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Chemistry

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Also known as: Hydrocyanic acid, Formonitrile, Prussic acid, Cyanwasserstoff, Blausaeure, Formic anammonide
Molecular Formula
CHN
Molecular Weight
27.025  g/mol
InChI Key
LELOWRISYMNNSU-UHFFFAOYSA-N
FDA UNII
2WTB3V159F

Hydrogen cyanide
Hydrogen cyanide (HCN); A toxic liquid or colorless gas. It is found in the smoke of various tobacco products and released by combustion of nitrogen-containing organic materials.
1 2D Structure

Hydrogen cyanide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
formonitrile
2.1.2 InChI
InChI=1S/CHN/c1-2/h1H
2.1.3 InChI Key
LELOWRISYMNNSU-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C#N
2.2 Other Identifiers
2.2.1 UNII
2WTB3V159F
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Acid, Hydrocyanic

2. Cyanide, Hydrogen

3. Hydrocyanic Acid

4. Zyklon B

2.3.2 Depositor-Supplied Synonyms

1. Hydrocyanic Acid

2. Formonitrile

3. Prussic Acid

4. Cyanwasserstoff

5. Blausaeure

6. Formic Anammonide

7. Evercyn

8. 74-90-8

9. Zaclondiscoids

10. Cyclon

11. Cyclone B

12. Aero Liquid Hcn

13. Agent Ac

14. Cyaanwaterstof

15. Cyjanowodor

16. Blauwzuur

17. Acido Cianidrico

18. Acide Cyanhydrique

19. Hydrogen Cyanide [iso]

20. Rcra Waste Number P063

21. Blausaeure [german]

22. Carbon Hydride Nitride (chn)

23. Methanenitrile

24. Hcn

25. Hydridonitridocarbon

26. [chn]

