WordNet

a nonmetallic univalent element that is normally a colorless and odorless highly flammable diatomic gas; the simplest and lightest and most abundant element in the universe (同)H, atomic number 1
an extremely poisonous salt of hydrocyanic acid

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『水素』(化学記号は『H』)
シアン化物,(特に)青酸カリ

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/08/06 23:59:11」(JST)

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Hydrogen cyanide (HCN), sometimes called prussic acid, is an organic compound^[8] with the chemical formula HCN. It is a colorless, extremely poisonous liquid that boils slightly above room temperature, at 25.6 °C (78.1 °F).^[9] HCN is produced on an industrial scale and is a highly valuable precursor to many chemical compounds ranging from polymers to pharmaceuticals.

1 Structure and general properties
2 History of discovery
3 Production and synthesis
- 3.1 Historical methods of production
4 Applications
5 Occurrence
- 5.1 HCN on the young Earth
- 5.2 HCN in mammals
- 5.3 HCN and the origin of life
- 5.4 HCN in space
6 As a poison and chemical weapon
7 References
8 External links

Structure and general properties

Hydrogen cyanide is a linear molecule, with a triple bond between carbon and nitrogen. A minor tautomer of HCN is HNC, hydrogen isocyanide.

Hydrogen cyanide is weakly acidic with a pK_a of 9.2. It partially ionizes in water solution to give the cyanide anion, CN⁻. A solution of hydrogen cyanide in water, represented as HCN, is called hydrocyanic acid. The salts of the cyanide anion are known as cyanides.

HCN has a faint bitter almond-like odor that some people are unable to detect owing to a genetic trait.^[10] The volatile compound has been used as inhalation rodenticide and human poison, as well as for killing whales.^[11] Cyanide ions interfere with iron-containing respiratory enzymes.

History of discovery

The red colored ferricyanide ion, one component of Prussian blue

Hydrogen cyanide was first isolated from a blue pigment (Prussian blue) which had been known since 1704 but whose structure was unknown. It is now known to be a coordination polymer with a complex structure and an empirical formula of hydrated ferric ferrocyanide. In 1752, the French chemist Pierre Macquer made the important step of showing that Prussian blue could be converted to iron oxide plus a volatile component and that these could be used to reconstitute it.^[12] The new component was what we now know as hydrogen cyanide. Following Macquer's lead, it was first prepared from Prussian blue by the Swedish chemist Carl Wilhelm Scheele in 1782,^[13] and was eventually given the German name Blausäure (lit. "Blue acid") because of its acidic nature in water and its derivation from Prussian blue. In English it became known popularly as Prussic acid.

In 1787 the French chemist Claude Louis Berthollet showed that Prussic acid did not contain oxygen,^[14] an important contribution to acid theory, which had hitherto postulated that acids must contain oxygen^[15] (hence the name of oxygen itself, which is derived from Greek elements that mean "acid-former" and are likewise calqued into German as Sauerstoff). In 1811 Joseph Louis Gay-Lussac prepared pure, liquified hydrogen cyanide.^[16] In 1815 Gay-Lussac deduced Prussic acid's chemical formula.^[17] The radical cyanide in hydrogen cyanide was given its name from cyan, not only an English word for a shade of blue but the Greek word for blue (Ancient Greek: κυανοῦς), again owing to its derivation from Prussian blue.

Production and synthesis

Hydrogen cyanide forms in at least limited amounts from many combinations of hydrogen, carbon, and ammonia. Hydrogen cyanide is currently produced in great quantities by several processes, as well as being a recovered waste product from the manufacture of acrylonitrile.^[8] In 2006 between 500 million and 1 billion pounds were produced in the US.^[18]

The most important process is the Andrussow oxidation invented by Leonid Andrussow at IG Farben in which methane and ammonia react in the presence of oxygen at about 1200 °C over a platinum catalyst:^[19]

2 CH₄ + 2 NH₃ + 3 O₂ → 2 HCN + 6 H₂O

The energy needed for the reaction is provided by the partial oxidation of methane and ammonia.

Of lesser importance is the Degussa process (BMA process) in which no oxygen is added and the energy must be transferred indirectly through the reactor wall:^[20]

CH₄ + NH₃ → HCN + 3H₂

This reaction is akin to steam reforming, the reaction of methane and water to give carbon monoxide and hydrogen.

In the Shawinigan Process, hydrocarbons, e.g. propane, are reacted with ammonia. In the laboratory, small amounts of HCN are produced by the addition of acids to cyanide salts of alkali metals:

H⁺ + NaCN → HCN + Na⁺

This reaction is sometimes the basis of accidental poisonings because the acid converts a nonvolatile cyanide salt into the gaseous HCN.

Historical methods of production

The large demand for cyanides for mining operations in the 1890s was met by George Thomas Beilby, who patented a method to produce hydrogen cyanide by passing ammonia over glowing coal in 1892. This method was used until Hamilton Castner in 1894 developed a synthesis starting from coal, ammonia, and sodium yielding sodium cyanide, which reacts with acid to form gaseous HCN.

