved 25 Septem-
ber 2016.
[3] Wolfgang Laue, Michael Thiemann, Erich Scheibler, Karl
Wilhelm Wiegand “Nitrates and Nitrites” in Ullmann’s
Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH,
Weinheim.doi:10.1002/14356007.a17_265. Article On-
line Posting Date: 15 June 2000
[4] Krakhmalev, S. I.; Vorotnikova, V. A.; Ten, N. V.;
Taranova, N. V. (1984). “Determination of sodium
nitrite in complex sodium grease”. Chemistry And
Technology Of Fuels And Oils. 20 (12): 612–613.
doi:10.1007/BF00726438.
[5] “Sodium Nitrite”. General Chemical. Retrieved 2012-09-
28.
4 6 REFERENCES
[6] WHO Model Formulary 2008 (PDF). World Health Orga-
nization. 2009. p. 65-66. ISBN 9789241547659. Re-
trieved 8 January 2017.
[7] Sindelar, Jeffrey; Milkowski, Andrew (March 2012).
“Human safety controversies surrounding nitrate and
nitrite in the diet”. Nitric Oxide. 26: 259–266.
doi:10.1016/j.niox.2012.03.011.
[8] UK Food Standards Agency: “Current EU approved addi-
tives and their E Numbers”. Retrieved 27 October 2011.
[9] http://ec.europa.eu/food/fs/sc/scf/reports/scf_reports_
38.pdf
[10] US Food and Drug Administration: “Listing of Food Ad-
ditives Status Part II”. Retrieved 27 October 2011.
[11] Australia New Zealand Food Standards Code“Standard
1.2.4 – Labelling of ingredients”. Retrieved 27 October
2011.
[12] Milkowski, Andrew; Garg, Harsha; Couglin, James;
Bryan, Nathan (January 2010). “Nutritional epidemiol-
ogy in the context of nitric oxide biology: Risk-Benefit
evaluation for dietary nitrite and nitrate”. Nitric Oxide. 22
(2): 110–119. doi:10.1016/j.niox.2009.08.004. PMID
19748594.
[13] Sindelar, Jeffrey; Milkowski, Andrew (November 2011).
“Sodium Nitrite in Processed Meat and Poultry Meats: A
Review of Curing and Examining the Risk/Benefit of Its
Use” (PDF). American Meat Science Association. 3: 1–14.
[14] http://msds.chem.ox.ac.uk/SO/sodium_nitrite.html
[15] Dennis, M. J.; Wilson, L. A. (2003). “Nitrates and
Nitrites”. Encyclopedia of Food Sciences and Nutrition.
p. 4136. doi:10.1016/B0-12-227055-X/00830-0. ISBN
978-0-12-227055-0.
[16] Leszczyńska, Teresa; Filipiak-Florkiewicz, Agnieszka;
Cieślik, Ewa; Sikora, ElżBieta; Pisulewski, Paweł M.
(2009). “Effects of some processing methods on nitrate
and nitrite changes in cruciferous vegetables”. Journal
of Food Composition and Analysis. 22 (4): 315–321.
doi:10.1016/j.jfca.2008.10.025.
[17] Correia, Manuela; Barroso, Ângela; Barroso, M. Fá-
tima; Soares, Débora; Oliveira, M. B. P. P.; Delerue-
Matos, Cristina (2010). “Contribution of different
vegetable types to exogenous nitrate and nitrite ex-
posure”. Food Chemistry. 120 (4): 960–966.
doi:10.1016/j.foodchem.2009.11.030.
[18] Meulemans, A.; Delsenne, F. (1994). “Measurement of
nitrite and nitrate levels in biological samples by capillary
electrophoresis”. Journal of Chromatography B. 660 (2):
401–404. doi:10.1016/0378-4347(94)00310-6.
[19] Southan, G; Srinivasan, A (1998). “Nitrogen Oxides and
Hydroxyguanidines: Formation of Donors of Nitric and
Nitrous Oxides and Possible Relevance to Nitrous Oxide
Formation by Nitric Oxide Synthase”. Nitric Oxide. 2 (4):
270–86. doi:10.1006/niox.1998.0187. PMID 9851368.
[20] Lapidge, Steven; Wishart, J.; Smith, M.; Staples, L.
(2009). “Is America Ready for a Humane Feral Pig Toxi-
cant?". Proceedings of the 13th Wildlife Damage Manage-
ment Conference: 49–59.
[21] Cowled, B. D.; Lapidge, S. J.; Humphrys, S.; Staples, L.
(2008). “Nitrite Salts as Poisons in Baits for Omnivores”.
International Patent WO/2008/104028.
[22] Porter, S.; Kuchel, T. (2010). Assessing the humaness and
efficacy of a new feral pig bait in domestic pigs. Study
PC0409 (PDF). Canberra, South Australia: Veterinary
Services Division, Institute of Medical and Veterinary
Science. p. 11.
[23] https://www.youtube.com/watch?v=GigpxLNbgeg&
spfreload=1
[24] “The epidemiological enigma of gastric cancer rates in the
US: was grandmother’s sausage the cause?". International
Journal of Epidemiology. 2000.
[25] Mackerness, C. W.; Leach, S. A.; Thompson, M.
