Product
Supplier
Encyclopedia
Inquiry
Home > Encyclopedia > Cyanamide

Cyanamide

Cyanamide structure

Cyanamide 

structure
  • CAS No:

    420-04-2

  • Formula:

    CH2N2

  • Chemical Name:

    Cyanamide

  • Synonyms:

    Cyanamide;Amidocyanogen;Cyanogenamide;Cyanogen nitride;Carbamonitrile;Cyanoamine;Hydrogen cyanamide;N-Cyanoamine;Alzogur;Carbimide;TsAKS;NSC 24133;Dormex;Deurbraak;Cyanamide F 1000;F 1000;Dyhard VP 111;Amino cyanide;CY 100;Dormax;32729-71-8;65931-45-5

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

white crystalline solid Cyanamide is a combustible crystalline solid, but it is usually found as a 25% liquid solution.


Cyanamide appears as colorless deliquescent crystals. Mp: 45°C; bp: 260°C. Density: 1.282 g cm-3. Quite soluble in water (77 g / 100 g solution at 15°C). Soluble in butanol, methyl ethyl ketone, ethyl acetate, alcohols, phenols, amines, ethers. Note: The term "cyanamide" is also used to refer to the important compound calcium cyanamide, which is a different chemical.|Liquid|COLOURLESS HYGROSCOPIC DELIQUESCENT CRYSTALS.|Crystalline solid.


Cyanamide appears as colorless deliquescent crystals. Mp: 45°C; bp: 260°C. Density: 1.282 g cm-3. Quite soluble in water (77 g / 100 g solution at 15°C). Soluble in butanol, methyl ethyl ketone, ethyl acetate, alcohols, phenols, amines, ethers. Note: The term "cyanamide" is also used to refer to the important compound calcium cyanamide, which is a different chemical.|Cyanamide is a nitrile that is hydrogen cyanide in which the hydrogen has been replaced by an amino group. It has a role as an EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor. It is a nitrile and a one-carbon compound. It is a conjugate acid of a cyanamide(2-).|Calcium cyanamide is used as a fertilizer, pesticide, and in the manufacture of other chemicals. It is irritating to the eyes, skin, and respiratory tract in humans. Acute (short-term) inhalation exposure may cause gastritis,rhinitis, pharyngitis, laryngitis, and tracheobronchitis. Acute oral exposure may cause a vasomotor reaction, resulting in intense flushing of the face, upper body, and arms. Tachycardia and hypotension have also been observed in humans following acute oral exposure. Chronic (long-term) occupational exposure has been reported to cause chronic rhinitis with perforation of the nasal septum in workers. EPA has not classified calcium cyanamide with respect to potential carcinogenicity.|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.

Cyanamide Basic Attributes

42.041

42.04

206-992-3

21CP7826LC

0424

267195|24133

2811

DTXSID6020353|DTXSID9034490|DTXSID90745933

Orthorhombic, elongated, six-sided tablets from dimethyl phthalate|Crystallizes from a variety of solvents as somewhat unstable, colorless, orthorhombic, deliquescent crystals.|Deliquescent crystals|Cyanamide forms colorless, orthorhombic crystals or long transparent needles (from water), large platelike crystals when allowed to crystallize spontaneously from water, and crystals from dimethyl phthalate solution.

29269090

Characteristics

49.8

-0.82 (20 deg C)

Cyanamide appears as colorless deliquescent crystals. Mp: 45°C; bp: 260°C. Density: 1.282 g cm-3. Quite soluble in water (77 g / 100 g solution at 15°C). Soluble in butanol, methyl ethyl ketone, ethyl acetate, alcohols, phenols, amines, ethers. Note: The term "cyanamide" is also used to refer to the important compound calcium cyanamide, which is a different chemical.

1.282 g/cm3 @ Temp: 20 °C

45-46 °C

83 °C @ Press: 0.5 Torr

286°F

1.397

775 g/L

Solid is stored in a cool, dry, place. Liquid is stored in pH4 added with phosphoric acid, sulfuric acid, or boric acid.

