cyanamide

Summary

Summary: A cyanide compound which has been used as a fertilizer, defoliant and in many manufacturing processes. It often occurs as the calcium salt, sometimes also referred to as cyanamide. The citrated calcium salt is used in the treatment of alcoholism.

Top Publications

  1. Bonner A, Dalwai S, Marway J, Preedy V. Acute exposure to the nutritional toxin alcohol reduces brain protein synthesis in vivo. Metabolism. 2003;52:389-96 pubmed
    ..In the event that some regions were refractory to the deleterious effects of ethanol, we also predosed rats with cyanamide, an aldehyde dehydrogenase inhibitor (ie, cyanamide + ethanol), to increase endogenous acetaldehyde, a potent ..
  2. Soltys D, Rudzińska Langwald A, Gniazdowska A, Wisniewska A, Bogatek R. Inhibition of tomato (Solanum lycopersicum L.) root growth by cyanamide is due to altered cell division, phytohormone balance and expansin gene expression. Planta. 2012;236:1629-38 pubmed publisher
    b>Cyanamide (CA) has been reported as a natural compound produced by hairy vetch (Vicia villosa Roth.) and it was shown also to be an allelochemical, responsible for strong allelopathic potential in this species...
  3. Zhang X, Zhong W, Widholm J. Expression of a fungal cyanamide hydratase in transgenic soybean detoxifies cyanamide in tissue culture and in planta to provide cyanamide resistance. J Plant Physiol. 2005;162:1064-73 pubmed
    ..of soybean were transformed by particle bombardment with a vector pCHZ-II that carries the coding sequence for cyanamide hydratase (Cah), an enzyme that converts toxic cyanamide to urea, from the soil fungus Myrothecium verrucaria...
  4. Walton E, Wu R, Richardson A, Davy M, Hellens R, Thodey K, et al. A rapid transcriptional activation is induced by the dormancy-breaking chemical hydrogen cyanamide in kiwifruit (Actinidia deliciosa) buds. J Exp Bot. 2009;60:3835-48 pubmed publisher
    ..Kiwifruit vines are often treated with the dormancy-breaking chemical hydrogen cyanamide (HC) to increase and synchronize budbreak...
  5. Wehrstedt K, Wildner W, Güthner T, Holzrichter K, Mertschenk B, Ulrich A. Safe transport of cyanamide. J Hazard Mater. 2009;170:829-35 pubmed publisher
    For many years cyanamide (CAS no. 420-04-2) was not commercially available due to its unstable nature...
  6. Kamo T, Endo M, Sato M, Kasahara R, Yamaya H, Hiradate S, et al. Limited distribution of natural cyanamide in higher plants: occurrence in Vicia villosa subsp. varia, V. cracca, and Robinia pseudo-acacia. Phytochemistry. 2008;69:1166-72 pubmed
    b>Cyanamide (NH2CN) has recently been proven to be a natural product, although it has been synthesized for over 100 years for agricultural and industrial purposes...
  7. Kamo T, Sato M, Kato K, Hiradate S, Nakajima E, Fujii Y, et al. Quantification of cyanamide contents in herbaceous plants. Biosci Biotechnol Biochem. 2006;70:2310-2 pubmed
    b>Cyanamide (NH2CN) is found in nature, although it has long been recognized as an industrial product...
  8. Ophir R, Pang X, Halaly T, Venkateswari J, Lavee S, Galbraith D, et al. Gene-expression profiling of grape bud response to two alternative dormancy-release stimuli expose possible links between impaired mitochondrial activity, hypoxia, ethylene-ABA interplay and cell enlargement. Plant Mol Biol. 2009;71:403-23 pubmed publisher
    ..for a large-scale comparative analysis of bud responses to two stimuli of grape-bud dormancy release, hydrogen cyanamide (HC) and heat shock (HS)...
  9. Lorenzo de la Peña L, Montero Santos J, Benito Lozano M, Martín Cabrera F. [Acetaldehyde syndrome after laboral exposition to hydrogen cyanamide]. Med Clin (Barc). 2006;127:717-8 pubmed

More Information

Publications92

  1. Tambour S, Closon C, Tirelli E, Quertemont E. Effects of cyanamide and acetaldehyde accumulation on the locomotor stimulant and sedative effects of ethanol in mice. Behav Pharmacol. 2007;18:777-84 pubmed
    ..A number of studies have used the drug cyanamide in an attempt to clarify the role of acetaldehyde in the behavioral effects of ethanol...
  2. Powner M, Gerland B, Sutherland J. Synthesis of activated pyrimidine ribonucleotides in prebiotically plausible conditions. Nature. 2009;459:239-42 pubmed publisher
    ..The starting materials for the synthesis-cyanamide, cyanoacetylene, glycolaldehyde, glyceraldehyde and inorganic phosphate-are plausible prebiotic feedstock ..