H.; Hill, M. J. (1989). “The inhibition of bacte-
rially mediated N-nitrosation by vitamin C: relevance
to the inhibition of endogenous N-nitrosation in the
achlorhydric stomach”. Carcinogenesis. 10 (2): 397–9.
doi:10.1093/carcin/10.2.397. PMID 2492212.
[26] Nitrosamines and Cancer by Richard A. Scanlan, Ph.D.
[27] Cancer Res. 43 (5 Suppl): 2435s–2440s. May 1983.
Missing or empty |title= (help)
[28] Nollet, Toldra, D (2015). Handbook of Food Analysis
(Third ed.). p. 290. ISBN 9781482297843.
[29] Williams, D (2004). “Reagents effecting nitrosation”. Ni-
trosation Reactions and the Chemistry of Nitric Oxide. p.
1. doi:10.1016/B978-044451721-0/50002-5. ISBN 978-
0-444-51721-0.
[30] “List of classifications, Volumes 1–116 - IARC Mono-
graphs on the Evaluation of Carcinogenic Risks to Hu-
mans”. International Agency for Research on Cancer
(IARC) - World Health Organization (WHO). 2010. Re-
trieved 25 September 2016.
[31] “VOLUME 94 - Ingested Nitrate and Nitrite, and
Cyanobacterial Peptide Toxins - IARC Monographs on
the Evaluation of Carcinogenic Risks to Humans”. Inter-
national Agency for Research on Cancer (IARC) - World
Health Organization (WHO). 2010. Retrieved 25 Septem-
ber 2016.
[32] “Heading Off Migraine Pain”. FDA Consumer magazine.
U.S. Food and Drug Administration. 1998.
[33] Hitti, Miranda (17 April 2007). “Study: Cured Meats,
COPD May Be Linked”. WebMD Medical News.
[34] Jiang, R.; Paik, D. C.; Hankinson, J. L.; Barr,
R. G. (2007). “Cured Meat Consumption, Lung
Function, and Chronic Obstructive Pulmonary Dis-
ease among United States Adults”. American Jour-
nal of Respiratory and Critical Care Medicine. 175
(8): 798–804. doi:10.1164/rccm.200607-969OC. PMC
1899290 . PMID 17255565.
5
[35] Najm, Issam; Trussell, R. Rhodes (February 2001).
“NDMA Formation in Water and Wastewater”. Journal
AWWA. 93 (2): 92–99.
[36] Bills, Donald D.; Hildrum, Kjell I.; Scanlan, Richard
A.; Libbey, Leonard M. (May 1973). “Potential pre-
cursors of N-nitrosopyrrolidine in bacon and other fried
foods”. J. Agric. Food Chem. 21 (5): 876–7.
doi:10.1021/jf60189a029. PMID 4739004.
[37] Hao, Zhi-wei; Xu, Xin-hua; Wang, Da-hui (March 2005).
“Reductive denitrification of nitrate by scrap iron filings”.
Journal of Zhejiang University SCIENCE. 6B (3): 182–
186. doi:10.1631/jzus.2005.B0182.
[38] “Sodium Azide”. Hazardous Waste Management.
Northeastern University. March 2003.
[39] Committee on Prudent Practices for Handling, Stor-
age, and Disposal of Chemicals in Laboratories, Board
on Chemical Sciences and Technology, Commission on
Physical Sciences, Mathematics, and Applications, Na-
tional Research Council (1995). Prudent practices in the
laboratory: handling and disposal of chemicals. Washing-
ton, D.C.: National Academy Press. ISBN 0-309-05229-
7.
[40] Stern, Kurt H. (1972). “High Temperature Properties and
Decomposition of Inorganic Salts; Part 3. Nitrates and
Nitrites” (PDF). J. Phys. Chem. US Naval Research Lab-
oratory. 1 (3): 750–751. doi:10.1063/1.3253104. Re-
trieved 15 March 2014.
7 External links
• ATSDR – Case Studies in Environmental Medicine
– Nitrate/Nitrite Toxicity U.S. Department of
Health and Human Services (public domain)
• International Chemical Safety Card 1120.
• National Center for Home Food Preservation Ni-
trates and Nitrites.
• TR-495: Toxicology and Carcinogenesis Studies
of Sodium Nitrite (CAS NO. 7632-00-0) Drinking
Water Studies in F344/N Rats and B6C3F1 Mice.