Vapour pressure, Pa at 20°C: 0.5

1.45 (Air = 1)

LD50 i.p. in male mice: 200-300 mg/kg (Doull)

Combustible Solid

1.03(at 25 °C)

Henry's Law constant = 2.66X10-11 atm-cu m/mole (est)

1.03 (at 25 °C)|Ka = 5.42X10-11; Kb = 2.5X10-12|pKa = 10.3

Deliquescent; optimum pH for storage of soln is approx 4; attacks various metals|Formation of dicyandiamide begins at 122 °C; dipole moment in benzene at 20 °C: 3.8|Cryoscopic constant (water) 26.8-28.4; specific heat 0.547 cal/g/deg C between 0 °C and 39 °C|Heat of formation 14.05 kcal/mole (25 °C); polymerizes at 122 °C; heat of fusion 2.1 kcal/mole|For more Other Experimental Properties (Complete) data for Cyanamide (7 total), please visit the HSDB record page.

No rapid reaction with air Slow reaction with water or mositure in air

Amines, Phosphines, and Pyridines

Polymerizable

CYANAMIDE is the amide of cyanic acid. Non-flammable but combustible (flash point: 140° C). Decomposes on warming above 49° C. Emits toxic fumes of CN- and NOx when heated to decomposition or on contact with acids or acid fumes (Hazardous Chemicals Desk Reference, p. 353 (1987)). Contact with moisture, acids or bases may cause a violent reaction at temperatures above about 40° C. Dry solid may polymerize at temperatures above 122° C. Rapid or explosive polymerization may occur during the evaporation of aqueous solutions. Reacts explosively with strong oxidizing agents and strong reducing agents. Attacks various metals (International Chemical Safety Card).

-176.4 kcal/mole (25 °C)

10.65eV|10.65 eV

Combustible Solid

Non-corrosive, as far as known

16.4 kcal/mole

Safety Information

III

8

UN 2811 6.1/PG 3

2

R21;R25;R36/38;R43

S3-S22-S36/37-S45

GS5950000

T:Toxic

Separated from food and feedstuffs and incompatible materials. See Chemical Dangers. Cool. Store at maximum 20 °C, never exceed 30 °C. Dry. Well closed. Keep in a well-ventilated room. Store only if stabilized. See Notes. Store in stainless steel, polyethylene or polypropylene.

Unstable - heat sensitive. Incompatible with strong oxidizing agents, strong reducing agents, bases, acids, iron and its salts, steel, brass, lead, moisture. Reacts with acids to produce very toxic gas.

P201-P280-P301 + P310 + P330-P303 + P361 + P353-P304 + P340 + P310-P305 + P351 + P338

H301 + H311-H314-H317-H361fd-H373-H412

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

... On contact with acid or fumes, it emits toxic fumes of cyanide and nitroxides.|Thermally unstable. Contact with moisture (water), acids, or alkalies may cause a violent reaction above 40 °C.|Cynamide solution easily reacts with metals.|Above 104 degrees F: Moisture, acids or alkalis; 1,2-phenylene diamine salts [Note: Polymerization may occur on evaporation of aqueous solutions].

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. For electric vehicles or equipment, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. (ERG, 2016)|Combustible only at increased temperature. Gives off irritating or toxic fumes (or gases) in a fire.|Flammable - 3rd degree, Reactive - 1st degree

|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P272, P273, P280, P281, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P312, P314, P321, P322, P330, P333+P313, P361, P363, P405, and P501|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P304+P340, P305+P351+P338, P310, P312, P330, P403+P233, P405, and P501|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P272, P273, P280, P281, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P312, P314, P321, P322, P330, P332+P313, P333+P313, P337+P313, P361, P362, P363, P405, and P501|Aggregated GHS information provided by 269 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P260, P261, P264, P270, P271, P272, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P314, P321, P330, P332+P313, P333+P313, P362, P363, P403+P233, P405, and P501|P201, P202, P260, P261, P264, P270, P271, P272, P273, P280, P281, P301+P310, P302+P352, P304+P340, P305+P351+P338, P307+P311, P308+P313, P312, P314, P321, P322, P330, P332+P313, P333+P313, P337+P313, P361, P362, P363, P391, P403+P233, P405, and P501|H261: In contact with water releases flammable gas [Danger Substances and mixtures which in contact with water, emit flammable gases]|P231+P232, P260, P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P309+P311, P310, P312, P321, P330, P332+P313, P362, P370+P378, P402+P404, P403+P233, P405, and P501|P201, P202, P261, P264, P270, P272, P280, P281, P301+P310, P302+P352, P308+P313, P321, P330, P333+P313, P363, P405, and P501