Applications

HCN is the precursor to sodium cyanide and potassium cyanide, which are used mainly in gold and silver mining and for the electroplating of those metals. Via the intermediacy of cyanohydrins, a variety of useful organic compounds are prepared from HCN including the monomer methyl methacrylate, from acetone, the amino acid methionine, via the Strecker synthesis, and the chelating agents EDTA and NTA. Via the hydrocyanation process, HCN is added to butadiene to give adiponitrile, a precursor to Nylon 66.^[8]

Occurrence

HCN is obtainable from fruits that have a pit, such as cherries, apricots, apples, and bitter almonds, from which almond oil and flavoring are made. Many of these pits contain small amounts of cyanohydrins such as mandelonitrile and amygdalin, which slowly release hydrogen cyanide.^[21]^[22] One hundred grams of crushed apple seeds can yield about 70 mg of HCN.^[23] Some millipedes release hydrogen cyanide as a defense mechanism,^[24] as do certain insects, such as some burnet moths. Hydrogen cyanide is contained in the exhaust of vehicles, in tobacco and wood smoke, and in smoke from burning nitrogen-containing plastics. So-called "bitter" roots of the cassava plant may contain up to 1 gram of HCN per kilogram.^[25]^[26]

HCN on the young Earth

It has been postulated that carbon from a cascade of asteroids (known as the Late Heavy Bombardment), resulting from interaction of Jupiter and Saturn, blasted the surface of young Earth and reacted with nitrogen in Earth’s atmosphere to form HCN.^[27]

HCN in mammals

Some authors have shown that neurons can produce hydrogen cyanide upon activation of their opioid receptors by endogenous or exogenous opioids. They have also shown that neuronal production of HCN activates NMDA receptors and plays a role in signal transduction between neuronal cells (neurotransmission). Moreover, increased endogenous neuronal HCN production under opioids was seemingly needed for adequate opioid analgesia, as analgesic action of opioids was attenuated by HCN scavengers. They considered endogenous HCN to be a neuromodulator.^[28]

It has also been shown that, while stimulating muscarinic cholinergic receptors in cultured pheochromocytoma cells increases HCN production, in a living organism (in vivo) muscarinic cholinergic stimulation actually decreases HCN production.^[29]

Leukocytes generate HCN during phagocytosis, and can kill bacteria, fungi, and other pathogens by generating several different toxic chemicals, one of which is hydrogen cyanide.^[28]

The vasodilatation, caused by sodium nitroprusside, has been shown to be mediated not only by NO generation, but also by endogenous cyanide generation, which adds not only toxicity, but also some additional antihypertensive efficacy compared to nitroglycerine and other non-cyanogenic nitrates which do not cause blood cyanide levels to rise.^[30]

HCN and the origin of life

Hydrogen cyanide has been discussed as a precursor to amino acids and nucleic acids, and is proposed to have played a part in the origin of life.^[31] Although the relationship of these chemical reactions to the origin of life theory remains speculative, studies in this area have led to discoveries of new pathways to organic compounds derived from the condensation of HCN.^[32]

HCN in space

HCN has been detected in the interstellar medium.^[33] Since then, extensive studies have probed formation and destruction pathways of HCN in various environments and examined its use as a tracer for a variety of astronomical species and processes. HCN can be observed from ground-based telescopes through a number of atmospheric windows.^[34] The J=1→0, J=3→2, J= 4→3, and J=10→9 pure rotational transitions have all been observed.^[33]^[35]^[36]

HCN is formed in interstellar clouds through one of two major pathways:^[37] via a neutral-neutral reaction (CH₂ + N → HCN + H) and via dissociative recombination (HCNH⁺ + e⁻ → HCN + H). The dissociative recombination pathway is dominant by 30%; however, the HCNH⁺ must be in its linear form. Dissociative recombination with its structural isomer, H₂NC⁺, exclusively produces hydrogen isocyanide (HNC).

HCN is destroyed in interstellar clouds through a number of mechanisms depending on the location in the cloud.^[37] In photon-dominated regions (PDRs), photodissociation dominates, producing CN (HCN + ν → CN + H). At further depths, photodissociation by cosmic rays dominate, producing CN (HCN + cr → CN + H). In the dark core, two competing mechanisms destroy it, forming HCN⁺ and HCNH⁺ (HCN + H⁺ → HCN⁺ + H; HCN + HCO⁺ → HCNH⁺ + CO). The reaction with HCO⁺ dominates by a factor of ~3.5. HCN has been used to analyze a variety of species and processes in the interstellar medium. It has been suggested as a tracer for dense molecular gas^[38]^[39] and as a tracer of stellar inflow in high-mass star-forming regions.^[40] Further, the HNC/HCN ratio has been shown to be an excellent method for distinguishing between PDRs and X-ray-dominated regions (XDRs).^[41]

On 11 August 2014, astronomers released studies, using the Atacama Large Millimeter/Submillimeter Array (ALMA) for the first time, that detailed the distribution of HCN, HNC, H₂CO, and dust inside the comae of comets C/2012 F6 (Lemmon) and C/2012 S1 (ISON).^[42]^[43]

As a poison and chemical weapon

A hydrogen cyanide concentration of 300 mg/m³ in air will kill a human within 10–60 minutes.^[44] A hydrogen cyanide concentration of 3500 ppm (about 3200 mg/m³) will kill a human in about 1 minute.^[44] The toxicity is caused by the cyanide ion, which halts cellular respiration by acting as a non-competitive inhibitor for an enzyme in mitochondria called cytochrome c oxidase. Specifically CN⁻ binds to Fe in the heme subunit in cytochromes, interrupting electron transfer.