  3. Halaly T, Pang X, Batikoff T, Crane O, Keren A, Venkateswari J, et al. Similar mechanisms might be triggered by alternative external stimuli that induce dormancy release in grape buds. Planta. 2008;228:79-88 pubmed publisher
    ..We compared the effects of heat shock (HS) and hydrogen cyanamide (HC) and demonstrated that HS leads to earlier and higher bud-break levels...
  4. Shahidullah M, Duncan A, Strachan P, Rafique K, Ball S, McPate M, et al. Role of catalase in the smooth muscle relaxant actions of sodium azide and cyanamide. Eur J Pharmacol. 2002;435:93-101 pubmed
    ..of this study was to determine the role of catalase in the smooth muscle relaxant actions of sodium azide and cyanamide. The effects of 3-amino-1,2,4-triazole suggested a role for this enzyme in the relaxant actions of sodium azide ..
  5. Maier Greiner U, Obermaier Skrobranek B, Estermaier L, Kammerloher W, Freund C, Wulfing C, et al. Isolation and properties of a nitrile hydratase from the soil fungus Myrothecium verrucaria that is highly specific for the fertilizer cyanamide and cloning of its gene. Proc Natl Acad Sci U S A. 1991;88:4260-4 pubmed
    ..hydrophobic chromatography to homogeneity; this protein catalyzed the stoichiometric hydration of the fertilizer cyanamide to urea with high substrate specificity. This cyanamide hydratase (urea hydro-lyase; EC 4.2.1...
  6. Mitani N, Aihara M, Yamakawa Y, Yamada M, Itoh N, Mizuki N, et al. Drug-induced hypersensitivity syndrome due to cyanamide associated with multiple reactivation of human herpesviruses. J Med Virol. 2005;75:430-4 pubmed
    ..A 46-year-old Japanese man is described in whom a generalized eruption developed about 1 month after taking cyanamide, a drug for alcoholism...
  7. Hashimoto K, Hoshii Y, Takahashi M, Mitsuno S, Hanai N, Watanabe Y, et al. Use of a monoclonal antibody against Lafora bodies for the immunocytochemical study of ground-glass inclusions in hepatocytes due to cyanamide. Histopathology. 2001;39:60-5 pubmed
    Ground-glass inclusions (GGIs) in hepatocytes are known to be associated with cyanamide treatment in patients with alcohol dependency...
  8. Soltys D, Rudzińska Langwald A, Kurek W, Gniazdowska A, Sliwinska E, Bogatek R. Cyanamide mode of action during inhibition of onion (Allium cepa L.) root growth involves disturbances in cell division and cytoskeleton formation. Planta. 2011;234:609-21 pubmed publisher
    b>Cyanamide is an allelochemical produced by hairy vetch (Vicia villosa Roth.). Its phyotoxic effect on plant growth was examined on roots of onion (Allium cepa L.) bulbs...
  9. Anastasi C, Buchet F, Crowe M, Helliwell M, Raftery J, Sutherland J. The search for a potentially prebiotic synthesis of nucleotides via arabinose-3-phosphate and its cyanamide derivative. Chemistry. 2008;14:2375-88 pubmed publisher
    ..The results of synthetic approaches involving phosphorylation, phosphate migration and 2,3-C--C bond construction are described herein...
  10. Or E, Vilozny I, Eyal Y, Ogrodovitch A. The transduction of the signal for grape bud dormancy breaking induced by hydrogen cyanamide may involve the SNF-like protein kinase GDBRPK. Plant Mol Biol. 2000;43:483-94 pubmed
    ..for an SNF-like protein kinase that is up-regulated upon chemical induction of dormancy release by hydrogen cyanamide (HC)...
  11. Niemela O, Parkkila S, Koll M, Preedy V. Generation of protein adducts with malondialdehyde and acetaldehyde in muscles with predominantly type I or type II fibers in rats exposed to ethanol and the acetaldehyde dehydrogenase inhibitor cyanamide. Am J Clin Nutr. 2002;76:668-74 pubmed
    ..Alcoholic myopathy is known to primarily affect type II muscle fibers (glycolytic, fast-twitch, anaerobic), whereas type I fibers (oxidative, slow-twitch, aerobic) are relatively protected...
  12. De Haro L. Disulfiram-like syndrome after hydrogen cyanamide professional skin exposure: two case reports in France. J Agromedicine. 2009;14:382-4 pubmed publisher
    Hydrogen cyanamide is a plant growth regulator used in agriculture to induce bud break in fruit trees...
  13. Kamo T, Hiradate S, Fujii Y. First isolation of natural cyanamide as a possible allelochemical from hairy vetch Vicia villosa. J Chem Ecol. 2003;29:275-83 pubmed
    b>Cyanamide was isolated from the leaves and stems of hairy vetch (Vicia villosa), guided by plant growth inhibitory activity against lettuce (Lectuca sativa) seedlings...
