Symmetrical dimethylhydrazine

Last updated
Symmetrical dimethylhydrazine
Dimethylhydrazin.svg
1,2-dimethylhydrazine-3D-balls.png
Names
Preferred IUPAC name
1,2-Dimethylhydrazine [1]
Other names
  • N,N'-Dimethylhydrazine [2]
  • sym-Dimethylhydrazine [2]
  • Hydrazomethane [2]
Identifiers
3D model (JSmol)
AbbreviationsSDMH [2]
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.149.162 OOjs UI icon edit-ltr-progressive.svg
KEGG
MeSH 1,2-Dimethylhydrazine
PubChem CID
RTECS number
  • MV2625000
UNII
UN number 2382
  • InChI=1S/C2H8N2/c1-3-4-2/h3-4H,1-2H3 Yes check.svgY
    Key: DIIIISSCIXVANO-UHFFFAOYSA-N Yes check.svgY
  • CNNC
Properties [3]
C2H8N2
Molar mass 60.100 g·mol−1
AppearanceColourless 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
Std molar
entropy
(S298)
199.15 J K−1 mol−1
−1987–−1978 kJ mol−1
Hazards
GHS labelling: [4]
GHS-pictogram-skull.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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. [1] [9] [10]

Related Research Articles

<span class="mw-page-title-main">Carcinogen</span> Substance, radionuclide, or radiation directly involved in causing cancer

A carcinogen is any agent that promotes the development of cancer. Carcinogens can include synthetic chemicals, naturally occurring substances, physical agents such as ionizing and non-ionizing radiation, and biologic agents such as viruses and bacteria. Most carcinogens act by creating mutations in DNA that disrupt a cell's normal processes for regulating growth, leading to uncontrolled cellular proliferation. This occurs when the cell's DNA repair processes fail to identify DNA damage allowing the defect to be passed down to daughter cells. The damage accumulates over time. This is typically a multi-step process during which the regulatory mechanisms within the cell are gradually dismantled allowing for unchecked cellular division.

<span class="mw-page-title-main">Mutagen</span> Physical or chemical agent that increases the rate of genetic mutation

In genetics, a mutagen is a physical or chemical agent that permanently changes genetic material, usually DNA, in an organism and thus increases the frequency of mutations above the natural background level. As many mutations can cause cancer in animals, such mutagens can therefore be carcinogens, although not all necessarily are. All mutagens have characteristic mutational signatures with some chemicals becoming mutagenic through cellular processes.

<span class="mw-page-title-main">Daminozide</span> Chemical compound

Daminozide, also known as aminozide, Alar, Kylar, SADH, B-995, B-nine, and DMASA, is an organic compound which acts as a plant growth regulator. It was produced in the U.S. by the Uniroyal Chemical Company, Inc.,, which registered daminozide for use on fruits intended for human consumption in 1963. It was primarily used on apples until 1989, when the manufacturer voluntarily withdrew it after the U.S. Environmental Protection Agency proposed banning it based on concerns about cancer risks to consumers. In addition to apples and ornamental plants, Uniroyal also registered daminozide for use on cherries, peaches, pears, Concord grapes, tomato transplants, and peanut vines.

Unsymmetrical dimethylhydrazine (abbreviated as UDMH; also known as 1,1-dimethylhydrazine, heptyl or Geptil) is a chemical compound with the formula H2NN(CH3)2 that is primarily used as a rocket propellant. At room temperature, UDMH is a colorless liquid, with a sharp, fishy, ammonia-like smell typical of organic amines. Samples turn yellowish on exposure to air and absorb oxygen and carbon dioxide. It is miscible with water, ethanol, and kerosene. At concentrations between 2.5% and 95% in air, its vapors are flammable. It is not sensitive to shock.

