Nitrite

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Nitrite
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Names
IUPAC name
Nitrite
Systematic IUPAC name
dioxidonitrate(1−)
Identifiers
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3D model (JSmol)
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  • InChI=1S/HNO2/c2-1-3/h(H,2,3)/p-1
    Key: IOVCWXUNBOPUCH-UHFFFAOYSA-M
  • InChI=1/HNO2/c2-1-3/h(H,2,3)/p-1
    Key: IOVCWXUNBOPUCH-REWHXWOFAR
  • N(=O)[O-]
Properties
Page Module:Chem2/styles.css has no content.NO−2
Molar mass 46.005 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Template:Chembox Footer/trackingTemplate:Short description

The nitrite ion has the chemical formula Page Module:Chem2/styles.css has no content.NO−2. Nitrite (mostly sodium nitrite) is widely used throughout chemical and pharmaceutical industries.[1] The nitrite anion is a pervasive intermediate in the nitrogen cycle in nature. The name nitrite also refers to organic compounds having the –ONO group, which are esters of nitrous acid.

Production

Sodium nitrite is made industrially by passing a mixture of nitrogen oxides into aqueous sodium hydroxide or sodium carbonate solution:[2][1]

Page Module:Chem2/styles.css has no content.NO + NO2 + 2 NaOH → 2 NaNO2 + H2O
Page Module:Chem2/styles.css has no content.NO + NO2 + Na2CO3 → 2 NaNO2 + CO2

The product is purified by recrystallization. Alkali metal nitrites are thermally stable up to and beyond their melting point (441 °C (826 °F) for Page Module:Chem2/styles.css has no content.KNO2). Ammonium nitrite can be made from dinitrogen trioxide, Page Module:Chem2/styles.css has no content.N2O3, which is formally the anhydride of nitrous acid:

Page Module:Chem2/styles.css has no content.2 NH3 + H2O + N2O3 → 2 NH4NO2

Structure

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The two canonical structures of Page Module:Chem2/styles.css has no content.NO−2, which contribute to the resonance hybrid for the nitrite ion
Dimensions of trans-HONO (from the microwave spectrum)

The nitrite ion has a symmetrical structure (C2v) symmetry), with both N–O bonds having equal length and a bond angle of about 115°. In valence bond theory, it is described as a resonance hybrid with equal contributions from two canonical forms that are mirror images of each other. In molecular orbital theory, there is a sigma bond between each oxygen atom and the nitrogen atom, and a delocalized pi bond made from the p orbitals on nitrogen and oxygen atoms, which is perpendicular to the plane of the molecule. The negative charge of the ion is equally distributed on the two oxygen atoms. Both nitrogen and oxygen atoms carry a lone pair of electrons. Therefore, the nitrite ion is a Lewis base.

In the gas phase, it exists predominantly as a trans-planar molecule.

Reactions

Acid-base properties

Nitrite is the conjugate base of the weak acid nitrous acid:

Page Module:Chem2/styles.css has no content.HNO2 ⇌ H+ + Page Module:Chem2/styles.css has no content.NO−2;      pKa ≈ 3.3 at 18 °C (64 °F)[citation needed]

Nitrous acid is also highly unstable, tending to disproportionate:

Page Module:Chem2/styles.css has no content.3 HNO2(aq) ⇌ H3O+ + 2 NO + Page Module:Chem2/styles.css has no content.NO−3

This reaction is slow at 0 °C (32 °F).[2] Addition of acid to a solution of a nitrite in the presence of a reducing agent, such as iron(II), is a way to make nitric oxide (NO) in the laboratory.

Oxidation and reduction

The formal oxidation state of the nitrogen atom in nitrite is +3. This means it can be either oxidized to oxidation states +4 and +5 or reduced to as low as −3. Standard reduction potentials for reactions directly involving nitrous acid are shown in the table below:[3]

Half-reaction E0 (V)
Page Module:Chem2/styles.css has no content.NO−3 + Page Module:Chem2/styles.css has no content.3 H+ + 2 e− ⇌ HNO2 + H2O +0.94
Page Module:Chem2/styles.css has no content.2 HNO2 + 4 H+ + 4 e− ⇌ H2N2O2 + 2 H2O +0.86
Page Module:Chem2/styles.css has no content.N2O4 + 2 H+ + 2 e− ⇌ 2 HNO2 +1.065
Page Module:Chem2/styles.css has no content.2 HNO2 + 4 H+ + 4 e− ⇌ N2O + 3 H2O +1.29

