アミノアセトニトリル
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/06/19 01:15:29」(JST)
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Aminoacetonitrile
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| Names |
| IUPAC name
2-Aminoacetonitrile[1]
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| Identifiers |
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CAS Number
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540-61-4 Y |
| ChemSpider |
10439 Y |
| EC Number |
208-751-8 |
| Jmol 3D model |
Interactive image |
| MeSH |
Aminoacetonitrile |
| PubChem |
10901 |
| RTECS number |
AL7750000 |
| UNII |
3739OQ10IJ Y |
InChI
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InChI=1S/C2H4N2/c3-1-2-4/h1,3H2 Y
Key: DFNYGALUNNFWKJ-UHFFFAOYSA-N Y
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| Properties |
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Chemical formula
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C2H4N2 |
| Molar mass |
56.07 g·mol−1 |
| Appearance |
Colourless liquid |
| Boiling point |
58.1 °C; 136.5 °F; 331.2 K at 2.0 kPa |
| Hazards |
| GHS pictograms |
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| GHS signal word |
WARNING |
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GHS hazard statements
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H302, H312, H332, H351 |
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GHS precautionary statements
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P280 |
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EU classification (DSD)
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Xn |
| R-phrases |
R20/21/22, R40 |
| S-phrases |
S36 |
| Related compounds |
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Related alkanenitriles
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- Hydrogen cyanide
- Thiocyanic acid
- Cyanogen iodide
- Cyanogen bromide
- Cyanogen chloride
- Cyanogen fluoride
- Acetonitrile
- Glycolonitrile
- Cyanogen
- Propanenitrile
- Aminopropionitrile
- Malononitrile
- Pivalonitrile
- Acetone cyanohydrin
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Related compounds
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DBNPA |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Y verify (what is YN ?) |
| Infobox references |
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Aminoacetonitrile is a simple organic compound containing both nitrile and amino groups. It is somewhat similar to the simplest amino acid, glycine. This compound is commercially available as the chloride and sulfate salts.
Contents
- 1 Production and applications
- 2 Occurrence in the interstellar medium
- 3 External links
- 4 References
Production and applications
Industrially aminoacetonitrile is produced from glycolonitrile by reaction with ammonia:
- HOCH2CN + NH3 → H2NCH2CN + H2O
The aminoacetonitrile can be hydrolysed to give glycine:[2]
Aminoacetonitrile derivatives are useful anthelmintics. They act as nematode specific ACh agonists[3] causing a spastic paralysis and rapid expulsion from the host.
Occurrence in the interstellar medium
In 2008, aminoacetonitrile was discovered in the Large Molecule Heimat, a giant gas cloud near the galactic center in the constellation Sagittarius by the Max Planck Institute for Radio Astronomy.[4] This discovery is significant to the debate on whether glycine exists widely in the universe.
External links
- Property data at the National Institute of Standards and Technology (NIST)
References
- ^ "Aminoacetonitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification. Retrieved 5 June 2012.
- ^ Peter Pollak, Gérard Romeder, Ferdinand Hagedorn, Heinz-Peter Gelbke "Nitriles" Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_363
- ^ Kaminsky, R.; Ducray, P.; Jung, M.; Clover, R.; Rufener, L.; Bouvier, J.; Weber, S. S.; Wenger, A.; Wieland-Berghausen, S.; et al. (2008). "A new class of anthelmintics effective against drug-resistant nematodes". Nature 452 (7184): 176–180. Bibcode:2008Natur.452..176K. doi:10.1038/nature06722. PMID 18337814.
- ^ Belloche, A.; Menten, K. M.; Comito, C.; Müller, H. S. P.; Schilke, P.; Ott, J.; Thorwirth, S.; Hieret, C. (2008). "Detection of amino acetonitrile in Sgr B2(N)" (pdf). Astronomy and Astrophysics 482 (1): 179–196. arXiv:0801.3219. Bibcode:2008A&A...482..179B. doi:10.1051/0004-6361:20079203.