Hydrogen cyanide has been absorbed into a carrier for use as a pesticide. Under IG Farben's brand name Zyklon B (German >Cyclone B, with the B standing for Blausäure - "Prussic Acid"),^[45] it was used in the German concentration camp mass killing during World War II. The same product is currently made in the Czech Republic under the trademark "Uragan D2". Hydrogen cyanide was also the agent employed in judicial execution in some U.S. states, where it was produced during the execution by the action of sulfuric acid on an egg-sized mass of potassium cyanide.^{[not specific enough to verify]}

Hydrogen cyanide is commonly listed amongst chemical warfare agents known as blood agents.^[46] As a substance listed under Schedule 3 of the Chemical Weapons Convention as a potential weapon which has large-scale industrial uses, manufacturing plants in signatory countries which produce more than 30 tonnes per year must be declared to, and can be inspected by, the Organisation for the Prohibition of Chemical Weapons. During the First World War, the United States and Italy used hydrogen cyanide against the Central Powers in 1918. France had used it in combat already in 1916, but this proved to be ineffective due to physical conditions.^[47]

Under the name prussic acid, HCN has been used as a killing agent in whaling harpoons.^[48] From the mid 18th century it was used in a number of poisoning murders and suicides.^[49] Cyanide has also been used in major occurrences of suicide in the 20th century, including the deaths of over 900 people at Jonestown and the mass suicides in 1945 Nazi Germany.

Hydrogen cyanide gas in air is explosive at concentrations over 5.6%.^[50] This is far above its toxicity level.