The data can be extended to include products in lower oxidation states. For example:

Page Module:Chem2/styles.css has no content.H2N2O2 + 2 H+ + 2 e− ⇌ N2 + 2 H2O;      E0 = +2.65 V

Oxidation reactions usually result in the formation of the nitrate ion, with nitrogen in oxidation state +5. For example, oxidation with permanganate ion can be used for quantitative analysis of nitrite (by titration):

Page Module:Chem2/styles.css has no content.5 NO−2 + 2 MnO−4 + 6 H+ → 2 Mn2+ + 3 H2O + 5 NO−3

The products of reduction reactions with the nitrite ion vary depending on the reducing agent used and its strength. With sulfur dioxide, the products are NO and Page Module:Chem2/styles.css has no content.N2O; with tin(II) (Page Module:Chem2/styles.css has no content.Sn2+) the product is hyponitrous acid (Page Module:Chem2/styles.css has no content.H2N2O2); reduction all the way to ammonia (Page Module:Chem2/styles.css has no content.NH3) occurs with hydrogen sulfide. With the hydrazinium cation (Page Module:Chem2/styles.css has no content.N2H+5) the product of nitrite reduction is hydrazoic acid (Page Module:Chem2/styles.css has no content.HN3), an unstable and explosive compound:

Page Module:Chem2/styles.css has no content.N2H+5 + HNO2 → HN3 + H2O + H3O+

which can also further react with nitrite:

Page Module:Chem2/styles.css has no content.HNO2 + HN3 → N2O + N2 + H2O

This reaction is unusual in that it involves compounds with nitrogen in four different oxidation states.[2]

Analysis of nitrite

Script error: No such module "Labelled list hatnote". Nitrite is detected and analyzed by the Griess Reaction, involving the formation of a deep red-colored azo dye upon treatment of a Page Module:Chem2/styles.css has no content.NO−2-containing sample with sulfanilic acid and naphthyl-1-amine in the presence of acid.[4]

Coordination complexes

Script error: No such module "Labelled list hatnote". Nitrite is an ambidentate ligand and can form a wide variety of coordination complexes by binding to metal ions in several ways. For example, the red nitrito pentaamminecobalt complex Page Module:Chem2/styles.css has no content.[Co(NH3)5(ONO)]2+ is metastable, isomerizing to the yellow nitro complex Page Module:Chem2/styles.css has no content.[Co(NH3)5(NO2)]2+.[2]

Nitrite is processed by several enzymes, all of which utilize coordination complexes.[citation needed]

Hazardous reactions

When heated with cyanides or thiosulfates, nitrites violently explode.[5]

Biochemistry

A schematic representation of the microbial nitrogen cycle.[6][7] ANAMMOX is anaerobic ammonium oxidation, DNRA is dissimilatory nitrate reduction to ammonium, and COMMAMOX is complete ammonium oxidation.

In nitrification, ammonium is converted to nitrite. Important species include Nitrosomonas. Other bacterial species, such as Nitrobacter, are responsible for oxidizing nitrite to nitrate.[citation needed]

Nitrite can be reduced to nitric oxide or ammonia by many species of bacteria. Under hypoxic conditions, nitrite may release nitric oxide, which causes potent vasodilation. Several mechanisms for nitrite conversion to NO have been described, including enzymatic reduction by xanthine oxidoreductase, nitrite reductase, and NO synthase (NOS), as well as nonenzymatic acidic disproportionation reactions.[citation needed]

Uses

Chemical precursor

Azo dyes and other colorants are prepared by the process called diazotization, which requires nitrite.[1]

Nitrite in food preservation and biochemistry

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Script error: No such module "Labelled list hatnote". The addition of nitrites and nitrates to processed meats such as ham, bacon, and sausages speeds up the curing of meat and also imparts an attractive colour. Nitrite reacts with the meat's myoglobin by attaching to the heme iron atom, forming reddish-brown nitrosomyoglobin and the characteristic pink "fresh" color of nitrosohemochrome or nitrosyl-heme upon cooking.[8] [9]

The academic and industrial consensus is that nitrites also reduce the growth and toxin production of Clostridium botulinum.[10][11][12]

