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Chemical Compound Review

Allylkyanid     but-3-enenitrile

Synonyms: Allylnitrile, Allyl cyanide, NSC-2583, AG-K-61474, ACMC-209949, ...
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Disease relevance of Allyl cyanide

  • Allylnitrile: a compound which induces long-term dyskinesia in mice following a single administration [1].
  • This inhibition was reversed by either sulpiride (0.15 mumol/kg i.v.) or haloperidol (0.13 mumol/kg i.v.) but not by yohimbine (0.14 mumol/kg i.v.). TL-350 did not change isoproterenol-induced tachycardia and hypotensive responses [2].
  • In a dose-dependent manner, allylnitrile caused corneal opacity and gliosis in the retina and olfactory bulbs, decreased rearing activity and increased the rating scores in tests of vestibular dysfunction, and induced hair cell loss in both the vestibular sensory epithelia and the organ of Corti [3].
  • The daily dietary intake of allylnitrile was estimated to be at least 0.12 micromol/kg body weight for Japanese, based on its generation from the vegetables, broccoli, cabbage, cauliflower and Chinese cabbage and their daily dietary consumption [4].
  • A dose-dependent inhibition of cyanide formation arising from allylnitrile in the liver and a dose-dependent attenuation of acute toxicity of allylnitrile were observed when CCl4 was given just prior to the nitrile administration in rats and mice [5].

High impact information on Allyl cyanide


Chemical compound and disease context of Allyl cyanide


Biological context of Allyl cyanide

  • It is conceivable that allylnitrile caused apoptotic changes in neurons but did not always lead them to cell death immediately [10].
  • The results suggest that active metabolites of allylnitrile are responsible for the head twitching, and that CCl4 prevents the metabolic process in the liver by forming conjugates with allylnitrile, resulting in the inhibition of the head twitching [5].

Anatomical context of Allyl cyanide


Associations of Allyl cyanide with other chemical compounds


Gene context of Allyl cyanide


Analytical, diagnostic and therapeutic context of Allyl cyanide

  • Using a combination of local -- scanning tunneling microscopy -- and spatially integrated, but chemically sensitive probes -- X-ray photoelectron spectroscopy and near edge X-ray absorption fine structure spectroscopy -- we have examined how 3-butenenitrile reacts with the Si(001)-2 x 1 surface at room temperature [15].


  1. Allylnitrile: a compound which induces long-term dyskinesia in mice following a single administration. Tanii, H., Kurosaka, Y., Hayashi, M., Hashimoto, K. Exp. Neurol. (1989) [Pubmed]
  2. TL-350, an ergoline derivative with dopamine receptor agonist properties. Ilhan, M., Long, J.P., Bhatnagar, R., Flynn, J., Cannon, J.G., Lee, T. J. Pharmacol. Exp. Ther. (1984) [Pubmed]
  3. Behavioural disturbances and sensory pathology following allylnitrile exposure in rats. Balbuena, E., Llorens, J. Brain Res. (2001) [Pubmed]
  4. Allylnitrile: generation from cruciferous vegetables and behavioral effects on mice of repeated exposure. Tanii, H., Takayasu, T., Higashi, T., Leng, S., Saijoh, K. Food Chem. Toxicol. (2004) [Pubmed]
  5. Effect of carbon tetrachloride on allylnitrile-induced head twitching. Tanii, H., Hashimoto, K., Harada, A. Environmental research. (1993) [Pubmed]
  6. Kinetics, thermodynamics, and effect of BPh3 on competitive C-C and C-H bond activation reactions in the interconversion of allyl cyanide by [Ni(dippe)]. Brunkan, N.M., Brestensky, D.M., Jones, W.D. J. Am. Chem. Soc. (2004) [Pubmed]
  7. Behavioral syndrome induced by allylnitrile, crotononitrile or 2-pentenenitrile in rats. Tanii, H., Hayashi, M., Hashimoto, K. Neuropharmacology (1991) [Pubmed]
  8. Alterations in the metabolism of serotonin and dopamine in the mouse brain following a single administration of allylnitrile, which induces long-term dyskinesia. Tanii, H., Okayama, A., Yamatodani, A., Hayashi, M., Hashimoto, K. Toxicol. Lett. (1991) [Pubmed]
  9. Removal of nitriles from synthetic wastewater by acrylonitrile utilizing bacteria. Wang, C.C., Lee, C.M., Chen, L.J. Journal of environmental science and health. Part A, Toxic/hazardous substances & environmental engineering. (2004) [Pubmed]
  10. Behavioral abnormalities and apoptotic changes in neurons in mice brain following a single administration of allylnitrile. Zang, X.P., Tanii, H., Kobayashi, K., Higashi, T., Oka, R., Koshino, Y., Saijoh, K. Arch. Toxicol. (1999) [Pubmed]
  11. Involvement of GABA neurons in allylnitrile-induced dyskinesia. Tanii, H., Zang, X., Saito, N., Saijoh, K. Brain Res. (2000) [Pubmed]
  12. In vitro digestion of sinigrin and glucotropaeolin by single strains of Bifidobacterium and identification of the digestive products. Cheng, D.L., Hashimoto, K., Uda, Y. Food Chem. Toxicol. (2004) [Pubmed]
  13. Metabolism of allylnitrile to cyanide: in vitro studies. Farooqui, M.Y., Ybarra, B., Piper, J. Res. Commun. Chem. Pathol. Pharmacol. (1993) [Pubmed]
  14. Fos induction in the brain of mice exhibiting behavioral abnormalities following administration of allylnitrile or crotononitrile. Tanii, H., Higashi, T., Oka, R., Saijoh, K. Brain Res. (2000) [Pubmed]
  15. Surface reactions of 3-butenenitrile on the Si(001)-2 x 1 surface at room temperature. Rangan, S., Bournel, F., Gallet, J.J., Kubsky, S., Le Guen, K., Dufour, G., Rochet, F., Sirotti, F., Piaszenski, G., Funke, R., Kneppe, M., Köhler, U. The journal of physical chemistry. B, Condensed matter, materials, surfaces, interfaces & biophysical. (2005) [Pubmed]
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