References

^ "Hydrogen Cyanide - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification. Retrieved 2012-06-04.
^ "hydrogen cyanide (CHEBI:18407)". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 18 October 2009. Main. Retrieved 2012-06-04.
^ ^a ^b ^c ^d ^e "NIOSH Pocket Guide to Chemical Hazards #0333". National Institute for Occupational Safety and Health (NIOSH).
^ Perrin, D. D. (1982). Ionisation Constants of Inorganic Acids and Bases in Aqueous Solution (2nd ed.). Oxford: Pergamon Press.
^ Patnaik, P. (2002). Handbook of Inorganic Chemicals. McGraw-Hill. ISBN 0-07-049439-8.
^ NIST Chemistry WebBook
^ ^a ^b "Hydrogen cyanide". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b ^c Gail, E.; Gos, S.; Kulzer, R.; Lorösch, J.; Rubo, A.; Sauer, M. (2005), "Cyano Compounds, Inorganic", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a08_159.pub2
^ http://www.wolframalpha.com/input/?i=boiling+point+of+Hydrogen+cyanide
^ "Cyanide, inability to smell". Online Mendelian Inheritance in Man. Retrieved 2010-03-31.
^ Lytle, Thomas. "Poison Harpoons". Retrieved 28 October 2013.
^ Pierre-Joseph Macquer (presented: 1752 ; published: 1756) "Éxamen chymique de bleu de Prusse" (Chemical examination of Prussian blue), Mémoires de l'Académie royale des Sciences , pages 60-77.
^ See:
- Carl W. Scheele (1782) "Försök, beträffande det färgande ämnet uti Berlinerblå" (Experiment concerning the coloring substance in Berlin blue), Kungliga Svenska Vetenskapsakademiens handlingar (Royal Swedish Academy of Science's Proceedings), 3: 264-275 (in Swedish).
- Reprinted in Latin as: "De materia tingente caerulei berolinensis" in: Carl Wilhelm Scheele with Ernst Benjamin Gottlieb Hebenstreit (ed.) and Gottfried Heinrich Schäfer (trans.), Opuscula Chemica et Physica (Leipzig ("Lipsiae"), (Germany): Johann Godfried Müller, 1789), vol. 2, pages 148-174.
^ See:
- Berthollet (presented: 1787 ; published: 1789)
"Mémoire sur l'acide prussique" (Memoir on prussic acid), Mémoires de l'Académie Royale des Sciences, pages 148-161.
- Reprinted in: Berthollet (1789) "Extrait d'un mémoire sur l'acide prussique" (Extract of a memoir on prussic acid), Annales de chimie 1: 30-39.
^ Newbold, B. T. (1999-11-01). "Claude Louis Berthollet: A Great Chemist in the French Tradition". Canadian Chemical News. Retrieved 2010-03-31.
^ Gay-Lussac (1811) "Note sur l'acide prussique" (Note on prussic acid), Annales de chimie, 44: 128 - 133.
^ Gay-Lussac (1815) "Recherche sur l'acide prussique" (Research on prussic acid) Annales de Chimie 95: 136-231.
^ [1]. EPA. Retrieved on 2013-01-31.
^ Andrussow, L. (1935). "The catalytic oxydation of ammonia-methane-mixtures to hydrogen cyanide". Angewandte Chemie 48 (37): 593–595. doi:10.1002/ange.19350483702.
^ Endter, F. (1958). "Die technische Synthese von Cyanwasserstoff aus Methan und Ammoniak ohne Zusatz von Sauerstoff". Chemie Ingenieur Technik 30 (5): 305–310. doi:10.1002/cite.330300506.
^ Vetter, J. (2000). "Plant cyanogenic glycosides". Toxicon 38 (1): 11–36. doi:10.1016/S0041-0101(99)00128-2. PMID 10669009.
^ Jones, D. A. (1998). "Why are so many food plants cyanogenic?". Phytochemistry 47 (2): 155–162. doi:10.1016/S0031-9422(97)00425-1. PMID 9431670.
^ "Are Apple Cores Poisonous? The Naked Scientists September 2010". Retrieved 6 March 2014.
^ Blum, M. S.; Woodring, J. P. (1962). "Secretion of Benzaldehyde and Hydrogen Cyanide by the Millipede Pachydesmus crassicutis (Wood)". Science 138 (3539): 512–513. Bibcode:1962Sci...138..512B. doi:10.1126/science.138.3539.512. PMID 17753947.
^ Aregheore, E. M.; Agunbiade, O. O. (1991). "The toxic effects of cassava (manihot esculenta grantz) diets on humans: a review". Veterinary and Human Toxicology 33 (3): 274–275. PMID 1650055.
^ White, W. L. B.; Arias-Garzon, D. I.; McMahon, J. M.; Sayre, R. T. (1998). "Cyanogenesis in Cassava, The Role of Hydroxynitrile Lyase in Root Cyanide Production". Plant Physiology 116 (4): 1219–1225. doi:10.1104/pp.116.4.1219. PMC 35028. PMID 9536038.
^ "Making Sense of the Chemistry That Led to Life on Earth". Retrieved 5 May 2015.
^ ^a ^b Borowitz JL, Gunasekar PG, Isom GE. (12 Sep 1997). "Hydrogen cyanide generation by mu-opiate receptor activation: possible neuromodulatory role of endogenous cyanide.". Brain Res. 768 (1-2): 294–300. doi:10.1016/S0006-8993(97)00659-8. PMID 9369328.
^ Gunasekar PG, Prabhakaran K, Li L, Zhang L, Isom GE, Borowitz JL. (May 2004). "Receptor mechanisms mediating cyanide generation in PC12 cells and rat brain.". Neurosci Res. 49 (1): 13–18. doi:10.1016/j.neures.2004.01.006. PMID 15099699.
^ Smith RP, Kruszyna H. (Jan 1976). "Toxicology of some inorganic antihypertensive anions.". Fed Proc. 35 (1): 69–72. PMID 1245233.
^ Matthews, C. N. (2004). "The HCN World: Establishing Protein - Nucleic Acid Life via Hydrogen Cyanide Polymers". Origins: Genesis, Evolution and Diversity of Life. Cellular Origin and Life in Extreme Habitats and Astrobiology 6. pp. 121–135. doi:10.1007/1-4020-2522-X_8. ISBN 978-1-4020-2522-8.
^ Al-Azmi, A.; Elassar, A.-Z. A.; Booth, B. L. (2003). "The Chemistry of Diaminomaleonitrile and its Utility in Heterocyclic Synthesis". Tetrahedron 59 (16): 2749–2763. doi:10.1016/S0040-4020(03)00153-4.
^ ^a ^b Snyder, L. E.; Buhl, D. (1971). "Observations of Radio Emission from Interstellar Hydrogen Cyanide" (pdf). Astrophysical Journal 163: L47–L52. Bibcode:1971ApJ...163L..47S. doi:10.1086/180664.
^ Treffers, R.; Larson, H. P.; Fink, U.; Gautier, T. N. (1978). "Upper limits to trace constituents in Jupiter's atmosphere from an analysis of its 5-μm spectrum". Icarus 34 (2): 331–343. Bibcode:1978Icar...34..331T. doi:10.1016/0019-1035(78)90171-9.
^ Bieging, J. H.; Shaked, S.; Gensheimer, P. D. (2000). "Submillimeter‐ and Millimeter‐Wavelength Observations of SiO and HCN in Circumstellar Envelopes of AGB Stars" (pdf). Astrophysical Journal 543 (2): 897–921. Bibcode:2000ApJ...543..897B. doi:10.1086/317129.
^ Schilke, P.; Menten, K. M. (2003). "Detection of a Second, Strong Sub-millimeter HCN Laser Line toward Carbon Stars" (pdf). Astrophysical Journal 583 (1): 446–450. Bibcode:2003ApJ...583..446S. doi:10.1086/345099.
^ ^a ^b Boger, G. I.; Sternberg, A. (2005). "CN and HCN in Dense Interstellar Clouds" (pdf). Astrophysical Journal 632 (1): 302–315. arXiv:astro-ph/0506535. Bibcode:2005ApJ...632..302B. doi:10.1086/432864.
^ Gao, Y.; Solomon, P. M. (2004). "The Star Formation Rate and Dense Molecular Gas in Galaxies" (pdf). Astrophysical Journal 606 (1): 271–290. arXiv:astro-ph/0310339. Bibcode:2004ApJ...606..271G. doi:10.1086/382999.
^ Gao, Y.; Solomon, P. M. (2004). "HCN Survey of Normal Spiral, Infrared‐luminous, and Ultraluminous Galaxies" (pdf). Astrophysical Journal Supplements 152: 63–80. arXiv:astro-ph/0310341. Bibcode:2004ApJS..152...63G. doi:10.1086/383003.
^ Wu, J.; Evans, N. J. (2003). "Indications of Inflow Motions in Regions Forming Massive Stars" (pdf). Astrophysical Journal 592 (2): L79–L82. arXiv:astro-ph/0306543. Bibcode:2003ApJ...592L..79W. doi:10.1086/377679.
^ Loenen, A. F. (2007). Proceedings IAU Symposium 202. Missing or empty |title= (help)
^ Zubritsky, Elizabeth; Neal-Jones, Nancy (11 August 2014). "RELEASE 14-038 - NASA’s 3-D Study of Comets Reveals Chemical Factory at Work". NASA. Retrieved 12 August 2014.
^ Cordiner, M.A. et al. (11 August 2014). "Mapping the Release of Volatiles in the Inner Comae of Comets C/2012 F6 (Lemmon) and C/2012 S1 (ISON) Using the Atacama Large Millimeter/Submillimeter Array". The Astrophysical Journal 792 (1). doi:10.1088/2041-8205/792/1/L2. Retrieved 12 August 2014.
^ ^a ^b Environmental and Health Effects. Cyanidecode.org. Retrieved on 2012-06-02.
^ Dwork, D.; van Pelt, R. J. (1996). Auschwitz, 1270 to the present. Norton. p. 443. ISBN 0-393-03933-1.
^ "Hydrogen Cyanide". Organisation for the Prohibition of Chemical Weapons. Retrieved 2009-01-14.
^ Markus Schnedlitz (2008) Chemische Kampfstoffe: Geschichte, Eigenschaften, Wirkung. GRIN Verlag, ISBN 364023360-3, p. 13
^ Poison Hand Darted Harpoons and Lances.
^ The Poison Garden website http://www.thepoisongarden.co.uk/atoz/prunus_laurocerasus.htm. Retrieved 18 October 2014. Missing or empty |title= (help)
^ "Documentation for Immediately Dangerous to Life or Health Concentrations (IDLHs) – 74908". NIOSH.