• Nitrite in Meat
6 8 TEXT AND IMAGE SOURCES, CONTRIBUTORS, AND LICENSES
8 Text and image sources, contributors, and licenses
8.1 Text
• Sodium nitrite Source: https://en.wikipedia.org/wiki/Sodium_nitrite?oldid=764697480 Contributors: Karada, Tristanb, Malbi, Ike9898,
Dysprosia, Calden, Riddley, TomDowden, Giftlite, Duncharris, Eequor, D3, Andycjp, Beland, Onco p53, Iantresman, Clemwang, Rich
Farmbrough, Grillo7, Kjoonlee, CanisRufus, Smalljim, Davidruben, Mikemsd, Arcadian, Hooperbloob, Nicolasbock, Keenan Pepper,
ABCD, Fasten, RJFJR, Vuo, Sivar, DePiep, Rjwilmsi, Hermione1980, Titoxd, FlaBot, RexNL, Physchim62, Antilived, WriterHound,
YurikBot, Hairy Dude, Farnkerl, Gaius Cornelius, Shaddack, E rulez, RyanJones, 2over0, Wizard IT, SmackBot, Anastrophe, Edgar181,
Apers0n, Fueled~enwiki, Eug, Dkechag, Darnoconrad, MalafayaBot, Uthbrian, Nick Levine, Rfwoolf, Homestarmy, Smokefoot, DMacks,
A5b, Kukini, Beetstra, Maelor, Thricecube, Tawkerbot2, Fvasconcellos, W guice, Cybernetic, Dr Zak, Cydebot, Robinatron, Rifleman
82, Bazzargh, Christian75, Trev M, GentlemanGhost, Headbomb, Dikteren, OSX, Mrs smartygirl, JAnDbot, Instinct, Arch dude, Igodard,
Ramurf, VoABot II, J.P.Lon, Smash1gordon, Philg88, ChemNerd, J.delanoy, Captain panda, 4johnny, DarkFalls, Cosmolux, DadaNeem,
Thioxane, Bcostley, MartinBotIII, Idioma-bot, Vmaldia, Deor, Shiggity, Philip Trueman, TXiKiBoT, JhsBot, Tanner-Christopher, Envi-
roboy, Doc James, AlleborgoBot, Logan, Wikiscottcha, Mayfare, Caltas, Yintan, Chem-awb, ClueBot, Boing! said Zebedee, Shjacks45,
Shinkolobwe, Plasmic Physics, DumZiBoT, Gardenparty, PSimeon, Dthomsen8, Addbot, C6541, DOI bot, EjsBot, Woelen, H92Bot,
CarsracBot, SamatBot, Sp80, Zorrobot, Ben Ben, Legobot, Luckas-bot, Yobot, Fraggle81, CheMoBot, Anypodetos, QueenCake, Up-
standingj, Cormorant 80, EryZ, Materialscientist, Citation bot, ArthurBot, Xqbot, Skaaii, Esmu Igors, Jehholivee94, FrescoBot, NSH002,
Riventree, ДмитрОст, D'ohBot, DivineAlpha, Citation bot 1, I dream of horses, Mutinus, Babahu, MastiBot, HowardJWilk, SpaceFlight89,
Mikespedia, Mowsala, Oktanyum, Blind cyclist, Jynto, Minimac, Onel5969, RjwilmsiBot, Nyxaus, EmausBot, John of Reading, Wikitan-
virBot, Sxoa, TexBrazos, Bobkart, PsychoHipE, Dcirovic, ZéroBot, Chemicalinterest, Alexsmith44, Donner60, Orange Suede Sofa, Chuis-
pastonBot, Whoop whoop pull up, Louisajb, ClueBot NG, Szfjozsef, Rosommer, Rycecube57, Snotbot, Kilterwind, Helpful Pixie Bot,
JohnSRoberts99, Titodutta, Simonnem, Carlstak, Newmanrs, Glacialfox, BattyBot, LegacyOfValor, Maple leaf eh, Gareth CHEBI, Jes-
salynShamess, Francesca Cattaneo, Mysterious Whisper, AAMCasilli, Sriharsh1234, Project Osprey, ChaseAm, Stamptrader, JaconaFrere,
Monkbot, Deren holmes chu, Matyson, Qwertyxp2000, Crystallizedcarbon, Konabruce01, VexorAbVikipædia, Adam9007, TerpeneOtto,
Brock6988 and Anonymous: 164
8.2 Images
• File:Hazard_N.svg Source: https://upload.wikimedia.org/wikipedia/commons/6/6a/Hazard_N.svg License: Public domain Contributors:
Converted from EPS file at http://forum.cptec.org/index.php?showtopic=368 Original artist: See historic
• File:Hazard_O.svg Source: https://upload.wikimedia.org/wikipedia/commons/a/ad/Hazard_O.svg License: Public domain Contributors:
? Original artist: ?
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tributors: Own work using: ChemDraw 8.0 Original artist: Eschenmoser
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Contributors: ? Original artist: ?