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Molecules detected in outer space
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| Molecules |
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Deuterated
molecules |
- Ammonia
- Ammonium ion
- Formaldehyde
- Formyl radical
- Heavy water
- Hydrogen cyanide
- Hydrogen deuteride
- Hydrogen isocyanide
- Methylacetylene
- N2D+
- Trihydrogen cation
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| Unconfirmed |
- Anthracene
- Dihydroxyacetone
- Ethyl methyl ether
- Glycine
- Graphene
- H2NCO+
- Linear C5
- Naphthalene cation
- Phosphine
- Pyrene
- Silylidine
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| Related |
- Abiogenesis
- Astrobiology
- Astrochemistry
- Atomic and molecular astrophysics
- Chemical formula
- Circumstellar envelope
- Cosmic dust
- Cosmic ray
- Cosmochemistry
- Diffuse interstellar band
- Extraterrestrial life
- Extraterrestrial liquid water
- Forbidden mechanism
- Helium hydride ion
- Homochirality
- Intergalactic dust
- Interplanetary medium
- Interstellar medium
- Iron–sulfur world theory
- Kerogen
- Life
- Molecules in stars
- Nexus for Exoplanet System Science
- Organic compound
- Outer space
- PAH world hypothesis
- Panspermia
- Polycyclic aromatic hydrocarbon (PAH)
- RNA world hypothesis
- Spectroscopy
- Tholin
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- Book:Chemistry
- Category:Astrochemistry
- Category:Molecules
- Portal:Astrobiology
- Portal:Chemistry
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English Journal
- Comparison of biotransformation and efficacy of aminoacetonitrile anthelmintics in vitro.
- Stuchlíková L1, Lecová L, Jirásko R, Lamka J, Vokřál I, Szotáková B, Holčapek M, Skálová L.
- Drug testing and analysis.Drug Test Anal.2015 Apr 28. doi: 10.1002/dta.1806. [Epub ahead of print]
- The present in vitro study was designed to test and compare anthelmintic activity, hepatotoxicity, and biotransformation of four selected aminoacetonitrile derivatives (AADs): monepantel (MOP, anthelmintic approved for the treatment), AAD-970, AAD-1154, and AAD-1336. Micro-agar larval development te
- PMID 25922167
- Catalytic asymmetric mannich-type reaction of N-alkylidene-α-aminoacetonitrile with ketimines.
- Lin S1, Kawato Y, Kumagai N, Shibasaki M.
- Angewandte Chemie (International ed. in English).Angew Chem Int Ed Engl.2015 Apr 20;54(17):5183-6. doi: 10.1002/anie.201412377. Epub 2015 Mar 3.
- Optically active vicinal diamines are versatile chiral building blocks in organic synthesis. A soft Lewis acid/hard Brønsted base cooperative catalyst allows for an efficient stereoselective coupling of N-alkylidene-α-aminoacetonitrile and ketimines to access this class of compounds bearing consec
- PMID 25736268
- Monepantel induces hepatic cytochromes p450 in sheep in vitro and in vivo.
- Stuchlíková L1, Matoušková P1, Bártíková H1, Vokřál I2, Lamka J2, Štolcová T1, Pětníková H1, Szotáková B1, Kubíček V3, Skálová L4.
- Chemico-biological interactions.Chem Biol Interact.2015 Feb 5;227:63-8. doi: 10.1016/j.cbi.2014.12.025. Epub 2014 Dec 31.
- Monepantel (MOP), a new amino-acetonitrile anthelmintic for the treatment and control of gastrointestinal nematode infections and associated diseases in sheep, is approved and marketed as oral solution under the trade name Zolvix® (Novartis Animal Health Inc., Switzerland). The effect of MOP on hep
- PMID 25555458
Japanese Journal
- "P-28 Study of reversibility in rat bone changes induced by beta-aminopropionitrile or aminoacetonitrile
- Teranishi Munehiro,Sato Satoko,Igarashi Isao,Matsumoto Etsuji,Yamoto Takashi,Manabe Sunao
- Journal of toxicological sciences 21(5), 380, 1996-12-20
- NAID 110001805942
- Involvement of CYP2E in 8-Hydroxylation of Theophylline in Mouse Hepatic Microsomes-Difference from Its N-Demethylations
- KONISHI Hiroki,MORITA Kunihiko,YAMAJI Akira
- Biological & pharmaceutical bulletin 19(4), 593-598, 1996-04-15
- … The 8-hydroxylation at a substrate concentration, where most of the total activity was attributed to the catalysis of the high-capacity phase, was markedly impaired by CYP2E inhibitors such as 4-methylpyrazole and aminoacetonitrile, whereas the N-demethylations were little affected by these agents. …
- NAID 110003641220
- メタンとアンモニヤからアミノアセトニトリルと2-アミノプロピオニトリルの生成について
Related Links
- Aminoacetonitrileとは？goo Wikipedia (ウィキペディア) 。出典：Wikipedia（ウィキペディア）フリー百科事典。 Aminoacetonitrileとは - goo Wikipedia (ウィキペディア) gooトップ サイトマップ スタートページに設定 RSS ヘルプ メニューへ ...
- [Aminoacetonitrile Hydrogen Sulfate] [151-63-3] | 価格や在庫、物性値などの詳細情報ページです。 ... 別名 (英名) Aminomethylcyanide Hydrogen Sulfate 別名 (英名) Cyanomethylamine Hydrogen Sulfate 別名 (英名) Glycinonitrile ...
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