27. Un 1051

28. Hydrogen(nitridocarbonate)

29. Zyklon B

30. 2wtb3v159f

31. Chembl183419

32. Chebi:18407

33. Blausaeure (german)

34. Blauwzuur [dutch]

35. Cyjanowodor [polish]

36. Caswell No. 483

37. Cyaanwaterstof [dutch]

38. Cyanwasserstoff [german]

39. Acido Cianidrico [italian]

40. Acide Cyanhydrique [french]

41. Ac [cyanide]

42. Hsdb 165

43. Acide Cyanhydrique [iso-french]

44. Einecs 200-821-6

45. Na1613

46. Un1051

47. Un1613

48. Un1614

49. Un3294

50. Rcra Waste No. P063

51. Epa Pesticide Chemical Code 045801

52. Ai3-31100-x

53. Brn 1718793

54. Unii-2wtb3v159f

55. Zootic Acid

56. Nitrilomethane #

57. Prussic Acid, Anhydrous, Stabilized

58. Carbon Hydride Nitride

59. Hydrocyanic Acid, Anhydrous, Stabilized

60. Hydrogen Cyanide, Anhydrous, Stabilized

61. Prussic Acid, Unstabilized

62. Hydrocyanicum Acidum

63. Ec 200-821-6

64. 143334-20-7

65. Un 1613 (salt/mix)

66. Un 1614 (salt/mix)

67. Hydrogen Cyanide [mi]

68. Hydrocyanic Acid (prussic), Unstabilized [forbidden]

69. Hydrogen Cyanide [hsdb]

70. Dtxsid9024148

71. Hydrogen Cyanide [who-dd]

72. Hydrocyanicum Acidum [hpus]

73. Ac (chemical Warfare Agent)

74. Bdbm50152968

75. Hydrocyanic Acid Aqueous Solutions, With Not >20% Hydrocyanic Acid

76. Hydrocyanic Acid, Anhydrous, Stabilized, Absorbed In A Porous Inert Material

77. Hydrogen Cyanide, Anhydrous, Stabilized, Absorbed In A Porous Inert Material

78. Prussic Acid, Anhydrous, Stabilized, Absorbed In A Porous Inert Material

79. Na 1051

80. Hydrocyanic Acid (prussic), Unstabilized

81. Hydrogen Cyanide, Stabilized With <3% Water

82. C01326

83. Q3416481

84. Graphitic Carbon Nitride, 99%, Length: 1 - 10 Mum

85. Hydrocyanic Acid, Aqueous Solutions <5% Hydrogen Cyanide

86. Hydridonitridocarbonhydrogen(nitridocarbonate)methanenitrile

87. Hydrogen Cyanide, Stabilized With <3% Water [un1051] [poison]

88. Hydrogen Cyanide, Solution In Alcohol With Not >45% Hydrogen Cyanide

89. Hydrocyanic Acid, Aqueous Solutions <5% Hydrogen Cyanide [na1613] [poison]

90. Hydrogen Cyanide, Solution In Alcohol With Not >45% Hydrogen Cyanide [un3294] [poison]

91. Hydrogen Cyanide, Stabilized, With <3% Water And Absorbed In A Porous Inert Material

92. Hydrocyanic Acid, Aqueous Solutions Or Hydrogen Cyanide, Aqueous Solutions With Not > 20% Hydrogen Cyanide

93. Hydrocyanic Acid, Aqueous Solutions Or Hydrogen Cyanide, Aqueous Solutions With Not > 20% Hydrogen Cyanide [un1613] [poison]

94. Hydrogen Cyanide, Stabilized, With <3% Water And Absorbed In A Porous Inert Material [un1614] [poison]

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 27.025 g/mol
Molecular Formula CHN
XLogP30.1
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Exact Mass27.010899036 g/mol
Monoisotopic Mass27.010899036 g/mol
Topological Polar Surface Area23.8 Ų
Heavy Atom Count2
Formal Charge0
Complexity10
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Minimum/Potential Fatal Human Dose

Cyanide is the least toxic of the "lethal" chemical agents. The LCt50s of hydrogen cyanide (AC) and cyanogen chloride (CK) by inhalation have been estimated to be 2500-5000 mg x min/cu m for AC and about 11,000 mg x min/cu m for CK. LD50s for hydrogen cyanide have been estimated to be 1.1 mg/kg for IV administration and 100 mg/kg after skin exposure. ... Cyanide is unique among military chemical agents because it is detoxified at a rate that is of practical importance, about 17 ug/kg x min. As a result the LCt50 is greater for a long exposure (e.g., 60 minutes) than for a short exposure (e.g., 2 minutes).

U.S. Army Research Institute of Chemical Defense, Chemical Casualty Care Division; Medical Management of Chemical Casualties Handbook, 3rd Ed. Aberdeen Proving Ground, MD (August 1999) Available from, as of January 5, 2018: https://www.brooksidepress.org/Products/OperationalMedicine/DATA/operationalmed/Manuals/RedHandbook/001TitlePage.htm


Cyanide is a potent oral poison producing symptoms in minutes and death in minutes to hours. One teaspoon of 29% liquid hydrogen cyanide has been fatal.

Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 1477


Lethal adult dose of hydrogen cyanide is 50 mg.

Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 1477


An average LD50 value for dermal exposure of 100 mg CN per kg as hydrogen cyanide was estimated for humans.

U.S. Dept Health & Human Services/Agency for Toxic Substances & Disease Registry; Toxicological Profile for Cyanide p.66 (July 2006)


An average fatal concentration for humans was estimated as 546 ppm hydrogen cyanide after a 10-minute exposure.

U.S. Dept Health & Human Services/Agency for Toxic Substances & Disease Registry; Toxicological Profile for Cyanide. p.27 (July 2006)


An average LD50 value for dermal exposure of 100 mg/kg body weight was estimated for humans. Concentrations of 7000 to 12,000 mg/cu m were estimated to be fatal after a 5-min exposure of workers with self-contained respirators without effective skin protection.

International Programme on Chemical Safety; Concise International Chemical Assessment Document 61: Hydrogen Cyanide and Cyanides: Human Health Aspects (2004) Available from, as of January 5, 2018: https://www.inchem.org/documents/cicads/cicads/cicad61.htm


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Chemical Warfare Agents

Chemicals that are used to cause the disturbance, disease, or death of humans during WARFARE. (See all compounds classified as Chemical Warfare Agents.)


5.2 Absorption, Distribution and Excretion

Cyanide as hydrogen cyanide is rapidly absorbed (within seconds) following inhalation exposure. Humans retained 58% of hydrogen cyanide in the lungs after inhaling the gas through normal breathing.

