Symmetrical dimethylhydrazine

Symmetrical dimethylhydrazine
Names
	Preferred IUPAC name 1,2-Dimethylhydrazine
	Other names N,N'-Dimethylhydrazine; sym-Dimethylhydrazine; Hydrazomethane;
Identifiers
CAS Number	540-73-8 ;
3D model (JSmol)	Interactive image;
Abbreviations	SDMH
ChEBI	CHEBI:73755 ;
ChEMBL	ChEMBL162921 ;
ChemSpider	1282 ;
KEGG	C19176 ;
MeSH	1,2-Dimethylhydrazine
PubChem CID	1322;
RTECS number	MV2625000;
UNII	IX068S9745 ;
UN number	2382
	InChI InChI=1S/C2H8N2/c1-3-4-2/h3-4H,1-2H3 Key: DIIIISSCIXVANO-UHFFFAOYSA-N ;
	SMILES CNNC;
Properties
Chemical formula	C2H8N2
Molar mass	60.100 g·mol−1
Appearance	Colourless liquid
Odor	Ichtyal, 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 (So298)	199.15 J K−1 mol−1
Std enthalpy of; combustion (ΔcH⦵298)	−1987–−1978 kJ mol−1
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H301, H311, H331, H350, H411
GHS precautionary statements	P201, P202, P261, P264, P270, P271, P273, P280, P281, P301+310, P302+352, P304+340, P308+313, P311, P312, P322, P330, P361, P363, P391, P403+233, 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).
	verify (what is ?)
	Infobox references

symmetrical dimethylhydrazine, 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), which is used as a rocket fuel.^[7]

It is used to induce colon tumors in experimental animals - particularly mice and feline cell samples.^[2]^[8]^[9]

References

↑ ^1.0 ^1.1 ^1.2 ^1.3 74-79-3 1,2-Dimethylhydrazine
↑ ^2.0 ^2.1 1,2-Dimethylhydrazine from PubChem
↑ Record of 1,2-Dimethylhydrazin in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 21 March 2008.
↑ "1,2-Dimethylhydrazine" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/1322#section=Safety-and-Hazards.
↑ Salehi, Alireza; Hosseini, Seyed Mohammad; Kazemi, Sohrab (2022-06-23). "Antioxidant and Anticarcinogenic Potentials of Propolis for Dimethylhydrazine-Induced Colorectal Cancer in Wistar Rats" (in en). BioMed Research International 2022: e8497562. doi:10.1155/2022/8497562. ISSN 2314-6133. PMID 35782078.
↑ 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" (in en). BioMed Research International 2022: e5440773. doi:10.1155/2022/5440773. ISSN 2314-6133. PMID 36262974.
↑ Gangadhar Choudhary, Hugh Hansen (1998). "Human health perspective of environmental exposure to hydrazines: A review". Chemosphere 37 (5): 801–843. doi:10.1016/S0045-6535(98)00088-5. PMID 9717244. Bibcode: 1998Chmsp..37..801C.
↑ Cruse, J. P.; Lewin, M. R.; Ferulano, G. P.; Clark, C. G. (1978). "Co-carcinogenic effects of dietary cholesterol in experimental colon cancer". Nature 276 (5690): 822–5. doi:10.1038/276822a0. PMID 723955. Bibcode: 1978Natur.276..822C.
↑ Wijnands, M.V.W. (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.

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Original source: https://en.wikipedia.org/wiki/Symmetrical dimethylhydrazine. Read more

[CAS-1] 1.0 ^1.1 ^1.2 ^1.3 74-79-3 1,2-Dimethylhydrazine

[PubChem_Compound-2] 2.0 ^2.1 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" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/1322#section=Safety-and-Hazards.

[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" (in en). BioMed Research International 2022: e8497562. doi:10.1155/2022/8497562. ISSN 2314-6133. 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" (in en). BioMed Research International 2022: e5440773. doi:10.1155/2022/5440773. ISSN 2314-6133. PMID 36262974.

[7] Gangadhar Choudhary, Hugh Hansen (1998). "Human health perspective of environmental exposure to hydrazines: A review". Chemosphere 37 (5): 801–843. doi:10.1016/S0045-6535(98)00088-5. PMID 9717244. Bibcode: 1998Chmsp..37..801C.

[8] Cruse, J. P.; Lewin, M. R.; Ferulano, G. P.; Clark, C. G. (1978). "Co-carcinogenic effects of dietary cholesterol in experimental colon cancer". Nature 276 (5690): 822–5. doi:10.1038/276822a0. PMID 723955. Bibcode: 1978Natur.276..822C.

[9] Wijnands, M.V.W. (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.

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Names


Preferred IUPAC name 1,2-Dimethylhydrazine^[2]
Other names N,N'-Dimethylhydrazine^[1] sym-Dimethylhydrazine^[1] Hydrazomethane^[1]
Identifiers
CAS Number	540-73-8^Y
3D model (JSmol)	Interactive image
Abbreviations	SDMH^[1]
ChEBI	CHEBI:73755^Y
ChEMBL	ChEMBL162921^Y
ChemSpider	1282^Y
KEGG	C19176^Y
MeSH	1,2-Dimethylhydrazine
PubChem CID	1322
RTECS number	MV2625000
UNII	IX068S9745^Y
UN number	2382
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	Ichtyal, 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^o₂₉₈)	199.15 J K⁻¹ mol⁻¹
Std enthalpy of combustion (Δ_cH^⦵₂₉₈)	−1987–−1978 kJ mol⁻¹
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H301, H311, H331, H350, H411
GHS precautionary statements	P201, P202, P261, P264, P270, P271, P273, P280, P281, P301+310, P302+352, P304+340, P308+313, P311, P312, P322, P330, P361, P363, P391, P403+233, 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

Symmetrical dimethylhydrazine

Topic: Chemistry

References