External links

Institut national de recherche et de sécurité (1997). "Cyanure d'hydrogène et solutions aqueuses". Fiche toxicologique n° 4, Paris:INRS, 5pp. (PDF file, in French)
International Chemical Safety Card 0492
Hydrogen cyanide and cyanides (CICAD 61)
National Pollutant Inventory: Cyanide compounds fact sheet
NIOSH Pocket Guide to Chemical Hazards
Department of health review

UpToDate Contents

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1. シアン化物中毒 cyanide poisoning
2. 化学テロ：早急な認識および初回薬物治療マネージメント chemical terrorism rapid recognition and initial medical management
3. 煙の吸入 smoke inhalation
4. 小児での潜在的に毒性を持つ植物の摂取による臨床症状および評価 clinical manifestations and evaluation of potentially toxic plant ingestions in children
5. 小児における毒性植物摂取およびニコチン中毒のマネージメント management of toxic plant ingestions and nicotine poisoning in children

English Journal

Dormancy alleviation by NO or HCN leading to decline of protein carbonylation levels in apple (Malus domestica Borkh.) embryos.

Krasuska U1, Ciacka K2, Dębska K2, Bogatek R3, Gniazdowska A4.
Journal of plant physiology.J Plant Physiol.2014 Aug 15;171(13):1132-41. doi: 10.1016/j.jplph.2014.04.015. Epub 2014 May 21.
Deep dormancy of apple (Malus domestica Borkh.) embryos can be overcome by short-term pre-treatment with nitric oxide (NO) or hydrogen cyanide (HCN). Dormancy alleviation of embryos modulated by NO or HCN and the first step of germination depend on temporary increased production of reactive oxygen s
PMID 24973585

Adaptive gains through repeated gene loss: parallel evolution of cyanogenesis polymorphisms in the genus Trifolium (Fabaceae).

Olsen KM1, Kooyers NJ2, Small LL2.
Philosophical transactions of the Royal Society of London. Series B, Biological sciences.Philos Trans R Soc Lond B Biol Sci.2014 Aug 5;369(1648). pii: 20130347. doi: 10.1098/rstb.2013.0347.
Variation in cyanogenesis (hydrogen cyanide release following tissue damage) was first noted in populations of white clover more than a century ago, and subsequent decades of research have established this system as a classic example of an adaptive chemical defence polymorphism. Here, we document po
PMID 24958921

Redox equilibration after one-electron reduction of cytochrome c oxidase: Radical formation and a possible hydrogen relay mechanism.

Ashe D1, Alleyne T1, Wilson M2, Svistunenko D2, Nicholls P3.
Archives of biochemistry and biophysics.Arch Biochem Biophys.2014 Jul 15;554:36-43. doi: 10.1016/j.abb.2014.04.015. Epub 2014 May 5.
Kinetic studies using UV/visible and EPR spectroscopy were carried out to follow the distribution of electrons within beef heart cytochrome c oxidase (CcO), both active and cyanide-inhibited, following addition of reduced cytochrome c as electron donor. In the initial one-electron reduced state the
PMID 24811894

Japanese Journal

杏仁のエタノール水溶液浸漬によるアミグダリンの低減

山崎慎也,澁澤登,栗林剛 [他],唐沢秀行,大日方洋
日本食品科学工学会誌 : Nippon shokuhin kagaku kogaku kaishi = Journal of the Japanese Society for Food Science and Technology 59(10), 522-527, 2012-10-15
… Since amygdalin generates harmful hydrogen cyanide upon hydrolysis by emulsin, an enzyme found in apricot kernels or <I>β</I> … Moreover, we established a method for reducing the hydrogen cyanide generated by hydrolysis of amygdalin. …
NAID 10031122187

3-14-1 高窒素含有バイオマス系廃棄物の熱分解における窒素の挙動に関する研究(Session 3 バイオマス等)

陳鴻芳,汪印,許光文,吉川邦夫
日本エネルギー学会大会講演要旨集 (21), 166-167, 2012-07-30
… Nitrogen content in biomass is usually higher than that in fossil fuel, and that nitrogen in biomass can form NOx precursors like ammonia (NH3) and hydrogen cyanide (HCN), and toxic contaminant like organic nitrogenated compounds (N-Tar) during the primary thermal conversion processes. …
NAID 110009560750

植物検疫における病害虫防除技術

三角隆
都市有害生物管理 1(2), 137-145, 2011-12-20
国内農業強化を目指しているが,低い食糧自給率から輸入農産物に依存する日本にとって,病害虫の侵入を防ぐ植物検疫制度は重要である.検疫処理では,青酸ガス,臭化メチル(MB)及びリン化アルミニウムによるくん蒸処理が主に実施される.青酸ガスでは,種苗類と青果物に対し,液体青酸1.8g/m^3,30分処理,MBでは,穀類等・青果物及び木材に対し,品目,温度などに応じた単位薬量(一部を除き,15-8.5g/m …
NAID 110008798936