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tors: Derived from File:Sodium-hydride-monomer-CRC-MW-3D-balls.png. Original artist: Ben Mills and Jynto
• File:Sodium_nitrite_crystals.jpg Source: https://upload.wikimedia.org/wikipedia/commons/f/f9/Sodium_nitrite_crystals.jpg License:
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Sodium Nitrite

  • 1. Sodium nitrite Not to be confused with sodium nitrate, sodium nitride, or nitratine. “E250” redirects here. For the mobile phone, see Samsung SGH-E250. Sodium nitrite is the inorganic compound with the chemical formula NaNO2. It is a white to slightly yellow- ish crystalline powder that is very soluble in water and is hygroscopic. It is a useful precursor to a variety of organic compounds, such as pharmaceuticals, dyes, and pesticides, but it is probably best known as a food addi- tive to prevent botulism. It is on the World Health Organization’s List of Essential Medicines, the most important medications needed in a basic health system.[2] 1 Uses 1.1 Industrial chemistry The main use of sodium nitrite is for the industrial pro- duction of organonitrogen compounds. It is a reagent for conversion of amines into diazo compounds, which are key precursors to many dyes, such as diazo dyes. Nitroso compounds are produced from nitrites. These are used in the rubber industry.[3] Other applications include uses in photography. It may also be used as an electrolyte in electrochemical grinding manufacturing processes, typically diluted to about 10% concentration in water. It is used in a variety of metallur- gical applications, for phosphatizing and detinning. Sodium nitrite is an effective corrosion inhibitor and is used as an additive in industrial greases,[4] as an aqueous solution in closed loop cooling systems, and in a molten state as a heat transfer medium.[5] 1.2 Medicine Main article: Sodium nitrite (medical use) Sodium nitrite is used together with sodium thiosulfate to treat cyanide poisoning.[6] It is in the section "antidotes and other substances used in poisonings" of the World Health Organization’s List of Essential Medicines, the most important medications needed in a basic health system.[2] 1.3 Food additive In the early 1900s, irregular curing was commonplace. This led to further research surrounding the use of sodium nitrite as an additive in food, standardizing the amount present in foods to minimize the amount needed while maximizing its food additive role.[7] Through this re- search, sodium nitrite has been found to inhibit growth of disease-causing microorganisms; give taste and color to the meat; and inhibit lipid oxidation that leads to rancidity.[7] The ability of sodium nitrite to address the above-mentioned issues has led to production of meat with improved food safety, extended storage life and im- proving desirable color/taste.[7] It has the E number E250. Potassium nitrite (E249) is used in the same way. It is approved for usage in the EU,[8][9] USA[10] and Australia and New Zealand.[11] 1.3.1 Inhibition of microbial growth Sodium nitrite is well known for its role in inhibiting the growth of Clostridium botulinum spores in refriger- ated meats.[12] The mechanism for this activity results from the inhibition of iron-sulfur clusters essential to en- ergy metabolism of Clostridium botulinum.[12] However, sodium nitrite has had varying degrees of effectiveness for controlling growth of other spoilage or disease caus- ing microorganisms.[7] Even though the inhibitory mech- anisms for sodium nitrite are not well known, its effec- tiveness depends on several factors including residual ni- trite level, pH, salt concentration, reductants present and iron content.[13] Furthermore, the type of bacteria also affects sodium nitrites effectiveness.[13] It is generally agreed upon that sodium nitrite is not considered effec- tive for controlling gram-negative enteric pathogens such as Salmonella and Escherichia coli.[13] 1.3.2 Taste and color The appearance and taste of meat is an important com- ponent of consumer acceptance.[7] Sodium nitrite is re- sponsible for the desirable red color (or shaded pink) of meat.[7] Very little nitrite is needed to induce this change.[7] It has been reported that as little as 2 to 14 parts per million (ppm) is needed to induce this desirable color change.[13] However, to extend the lifespan of this 1
  • 2. 2 2 TOXICITY color change, significantly higher levels are needed.[13] The mechanism responsible for this color change is the formation of nitrosylating agents by nitrite, which has the ability to transfer nitric oxide that subsequently re- acts with myoglobin to produce the cured meat color.[13] The unique taste associated with cured meat is also af- fected by the addition of sodium nitrite.[7] However, the mechanism underlying this change in taste is still not fully understood.[13] 1.3.3 Inhibition of lipid oxidation Sodium nitrite is also able to effectively delay the de- velopment of oxidative rancidity.[13] Lipid oxidation is considered to be a major reason for the deterioration of quality of meat products (rancidity and unappetiz- ing flavors).[13] Sodium nitrite acts as an antioxidant in a mechanism similar to the one responsible for the col- oring affect.[13] Nitrite reacts with heme proteins and metal ions, neutralizing free radicals by nitric oxide (one of its byproducts).[13] Neutralization of these free radi- cals terminates the cycle of lipid oxidation that leads to rancidity.[13] 2 Toxicity While this chemical will prevent the growth of bacteria, it can be toxic in high amounts for animals and humans. Sodium nitrite’s LD50 in rats is 180 mg/kg and its human LDLₒ is 71 mg/kg, meaning a 65 kg person would likely have to consume at least 4.6 g to result in death.[14] To prevent toxicity, sodium nitrite (blended with salt) sold as a food additive is dyed bright pink to avoid mistak- ing it for plain salt or sugar. Nitrites are not naturally occurring in vegetables in significant quantities.[15] How- ever, nitrates are found in commercially available veg- etables and a study in an intensive agricultural area in northern Portugal found residual nitrate levels in 34 veg- etable samples, including different varieties of cabbage, lettuce, spinach, parsley and turnips ranged between 54 and 2440 mg/kg, e.g. curly kale (302.0 mg/kg) and green cauliflower (64 mg/kg).[16][17] Boiling vegetables lowers nitrate but not nitrite.