On the other hand, a 2018 study by the British Meat Producers Association determined that legally permitted levels of nitrite do not affect the growth of C. botulinum.[13]

Addition of ascorbic acid, erythorbic acid, or one of their salts enhances the binding of nitrite to the iron atom in myoglobin.[8] These chemicals also reduce the formation of nitrosamine in the stomach, but only when the fat content of a meal is less than 10%, beyond which they instead increase the formation of nitrosamine.[14][15]

In the U.S., meat cannot be labeled "cured" unless it contains nitrite.[16][17][18] In the US, nitrite has been formally used since 1925. According to scientists working for the industry group American Meat Institute, this use of nitrite started in the Middle Ages.[19]

In some countries,[which?] cured-meat products are manufactured without nitrate or nitrite, and without nitrite from vegetable sources. Parma ham, produced without nitrite since 1993, was reported in 2018 to have caused no cases of botulism. This is because the muscle's interior is sterile, while its surface is exposed to oxygen.[9] Other manufacturing processes do not assure these conditions, and reduction of nitrite results in toxin production.[20]

Historians and epidemiologists argue[<span title="Script error: No such module "decodeEncode".">weasel words] that the widespread use of nitrite in meat-curing is closely linked to the development of industrial meat-processing.[21][22] French investigative journalist Guillaume Coudray asserts that the meat industry chooses to cure its meats with nitrite even though it is established that this chemical gives rise to cancer-causing nitroso-compounds.[citation needed] Some traditional and artisanal producers avoid nitrites. As many researchers[who?] nowadays[when?] try to point out the hazardous generation of nitrosamines as nitrites bind to free peptides in the gastrointestinal system, the EU published a regulation that requires lowering nitrite levels in meat curing from 150 to 80 ppm.[23]

In mice, food rich in nitrites together with unsaturated fats can prevent hypertension by forming nitro fatty acids that inhibit soluble epoxide hydrolase, which is one explanation for the apparent health effect of the Mediterranean diet.[24] Adding nitrites to meat has been shown to generate known carcinogens; the World Health Organization (WHO) advises that eating 50 g (1.8 oz) of nitrite processed meat a day would raise the risk of getting bowel cancer by 18% over a lifetime.[9]

The recommended maximum limits by the World Health Organization in drinking water are 3 mg/L and 50 mg/L for nitrite and nitrate ions, respectively. Ingesting too much nitrite and/or nitrate through well water is suspected to cause methemoglobinemia.[25][26]

95% of the nitrite ingested in modern diets comes from bacterial conversion of nitrates naturally found in vegetables.[27] However, potentially cancer-causing nitroso compounds are not formed in the pH-neutral colon. They are mostly produced in the acidic stomach.[28][29]

Since the 1980s, sorbic acid and its salts have been used to inhibit Clostridium botulinum in meat products, replacing nitrites to avoid the formation of carcinogenic nitrosamines.[30]

Antidote for cyanide poisoning

Nitrites in the form of sodium nitrite and amyl nitrite are components of many cyanide antidote kits.[31] Both of these compounds bind to hemoglobin and oxidize the Page Module:Chem2/styles.css has no content.Fe2+ ions to Page Module:Chem2/styles.css has no content.Fe3+ ions forming methemoglobin. Methemoglobin, in turn, binds to cyanide (CN), creating cyanmethemoglobin, effectively removing cyanide from the complex IV of the electron transport chain (ETC) in mitochondria, which is the primary site of disruption caused by cyanide. Another mechanism by which nitrites help treat cyanide toxicity is the generation of nitric oxide (NO). NO displaces the CN from the cytochrome c oxidase (ETC complex IV), making it available for methemoglobin to bind.[32]

Organic nitrites

A nitrite ester

In organic chemistry, alkyl nitrites are esters of nitrous acid and contain the nitrosoxy functional group. Nitro compounds contain the Page Module:Chem2/styles.css has no content.C−NO2 group. Nitrites have the general formula RONO, where R is an aryl or alkyl group. Amyl nitrite and other alkyl nitrites have a vasodilating action and must be handled in the laboratory with caution. They are sometimes used in medicine to treat heart disease. A classic named reaction for the synthesis of alkyl nitrites is the Meyer synthesis in which alkyl halides react with metallic nitrites to a mixture of nitroalkanes and nitrites.[33][34]