Monomethylhydrazine (MMH) is a highly toxic, volatile hydrazine derivative with the chemical formula CH6N2. It is used as a rocket propellant in bipropellant rocket engines because it is hypergolic with various oxidizers such as nitrogen tetroxide and nitric acid. As a propellant, it is described in specification MIL-PRF-27404.

Genotoxicity is the property of chemical agents that damage the genetic information within a cell causing mutations, which may lead to cancer. While genotoxicity is often confused with mutagenicity, all mutagens are genotoxic, but some genotoxic substances are not mutagenic. The alteration can have direct or indirect effects on the DNA: the induction of mutations, mistimed event activation, and direct DNA damage leading to mutations. The permanent, heritable changes can affect either somatic cells of the organism or germ cells to be passed on to future generations. Cells prevent expression of the genotoxic mutation by either DNA repair or apoptosis; however, the damage may not always be fixed leading to mutagenesis.

<span class="mw-page-title-main">Methylcholanthrene</span> Chemical compound

Methylcholanthrene is a highly carcinogenic polycyclic aromatic hydrocarbon produced by burning organic compounds at very high temperatures. Methylcholanthrene is also known as 3-methylcholanthrene, 20-methylcholanthrene or the IUPAC name 3-methyl-1,2-dyhydrobenzo[j]aceanthrylene. The short notation often used is 3-MC or MCA. This compound forms pale yellow solid crystals when crystallized from benzene and ether. It has a melting point around 180 °C and its boiling point is around 280 °C at a pressure of 80 mmHg. Methylcholanthrene is used in laboratory studies of chemical carcinogenesis. It is an alkylated derivative of benz[a]anthracene and has a similar UV spectrum. The most common isomer is 3-methylcholanthrene, although the methyl group can occur in other places.

<span class="mw-page-title-main">Nitrosamine</span> Organic compounds of the form >N–N=O

In organic chemistry, nitrosamines are organic compounds with the chemical structure R2N−N=O, where R is usually an alkyl group. They feature a nitroso group bonded to a deprotonated amine. Most nitrosamines are carcinogenic in nonhuman animals. A 2006 systematic review supports a "positive association between nitrite and nitrosamine intake and gastric cancer, between meat and processed meat intake and gastric cancer and oesophageal cancer, and between preserved fish, vegetable and smoked food intake and gastric cancer, but is not conclusive".

<span class="mw-page-title-main">Caffeic acid</span> Chemical compound

Caffeic acid is an organic compound with the formula (HO)2C6H3CH=CHCO2H. It is a polyphenol. It is a yellow solid. Structurally, it is classified as a hydroxycinnamic acid. The molecule consists of both phenolic and acrylic functional groups. It is found in all plants as an intermediate in the biosynthesis of lignin, one of the principal components of biomass and its residues. It is unrelated to caffeine.

<span class="mw-page-title-main">Nitroso</span> Class of functional groups with a –N=O group attached

In organic chemistry, nitroso refers to a functional group in which the nitric oxide group is attached to an organic moiety. As such, various nitroso groups can be categorized as C-nitroso compounds, S-nitroso compounds, N-nitroso compounds, and O-nitroso compounds.

<span class="mw-page-title-main">Hydrazines</span> Class of chemical compounds

Hydrazines (R2N−NR2) are a class of chemical compounds with two nitrogen atoms linked via a covalent bond and which carry from one up to four alkyl or aryl substituents. Hydrazines can be considered as derivatives of the inorganic hydrazine (H2N−NH2), in which one or more hydrogen atoms have been replaced by hydrocarbon groups.

<i>tert</i>-Butylhydroquinone Chemical compound

tert-Butylhydroquinone is a synthetic aromatic organic compound which is a type of phenol. It is a derivative of hydroquinone, substituted with a tert-butyl group.