[16] Fresh meat contains 0.4–0.5 mg/kg nitrite and 4–7 mg/kg of nitrate (10–30 mg/kg ni- trate in cured meats).[15] The presence of nitrite in animal tissue is a consequence of metabolism of nitric oxide, an important neurotransmitter.[18] Nitric oxide can be cre- ated de novo from nitric oxide synthase utilizing arginine or from ingested nitrate or nitrite.[19] 2.1 Humane toxin for feral hog/wild boar control Because of sodium nitrite’s high level of toxicity to swine (Sus scrofa) it is now being developed in Australia to con- trol feral pigs and wild boar.[20][21] The sodium nitrite in- duces methemoglobinemia in swine, i.e., it reduces the amount of oxygen that is released from hemoglobin, so the animal will feel faint and pass out, and then die in a hu- mane manner after first being rendered unconscious.[22] The Texas Parks and Wildlife Department operates a re- search facility at Kerr Wildlife Management Area, where they examine feral pig feeding preferences and bait tac- tics to administer sodium nitrite.[23] 2.2 Nitrosamines A principal concern about sodium nitrite is the formation of carcinogenic nitrosamines in meats containing sodium nitrite when meat is charred or overcooked. Such car- cinogenic nitrosamines can also be formed from the re- action of nitrite with secondary amines under acidic con- ditions (such as occurs in the human stomach) as well as during the curing process used to preserve meats. Di- etary sources of nitrosamines include US cured meats preserved with sodium nitrite as well as the dried salted fish eaten in Japan. In the 1920s, a significant change in US meat curing practices resulted in a 69% decrease in average nitrite content. This event preceded the begin- ning of a dramatic decline in gastric cancer mortality.[24] About 1970, it was found that ascorbic acid (vitamin C), an antioxidant, inhibits nitrosamine formation.[25] Con- sequently, the addition of at least 550 ppm of ascor- bic acid is required in meats manufactured in the United States. Manufacturers sometimes instead use erythorbic acid, a cheaper but equally effective isomer of ascor- bic acid. Additionally, manufacturers may include α- tocopherol (vitamin E) to further inhibit nitrosamine pro- duction. α-Tocopherol, ascorbic acid, and erythorbic acid all inhibit nitrosamine production by their oxidation- reduction properties. Ascorbic acid, for example, forms dehydroascorbic acid when oxidized, which when in the presence of nitrosonium, a potent nitrosating agent formed from sodium nitrite, reduces the nitrosonium into nitric oxide.[26] The nitrosonium ion formed in acidic ni- trite solutions is commonly[27][28] mislabeled nitrous an- hydride, an unstable nitrogen oxide that cannot exist in vitro.[29] Nitrate or nitrite (ingested) under conditions that result in endogenous nitrosation has been classified as “proba- bly carcinogenic to humans” by International Agency for Research on Cancer (IARC).[30][31] Sodium nitrite consumption has also been linked to the triggering of migraines in individuals who already suffer from them.[32] One study has found a correlation between highly fre- quent ingestion of meats cured with pink salt and the COPD form of lung disease. The study’s researchers sug- gest that the high amount of nitrites in the meats was re- sponsible; however, the team did not prove the nitrite the- ory. Additionally, the study does not prove that nitrites or
  • 3. 3 cured meat caused higher rates of COPD, merely a link. The researchers did adjust for many of COPD’s risk fac- tors, but they commented they cannot rule out all possible unmeasurable causes or risks for COPD.[33][34] 3 Mechanism of action Carcinogenic nitrosamines are formed when amines that occur naturally in food react with sodium nitrite found in cured meat products. R2NH (amines) + NaNO2 (sodium nitrite) → R2N–N=O (nitrosamine) In the presence of acid (such as in the stomach) or heat (such as via cooking), nitrosamines are converted to diazonium ions. R2N–N=O (nitrosamine) + (acid or heat) → R–N+ 2 (diazonium ion) Certain nitrosamines such as N-nitrosodimethylamine[35] and N-nitrosopyrrolidine[36] form carbocations that react with biological nucleophiles (such as DNA or an enzyme) in the cell. R–N+ 2 (diazonium ion) → R+ (carbocation) + N2 (leaving group) + Nu (biological nucleophiles) → R–Nu If this nucleophilic substitution reaction occurs at a cru- cial site in a biomolecule, it can disrupt normal cell func- tions, leading to cancer or cell death. 4 Production The salt is prepared by treating sodium hydroxide with mixtures of nitrogen dioxide and nitric oxide: 2 NaOH + NO2 + NO → 2 NaNO2 + H2O The conversion is sensitive to the presence of oxygen, which can lead to varying amounts of sodium nitrate. In former times, sodium nitrite was prepared by reduction of sodium nitrate with various metals.[3][37] 5 Chemical reactions In the laboratory, sodium nitrite can be used to destroy excess sodium azide.[38][39] 2 NaN3 + 2 NaNO2 + 2 H+ → 3 N2 + 2 NO + 2 Na+ + 2 H2O Above 330 °C sodium nitrite decomposes (in air) to sodium oxide, nitric oxide and nitrogen dioxide.[40] 2 NaNO2 → Na2O + NO + NO2 Sodium nitrite can also be used in the production of nitrous acid via sulfuric acid. This reaction first yields nitrous acid and sodium sulfate: 2 NaNO 2 + H 2SO 4 → 2 HNO 2 + Na 2SO 4 The nitrous acid then, under normal conditions, decom- poses: 2 HNO 2 → NO 2 + NO + H 2O The nitrogen dioxide of the prior decomposition is then routed through a condensor or fractional distillation ap- paratus to react with water and yield nitric acid: 2 NO 2 + H 2O → HNO 3 + HNO 2 6 References [1] Zumdahl, Steven S. (2009). Chemical Principles (6th ed.). Houghton Mifflin Company. p. A23. ISBN 0-618- 94690-X. [2] “WHO Model List of EssentialMedicines” (PDF). World Health Organization. April 2015. Retrieved 25 Septem- ber 2016. [3] Wolfgang Laue, Michael Thiemann, Erich Scheibler, Karl Wilhelm Wiegand “Nitrates and Nitrites” in Ullmann’s Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim.doi:10.1002/14356007.a17_265. Article On- line Posting Date: 15 June 2000 [4] Krakhmalev, S. I.; Vorotnikova, V. A.; Ten, N. V.; Taranova, N. V. (1984). “Determination of sodium nitrite in complex sodium grease”. Chemistry And Technology Of Fuels And Oils. 20 (12): 612–613. doi:10.1007/BF00726438. [5] “Sodium Nitrite”. General Chemical. Retrieved 2012-09- 28.