U.S. Dept Health & Human Services/Agency for Toxic Substances & Disease Registry; Toxicological Profile for Cyanide p.75 (July 2006)


Once cyanide is absorbed, it is rapidly distributed by the blood throughout the body. Tissue levels of hydrogen cyanide were 0.75, 0.42, 0.41, 0.33, and 0.32 mg/100 g of tissue in the lung, heart, blood, kidney, and brain, respectively, in a man who died following inhalation exposure to hydrogen cyanide gas. ... In another case, tissue cyanide levels from a man who died from inhalation of hydrogen cyanide were reported as 0.5 mg per 100 mL of blood and 0.11, 0.07, and 0.03 mg/100 g in the kidney, brain, and liver, respectively. Urinary cyanide levels were reported as 0.2 mg/100 mL, and 0.03 mg/100 g were found in the gastric contents ... .

U.S. Dept Health & Human Services/Agency for Toxic Substances & Disease Registry; Toxicological Profile for Cyanide p.77-8 (July 2006)


Rats exposed /by inhalation/ to hydrogen cyanide gas at 356 or 1,180 ppm died within 10 and 5 minutes, respectively. Samples taken immediately after respiration stopped showed that the pattern of tissue distribution of cyanide did not vary with the concentration used. In averaging data for both dose groups, tissue concentrations, reported as ug/g wet weight (ww), were 4.4 in the lungs, 3.0 in the blood, 2.15 in the liver, 1.4 in the brain, and 0.68 in the spleen. Thus, the highest cyanide concentrations were observed in the lung.

U.S. Dept Health & Human Services/Agency for Toxic Substances & Disease Registry; Toxicological Profile for Cyanide p.78 (July 2006)


Rabbits exposed /by inhalation/ to hydrogen cyanide at 2,714 ppm for 5 minutes had cyanide levels of 170/100 mL in blood and 48 ug/100 mL in plasma, and tissue levels (in units of ug/100 g) of 0 in the liver, 6 in the kidney, 50 in the brain, 62 in the heart, 54 in the lung, and 6 in the spleen. ... Six rabbits exposed dermally (area not reported) to 33.75 mg CN/kg as hydrogen cyanide had blood and serum cyanide levels of 310 and 144 ug/dL, respectively, and tissue levels (ug/100 g) of 26 in liver, 66 in kidney, 97 in brain, 110 in heart, 120 in lungs, and 21 in the spleen.

U.S. Dept Health & Human Services/Agency for Toxic Substances & Disease Registry; Toxicological Profile for Cyanide p.78, 80 (July 2006)


For more Absorption, Distribution and Excretion (Complete) data for Hydrogen cyanide (27 total), please visit the HSDB record page.


5.3 Metabolism/Metabolites

Reports of ingestion of cyanides by humans and reports of occupational exposure ... indicate that cyanide is transformed into thiocyanate. ... Conversion of cyanide to thiocyanate is enhanced when cyanide poisoning is treated by intravenous administration of a sulfur donor ... . The sulfur donor must have a sulfane sulfur, a sulfur bonded to another sulfur (e.g., sodium thiosulfate). During conversion by rhodanese, a sulfur atom is transferred from the donor to the enzyme, forming a persulfide intermediate. The persulfide sulfur is then transferred from the enzyme to cyanide, yielding thiocyanate. Thiocyanate is then readily excreted in the urine as the major metabolite. Once thiocyanate is formed, it is not converted back to cyanide. /Cyanide/

U.S. Dept Health & Human Services/Agency for Toxic Substances & Disease Registry; Toxicological Profile for Cyanide p.80-2 (July 2006)


The metabolism of cyanide has been studied in animals. The proposed metabolic pathways ... are (1) the major pathway, conversion to thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase; (2) conversion to 2-aminothiazoline-4-carboxylic acid; (3) incorporation into a 1-carbon metabolic pool; or (4) combining with hydroxocobalamin to form cyanocobalamin (vitamin B12). Thiocyanate has been shown to account for 60 to 80% of an administered cyanide dose while 2-aminothiazoline-4-carboxylic acid accounts for about 15% of the dose. /Cyanide/

U.S. Dept Health & Human Services/Agency for Toxic Substances & Disease Registry; Toxicological Profile for Cyanide p.80 (July 2006)