Safety

Script error: No such module "Labelled list hatnote". Large doses of nitrites cause acute poisoning in the form of methemoglobinemia, which can lead to death.[35]

See also

References

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  1. ^ a b c Script error: No such module "Template wrapper".
  2. ^ a b c d Page Module:Citation/CS1/styles.css has no content.Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. pp. 461–464. doi:10.1016/C2009-0-30414-6. ISBN 978-0-08-037941-8.
  3. ^ Page Module:Citation/CS1/styles.css has no content.Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. p. 431. doi:10.1016/C2009-0-30414-6. ISBN 978-0-08-037941-8.
  4. ^ Page Module:Citation/CS1/styles.css has no content.Ivanov, V. M. (1 October 2004). "The 125th Anniversary of the Griess Reagent". Journal of Analytical Chemistry. 59 (10): 1002–1005. doi:10.1023/B:JANC.0000043920.77446.d7. ISSN 1608-3199. S2CID 98768756.
  5. ^ Page Module:Citation/CS1/styles.css has no content.Kaye, Seymour M. (1 January 1978). "N – Nitrites". Encyclopedia of Explosives and Related Items (PDF) (Technical report). Vol. 8, M1 Thickener through Pyruvonitrolic Acid. Dover, NJ: Army Armament Research And Development Center – Large Caliber Weapon Systems Lab. p. N107. LCCN 61-61759. ADA057762, PATR 2700.
  6. ^ Page Module:Citation/CS1/styles.css has no content.Sparacino-Watkins, Courtney; Stolz, John F.; Basu, Partha (16 December 2013). "Nitrate and periplasmic nitrate reductases". Chem. Soc. Rev. 43 (2): 676–706. doi:10.1039/c3cs60249d. ISSN 1460-4744. PMC 4080430. PMID 24141308.
  7. ^ Page Module:Citation/CS1/styles.css has no content.Simon, Jörg; Klotz, Martin G. (2013). "Diversity and evolution of bioenergetic systems involved in microbial nitrogen compound transformations". Biochimica et Biophysica Acta (BBA) - Bioenergetics. 1827 (2): 114–135. doi:10.1016/j.bbabio.2012.07.005. PMID 22842521.
  8. ^ a b Page Module:Citation/CS1/styles.css has no content.Pappenberger, Günter; Hohmann, Hans-Peter (2013). "Industrial Production of L-Ascorbic Acid (Vitamin C) and D-Isoascorbic Acid". Biotechnology of Food and Feed Additives. Advances in Biochemical Engineering/Biotechnology. 143: 143–188. doi:10.1007/10_2013_243. ISBN 978-3-662-43760-5. PMID 24258144.
  9. ^ a b c Page Module:Citation/CS1/styles.css has no content.Wilson, Bee (1 March 2018). "Yes, bacon really is killing us". The Guardian. London. ISSN 0261-3077. Archived from the original on 10 February 2021. Retrieved 14 February 2021. In trade journals of the 1960s, the firms who sold nitrite powders to ham-makers spoke quite openly about how the main advantage was to increase profit margins by speeding up production.
  10. ^ Page Module:Citation/CS1/styles.css has no content.Christiansen LN, Johnston RW, Kautter DA, Howard JW, Aunan WJ (March 1973). "Effect of nitrite and nitrate on toxin production by Clostridium botulinum and on nitrosamine formation in perishable canned comminuted cured meat". Applied Microbiology. 25 (3): 357–362. doi:10.1128/AEM.25.3.357-362.1973. PMC 380811. PMID 4572891.
  11. ^ Page Module:Citation/CS1/styles.css has no content.Lee, Soomin; Lee, Heeyoung; Kim, Sejeong; Lee, Jeeyeon; Ha, Jimyeong; Choi, Yukyung; Oh, Hyemin; Choi, Kyoung-Hee; Yoon, Yohan (August 2018). "Microbiological safety of processed meat products formulated with low nitrite concentration — A review". Asian-Australasian Journal of Animal Sciences. 31 (8): 1073–1077. doi:10.5713/ajas.17.0675. ISSN 1011-2367. PMC 6043430. PMID 29531192.
