Symmetrical dimethylhydrazine

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]

Symmetrical dimethylhydrazine

Names
Preferred IUPAC name 1,2-Dimethylhydrazine[1]
Other names N,N'-Dimethylhydrazine[2] sym-Dimethylhydrazine[2] Hydrazomethane[2]
Identifiers
CAS Number	540-73-8 Y
3D model (JSmol)	Interactive image
Abbreviations	SDMH[2]
ChEBI	CHEBI:73755 Y
ChEMBL	ChEMBL162921 Y
ChemSpider	1282 Y
ECHA InfoCard	100.149.162
KEGG	C19176 Y
MeSH	1,2-Dimethylhydrazine
PubChem CID	1322
RTECS number	MV2625000
UNII	IX068S9745 Y
UN number	2382
CompTox Dashboard (EPA)	DTXSID0041228
InChI InChI=1S/C2H8N2/c1-3-4-2/h3-4H,1-2H3 Y Key: DIIIISSCIXVANO-UHFFFAOYSA-N Y
SMILES CNNC
Properties[3]
Chemical formula	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
Solubility in water	Miscible
Thermochemistry
Heat capacity (C)	171.04 J K−1 mol−1
Std molar entropy (S⦵298)	199.15 J K−1 mol−1
Std enthalpy of combustion (ΔcH⦵298)	−1987–−1978 kJ mol−1
Hazards
GHS labelling:[4]
Pictograms
Signal word	Danger
Hazard statements	H301, H311, H331, H350, H411
Precautionary statements	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	Biurea Daminozide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

It is used to induce colon tumors in experimental animals—particularly mice and feline cell samples.^[1][9][10]

References

1. 1,2-Dimethylhydrazine from PubChem
2. 74-79-3 1,2-Dimethylhydrazine
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.