4-Aminobiphenyl (4-ABP) is an organic compound with the formula C6H5C6H4NH2. It is an amine derivative of biphenyl. It is a colorless solid, although aged samples can appear colored. 4-Aminobiphenyl was commonly used in the past as a rubber antioxidant and an intermediate for dyes. Exposure to this aryl-amine can happen through contact with chemical dyes and from inhalation of cigarette smoke. Researches showed that 4-aminobiphenyl is responsible for bladder cancer in humans and dogs by damaging DNA. Due to its carcinogenic effects, commercial production of 4-aminobiphenyl ceased in the United States in the 1950s.

<span class="mw-page-title-main">DNA adduct</span> Segment of DNA bound to a cancer-causing chemical

In molecular genetics, a DNA adduct is a segment of DNA bound to a cancer-causing chemical. This process could lead to the development of cancerous cells, or carcinogenesis. DNA adducts in scientific experiments are used as biomarkers of exposure. They are especially useful in quantifying an organism's exposure to a carcinogen. The presence of such an adduct indicates prior exposure to a potential carcinogen, but it does not necessarily indicate the presence of cancer in the subject animal.

<span class="mw-page-title-main">Dibutyltryptamine</span> Chemical compound

N,N-Dibutyltryptamine (DBT) is a psychedelic drug belonging to the tryptamine family. It is found either as its crystalline hydrochloride salt or as an oily or crystalline base. DBT was first synthesized by the chemist Alexander Shulgin and reported in his book TiHKAL . Shulgin did not test DBT himself, but reports a human dosage of "1 mg/kg i.m." being active, but less so than DMT or DET. This suggests that an active dosage of DBT will be in the 100 mg range. This compound has been sold as a "research chemical" and has been confirmed to be an active hallucinogen although somewhat weaker than other similar tryptamine derivatives. It produces a head-twitch response in mice.

<i>o</i>-Toluidine Aryl amine

o-Toluidine (ortho-toluidine) is an organic compound with the chemical formula CH3C6H4NH2. It is the most important of the three isomeric toluidines. It is a colorless liquid although commercial samples are often yellowish. It is a precursor to the herbicides metolachlor and acetochlor.

<span class="mw-page-title-main">Methylated-DNA-protein-cysteine methyltransferase</span> Mammalian protein found in Homo sapiens

Methylated-DNA--protein-cysteine methyltransferase(MGMT), also known as O6-alkylguanine DNA alkyltransferaseAGT, is a protein that in humans is encoded by the MGMT gene. MGMT is crucial for genome stability. It repairs the naturally occurring mutagenic DNA lesion O6-methylguanine back to guanine and prevents mismatch and errors during DNA replication and transcription. Accordingly, loss of MGMT increases the carcinogenic risk in mice after exposure to alkylating agents. The two bacterial isozymes are Ada and Ogt.

<span class="mw-page-title-main">Aloe emodin</span> Chemical compound

Aloe emodin is an anthraquinone and an isomer of emodin present in aloe latex, an exudate from the aloe plant. It has a strong stimulant-laxative action. Aloe emodin is not carcinogenic when applied to the skin, although it may increase the carcinogenicity of some kinds of radiation.

Mouse models of colorectal cancer and intestinal cancer are experimental systems in which mice are genetically manipulated, fed a modified diet, or challenged with chemicals to develop malignancies in the gastrointestinal tract. These models enable researchers to study the onset, progression of the disease, and understand in depth the molecular events that contribute to the development and spread of colorectal cancer. They also provide a valuable biological system, to simulate human physiological conditions, suitable for testing therapeutics.

<span class="mw-page-title-main">Tetrachloro-1,2-difluoroethane</span> Chemical compound

Tetrachloro-1,2-difluoroethane is a chlorofluorocarbon known as Freon 112, CFC-112 or R-112. It has a symmetrical structure CCl2FCCl2F and so can be called symmetrical tetrachlorodifluoroethane. "Symmetrical" may also be abbreviated to "s-" or "sym-". In contrast an asymmetrical isomer has formula CCl3CClF2.

References

  1. 1 2 1,2-Dimethylhydrazine from PubChem
  2. 1 2 3 4 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.