  12. ^ Page Module:Citation/CS1/styles.css has no content.Sindelar, Jeffrey J.; Milkowski, Andrew L. (May 2012). "Human safety controversies surrounding nitrate and nitrite in the diet". Nitric Oxide. 26 (4): 259–266. doi:10.1016/j.niox.2012.03.011. PMID 22487433.
  13. ^ Page Module:Citation/CS1/styles.css has no content.Doward, Jamie (23 March 2019). "Revealed: no need to add cancer-risk nitrites to ham". The Observer. London. Archived from the original on 26 January 2021. Retrieved 14 February 2021. The results show that there is no change in levels of inoculated C. botulinum over the curing process, which implies that the action of nitrite during curing is not toxic to C. botulinum spores at levels of 150ppm [parts per million] ingoing nitrite and below.
  14. ^ Page Module:Citation/CS1/styles.css has no content.Combet, E.; Paterson, S.; Iijima, K.; Winter, J.; Mullen, W; Crozier, A.; Preston, T.; McColl, K. E. (2007). "Fat transforms ascorbic acid from inhibiting to promoting acid-catalysed N-nitrosation". Gut. 56 (12): 1678–1684. doi:10.1136/gut.2007.128587. PMC 2095705. PMID 17785370.
  15. ^ Page Module:Citation/CS1/styles.css has no content.Combet, E.; El Mesmari, A.; Preston, T.; Crozier, A.; McColl, K. E. (2010). "Dietary phenolic acids and ascorbic acid: Influence on acid-catalyzed nitrosative chemistry in the presence and absence of lipids". Free Radical Biology and Medicine. 48 (6): 763–771. doi:10.1016/j.freeradbiomed.2009.12.011. PMID 20026204.
  16. ^ Page Module:Citation/CS1/styles.css has no content.De Vries, John (1997). Food Safety and Toxicity. CRC Press. p. 70. ISBN 978-0-8493-9488-1.
  17. ^ sodium nitrite and nitrate facts Accessed 12 Dec 2014
  18. ^ Page Module:Citation/CS1/styles.css has no content.Doyle, Michael P.; Sperber, William H. (23 September 2009). Compendium of the Microbiological Spoilage of Foods and Beverages. Springer. p. 78. ISBN 978-1-4419-0826-1.
  19. ^ Page Module:Citation/CS1/styles.css has no content.Binkerd, E. F.; Kolari, O. E. (1 January 1975). "The history and use of nitrate and nitrite in the curing of meat". Food and Cosmetics Toxicology. 13 (6): 655–661. doi:10.1016/0015-6264(75)90157-1. ISSN 0015-6264. PMID 1107192.
  20. ^ Page Module:Citation/CS1/styles.css has no content.Lebrun, S.; Van Nieuwenhuysen, T.; Crèvecoeur, S.; Vanleyssem, R.; Thimister, J.; Denayer, S.; Jeuge, S.; Daube, G.; Clinquart, A.; Fremaux, B. (December 2020). "Influence of reduced levels or suppression of sodium nitrite on the outgrowth and toxinogenesis of psychrotrophic Clostridium botulinum Group II type B in cooked ham". International Journal of Food Microbiology. 334 108853. doi:10.1016/j.ijfoodmicro.2020.108853. PMID 32932195.
  21. ^ Page Module:Citation/CS1/styles.css has no content.Coudray, Guillaume (2017). Cochonneries: Comment la charcuterie est devenue un poison (in français). Paris: La Découverte. pp. 40–70. ISBN 978-2-7071-9358-2.
  22. ^ Page Module:Citation/CS1/styles.css has no content.Lauer, Klaus (1 January 1991). "The history of nitrite in human nutrition: A contribution from German cookery books". Journal of Clinical Epidemiology. 44 (3): 261–264. doi:10.1016/0895-4356(91)90037-A. ISSN 0895-4356. PMID 1999685.
  23. ^ Page Module:Citation/CS1/styles.css has no content."Commission Decision (EU) 2024/1225 of 30 April 2024 concerning national provisions notified by Denmark on the addition of nitrite to certain meat products".
  24. ^ Page Module:Citation/CS1/styles.css has no content.Charles, R. L.; Rudyk, O.; Prysyazhna, O.; Kamynina, A.; Yang, J.; Morisseau, C.; Hammock, B. D.; Freeman, B. A.; Eaton, P. (2014). "Protection from hypertension in mice by the Mediterranean diet is mediated by nitro fatty acid inhibition of soluble epoxide hydrolase". Proceedings of the National Academy of Sciences. 111 (22): 8167–8172. Bibcode:2014PNAS..111.8167C. doi:10.1073/pnas.1402965111. PMC 4050620. PMID 24843165.