  14. Nakahara T, Hunter R, Hirano M, Uchimura H, McArdle A, Broome C, et al. Alcohol alters skeletal muscle heat shock protein gene expression in rats: these effects are moderated by sex, raised endogenous acetaldehyde, and starvation. Metabolism. 2006;55:843-51 pubmed
    ..5 hours before sacrifice and compared to controls given a dose of saline (with or without pretreatment with cyanamide-an acetaldehyde dehydrogenase inhibitor which raises endogenous acetaldehyde); (iii) male rats starved for 1 or ..
  15. McVicker B, Tuma D, Kubik J, Tuma P, Casey C. Ethanol-induced apoptosis in polarized hepatic cells possibly through regulation of the Fas pathway. Alcohol Clin Exp Res. 2006;30:1906-15 pubmed
    ..The data presented here indicate that alcohol metabolism induces apoptosis in WIF-B cells that occurs, in part, by mechanisms involving signals emanating from death receptors. ..
  16. Tsanakopoulou M, Sutherland J. Cyanamide as a prebiotic phosphate activating agent - catalysis by simple 2-oxoacid salts. Chem Commun (Camb). 2017;53:11893-11896 pubmed publisher
    b>Cyanamide is a prebiotically plausible compound that has previously been invoked as a phosphate activating agent. However, its reactions with phosphate monoesters are very slow and tend to be low yielding...
  17. Wang C, Wang D, Xu F, Pan B, Wan B. Iron-catalyzed cycloaddition reaction of diynes and cyanamides at room temperature. J Org Chem. 2013;78:3065-72 pubmed publisher
    ..The lower reaction temperature, broad substrates scope, and inversed regioselectivity make it a complementary method to the previously developed iron catalytic system. ..
  18. Cheng C, Di S, Zhang W, Chen L, Tian Z, Zhou Z, et al. Determination of cyanamide residue in 21 plant-derived foods by liquid chromatography-tandem mass spectrometry. Food Chem. 2018;239:529-534 pubmed publisher
    b>Cyanamide is widely used in agriculture, and has a modest toxicity in humans. In the present study, a simple, sensitive, and widely applicable method for detecting cyanamide in 21 plant-derived foods was developed...
  19. Kamo T, Tokuoka Y, Miyazaki M. Quantification of canavanine, 2-aminoethanol, and cyanamide in Aphis craccivora and its host plants, Robinia pseudoacacia and Vicia angustifolia: effects of these compounds on larval survivorship of Harmonia axyridis. J Chem Ecol. 2012;38:1552-60 pubmed publisher
    ..In the present study, we determined the concentrations of cyanamide, canavanine, and 2-aminoethanol in A. craccivora infesting the two host plants. In the extracts of A...
  20. Kinoshita H, Ijiri I, Ameno S, Kubota T, Zhang X, Hishida S, et al. Cholinergic nerves mediate acetaldehyde action in the gastrointestinal tract. Alcohol Alcohol. 2001;36:377-80 pubmed
    ..AT), atropine methylbromide (ATMB), pirenzepine (PI), bethanechol (BE) and pilocarpine (PL) with or without cyanamide (CY; a potent inhibitor of aldehyde dehydrogenase, which induces high AcH concentration in blood)...
  21. Rodriguez A, Macia M, Navarro J. [Renal and hepatic failure secondary to cyanamide]. An Med Interna. 2003;20:603 pubmed
  22. Jagoda Cwiklik B, Wang X, Woo H, Yang J, Wang G, Zhou M, et al. Microsolvation of the dicyanamide anion: [N(CN)(2)(-)](H(2)O)n (n = 0-12). J Phys Chem A. 2007;111:7719-25 pubmed
    ..In all the hydrated clusters, the most stable structures consist of a water cluster solvating one end of the N(CN)(2)(-) anion. ..
  23. Liu L, Sun C, Liu X, He X, Liu M, Wu H, et al. Effect of calcium cyanamide, ammonium bicarbonate and lime mixture, and ammonia water on survival of Ralstonia solanacearum and microbial community. Sci Rep. 2016;6:19037 pubmed publisher
    The inorganic nitrogenous amendments calcium cyanamide (CC), ammonia water (AW), and a mixture of ammonium bicarbonate with lime (A+L) are popularly used as fumigants to control soil-borne disease in China...
  24. Barquero Romero J, Ruiz Calero R, Estepa Alonso M. [Carbimide overdosage: description of a case and review of the literature]. An Med Interna. 2005;22:607-8 pubmed
  25. Deaton D, Hassell A, McFadyen R, Miller A, Miller L, Shewchuk L, et al. Novel and potent cyclic cyanamide-based cathepsin K inhibitors. Bioorg Med Chem Lett. 2005;15:1815-9 pubmed
    ..from a PDE IV inhibitor hit derived from high throughput screening of the compound collection, a key pyrrolidine cyanamide pharmacophore was identified...