  • 4. 4 6 REFERENCES [6] WHO Model Formulary 2008 (PDF). World Health Orga- nization. 2009. p. 65-66. ISBN 9789241547659. Re- trieved 8 January 2017. [7] Sindelar, Jeffrey; Milkowski, Andrew (March 2012). “Human safety controversies surrounding nitrate and nitrite in the diet”. Nitric Oxide. 26: 259–266. doi:10.1016/j.niox.2012.03.011. [8] UK Food Standards Agency: “Current EU approved addi- tives and their E Numbers”. Retrieved 27 October 2011. [9] http://ec.europa.eu/food/fs/sc/scf/reports/scf_reports_ 38.pdf [10] US Food and Drug Administration: “Listing of Food Ad- ditives Status Part II”. Retrieved 27 October 2011. [11] Australia New Zealand Food Standards Code“Standard 1.2.4 – Labelling of ingredients”. Retrieved 27 October 2011. [12] Milkowski, Andrew; Garg, Harsha; Couglin, James; Bryan, Nathan (January 2010). “Nutritional epidemiol- ogy in the context of nitric oxide biology: Risk-Benefit evaluation for dietary nitrite and nitrate”. Nitric Oxide. 22 (2): 110–119. doi:10.1016/j.niox.2009.08.004. PMID 19748594. [13] Sindelar, Jeffrey; Milkowski, Andrew (November 2011). “Sodium Nitrite in Processed Meat and Poultry Meats: A Review of Curing and Examining the Risk/Benefit of Its Use” (PDF). American Meat Science Association. 3: 1–14. [14] http://msds.chem.ox.ac.uk/SO/sodium_nitrite.html [15] Dennis, M. J.; Wilson, L. A. (2003). “Nitrates and Nitrites”. Encyclopedia of Food Sciences and Nutrition. p. 4136. doi:10.1016/B0-12-227055-X/00830-0. ISBN 978-0-12-227055-0. [16] Leszczyńska, Teresa; Filipiak-Florkiewicz, Agnieszka; Cieślik, Ewa; Sikora, ElżBieta; Pisulewski, Paweł M. (2009). “Effects of some processing methods on nitrate and nitrite changes in cruciferous vegetables”. Journal of Food Composition and Analysis. 22 (4): 315–321. doi:10.1016/j.jfca.2008.10.025. [17] Correia, Manuela; Barroso, Ângela; Barroso, M. Fá- tima; Soares, Débora; Oliveira, M. B. P. P.; Delerue- Matos, Cristina (2010). “Contribution of different vegetable types to exogenous nitrate and nitrite ex- posure”. Food Chemistry. 120 (4): 960–966. doi:10.1016/j.foodchem.2009.11.030. [18] Meulemans, A.; Delsenne, F. (1994). “Measurement of nitrite and nitrate levels in biological samples by capillary electrophoresis”. Journal of Chromatography B. 660 (2): 401–404. doi:10.1016/0378-4347(94)00310-6. [19] Southan, G; Srinivasan, A (1998). “Nitrogen Oxides and Hydroxyguanidines: Formation of Donors of Nitric and Nitrous Oxides and Possible Relevance to Nitrous Oxide Formation by Nitric Oxide Synthase”. Nitric Oxide. 2 (4): 270–86. doi:10.1006/niox.1998.0187. PMID 9851368. [20] Lapidge, Steven; Wishart, J.; Smith, M.; Staples, L. (2009). “Is America Ready for a Humane Feral Pig Toxi- cant?". Proceedings of the 13th Wildlife Damage Manage- ment Conference: 49–59. [21] Cowled, B. D.; Lapidge, S. J.; Humphrys, S.; Staples, L. (2008). “Nitrite Salts as Poisons in Baits for Omnivores”. International Patent WO/2008/104028. [22] Porter, S.; Kuchel, T. (2010). Assessing the humaness and efficacy of a new feral pig bait in domestic pigs. Study PC0409 (PDF). Canberra, South Australia: Veterinary Services Division, Institute of Medical and Veterinary Science. p. 11. [23] https://www.youtube.com/watch?v=GigpxLNbgeg& spfreload=1 [24] “The epidemiological enigma of gastric cancer rates in the US: was grandmother’s sausage the cause?". International Journal of Epidemiology. 2000. [25] Mackerness, C. W.; Leach, S. A.; Thompson, M. H.; Hill, M. J. (1989). “The inhibition of bacte- rially mediated N-nitrosation by vitamin C: relevance to the inhibition of endogenous N-nitrosation in the achlorhydric stomach”. Carcinogenesis. 