  25. ^ Page Module:Citation/CS1/styles.css has no content.Bagheri, H.; Hajian, A.; Rezaei, M.; Shirzadmehr, A. (2017). "Composite of Cu metal nanoparticles—multiwall carbon nanotubes—reduced graphene oxide as a novel and high-performance platform of the electrochemical sensor for simultaneous determination of nitrite and nitrate". Journal of Hazardous Materials. 324 (Pt B): 762–772. Bibcode:2017JHzM..324..762B. doi:10.1016/j.jhazmat.2016.11.055. PMID 27894754.
  26. ^ Page Module:Citation/CS1/styles.css has no content.Powlson DS, Addiscott TM, Benjamin N, Cassman KG, de Kok TM, van Grinsven H, et al. (2008). "When does nitrate become a risk for humans?". Journal of Environmental Quality. 37 (2): 291–295. Bibcode:2008JEnvQ..37..291P. doi:10.2134/jeq2007.0177. PMID 18268290. S2CID 14097832. Archived from the original on 22 July 2018.
  27. ^ Page Module:Citation/CS1/styles.css has no content."Is celery juice a viable alternative to nitrites in cured meats?". Office for Science and Society. Retrieved 14 September 2022.
  28. ^ Page Module:Citation/CS1/styles.css has no content.Lee, L; Archer, MC; Bruce, WR (October 1981). "Absence of volatile nitrosamines in human feces". Cancer Res. 41 (10): 3992–3994. PMID 7285009.
  29. ^ Page Module:Citation/CS1/styles.css has no content.Kuhnle, GG; Story, GW; Reda, T; et al. (October 2007). "Diet-induced endogenous formation of nitroso compounds in the GI tract". Free Radic. Biol. Med. 43 (7): 1040–1047. doi:10.1016/j.freeradbiomed.2007.03.011. PMID 17761300.
  30. ^ Page Module:Citation/CS1/styles.css has no content.A. S. Naidu, ed. (2000). Natural food antimicrobial systems. CRC Press. p. 637. ISBN 0-8493-2047-X.
  31. ^ Page Module:Citation/CS1/styles.css has no content.Meillier, Andrew; Heller, Cara (2015). "Acute Cyanide Poisoning: Hydroxocobalamin and Sodium Thiosulfate Treatments with Two Outcomes following One Exposure Event". Case Reports in Medicine. 2015 217951. doi:10.1155/2015/217951. ISSN 1687-9627. PMC 4620268. PMID 26543483.
  32. ^ Page Module:Citation/CS1/styles.css has no content.Bebarta, Vikhyat S.; Brittain, Matthew; Chan, Adriano; Garrett, Norma; Yoon, David; Burney, Tanya; Mukai, David; Babin, Michael; Pilz, Renate B.; Mahon, Sari B.; Brenner, Matthew (June 2017). "Sodium Nitrite and Sodium Thiosulfate Are Effective Against Acute Cyanide Poisoning when Administered by Intramuscular Injection". Annals of Emergency Medicine. 69 (6): 718–725.e4. doi:10.1016/j.annemergmed.2016.09.034. ISSN 0196-0644. PMC 5446299. PMID 28041825.
  33. ^ Page Module:Citation/CS1/styles.css has no content.Victor Meyer (1872). "Über die Nitroverbindungen der Fettreihe". Justus Liebig's Annalen der Chemie (in german). 171 (1): 1–56. doi:10.1002/jlac.18741710102.{{cite journal}}: CS1 maint: unrecognized language (link)
  34. ^ Page Module:Citation/CS1/styles.css has no content.Reynolds, R.B.; Adkins, H. (1929). "The Relationship of the Constitution of Certain Alky Halides to the Formation of Nitroparaffins and Alkyl Nitrites". Journal of the American Chemical Society. 51 (1): 279–287. Bibcode:1929JAChS..51..279R. doi:10.1021/ja01376a037.
  35. ^ Page Module:Citation/CS1/styles.css has no content.Katabami K, Hayakawa M, Gando S (3 August 2016). "Severe Methemoglobinemia due to Sodium Nitrite Poisoning". Case Reports in Emergency Medicine. 2016 9013816. doi:10.1155/2016/9013816. PMC 4987464. PMID 27563472.

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