  26. Badejo A, Hodnette C, Dhaliwal J, Casey D, Pankey E, Murthy S, et al. Mitochondrial aldehyde dehydrogenase mediates vasodilator responses of glyceryl trinitrate and sodium nitrite in the pulmonary vascular bed of the rat. Am J Physiol Heart Circ Physiol. 2010;299:H819-26 pubmed publisher
    ..conditions and decreases in systemic arterial pressure in response to GTN and sodium nitrite were attenuated by cyanamide, an ALDH2 inhibitor, whereas responses to the NO donor, sodium nitroprusside (SNP), were not altered...
  27. Park P, Miller R, Shukla S. Acetylation of histone H3 at lysine 9 by ethanol in rat hepatocytes. Biochem Biophys Res Commun. 2003;306:501-4 pubmed
    ..Treatment of cells with ethanol metabolizing enzyme inhibitors (4-methylpyrazole and cyanamide) decreased ethanol-induced histone H3 acetylation at Lys(9)...
  28. Demko Z, Sharpless K. An intramolecular [2 + 3] cycloaddition route to fused 5-heterosubstituted tetrazoles. Org Lett. 2001;3:4091-4 pubmed
    ..Cyanates, thiocyanates, and cyanamides are all competent dipolarophiles for this reaction. A variety of scaffolds are tolerated when the new enclosed ring is five- or six-membered. ..
  29. West M, Biggs T, Tavares E, Lankford M, Myers R. Drinking patterns in genetic low-alcohol-drinking (LAD) rats after systemic cyanamide and cerebral injections of THP or 6-OHDA. Alcohol. 1998;15:239-47 pubmed
    ..Then a saline vehicle or either 10 or 20 mg/kg of the aldehyde dehydrogenase (AIDH) inhibitor, cyanamide, was injected s.c. twice daily for 3 days. Secondly, either 0.5 or 1...
  30. Austin P, Hall A, Snelgar W, Currie M. Modelling kiwifruit budbreak as a function of temperature and bud interactions. Ann Bot. 2002;89:695-706 pubmed
    ..Under this scenario, dormancy-breaking chemicals (such as hydrogen cyanamide, HC) enhance budbreak by diminishing the duration of suppression...
  31. Trébol I, Lasa O, Navajas B, Ratón J, Diaz Perez J. Allergic contact dermatitis from cyanamide. Dermatitis. 2005;16:32-3 pubmed
    b>Cyanamide (carbimide or calcium carbimide) has been used to treat chronic alcoholism for more than 45 years...
  32. Kamo T, Takemura T, Wasano N, Fujii Y, Hiradate S. Quantification of cyanamide in young seedlings of Vicia species, Lens culinaris, and Robinia pseudo-acacia by gas chromatography-mass spectrometry. Biosci Biotechnol Biochem. 2012;76:1416-8 pubmed
    We quantified the cyanamide content of young leaves of nine Vicia species, Lens culinaris, and Robinia pseudo-acacia using a modified analytical procedure that made it possible to measure the cyanamide content of a single leaf...
  33. Ghanayem B, Burka L, Matthews H. Metabolic basis of ethylene glycol monobutyl ether (2-butoxyethanol) toxicity: role of alcohol and aldehyde dehydrogenases. J Pharmacol Exp Ther. 1987;242:222-31 pubmed
    ..Pretreatment of rats with cyanamide (aldehyde dehydrogenase inhibitor) also significantly protected rats against BE-induced hematotoxicity and ..
  34. Åkerbladh L, Chow S, Odell L, Larhed M. Synthesis of 4H-Benzo[e][1,3]oxazin-4-ones by a Carbonylation-Cyclization Domino Reaction of ortho-Halophenols and Cyanamide. ChemistryOpen. 2017;6:620-628 pubmed publisher
    ..i>ortho-iodophenols are subjected to palladium-catalyzed carbonylative coupling with Mo(CO)6 and cyanamide, followed by a spontaneous, intramolecular cyclization to afford 4H-1,3-benzoxazin-4-ones in moderate to ..
  35. Nakagawa H. Photocontrollable nitric oxide (NO) and nitroxyl (HNO) donors and their release mechanisms. Nitric Oxide. 2011;25:195-200 pubmed publisher
    ..This review of photocontrollable NO and HNO donors and their mechanisms also covers spontaneous-release donors to the extent necessary to understand their contribution to the development of the photocontrollable donors. ..
  36. Pirali T, Tron G, Masson G, Zhu J. Ammonium chloride promoted three-component synthesis of 5-iminooxazoline and its subsequent transformation to macrocyclodepsipeptide. Org Lett. 2007;9:5275-8 pubmed
  37. Jamal M, Ameno K, Uekita I, Kumihashi M, Wang W, Ijiri I. Catalase mediates acetaldehyde formation in the striatum of free-moving rats. Neurotoxicology. 2007;28:1245-8 pubmed
    ..inhibitor), and/or catalase inhibitor sodium azide (AZ, 10mg/kg) or 3-amino-1,2,4-triazole (AT, 1g/kg), and/or cyanamide (CY, 50mg/kg, an aldehyde dehydrogenase inhibitor)...