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リンク元	「シアン化水素」「青酸」

「シアン化水素」

Hydrogen cyanide
Names
	IUPAC name Formonitrile (substitutive); Hydridonitridocarbon (additive);
	Other names Formic anammonide; Hydrocyanic acid; Prussic acid; Methanenitrile;
Identifiers
CAS Registry Number	74-90-8
3DMet	B00275
ChEBI	CHEBI:18407
ChemSpider	748
EC number	200-821-6
	InChI InChI=1S/CHN/c1-2/h1H ; Key: LELOWRISYMNNSU-UHFFFAOYSA-N ;
Jmol-3D images	Image
KEGG	C01326
MeSH	Hydrogen+Cyanide
PubChem	768
RTECS number	MW6825000
	SMILES C#N ;
UNII	2WTB3V159F
UN number	1051
Properties
Chemical formula	CHN
Molar mass	27.03 g·mol−1
Appearance	Very pale, blue, transparent liquid or colorless gas
Odor	Oil of bitter almond
Density	0.687 g mL−1
Melting point	−14 to −12 °C; 7 to 10 °F; 259 to 261 K
Boiling point	25.6 to 26.6 °C; 78.0 to 79.8 °F; 298.7 to 299.7 K
Solubility in water	Miscible
Solubility in ethanol	Miscible
Vapor pressure	630 mmHg (20°C)
Henry's law; constant (kH)	75 μmol Pa−1 kg−1
Acidity (pKa)	9.21
Basicity (pKb)	4.79
Refractive index (nD)	1.2675
Viscosity	201 μPa s
Structure
Molecular shape	Linear
Dipole moment	2.98 D
Thermochemistry
Specific; heat capacity (C)	71.00 kJ K−1 mol−1 (at 27 °C)
Std molar; entropy (So298)	113.01 J K−1 mol−1
Std enthalpy of; formation (ΔfHo298)	109.9 kJ mol−1
Std enthalpy of; combustion (ΔcHo298)	-426.5 kJ mol−1
Hazards
EU classification	F+ T+ N
R-phrases	R12, R26/27/28, R50/53
S-phrases	(S1/2), S16, S36/37, S38, S45, S53, S59, S61
NFPA 704	4 4 1
Flash point	−17.8 °C (0.0 °F; 255.3 K)
Autoignition; temperature	538 °C (1,000 °F; 811 K)
Explosive limits	5.6% - 40.0%
	Lethal dose or concentration (LD, LC):
LC50 (Median concentration)	501 ppm (rat, 5 min); 323 ppm (mouse, 5 min); 275 ppm (rat, 15 min); 170 ppm (rat, 30 min); 160 ppm (rat, 30 min); 323 ppm (rat, 5 min)
LCLo (Lowest published)	200 ppm (mammal, 5 min); 36 ppm (mammal, 2 hr); 107 ppm (human, 10 min); 759 ppm (rabbit, 1 min); 759 ppm (cat, 1 min); 357 ppm (human, 2 min); 179 ppm (human, 1 hr)
	US health exposure limits (NIOSH):
PEL (Permissible)	TWA 10 ppm (11 mg/m3) [skin]
REL (Recommended)	ST 4.7 ppm (5 mg/m3) [skin]
IDLH (Immediate danger	50 ppm
Related compounds
Related alkanenitriles	Hydrogen isocyanide; Isocyanic acid; Thiocyanic acid; Cyanogen iodide; Cyanogen bromide; Cyanogen chloride; Cyanogen fluoride; Acetonitrile; Aminoacetonitrile; Glycolonitrile; Cyanogen;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is: /?)
	Infobox references

　　[★]

英: hydrogen cyanide
同: 青酸？
関: シアン化水素中毒、シアン化合物、(コナンをはじめとした探偵物で大人気)シアン化カリウム

分子式：HCN、分子量27.03。
常温で無色、甘い臭い(苦いアーモンド臭)、揮発性液体。
船内、食品などの消毒に用いられる。ないし、窒素化合物(プラスチック、ポリウレタン、ナイロン、アクリル)の燃焼により生じうる。
シアン化水素の経口接触による最低致死濃度は50mg。
気体としての許容濃度5ppm、中毒濃度50ppm、致死濃度150-200ppm。

臨床中毒学 p.405

「青酸」

　　[★]

英: hydrogen cyanide
関: シアン、シアン化物 cyanide CN^-、シアン化水素

HCN

[1] "Hydrogen Cyanide - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification. Retrieved 2012-06-04.

[2] "hydrogen cyanide (CHEBI:18407)". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 18 October 2009. Main. Retrieved 2012-06-04.

[PGCH-3] "NIOSH Pocket Guide to Chemical Hazards #0333". National Institute for Occupational Safety and Health (NIOSH).

[4] Perrin, D. D. (1982). Ionisation Constants of Inorganic Acids and Bases in Aqueous Solution (2nd ed.). Oxford: Pergamon Press.

[5] Patnaik, P. (2002). Handbook of Inorganic Chemicals. McGraw-Hill. ISBN 0-07-049439-8.

[6] NIST Chemistry WebBook

[IDLH-7] "Hydrogen cyanide". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).

[Ullmann-8] Gail, E.; Gos, S.; Kulzer, R.; Lorösch, J.; Rubo, A.; Sauer, M. (2005), "Cyano Compounds, Inorganic", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a08_159.pub2

[9] ttp://www.wolframalpha.com/input/?i=boiling+point+of+Hydrogen+cyanide

[10] "Cyanide, inability to smell". Online Mendelian Inheritance in Man. Retrieved 2010-03-31.