Although cyanide can interact with substances such as methemoglobin in the bloodstream, the majority of cyanide metabolism occurs within the tissues. Cyanide is metabolized in mammalian systems by one major route and several minor routes. The major route of metabolism for hydrogen cyanide and cyanides is detoxification in the liver by the mitochondrial enzyme rhodanese, which catalyses the transfer of the sulfane sulfur of thiosulfate to the cyanide ion to form thiocyanate ... . About 80% of cyanide is detoxified by this route. The rate-limiting step is the amount of thiosulfate. While rhodanese is present in the mitochondria of all tissues, the species and tissue distributions of rhodanese are highly variable. In general, the highest concentrations of rhodanese are found in the liver, kidney, brain, and muscle, but the supply of thiosulfate is limited. Rhodanese is present in rat nasal mucosal tissues, particularly in the olfactory region, at a 7-fold higher concentration (on a per milligram of mitochondrial protein basis) than in the liver. Dogs have a lower overall activity of rhodanese than monkeys, rats, and rabbits. A number of other sulfur transferases can also metabolize cyanide, and albumin, which carries elemental sulfur in the body in the sulfane form, can assist in the catalysis of cyanide to thiocyanate as well. Cyanide and thiocyanate can also be metabolized by several minor routes, including the combination of cyanide with hydroxycobalamin (vitamin B12a) to yield cyanocobalamin (vitamin B12) and the non-enzymatic combination of cyanide with cystine, forming 2-iminothiazoline-4-carboxylic acid, which appears to be excreted without further change. /Cyanide/

International Programme on Chemical Safety; Concise International Chemical Assessment Document 61: Hydrogen Cyanide and Cyanides: Human Health Aspects (2004) Available from, as of January 5, 2018: https://www.inchem.org/documents/cicads/cicads/cicad61.htm


While absorbed cyanide is principally excreted as thiocyanate in the urine, traces of free hydrogen cyanide may also be excreted unchanged in the lungs, saliva, sweat, or urine, as carbon dioxide in expired air, or as beta-thiocyanoalanine in saliva and sweat. /Cyanide/

International Programme on Chemical Safety; Concise International Chemical Assessment Document 61: Hydrogen Cyanide and Cyanides: Human Health Aspects (2004) Available from, as of January 5, 2018: https://www.inchem.org/documents/cicads/cicads/cicad61.htm


For more Metabolism/Metabolites (Complete) data for Hydrogen cyanide (17 total), please visit the HSDB record page.


5.4 Biological Half-Life

The time-course of cyanide in exhaled air was measured with an electrochemical detector in 10 volunteers during and after a 1 min x 10 ppm exposure to HCN. The experiment revealed an average half-life of 16s (range 10-24s) in breath.

PMID:18490114 Stamyr K et al; Toxicol Lett 179 (1): 59-62 (2008)


A plasma half-life of 20 minutes to 1 hour has been estimated for cyanides in humans after nonlethal exposures /Cyanides/

U.S. Dept Health & Human Services/Agency for Toxic Substances & Disease Registry; Toxicological Profile for Cyanide p.80 (July 2006)


Half-time values of the principal metabolite thiocyanate in humans have been reported as 4 hr, 2 days, and 2.7 days. In patients with renal insufficiency, a mean half-time of 9 days was reported.

International Programme on Chemical Safety; Concise International Chemical Assessment Document 61: Hydrogen Cyanide and Cyanides: Human Health Aspects (2004) Available from, as of January 5, 2018: https://www.inchem.org/documents/cicads/cicads/cicad61.htm


Half-life for the conversion of cyanide to thiocyanate from a non-lethal dose in man is between 20 min and 1 hr. /Cyanide/

Feldstein M, Klendshoj NC; J Lab Chin Med 44: 166-70 (1954) as cited in NIOSH; Criteria Document: Hydrogen Cyanide and Cyanide Salts p.45 (1976) DHEW Pub. NIOSH 77-108