  38. McCall W, Grillo T, Comins D. Stereoselective synthesis of acyclic amino alcohols via von Braun ring opening of chiral piperidines. Org Lett. 2008;10:3255-7 pubmed publisher
    ..The ring-opened products contain useful cyanamide and benzylic bromide functional groups...
  39. Soltys D, Gniazdowska A, Bogatek R. Inhibition of tomato (Solanum lycopersicum L.) root growth by cyanamide is not always accompanied with enhancement of ROS production. Plant Signal Behav. 2013;8:e23994 pubmed publisher
    Mode of action of allelochemicals in target plants is currently widely studied. Cyanamide is one of the newly discovered allelochemical, biosynthesized in hairy vetch...
  40. Escuer A, Mc Kee V, Nelson J, Ruiz E, Sanz N, Vicente R. Ferromagnetic interaction in mu1,3-cyanamido-derived copper(II) cryptates. Chemistry. 2004;11:398-405 pubmed
    The reaction of dinuclear copper(II) cryptates with calcium cyanamide, CaNCN, and sodium dicyanamide, Na[N(CN)(2)] results in dinuclear compounds of formulae [Cu(2)(HNCN)(R3Bm)](ClO(4))(3) (1), [Cu(2)(dca)(R3Bm)](ClO(4))(3)4H(2)O (2), ..
  41. De la Pinta N, Martin S, Urtiaga M, Barandika M, Arriortua M, Lezama L, et al. Structural analysis, spectroscopic, and magnetic properties of the 1D triple-bridged compounds [M(dca)2(bpa)] (M = Mn, Fe, Co, Zn; dca = dicyanamide; bpa = 1,2-bis(4-pyridyl)ethane) and the 3D [Ni(dca)(bpa)2]dca·6H2O. Inorg Chem. 2010;49:10445-54 pubmed publisher
    ..Magnetic susceptibility measurements show antiferromagnetic couplings, increasing for 1-3. Compound 5 shows very slight antiferromagnetic interactions. ..
  42. Jänkälä H, Eriksson C, Eklund K, Harkonen M, Maki T. Combined calcium carbimide and ethanol treatment induces high blood acetaldehyde levels, myocardial apoptosis and altered expression of apoptosis-regulating genes in rat. Alcohol Alcohol. 2002;37:222-8 pubmed
    ..These results indicate that acetaldehyde might regulate the expression of apoptosis-linked genes and that apoptosis of myocardial cells may be involved in the development of alcoholic heart disease. ..
  43. Perez F, Kuhn N, Vergara R. Expression analysis of phytochromes A, B and floral integrator genes during the entry and exit of grapevine-buds from endodormancy. J Plant Physiol. 2011;168:1659-66 pubmed publisher
    ..into ED, and its subsequent up-regulation following the application of dormancy-breaking compounds, hydrogen cyanamide (HC) and sodium azide, suggests that VvFT could play a key role in stimulating bud-growth by repressing their ..
  44. Pramanik S, Dutta S, Bhattacharyya A. Studies on the residue of hydrogen cyanamide in grape berries. Bull Environ Contam Toxicol. 2009;82:644-6 pubmed publisher
    Multilocational field trials were conducted in grapevines at four different locations by applying hydrogen cyanamide 50% SL during 2006-2007...
  45. Dutta S, Higginson C, Ho B, Rynearson K, Dibrov S, Hermann T. 1,3-Diazepanes of natural product-like complexity from cyanamide-induced rearrangement of epoxy-delta-lactams. Org Lett. 2010;12:360-3 pubmed publisher
    ..The synthesis of the 1,3-diazepane scaffold was achieved via an unprecedented cyanamide-induced rearrangement of epoxy-delta-lactams.
  46. Ziegler Skylakakis K, Nill S, Pan J, Andrae U. S-oxygenation of thiourea results in the formation of genotoxic products. Environ Mol Mutagen. 1998;31:362-73 pubmed
    ..b>Cyanamide did not elicit repair...
  47. Supuran C, Scozzafava A, Briganti F. Carbonic anhydrase inhibitors: N-cyanosulfonamides, a new class of high affinity isozyme II and IV inhibitors. J Enzyme Inhib. 1999;14:289-306 pubmed
    ..has been prepared by reaction of alkyl-, arylalkyl- and arylsulfonyl halides or sulfonic acid anhydrides with cyanamide, or by reaction of cyanogen bromide with sulfamide/sulfamic acid...
  48. Bogel Łukasik E, Lourenço C, Zakrzewska M, Bogel Łukasik R. Insight into the phase equilibrium phenomena of systems containing dienes and dicyanamide ionic liquids as a new potential application. J Phys Chem B. 2010;114:15605-9 pubmed publisher
    ..19 mol fraction of the diene. The attained results demonstrate that nonpolar compounds can be dissolved to some extent in highly charged and polar solvents such as ionic liquids...