[11] Lytle, Thomas. "Poison Harpoons". Retrieved 28 October 2013.

[12] Pierre-Joseph Macquer (presented: 1752 ; published: 1756) "Éxamen chymique de bleu de Prusse" (Chemical examination of Prussian blue), Mémoires de l'Académie royale des Sciences , pages 60-77.

[13] See:

Carl W. Scheele (1782) "Försök, beträffande det färgande ämnet uti Berlinerblå" (Experiment concerning the coloring substance in Berlin blue), Kungliga Svenska Vetenskapsakademiens handlingar (Royal Swedish Academy of Science's Proceedings), 3: 264-275 (in Swedish).

Reprinted in Latin as: "De materia tingente caerulei berolinensis" in: Carl Wilhelm Scheele with Ernst Benjamin Gottlieb Hebenstreit (ed.) and Gottfried Heinrich Schäfer (trans.), Opuscula Chemica et Physica (Leipzig ("Lipsiae"), (Germany): Johann Godfried Müller, 1789), vol. 2, pages 148-174.

[14] Carl W. Scheele (1782) "Försök, beträffande det färgande ämnet uti Berlinerblå" (Experiment concerning the coloring substance in Berlin blue), Kungliga Svenska Vetenskapsakademiens handlingar (Royal Swedish Academy of Science's Proceedings), 3: 264-275 (in Swedish).

[15] Reprinted in Latin as: "De materia tingente caerulei berolinensis" in: Carl Wilhelm Scheele with Ernst Benjamin Gottlieb Hebenstreit (ed.) and Gottfried Heinrich Schäfer (trans.), Opuscula Chemica et Physica (Leipzig ("Lipsiae"), (Germany): Johann Godfried Müller, 1789), vol. 2, pages 148-174.

[14] See:

Berthollet (presented: 1787 ; published: 1789)

"Mémoire sur l'acide prussique" (Memoir on prussic acid), Mémoires de l'Académie Royale des Sciences, pages 148-161.

Reprinted in: Berthollet (1789) "Extrait d'un mémoire sur l'acide prussique" (Extract of a memoir on prussic acid), Annales de chimie 1: 30-39.

[17] Berthollet (presented: 1787 ; published: 1789)

[18] Reprinted in: Berthollet (1789) "Extrait d'un mémoire sur l'acide prussique" (Extract of a memoir on prussic acid), Annales de chimie 1: 30-39.

[15] Newbold, B. T. (1999-11-01). "Claude Louis Berthollet: A Great Chemist in the French Tradition". Canadian Chemical News. Retrieved 2010-03-31.

[16] Gay-Lussac (1811) "Note sur l'acide prussique" (Note on prussic acid), Annales de chimie, 44: 128 - 133.

[17] Gay-Lussac (1815) "Recherche sur l'acide prussique" (Research on prussic acid) Annales de Chimie 95: 136-231.

[18] [1]. EPA. Retrieved on 2013-01-31.

[19] Andrussow, L. (1935). "The catalytic oxydation of ammonia-methane-mixtures to hydrogen cyanide". Angewandte Chemie 48 (37): 593–595. doi:10.1002/ange.19350483702.

[20] Endter, F. (1958). "Die technische Synthese von Cyanwasserstoff aus Methan und Ammoniak ohne Zusatz von Sauerstoff". Chemie Ingenieur Technik 30 (5): 305–310. doi:10.1002/cite.330300506.

[21] Vetter, J. (2000). "Plant cyanogenic glycosides". Toxicon 38 (1): 11–36. doi:10.1016/S0041-0101(99)00128-2. PMID 10669009.

[22] Jones, D. A. (1998). "Why are so many food plants cyanogenic?". Phytochemistry 47 (2): 155–162. doi:10.1016/S0031-9422(97)00425-1. PMID 9431670.

[23] "Are Apple Cores Poisonous? The Naked Scientists September 2010". Retrieved 6 March 2014.

[24] Blum, M. S.; Woodring, J. P. (1962). "Secretion of Benzaldehyde and Hydrogen Cyanide by the Millipede Pachydesmus crassicutis (Wood)". Science 138 (3539): 512–513. Bibcode:1962Sci...138..512B. doi:10.1126/science.138.3539.512. PMID 17753947.

[25] Aregheore, E. M.; Agunbiade, O. O. (1991). "The toxic effects of cassava (manihot esculenta grantz) diets on humans: a review". Veterinary and Human Toxicology 33 (3): 274–275. PMID 1650055.

[26] White, W. L. B.; Arias-Garzon, D. I.; McMahon, J. M.; Sayre, R. T. (1998). "Cyanogenesis in Cassava, The Role of Hydroxynitrile Lyase in Root Cyanide Production". Plant Physiology 116 (4): 1219–1225. doi:10.1104/pp.116.4.1219. PMC 35028. PMID 9536038.

[27] "Making Sense of the Chemistry That Led to Life on Earth". Retrieved 5 May 2015.

[pmid9369328-28] Borowitz JL, Gunasekar PG, Isom GE. (12 Sep 1997). "Hydrogen cyanide generation by mu-opiate receptor activation: possible neuromodulatory role of endogenous cyanide.". Brain Res. 768 (1-2): 294–300. doi:10.1016/S0006-8993(97)00659-8. PMID 9369328.

[29] Gunasekar PG, Prabhakaran K, Li L, Zhang L, Isom GE, Borowitz JL. (May 2004). "Receptor mechanisms mediating cyanide generation in PC12 cells and rat brain.". Neurosci Res. 49 (1): 13–18. doi:10.1016/j.neures.2004.01.006. PMID 15099699.

