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Revision as of 16:14, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 471859728 of page 1,2-Dimethylhydrazine for the Chem/Drugbox validation project (updated: '').  Latest revision as of 18:31, 29 October 2024 edit Trasheater Midir (talk | contribs)Extended confirmed users3,426 edits Reference edited with ProveIt #proveit - something can be more toxic than geptylTag: ProveIt edit 
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{{chembox
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
| Verifiedfields = changed
{{Chembox
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 443340302 | verifiedrevid = 477204010
| ImageFile = Dimethylhydrazin.svg | ImageFile = Dimethylhydrazin.svg
| ImageFile_Ref = {{chemboximage|correct|??}} | ImageFile_Ref = {{chemboximage|correct|??}}
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| ImageFile1 = 1,2-dimethylhydrazine-3D-balls.png | ImageFile1 = 1,2-dimethylhydrazine-3D-balls.png
| ImageFile1_Ref = {{chemboximage|correct|??}} | ImageFile1_Ref = {{chemboximage|correct|??}}
| ImageSize1 = 160 | ImageSize1 = 100
| ImageName1 = Ball and stick model of 1,2-dimethylhydrazine | ImageName1 = Ball and stick model of 1,2-dimethylhydrazine
| IUPACName = 1,2-Dimethylhydrazine<ref name="PubChem Compound">{{Cite web|title=1,2-Dimethylhydrazine - Compound Summary|url=http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=1322&loc=ec_rcs|work=PubChem Compound|publisher=National Center for Biotechnology Information|accessdate=8 January 2012|location=USA|date=25 March 2005|at=Identification and Related Records}}</ref> | PIN = 1,2-Dimethylhydrazine<ref name="PubChem Compound">{{PubChem|1322|1,2-Dimethylhydrazine}}</ref>
| OtherNames = {{Unbulleted list|''N'',''N'''-Dimethylhydrazine<ref name = CAS>Chemical Abstracts Service: American Chemical Society, Columbus, OH, 2004; RN 540-73-8; Version 2007.3 (accessed November 4, 2011)</ref>|''sym''-Dimethylhydrazine<ref name = CAS/>|Hydrazomethane<ref name = CAS/>}} | OtherNames = {{Unbulleted list|''N'',''N'''-Dimethylhydrazine<ref name = CAS>{{CAS|74-79-3|1,2-Dimethylhydrazine}}</ref>|''sym''-Dimethylhydrazine<ref name = CAS/>|Hydrazomethane<ref name = CAS/>}}
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| Abbreviations = SDMH<ref name = CAS/> | Abbreviations = SDMH<ref name = CAS/>
| CASNo = 540-73-8 | CASNo = 540-73-8
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 1322 | PubChem = 1322
⚫ | ChemSpiderID = 1282
| PubChem_Ref = {{Pubchemcite|correct|Pubchem}}
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | ChemSpiderID = 1282
⚫ | UNII = IX068S9745
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | UNII = IX068S9745
| UNII_Ref = {{fdacite|correct|FDA}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| KEGG = C19176 | ChEBI = 73755
| KEGG_Ref = {{keggcite|correct|kegg}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 162921
⚫ | MeSHName = 1,2-Dimethylhydrazine
| SMILES = CNNC | KEGG = C19176
| KEGG_Ref = {{keggcite|correct|kegg}}
⚫ | StdInChI = 1S/C2H8N2/c1-3-4-2/h3-4H,1-2H3
⚫ | MeSHName = 1,2-Dimethylhydrazine
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| RTECS = MV2625000
⚫ | StdInChIKey = DIIIISSCIXVANO-UHFFFAOYSA-N
| UNNumber = 2382
⚫ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| SMILES = CNNC
⚫ | StdInChI = 1S/C2H8N2/c1-3-4-2/h3-4H,1-2H3
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChIKey = DIIIISSCIXVANO-UHFFFAOYSA-N
⚫ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Reference = <ref>{{GESTIS|ZVG=34110|CAS=540-73-8|Name=1,2-Dimethylhydrazin|Datum=21. März. 2008}}</ref> | Properties_ref = <ref>{{GESTIS|ZVG=34110|CAS=540-73-8|Name=1,2-Dimethylhydrazin|Date=21 March 2008}}</ref>
| C=2|N=2|H=8 | C=2 | H=8 | N=2
⚫ | Appearance = Colourless liquid
| ExactMass = 60.068748266 g mol<sup>−1</sup>
| Odor = Fishy, ammoniacal
⚫ | Appearance = Colourless, transparent liquid
| Density = 830 mg mL<sup>−1</sup> | Density = 827.4 kg m{{sup|−3}} (at 20 °C)
| MeltingPtC = −9 | MeltingPtC = −9
| BoilingPtK = 360 | BoilingPtK = 360
| Solubility = Miscible | Solubility = Miscible
}} }}
| Section3 = {{Chembox Thermochemistry |Section3={{Chembox Thermochemistry
| DeltaHc = −1.9872–−1.9788 kJ mol<sup>−1</sup> | DeltaHc = −1987–−1978 kJ mol{{sup|−1}}
| Entropy = 199.15 J K<sup>−1</sup> mol<sup>−1</sup> | Entropy = 199.15 J K{{sup|−1}} mol{{sup|−1}}
| HeatCapacity = 171.04 J K<sup>−1</sup> mol<sup>−1</sup> | HeatCapacity = 171.04 J K{{sup|−1}} mol{{sup|−1}}
}}
|Section7={{Chembox Hazards
| GHS_ref=<ref>{{cite web |title=1,2-Dimethylhydrazine |url=https://pubchem.ncbi.nlm.nih.gov/compound/1322#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=22 December 2021 |language=en}}</ref>
| GHSPictograms = {{GHS06}}{{GHS08}}{{GHS09}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|301|311|331|350|411}}
| PPhrases = {{P-phrases|201|202|261|264|270|271|273|280|281|301+310|302+352|304+340|308+313|311|312|322|330|361|363|391|403+233|405}}
}}
|Section8={{Chembox Related
| OtherCompounds = {{unbulleted list|]|]}}
}} }}
}} }}