  49. Madaghiele M, Piccinno A, Saponaro M, Maffezzoli A, Sannino A. Collagen- and gelatine-based films sealing vascular prostheses: evaluation of the degree of crosslinking for optimal blood impermeability. J Mater Sci Mater Med. 2009;20:1979-89 pubmed publisher
    ..The presence of glycerol in crosslinked collagen films was found to have plasticizing effects, which are likely to facilitate blood impermeability, and to increase the thermal stability of collagen...
  50. Ghosh S, Mukherjee S, Seth P, Mukherjee P, Ghosh A. Solvent-templated supramolecular isomerism in 2D coordination polymer constructed by Ni(II)2Co(II) nodes and dicyanamido spacers: drastic change in magnetic behaviours. Dalton Trans. 2013;42:13554-64 pubmed publisher
    ..The DFT calculations of exchange interactions between metal centres provide a clear evidence of the role played by the fundamental geometrical factors on the nature and magnitude of the magnetic coupling in these pseudo-polymorphic CPs...
  51. Kamo T, Kato K, Hiradate S, Nakajima E, Fujii Y, Hirota M. Evidence of cyanamide production in hairy vetch Vicia villosa. Nat Prod Res. 2006;20:429-33 pubmed
    b>Cyanamide (NH(2)CN) has recently been isolated as a plant growth inhibitor from Vicia villosa, which is the first discovery of cyanamide from natural sources. To reveal the presence of the biosynthesized cyanamide in plants, 3...
  52. Jamal M, Ameno K, Kumihashi M, Wang W, Ameno S, Kubota T, et al. Failure of ethanol and acetaldehyde to alter in vivo norepinephrine release in the striatum and hippocampus of rats. Arch Toxicol. 2004;78:723-7 pubmed
    ..Rats were treated intraperitoneally with EtOH (1 g/kg) or cyanamide (CY, 50 mg/kg, a potent aldehyde dehydrogenase inhibitor) plus EtOH (1 g/kg)...
  53. Kamijo S, Yamamoto Y. Synthesis of allyl cyanamides and N-cyanoindoles via the palladium-catalyzed three-component coupling reaction. J Am Chem Soc. 2002;124:11940-5 pubmed
  54. Jamal M, Ameno K, Ikuo U, Kumihashi M, Wang W, Ijiri I. Ethanol and acetaldehyde: in vivo quantitation and effects on cholinergic function in rat brain. Novartis Found Symp. 2007;285:137-41; discussion 141-4, 198-9 pubmed
    ..The results showed that acetaldehyde was present in the cyanamide (CY) + EtOH, CY + 4-methylpyrazole (4-MP) + EtOH and CY + sodium azide + EtOH groups...
  55. Hiradate S, Kamo T, Nakajima E, Kato K, Fujii Y. Direct quantitative determination of cyanamide by stable isotope dilution gas chromatography-mass spectrometry. J Chromatogr A. 2005;1098:138-43 pubmed
    b>Cyanamide is a multifunctional agrochemical used, for example, as a pesticide, herbicide, and fertilizer. Recent research has revealed that cyanamide is a natural product biosynthesized in a leguminous plant, hairy vetch (Vicia villosa)...
  56. Patel V, Worrall S, Emery P, Preedy V. Protein adduct species in muscle and liver of rats following acute ethanol administration. Alcohol Alcohol. 2005;40:485-93 pubmed
    ..Our objective was to test the hypothesis that in muscle a variety of different adduct species are formed after acute alcohol exposure and that unreduced adducts predominate...
  57. Giles R, Nkansah R, Looper R. Synthesis of 2-thio- and 2-oxoimidazoles via cascade addition-cycloisomerization reactions of propargylcyanamides. J Org Chem. 2010;75:261-4 pubmed publisher
    ..In general, the reaction sequence allows for the rapid formation of highly substituted 2-thio- and 2-oxoimidazoles in good to excellent yields...
  58. Brewer C. Cyanamide or disulfiram in the treatment of adolescent alcohol misusers?. Alcohol Alcohol. 2003;38:442; author reply 442-3 pubmed
  59. Dierolf D, Scheitza S, Bonifas J, Blomeke B. Cyanamide-mediated Inhibition of N-acetyltransferase 1. Toxicology. 2012;302:1-10 pubmed publisher
    b>Cyanamide has been used for decades for medical intentions in the treatment of alcoholism and for agricultural purposes as a plant growth regulator and bud-breaking agent...
  60. Nagumo Y, Tanaka K, Tewari K, Thiraporn K, Tsuchida T, Honma T, et al. Rapid quantification of cyanamide by ultra-high-pressure liquid chromatography in fertilizer, soil or plant samples. J Chromatogr A. 2009;1216:5614-8 pubmed publisher
    A rapid and simple method for determination of cyanamide in fertilizer, soil and plants has been developed. In this method, cyanamide is extracted with 2% acetic acid and the extract separated by centrifugation...
  61. Mar A, Oro J. Synthesis of the coenzymes adenosine diphosphate glucose, guanosine diphosphate glucose, and cytidine diphosphoethanolamine under primitive Earth conditions. J Mol Evol. 1991;32:201-10 pubmed
    ..to react under aqueous solutions, at moderate temperatures and short periods of time, with mediation by cyanamide or urea...
