Symmetrical dimethylhydrazine

Symmetrical dimethylhydrazine
Skeletal formula of 1,2-dimethylhydrazine with all implicit hydrogens shown
Ball and stick model of 1,2-dimethylhydrazine
Names
Preferred IUPAC name
1,2-Dimethylhydrazine[2]
Other names
  • N,N'-Dimethylhydrazine[1]
  • sym-Dimethylhydrazine[1]
  • Hydrazomethane[1]
Identifiers
3D model (JSmol)
Abbreviations SDMH[1]
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.149.162 Edit this at Wikidata
KEGG
MeSH 1,2-Dimethylhydrazine
RTECS number
  • MV2625000
UNII
UN number 2382
  • InChI=1S/C2H8N2/c1-3-4-2/h3-4H,1-2H3 checkY
    Key: DIIIISSCIXVANO-UHFFFAOYSA-N checkY
  • CNNC
Properties[3]
C2H8N2
Molar mass 60.100 g·mol−1
Appearance Colourless liquid
Odor Fishy, ammoniacal
Density 827.4 kg m−3 (at 20 °C)
Melting point −9 °C (16 °F; 264 K)
Boiling point 87 °C; 188 °F; 360 K
Miscible
Thermochemistry
171.04 J K−1 mol−1
199.15 J K−1 mol−1
−1987–−1978 kJ mol−1
Hazards
GHS labelling:[4]
GHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Danger
H301, H311, H331, H350, H411
P201, P202, P261, P264, P270, P271, P273, P280, P281, P301+P310, P302+P352, P304+P340, P308+P313, P311, P312, P322, P330, P361, P363, P391, P403+P233, P405
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Symmetrical dimethylhydrazine (SDMH), or 1,2-dimethylhydrazine, is the organic compound with the formula (CH3NH)2. It is one of the two isomers of dimethylhydrazine. Both isomers are colorless liquids at room temperature, with properties similar to those of methylamines. Symmetrical dimethylhydrazine is a potent carcinogen that acts as a DNA methylating agent.[5][6] The compound has no commercial value, in contrast to its isomer unsymmetrical dimethylhydrazine (1,1-dimethylhydrazine, UDMH), which is used as a rocket fuel.[7] Symmetrical dimethylhydrazine is more toxic than unsymmetrical dimethylhydrazine and is therefore an unwanted impurity in UDMH.[8]

It is used to induce colon tumors in experimental animals—particularly mice and feline cell samples.[2][9][10]

  1. ^ a b c d 74-79-3 1,2-Dimethylhydrazine
  2. ^ a b 1,2-Dimethylhydrazine from PubChem
  3. ^ Record of 1,2-Dimethylhydrazin in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 21 March 2008.
  4. ^ "1,2-Dimethylhydrazine". pubchem.ncbi.nlm.nih.gov. Retrieved 22 December 2021.
  5. ^ Salehi, Alireza; Hosseini, Seyed Mohammad; Kazemi, Sohrab (2022-06-23). "Antioxidant and Anticarcinogenic Potentials of Propolis for Dimethylhydrazine-Induced Colorectal Cancer in Wistar Rats". BioMed Research International. 2022: e8497562. doi:10.1155/2022/8497562. ISSN 2314-6133. PMC 9246617. PMID 35782078.
  6. ^ Valaei, Amirhasan; Azadeh, Fatemeh; Mostafavi Niaki, Seyedeh Talayeh; Salehi, Alireza; Shakib Khoob, Maede; Mirebrahimi, Seyed Hesam odin; Kazemi, Sohrab; Hosseini, Seyed Mohammad (2022-10-10). "Antioxidant and Anticancer Potentials of the Olive and Sesame Mixture against Dimethylhydrazine-Induced Colorectal Cancer in Wistar Rats". BioMed Research International. 2022: e5440773. doi:10.1155/2022/5440773. ISSN 2314-6133. PMC 9576397. PMID 36262974.
  7. ^ Gangadhar Choudhary, Hugh Hansen (August 1998). "Human health perspective of environmental exposure to hydrazines: A review". Chemosphere. 37 (5): 801–843. Bibcode:1998Chmsp..37..801C. doi:10.1016/S0045-6535(98)00088-5. PMID 9717244.
  8. ^ Schmidt, Eckart W. (2022). "Dimethylhydrazines". Encyclopedia of Liquid Fuels. De Gruyter. pp. 1333–1499. doi:10.1515/9783110750287-016. ISBN 978-3-11-075028-7.
  9. ^ Cruse, J. P.; Lewin, M. R.; Ferulano, G. P.; Clark, C. G. (December 1978). "Co-carcinogenic effects of dietary cholesterol in experimental colon cancer". Nature. 276 (5690): 822–5. Bibcode:1978Natur.276..822C. doi:10.1038/276822a0. PMID 723955. S2CID 4303843.
  10. ^ Wijnands, M.V.W. (April 1999). "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". Carcinogenesis. 20 (4): 651–6. doi:10.1093/carcin/20.4.651. PMID 10223195.