[30] Smith RP, Kruszyna H. (Jan 1976). "Toxicology of some inorganic antihypertensive anions.". Fed Proc. 35 (1): 69–72. PMID 1245233.

[31] Matthews, C. N. (2004). "The HCN World: Establishing Protein - Nucleic Acid Life via Hydrogen Cyanide Polymers". Origins: Genesis, Evolution and Diversity of Life. Cellular Origin and Life in Extreme Habitats and Astrobiology 6. pp. 121–135. doi:10.1007/1-4020-2522-X_8. ISBN 978-1-4020-2522-8.

[32] Al-Azmi, A.; Elassar, A.-Z. A.; Booth, B. L. (2003). "The Chemistry of Diaminomaleonitrile and its Utility in Heterocyclic Synthesis". Tetrahedron 59 (16): 2749–2763. doi:10.1016/S0040-4020(03)00153-4.

[Snyder.2C_Lewis_E..3B_Buhl.2C_David_1971_L47-33] Snyder, L. E.; Buhl, D. (1971). "Observations of Radio Emission from Interstellar Hydrogen Cyanide" (pdf). Astrophysical Journal 163: L47–L52. Bibcode:1971ApJ...163L..47S. doi:10.1086/180664.

[Treffers.2C_Richard.3B_Larson.2C_Harold.3B_Fink.2C_Uwe.3B_Gautier.2C_Thomas_1978-34] Treffers, R.; Larson, H. P.; Fink, U.; Gautier, T. N. (1978). "Upper limits to trace constituents in Jupiter's atmosphere from an analysis of its 5-μm spectrum". Icarus 34 (2): 331–343. Bibcode:1978Icar...34..331T. doi:10.1016/0019-1035(78)90171-9.

[35] Bieging, J. H.; Shaked, S.; Gensheimer, P. D. (2000). "Submillimeter‐ and Millimeter‐Wavelength Observations of SiO and HCN in Circumstellar Envelopes of AGB Stars" (pdf). Astrophysical Journal 543 (2): 897–921. Bibcode:2000ApJ...543..897B. doi:10.1086/317129.

[36] Schilke, P.; Menten, K. M. (2003). "Detection of a Second, Strong Sub-millimeter HCN Laser Line toward Carbon Stars" (pdf). Astrophysical Journal 583 (1): 446–450. Bibcode:2003ApJ...583..446S. doi:10.1086/345099.

[Boger.2C_G._I._and_Sternberg.2C_A._2005_302-37] Boger, G. I.; Sternberg, A. (2005). "CN and HCN in Dense Interstellar Clouds" (pdf). Astrophysical Journal 632 (1): 302–315. arXiv:astro-ph/0506535. Bibcode:2005ApJ...632..302B. doi:10.1086/432864.

[38] Gao, Y.; Solomon, P. M. (2004). "The Star Formation Rate and Dense Molecular Gas in Galaxies" (pdf). Astrophysical Journal 606 (1): 271–290. arXiv:astro-ph/0310339. Bibcode:2004ApJ...606..271G. doi:10.1086/382999.

[39] Gao, Y.; Solomon, P. M. (2004). "HCN Survey of Normal Spiral, Infrared‐luminous, and Ultraluminous Galaxies" (pdf). Astrophysical Journal Supplements 152: 63–80. arXiv:astro-ph/0310341. Bibcode:2004ApJS..152...63G. doi:10.1086/383003.

[40] Wu, J.; Evans, N. J. (2003). "Indications of Inflow Motions in Regions Forming Massive Stars" (pdf). Astrophysical Journal 592 (2): L79–L82. arXiv:astro-ph/0306543. Bibcode:2003ApJ...592L..79W. doi:10.1086/377679.

[41] Loenen, A. F. (2007). Proceedings IAU Symposium 202. Missing or empty |title= (help)

[NASA-20140811-42] Zubritsky, Elizabeth; Neal-Jones, Nancy (11 August 2014). "RELEASE 14-038 - NASA’s 3-D Study of Comets Reveals Chemical Factory at Work". NASA. Retrieved 12 August 2014.

[AJL-20140811-43] Cordiner, M.A. et al. (11 August 2014). "Mapping the Release of Volatiles in the Inner Comae of Comets C/2012 F6 (Lemmon) and C/2012 S1 (ISON) Using the Atacama Large Millimeter/Submillimeter Array". The Astrophysical Journal 792 (1). doi:10.1088/2041-8205/792/1/L2. Retrieved 12 August 2014.

[cyanidecode1-44] Environmental and Health Effects. Cyanidecode.org. Retrieved on 2012-06-02.

[45] Dwork, D.; van Pelt, R. J. (1996). Auschwitz, 1270 to the present. Norton. p. 443. ISBN 0-393-03933-1.

[46] "Hydrogen Cyanide". Organisation for the Prohibition of Chemical Weapons. Retrieved 2009-01-14.

[47] Markus Schnedlitz (2008) Chemische Kampfstoffe: Geschichte, Eigenschaften, Wirkung. GRIN Verlag, ISBN 364023360-3, p. 13

[48] Poison Hand Darted Harpoons and Lances.

[49] The Poison Garden website http://www.thepoisongarden.co.uk/atoz/prunus_laurocerasus.htm. Retrieved 18 October 2014. Missing or empty |title= (help)

[http:.2F.2Fwww.cdc.gov.2Fniosh.2Fidlh.2F74908.html-50] "Documentation for Immediately Dangerous to Life or Health Concentrations (IDLHs) – 74908". NIOSH.

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hydrogen cyanide