  62. Stanek J, Symanowicz P, Olsen J, Gianutsos G, Morris J. Sensory-nerve-mediated nasal vasodilatory response to inspired acetaldehyde and acetic acid vapors. Inhal Toxicol. 2001;13:807-22 pubmed
    ..Pretreatment with the aldehyde dehydrogenase inhibitor cyanamide (10 mg/kg, 1 h prior to exposure) reduced the vasodilatory response to 200 ppm but not to 50 ppm acetaldehyde...
  63. Giles R, Sullivan J, Steiner A, Looper R. Addition-hydroamination reactions of propargyl cyanamides: rapid access to highly substituted 2-aminoimidazoles. Angew Chem Int Ed Engl. 2009;48:3116-20 pubmed publisher
    ..The synthesis of the propargyl cyanamide precursors through a three-component coupling enables the preparation of this important heterocyclic core ..
  64. Cervia D, Martini D, Ristori C, Catalani E, Timperio A, Bagnoli P, et al. Modulation of the neuronal response to ischaemia by somatostatin analogues in wild-type and knock-out mouse retinas. J Neurochem. 2008;106:2224-35 pubmed publisher
    ..In contrast, cell death was increased by blocking sst(2) with cyanamide. In sst(2) over-expressing ischaemic retinas, somatostatin analogues increased cell death, and octreotide also ..
  65. Launay M, Dronskowski R. A theoretical study on the structures and energetics of hypothetical TiM(NCN)3 compounds of the 3d transition metals. J Comput Chem. 2005;26:1180-8 pubmed
    ..The best models are characterized by low-spin magnetic transition metals found in octahedral coordination, and the TiN(6) and MN(6) polyhedra either share faces or edges...
  66. Tambour S, Didone V, Tirelli E, Quertemont E. Dissociation between the locomotor and anxiolytic effects of acetaldehyde in the elevated plus-maze: evidence that acetaldehyde is not involved in the anxiolytic effects of ethanol in mice. Eur Neuropsychopharmacol. 2005;15:655-62 pubmed
    ..In an independent experiment, cyanamide, an aldehyde dehydrogenase inhibitor, prevented the locomotor stimulant effects of ethanol, although it failed ..
  67. Adachi J, Kudo R, Nushida H, Ueno Y, Koll M, Preedy V. Fatty acid profile in skeletal muscle of the rat in response to acute (2.5 hours) and prolonged (6 weeks) ethanol-dosage. Addict Biol. 2003;8:181-9 pubmed
    ..There were four groups: (A) saline (control); (B) cyanamide (an aldehyde dehydrogenase inhibitor); (C) ethanol; and (D) cyanamide + ethanol...
  68. Ishibashi T, Nomura Nakamoto M, Abe F, Masuoka T, Imaizumi N, Yoshida J, et al. Effects of cyanamide, an aldehyde dehydrogenase type 2 inhibitor, on glyceryl trinitrate- and isosorbide dinitrate-induced vasodilation in rabbit excised aorta and in anesthetized whole animal. Biol Pharm Bull. 2013;36:556-63 pubmed
    ..dinitrate (ISDN) was systematically examined in excised rabbit aorta and anesthetized whole animal with cyanamide, an ALDH2 inhibitor...
  69. Izco M, Orio L, O Shea E, Colado M. Binge ethanol administration enhances the MDMA-induced long-term 5-HT neurotoxicity in rat brain. Psychopharmacology (Berl). 2007;189:459-70 pubmed
    ..Ecstasy abuse commonly occurs in hot, overcrowded environments in combination with alcohol. Around 90% of ecstasy users take ethanol; over 70% of these users also often drink alcohol at hazardous levels...
  70. Golwala N, Hodenette C, Murthy S, Nossaman B, Kadowitz P. Vascular responses to nitrite are mediated by xanthine oxidoreductase and mitochondrial aldehyde dehydrogenase in the rat. Can J Physiol Pharmacol. 2009;87:1095-101 pubmed publisher
    ..of the xanthine oxidoreductase inhibitor allopurinol and the mitochondrial aldehyde dehydrogenase inhibitor cyanamide on decreases in mean systemic arterial pressure in response to i.v...
  71. Closon C, Didone V, Tirelli E, Quertemont E. Acetaldehyde and the hypothermic effects of ethanol in mice. Alcohol Clin Exp Res. 2009;33:2005-14 pubmed publisher
    ..The aim of the present study is to better understand the hypothermic effects of acetaldehyde and the possible contribution of acetaldehyde in ethanol-induced hypothermia, especially under conditions leading to acetaldehyde accumulation...
