Symmetrical dimethylhydrazine

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 ~~o~~ 298)

| 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).

N verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

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. ↑ 1.0 1.1 1.2 1.3 74-79-3 1,2-Dimethylhydrazine
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.

* v
* t
* e

Hydrazines

* 4-PTSC
* Acylhydrazine
* ADH
* Adjudin
* Agaritine
* Benmoxin
* Cadralazine
* Carbazide
* Carbidopa
* Carbohydrazide
* Daminozide
* Dihydralazine
* DNPH
* Endralazine
* Gyromitrin
* HBT
* Hydralazine
* Hydrazide
* Hydrazine
* Hydrazone
* Iproclozide
* Iproniazid
* Isocarboxazid
* Isoniazid
* Mebanazine
* Metfendrazine
* MMH
* Nialamide
* Octamoxin
* PEH
* Phenelzine
* Pheniprazine
* Phenoxypropazine
* Phenylhydrazine
* Pildralazine
* Pimagedine
* Pivalylbenzhydrazine
* Procarbazine
* Safrazine
* Semicarbazide
* Semicarbazone
* SDMH
* Tetrafluorohydrazine
* UDMH

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*[CID]: Compound ID
*[H301]: Toxic if swallowed
*[H311]: Toxic in contact with skin
*[H331]: Toxic if inhaled
*[H350]: May cause cancer
*[H411]: Toxic to aquatic life with long lasting effects
*[P201]: Obtain special instructions before use
*[P202]: Do not handle until all safety precautions have been read and understood
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P270]: Do not eat, drink or smoke when using this product
*[P271]: Use only outdoors or in a well-ventilated area
*[P273]: Avoid release to the environment
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P281]: Use personal protective equipment as required
*[P301+310]: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P308+313]: IF exposed or concerned: Get medical advice/attention
*[P311]: Call a POISON CENTER or doctor/physician
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P322]: Specific measures (see … on this label)
*[P330]: Rinse mouth
*[P361]: Remove/Take off immediately all contaminated clothing
*[P363]: Wash contaminated clothing before reuse
*[P391]: Collect spillage
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P405]: Store locked up
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