10 (2): 397–9. doi:10.1093/carcin/10.2.397. PMID 2492212. [26] Nitrosamines and Cancer by Richard A. Scanlan, Ph.D. [27] Cancer Res. 43 (5 Suppl): 2435s–2440s. May 1983. Missing or empty |title= (help) [28] Nollet, Toldra, D (2015). Handbook of Food Analysis (Third ed.). p. 290. ISBN 9781482297843. [29] Williams, D (2004). “Reagents effecting nitrosation”. Ni- trosation Reactions and the Chemistry of Nitric Oxide. p. 1. doi:10.1016/B978-044451721-0/50002-5. ISBN 978- 0-444-51721-0. [30] “List of classifications, Volumes 1–116 - IARC Mono- graphs on the Evaluation of Carcinogenic Risks to Hu- mans”. International Agency for Research on Cancer (IARC) - World Health Organization (WHO). 2010. Re- trieved 25 September 2016. [31] “VOLUME 94 - Ingested Nitrate and Nitrite, and Cyanobacterial Peptide Toxins - IARC Monographs on the Evaluation of Carcinogenic Risks to Humans”. Inter- national Agency for Research on Cancer (IARC) - World Health Organization (WHO). 2010. Retrieved 25 Septem- ber 2016. [32] “Heading Off Migraine Pain”. FDA Consumer magazine. U.S. Food and Drug Administration. 1998. [33] Hitti, Miranda (17 April 2007). “Study: Cured Meats, COPD May Be Linked”. WebMD Medical News. [34] Jiang, R.; Paik, D. C.; Hankinson, J. L.; Barr, R. G. (2007). “Cured Meat Consumption, Lung Function, and Chronic Obstructive Pulmonary Dis- ease among United States Adults”. American Jour- nal of Respiratory and Critical Care Medicine. 175 (8): 798–804. doi:10.1164/rccm.200607-969OC. PMC 1899290 . PMID 17255565.
  • 5. 5 [35] Najm, Issam; Trussell, R. Rhodes (February 2001). “NDMA Formation in Water and Wastewater”. Journal AWWA. 93 (2): 92–99. [36] Bills, Donald D.; Hildrum, Kjell I.; Scanlan, Richard A.; Libbey, Leonard M. (May 1973). “Potential pre- cursors of N-nitrosopyrrolidine in bacon and other fried foods”. J. Agric. Food Chem. 21 (5): 876–7. doi:10.1021/jf60189a029. PMID 4739004. [37] Hao, Zhi-wei; Xu, Xin-hua; Wang, Da-hui (March 2005). “Reductive denitrification of nitrate by scrap iron filings”. Journal of Zhejiang University SCIENCE. 6B (3): 182– 186. doi:10.1631/jzus.2005.B0182. [38] “Sodium Azide”. Hazardous Waste Management. Northeastern University. March 2003. [39] Committee on Prudent Practices for Handling, Stor- age, and Disposal of Chemicals in Laboratories, Board on Chemical Sciences and Technology, Commission on Physical Sciences, Mathematics, and Applications, Na- tional Research Council (1995). Prudent practices in the laboratory: handling and disposal of chemicals. Washing- ton, D.C.: National Academy Press. ISBN 0-309-05229- 7. [40] Stern, Kurt H. (1972). “High Temperature Properties and Decomposition of Inorganic Salts; Part 3. Nitrates and Nitrites” (PDF). J. Phys. Chem. US Naval Research Lab- oratory. 1 (3): 750–751. doi:10.1063/1.3253104. Re- trieved 15 March 2014. 7 External links • ATSDR – Case Studies in Environmental Medicine – Nitrate/Nitrite Toxicity U.S. Department of Health and Human Services (public domain) • International Chemical Safety Card 1120. • National Center for Home Food Preservation Ni- trates and Nitrites. • TR-495: Toxicology and Carcinogenesis Studies of Sodium Nitrite (CAS NO. 7632-00-0) Drinking Water Studies in F344/N Rats and B6C3F1 Mice. • Nitrite in Meat
  • 6. 6 8 TEXT AND IMAGE SOURCES, CONTRIBUTORS, AND LICENSES 8 Text and image sources, contributors, and licenses 8.1 Text • Sodium nitrite Source: https://en.wikipedia.org/wiki/Sodium_nitrite?oldid=764697480 Contributors: Karada, Tristanb, Malbi, Ike9898, Dysprosia, Calden, Riddley, TomDowden, Giftlite, Duncharris, Eequor, D3, Andycjp, Beland, Onco p53, Iantresman, Clemwang, Rich Farmbrough, Grillo7, Kjoonlee, CanisRufus, Smalljim, Davidruben, Mikemsd, Arcadian, Hooperbloob, Nicolasbock, Keenan Pepper, ABCD, Fasten, RJFJR, Vuo, Sivar, DePiep, Rjwilmsi, Hermione1980, Titoxd, FlaBot, RexNL, Physchim62, Antilived, WriterHound, YurikBot, Hairy Dude, Farnkerl, Gaius Cornelius, Shaddack, E rulez, RyanJones, 2over0, Wizard IT, SmackBot, Anastrophe, Edgar181, Apers0n, Fueled~enwiki, Eug, Dkechag, Darnoconrad, MalafayaBot, Uthbrian, Nick