  72. Mowafy E, Aly H. Extraction and separation of Pd(II), Pt(IV), Fe(III), Zn(II), Cu(II) and Ag(I) from hydrochloric acid solutions with selected cyanamides as novel extractants. J Hazard Mater. 2007;149:465-70 pubmed
    Three structurally related novel extractants namely: N,N-dihexylcyanamide (DHCY), N,N-di(2-ethylhexyl)cyanamide (DEHCY) and N,N-di-octylcyanamide (DOCY) were synthesized in our laboratory and characterized by different techniques...
  73. Hammond A, Fry J. Effect of cyanamide on toxicity and glutathione depletion in rat hepatocyte cultures: differences between two dichloropropanol isomers. Chem Biol Interact. 1999;122:107-15 pubmed
    The effect of aldehyde dehydrogenase inhibition by cyanamide pre-treatment in vitro on dichloropropanol-dependent toxicity and glutathione depletion was investigated in 24 h rat hepatocyte cultures...
  74. Adachi J, Asano M, Ueno Y, Marway J, Camilleri P, Peters T, et al. Acute effect of ethanol on 7-hydroperoxycholesterol in muscle and liver. Lipids. 2001;36:267-71 pubmed
    ..in the initial periods of ethanol exposure, especially when acetaldehyde levels are markedly raised with cyanamide, an aldehyde dehydrogenase inhibitor...
  75. Nakamura Y, Yokoyama H, Higuchi S, Hara S, Kato S, Ishii H. Acetaldehyde accumulation suppresses Kupffer cell release of TNF-Alpha and modifies acute hepatic inflammation in rats. J Gastroenterol. 2004;39:140-7 pubmed
    ..This study was designed to clarify the role of acetaldehyde in liver injury, specifically in vivo and in vitro effects on Kupffer cell release of the inflammatory cytokine tumor necrosis factor-alpha (TNF-Alpha)...
  76. Kohn F, Landkamer G, Sladek N. Effect of the aldehyde dehydrogenase inhibitor, cyanamide, on the ex vivo sensitivity of murine multipotent and committed hematopoietic progenitor cells to mafosfamide (ASTA Z 7557). Immunopharmacol Immunotoxicol. 1987;9:163-76 pubmed
    ..and CFU-E) hematopoietic progenitor cells to mafosfamide was quantified with and without concurrent exposure to cyanamide, an inhibitor of aldehyde dehydrogenase activity...
  77. Kawai T, Mihara T, Kawashima I, Fujita Y, Ikeda C, Negishi H, et al. Endogenous acetaldehyde toxicity during antral follicular development in the mouse ovary. Reprod Toxicol. 2012;33:322-30 pubmed publisher
    ..When immature mice were co-injected with the ALDH inhibitor, cyanamide, and eCG, the expression of genes involved in the differentiations of granulosa cells was suppressed and the ..
  78. Chen C, Budas G, Churchill E, Disatnik M, Hurley T, Mochly Rosen D. Activation of aldehyde dehydrogenase-2 reduces ischemic damage to the heart. Science. 2008;321:1493-5 pubmed publisher
    ..Thus, pharmacologic enhancement of ALDH2 activity may be useful for patients with wild-type or mutant ALDH2 who are subjected to cardiac ischemia, such as during coronary bypass surgery...
  79. Vary T, Lang C. Differential phosphorylation of translation initiation regulators 4EBP1, S6k1, and Erk 1/2 following inhibition of alcohol metabolism in mouse heart. Cardiovasc Toxicol. 2008;8:23-32 pubmed publisher
    ..Pretreatment with cyanamide, an inhibitor of aldehyde dehydrogenase, did not attenuate the ethanol-induced decrease in phosphorylation S6k1(..
  80. Servais A, Azzouz M, Lopes D, Courillon C, Malacria M. Radical cyclization of N-acylcyanamides: total synthesis of luotonin A. Angew Chem Int Ed Engl. 2007;46:576-9 pubmed
  81. Ballarín E, Ibáñez L, Hernandez J, Force L, Laporte J. Cyanamide-induced aplastic anemia. Eur J Clin Pharmacol. 2005;61:467-9 pubmed
    To report a case of aplastic anemia in a patient treated with cyanamide, an alcohol-aversive drug. A 67-year-old man was admitted to hospital because of fever and pancytopenia. He had taken cyanamide for 6 months as an alcohol deterrent...
  82. Zhang J, Chen Z, Cobb F, Stamler J. Role of mitochondrial aldehyde dehydrogenase in nitroglycerin-induced vasodilation of coronary and systemic vessels: an intact canine model. Circulation. 2004;110:750-5 pubmed
    ..However, whether this mechanism operates in the systemic and coronary beds that subserve the antianginal action of GTN is not known. In this study, we address this question in an intact canine model...
  83. van Mourik T, Dingley A. Geometry dependence of spin-spin couplings in cyanamide by DFT analysis. Chemphyschem. 2007;8:288-96 pubmed
    ..Herein, the geometric dependencies of the one-bond amino N-H spin-spin coupling constants [(1)J(NH)] in the cyanamide monomer and dimer have been computed with B3LYP and the aug-cc-pVTZ-su0 basis set...