'''Symmetrical dimethylhydrazine''' (SDMH), or '''1,2-dimethylhydrazine''', is the organic compound with the formula (CH<sub>3</sub>NH)<sub>2</sub>. It is one of the two isomers of ]. Both isomers are colorless liquids at room temperature, with properties similar to those of ]s. Symmetrical dimethylhydrazine is a potent ] that acts as a ].<ref>{{Cite journal |last1=Salehi |first1=Alireza |last2=Hosseini |first2=Seyed Mohammad |last3=Kazemi |first3=Sohrab |date=2022-06-23 |title=Antioxidant and Anticarcinogenic Potentials of Propolis for Dimethylhydrazine-Induced Colorectal Cancer in Wistar Rats |journal=BioMed Research International |language=en |volume=2022 |pages=e8497562 |doi=10.1155/2022/8497562 |issn=2314-6133 |pmc=9246617 |pmid=35782078 |doi-access=free }}</ref><ref>{{Cite journal |last1=Valaei |first1=Amirhasan |last2=Azadeh |first2=Fatemeh |last3=Mostafavi Niaki |first3=Seyedeh Talayeh |last4=Salehi |first4=Alireza |last5=Shakib Khoob |first5=Maede |last6=Mirebrahimi |first6=Seyed Hesam odin |last7=Kazemi |first7=Sohrab |last8=Hosseini |first8=Seyed Mohammad |date=2022-10-10 |title=Antioxidant and Anticancer Potentials of the Olive and Sesame Mixture against Dimethylhydrazine-Induced Colorectal Cancer in Wistar Rats |journal=BioMed Research International |language=en |volume=2022 |pages=e5440773 |doi=10.1155/2022/5440773 |issn=2314-6133 |pmc=9576397 |pmid=36262974 |doi-access=free }}</ref> The compound has no commercial value, in contrast to its isomer ] (1,1-dimethylhydrazine, UDMH), which is used as a rocket fuel.<ref>{{cite journal|title=Human health perspective of environmental exposure to hydrazines: A review
|author=Gangadhar Choudhary, Hugh Hansen
|date=August 1998
|journal=Chemosphere
|volume=37
|issue=5
|pages=801–843
|doi=10.1016/S0045-6535(98)00088-5|pmid=9717244
|bibcode=1998Chmsp..37..801C
}}</ref> Symmetrical dimethylhydrazine is more toxic than unsymmetrical dimethylhydrazine and is therefore an unwanted impurity in UDMH.<ref>{{Cite encyclopedia |title=Dimethylhydrazines |encyclopedia=Encyclopedia of Liquid Fuels |publisher=De Gruyter |url=https://www.degruyter.com/document/doi/10.1515/9783110750287-016/html |last=Schmidt |first=Eckart W. |date=2022 |pages=1333–1499 |doi=10.1515/9783110750287-016 |isbn=978-3-11-075028-7}}</ref>

It is used to induce colon tumors in experimental animals—particularly mice and feline cell samples.<ref name="PubChem Compound" /><ref>{{Cite journal |last1=Cruse |first1=J. P. |last2=Lewin |first2=M. R. |last3=Ferulano |first3=G. P. |last4=Clark |first4=C. G. |date=December 1978 |title=Co-carcinogenic effects of dietary cholesterol in experimental colon cancer |journal=Nature |volume=276 |issue=5690 |pages=822–5 |pmid=723955 |doi=10.1038/276822a0 |bibcode=1978Natur.276..822C |s2cid=4303843 }}</ref><ref>{{Cite journal |last1=Wijnands |first1=M.V.W. |date=April 1999 |title=A comparison of the effects of dietary cellulose and fermentable galacto-oligosaccharide, in a rat model of colorectal carcinogenesis: fermentable fibre confers greater protection than non-fermentable fibre in both high and low fat backgrounds |journal=Carcinogenesis |volume=20 |issue=4 |pages=651–6 |pmid=10223195 |doi=10.1093/carcin/20.4.651 |doi-access= }}</ref>

==References==
{{reflist}}

{{hydrazines}}

]
]
]


{{organic-compound-stub}}