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{{chembox |
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| verifiedrevid = 414455401 |
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|Reference=<ref name="Merck">'']'', 11th Edition, '''6017'''.</ref> |
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| verifiedrevid = 433348561 |
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|ImageFile=MNNG skeletal.png |
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| Reference =<ref name="Merck">'']'', 11th Edition, '''6017'''.</ref> |
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|ImageSize=150px |
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| ImageFile =MNNG skeletal.png |
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|IUPACName=1-methyl-2-nitro-1-nitrosoguanidine |
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| ImageSize =150px |
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|OtherNames=''N''-Methyl-''N''-nitroso-''N′''-nitroguanidine; ''N''-Methlyl-''N′''-nitro-''N''-nitrosoguanidine |
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| ImageAlt = Structural formula of methylnitronitrosoguanidine |
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| ImageFile1 = Methylnitronitrosoguanidine 3D spacefill.png |
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| ImageSize1 = 160 |
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| ImageAlt1 = Space-filling model of the methylnitronitrosoguanidine molecule |
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| PIN = ''N''-Methyl-''N''′-nitro-''N''-nitrosoguanidine |
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| OtherNames = 1-Methyl-3-nitro-1-nitrosoguanidine<br />''N''-Methyl-''N''-nitroso-''N''′-nitroguanidine |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| Abbreviations = MNNG |
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| Abbreviations = MNNG |
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| CASNo_Ref = {{cascite}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=70-25-7 |
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| CASNo =70-25-7 |
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| UNII_Ref = {{fdacite|correct|CAS}} |
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| PubChem=9562060 |
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| UNII = 12H3O2UGSF |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C14592 |
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| KEGG = C14592 |
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| SMILES=CN(C(=N(=O))N)N=O |
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| SMILES =CN(C(=N(=O))N)N=O |
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| PubChem = 6261 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 6025 |
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| InChI = 1/C2H5N5O3/c1-6(5-8)2(3)4-7(9)10/h1H3,(H2,3,4) |
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| InChIKey = VZUNGTLZRAYYDE-UHFFFAOYAT |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C2H5N5O3/c1-6(5-8)2(3)4-7(9)10/h1H3,(H2,3,4) |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = VZUNGTLZRAYYDE-UHFFFAOYSA-N |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>2</sub>H<sub>5</sub>N<sub>5</sub>O<sub>3</sub> |
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| Formula =C<sub>2</sub>H<sub>5</sub>N<sub>5</sub>O<sub>3</sub> |
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| MolarMass=147.09 g/mol |
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| MolarMass =147.09 g/mol |
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| Appearance=Yellow crystals |
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| Appearance =Yellow crystals |
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| Density= |
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| Density = |
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| MeltingPtC = 118 |
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| MeltingPt=118 °C (dec.) |
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| MeltingPt_notes = (decomposes) |
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| BoilingPt= |
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| BoilingPt = |
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| Solubility= reacts violently, slowly hydrolysed |
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| Solubility = reacts violently, slowly hydrolysed |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards= |
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| MainHazards = |
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| FlashPt= |
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| FlashPt = |
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| AutoignitionPt = |
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| Autoignition= |
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'''Methylnitronitrosoguanidine''' (MNNG) is a biochemical tool used experimentally as a ] and ].<ref name="Merck"/> It acts by adding ] to the O<sup>6</sup> of guanine and O<sup>4</sup> of thymine. These changes do not cause a heavy distortion in the double helix of DNA and thus are hard to detect by the ] system. |
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'''Methylnitronitrosoguanidine''' ('''MNNG'''<ref name="Lawley Thatcher pp. 693–707">{{cite journal | last1=Lawley | first1=P. D. | last2=Thatcher | first2=Carolyn J. | title=Methylation of deoxyribonucleic acid in cultured mammalian cells by ''N''-methyl-''N''′-nitro-''N''-nitrosoguanidine. The influence of cellular thiol concentrations on the extent of methylation and the 6-oxygen atom of guanine as a site of methylation | journal=Biochemical Journal | publisher=Portland Press Ltd. | volume=116 | issue=4 | date=1970-02-01 | issn=0306-3283 | doi=10.1042/bj1160693 | pages=693–707| pmid=5435496 | pmc=1185415 }}</ref> or '''MNG''', '''NTG''' when referred to colloquially as nitrosoguanidine<ref name="WormBook">{{cite web | title=Forward and reverse mutagenesis in ''C. elegans'' | website=WormBook | url=http://www.wormbook.org/chapters/www_frmutagenesis/frmutagenesis.html | access-date=2021-12-01}}</ref>) is a biochemical tool used experimentally as a ] and ].<ref name="Merck"/> It acts by adding ] to the O<sup>6</sup> of ] and O<sup>4</sup> of ], which can lead to ] between GC and AT. These changes do not cause a heavy distortion in the double helix of DNA and thus are hard to detect by the ] system. |
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In organic chemistry, MNNG is used as a source of ] when reacted with aqueous ].<ref>{{cite journal | journal = Aldrichimica Acta | volume = 16 | issue = 3 | year = 1983}}</ref> |
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In organic chemistry, MNNG is used as a source of ] when reacted with aqueous ].<ref>{{cite journal | journal = Aldrichimica Acta | volume = 16 | number = 1 | year = 1983 | pages=3–10 | title = The Preparation and Reactions of Diazomethane | author = T. Howard Black | url = https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/187/633/acta-vol16.pdf#page=4 | access-date = 2024-10-13 | archive-date = 2019-02-03 | archive-url = https://web.archive.org/web/20190203030451/http://www.thblack.com/chemistry/AActa1983_16_3.pdf }}</ref> |
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MNNG is a probable human carcinogen listed as an ].<ref>, ]</ref> |
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MNNG is a probable human carcinogen listed as an ].<ref>, ]</ref> |
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==Stability== |
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MNNG produces diazomethane, a known methylating agent of DNA and other substrates, in basic aqueous solutions, and ], a ], in acidic solutions.<ref name="Hollaender1971">{{cite book | last=Hollaender | first=Alexander | title=Chemical Mutagens: Principles and Methods for Their Detection |volume=1 | publisher=] | year=1971 | isbn=978-1-4615-8966-2 | oclc=851813793 | page=188}}</ref> |
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==References== |
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==References== |
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