Levine, Rfwoolf, Homestarmy, Smokefoot, DMacks, A5b, Kukini, Beetstra, Maelor, Thricecube, Tawkerbot2, Fvasconcellos, W guice, Cybernetic, Dr Zak, Cydebot, Robinatron, Rifleman 82, Bazzargh, Christian75, Trev M, GentlemanGhost, Headbomb, Dikteren, OSX, Mrs smartygirl, JAnDbot, Instinct, Arch dude, Igodard, Ramurf, VoABot II, J.P.Lon, Smash1gordon, Philg88, ChemNerd, J.delanoy, Captain panda, 4johnny, DarkFalls, Cosmolux, DadaNeem, Thioxane, Bcostley, MartinBotIII, Idioma-bot, Vmaldia, Deor, Shiggity, Philip Trueman, TXiKiBoT, JhsBot, Tanner-Christopher, Envi- roboy, Doc James, AlleborgoBot, Logan, Wikiscottcha, Mayfare, Caltas, Yintan, Chem-awb, ClueBot, Boing! said Zebedee, Shjacks45, Shinkolobwe, Plasmic Physics, DumZiBoT, Gardenparty, PSimeon, Dthomsen8, Addbot, C6541, DOI bot, EjsBot, Woelen, H92Bot, CarsracBot, SamatBot, Sp80, Zorrobot, Ben Ben, Legobot, Luckas-bot, Yobot, Fraggle81, CheMoBot, Anypodetos, QueenCake, Up- standingj, Cormorant 80, EryZ, Materialscientist, Citation bot, ArthurBot, Xqbot, Skaaii, Esmu Igors, Jehholivee94, FrescoBot, NSH002, Riventree, ДмитрОст, D'ohBot, DivineAlpha, Citation bot 1, I dream of horses, Mutinus, Babahu, MastiBot, HowardJWilk, SpaceFlight89, Mikespedia, Mowsala, Oktanyum, Blind cyclist, Jynto, Minimac, Onel5969, RjwilmsiBot, Nyxaus, EmausBot, John of Reading, Wikitan- virBot, Sxoa, TexBrazos, Bobkart, PsychoHipE, Dcirovic, ZéroBot, Chemicalinterest, Alexsmith44, Donner60, Orange Suede Sofa, Chuis- pastonBot, Whoop whoop pull up, Louisajb, ClueBot NG, Szfjozsef, Rosommer, Rycecube57, Snotbot, Kilterwind, Helpful Pixie Bot, JohnSRoberts99, Titodutta, Simonnem, Carlstak, Newmanrs, Glacialfox, BattyBot, LegacyOfValor, Maple leaf eh, Gareth CHEBI, Jes- salynShamess, Francesca Cattaneo, Mysterious Whisper, AAMCasilli, Sriharsh1234, Project Osprey, ChaseAm, Stamptrader, JaconaFrere, Monkbot, Deren holmes chu, Matyson, Qwertyxp2000, Crystallizedcarbon, Konabruce01, VexorAbVikipædia, Adam9007, TerpeneOtto, Brock6988 and Anonymous: 164 8.2 Images • File:Hazard_N.svg Source: https://upload.wikimedia.org/wikipedia/commons/6/6a/Hazard_N.svg License: Public domain Contributors: Converted from EPS file at http://forum.cptec.org/index.php?showtopic=368 Original artist: See historic • File:Hazard_O.svg Source: https://upload.wikimedia.org/wikipedia/commons/a/ad/Hazard_O.svg License: Public domain Contributors: ? Original artist: ? • File:Hazard_T.svg Source: https://upload.wikimedia.org/wikipedia/commons/3/39/Hazard_T.svg License: Public domain Contributors: ? Original artist: ? • File:Lock-green.svg Source: https://upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg License: CC0 Contributors: en:File: Free-to-read_lock_75.svg Original artist: User:Trappist the monk • File:Natriumnitrit.png Source: https://upload.wikimedia.org/wikipedia/commons/6/6c/Natriumnitrit.png License: Public domain Con- tributors: Own work using: ChemDraw 8.0 Original artist: Eschenmoser • File:Nitrite-3D-vdW.png Source: https://upload.wikimedia.org/wikipedia/commons/a/a6/Nitrite-3D-vdW.png License: Public domain Contributors: ? Original artist: ? • File:Sodium-3D.png Source: https://upload.wikimedia.org/wikipedia/commons/0/05/Sodium-3D.png License: Public domain Contribu- tors: Derived from File:Sodium-hydride-monomer-CRC-MW-3D-balls.png. Original artist: Ben Mills and Jynto • File:Sodium_nitrite_crystals.jpg Source: https://upload.wikimedia.org/wikipedia/commons/f/f9/Sodium_nitrite_crystals.jpg License: CC BY-SA 3.0 Contributors: http://woelen.homescience.net/science/index.html Original artist: W. Oelen • File:X_mark.svg Source: https://upload.wikimedia.org/wikipedia/commons/a/a2/X_mark.svg License: Public domain Contributors: Own work Original artist: User:Gmaxwell • File:Yes_check.svg Source: https://upload.wikimedia.org/wikipedia/en/f/fb/Yes_check.svg License: PD Contributors: ? Original artist: ? 8.3 Content license • Creative Commons Attribution-Share Alike 3.0