5.5 Mechanism of Action

Cyanide (as hydrogen cyanide), originating in vivo by dissociation of potassium cyanide, sodium cyanide, and other cyanogenic compounds or arising from catabolism of cyanogenic glycosides, exerts its acute toxic effects by complexing with the ferric iron atom in metalloenzymes, resulting in histotoxic anoxia through inhibition of cytochrome c oxidase, metalloenzymes that function as the terminal oxidase of the inner mitochondrial membrane respiratory chain. A two-step process has been proposed: cyanide as hydrogen cyanide first penetrates a protein crevice of cytochrome c oxidase and binds to the protein. Hydrogen cyanide then binds to the trivalent iron ion of the enzyme, forming a relatively stable (but reversible) coordination complex. One mole of hydrogen cyanide is bound to one mole of cytochrome c oxidase. As a result, the enzyme becomes unable to catalyze the reactions in which electrons would be transferred from reduced cytochrome to oxygen. Cellular oxygen utilization is thus impaired, with resultant reduction in or cessation of aerobic metabolism. Glucose catabolism then shifts from the aerobic pathway to anaerobic metabolism including the pentose phosphate pathway, resulting in increased blood glucose, pyruvic acid, lactic acid, and nicotinamide adenine dinucleotide (NADPH) levels, and a decrease in the adenosine triphosphate/adenosine diphosphate (ATP/ADP) ratio. /Some investigators/ suggest that it is the binding of cyanide to oxidized CuB, the copper ion that is part of the dioxygen binding-site that leads to the inhibition of cytochrome c oxidase. The inhibition of oxygen use by cells (termed histoxic hypoxia) causes oxygen tensions to rise in peripheral tissues. This results in a decrease in the unloading gradient for oxyhemoglobin; thus, oxyhemoglobin is carried in the venous blood. Inhibition of oxygen utilization is thought to occur rapidly after cyanide exposure. ... In addition to binding to cytochrome c oxidase, cyanide also binds to catalase, peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, and succinic dehydrogenase. These reactions may also contribute to the classic signs of cyanide toxicity. ...

U.S. Dept Health & Human Services/Agency for Toxic Substances & Disease Registry; Toxicological Profile for Cyanide p.90-1(July 2006)


The mitochondrial electron transport system may also be seriously disturbed by cyanide through the inhibition of succinate dehydrogenase, which is a nonheme flavin-containing iron-sulfur protein which passes electrons to the cytochrome system. The peculiarity of this enzyme is its sulfur linkages which are of the persulfide or sulfane type, favoring a "labile sulfur" condition that is essential for activity. Cyanide is a strong thiophile reacting with the "labile" sulfur thus breaking the persulfide bond.

Nat'l Research Council Canada; The Effect of Cyanides on Aquatic Organisms with Emphasis Upon Fresh Water Fishes p.59 (1982) NRCC No.19246


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Hydrogen cyanide manufacturers, exporters & distributors 1

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Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Hydrogen cyanide manufacturer or Hydrogen cyanide supplier.

PharmaCompass also assists you with knowing the Hydrogen cyanide API Price utilized in the formulation of products. Hydrogen cyanide API Price is not always fixed or binding as the Hydrogen cyanide Price is obtained through a variety of data sources. The Hydrogen cyanide Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Hydrogen cyanide

Synonyms

Hydrocyanic acid, Formonitrile, Prussic acid, Cyanwasserstoff, Blausaeure, Formic anammonide

Cas Number

74-90-8

Unique Ingredient Identifier (UNII)

2WTB3V159F

About Hydrogen cyanide

Hydrogen cyanide (HCN); A toxic liquid or colorless gas. It is found in the smoke of various tobacco products and released by combustion of nitrogen-containing organic materials.

Hydrogen cyanide Manufacturers

A Hydrogen cyanide manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Hydrogen cyanide, including repackagers and relabelers. The FDA regulates Hydrogen cyanide manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Hydrogen cyanide API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Hydrogen cyanide Suppliers

A Hydrogen cyanide supplier is an individual or a company that provides Hydrogen cyanide active pharmaceutical ingredient (API) or Hydrogen cyanide finished formulations upon request. The Hydrogen cyanide suppliers may include Hydrogen cyanide API manufacturers, exporters, distributors and traders.

Hydrogen cyanide GMP

Hydrogen cyanide Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Hydrogen cyanide GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Hydrogen cyanide GMP manufacturer or Hydrogen cyanide GMP API supplier for your needs.

Hydrogen cyanide CoA

A Hydrogen cyanide CoA (Certificate of Analysis) is a formal document that attests to Hydrogen cyanide's compliance with Hydrogen cyanide specifications and serves as a tool for batch-level quality control.

Hydrogen cyanide CoA mostly includes findings from lab analyses of a specific batch. For each Hydrogen cyanide CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Hydrogen cyanide may be tested according to a variety of international standards, such as European Pharmacopoeia (Hydrogen cyanide EP), Hydrogen cyanide JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Hydrogen cyanide USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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