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premise. Provide: Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection. Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.] (NIOSH, 2016)|Wear long rubber gloves, a self-contained breathing apparatus, and coveralls or aprons.|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.|Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. (Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.)|(See protection codes)

Cyanamide may burn, but does not readily ignite.

Use dry chemical or CO2 extinguishers. Containers may explode in fire. If material or contaminated runoff enters waterways, notify downstream users or potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors or shows any signs of deforming), withdraw immediately to a secure position ... The only respirators recommended for fire fighting are self-contained breathing apparatuses that have full facepieces and are operated in a pressure-demand or other positive-pressure mode.

Spill handling: evacuate persons not wearing protective equipment from area of spill or leak until clean-up is complete. Remove all ignition sources. Ventilate area of spill or leak. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or a similar material and deposit in sealed containers. It may be necessary to contain and dispose of this chemical as a hazardous waste. Keep cyanamide out of a confined space, such as a sewer, because of the possibility of an explosion, unless the sewer is designed to prevent the build-up of explosive concentrations. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations.

The worker should immediately wash the skin when it becomes contaminated.|Work clothing that becomes wet or significantly contaminated should be removed and replaced.|Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.|Local exhaust or breathing protection.|For more Preventive Measures (Complete) data for Cyanamide (8 total), please visit the HSDB record page.

Short term exposure: cyanamide is caustic and severely irritates the eyes, skin, and respiratory tracts, and may affect the liver. Ingestion or inhalation may cause transitory intense redness of the face, headache, vertio, increased respiration, tachycardia, and hypotension. The adverse effects of cyanamide are potentiated by the ingestion of alcohol (beer, wine, or liquor) within 1-2 days before or after exposure. Cyanamide is a highly reactive chemical and is a dangerous explosion hazard. Long term exposure: Repeated or prolonged contact may cause skin sensitization and allergy. Exposure may cause liver and nervous system damage.|The dust irritates eyes and respiratory tract.

Recommended Exposure Limits: 10 Hour Time-Weighted Average: 2 mg/cu m.

Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Vacuum spilled material with specialist equipment. Carefully collect remainder. Then store and dispose of according to local regulations.

Separated from food and feedstuffs and incompatible materials. See Chemical Dangers. Cool. Store at maximum 20 °C, never exceed 30 °C. Dry. Well closed. Keep in a well-ventilated room. Store only if stabilized. Store in stainless steel, polyethylene or polypropylene.

A harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered.

The substance is severely irritating to the eyes and skin. The substance is irritating to the respiratory tract.

Repeated or prolonged contact may cause skin sensitization. Animal tests show that this substance possibly causes toxicity to human reproduction or development.

NO open flames.

PREVENT DISPERSION OF DUST! AVOID ALL CONTACT! IN ALL CASES CONSULT A DOCTOR!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield.

| 4 - Materials that, under emergency conditions, can be lethal.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 3 - Materials that in themselves are capable of detonation or explosive decomposition or explosive reaction but that require a strong initiating source or must be heated under confinement before initiation.

Calcium cyanamide is used as a fertilizer, pesticide, and in the manufacture of other chemicals. It is irritating to the eyes, skin, and respiratory tract in humans. Acute (short-term) inhalation exposure may cause gastritis,rhinitis, pharyngitis, laryngitis, and tracheobronchitis. Acute oral exposure may cause a vasomotor reaction, resulting in intense flushing of the face, upper body, and arms. Tachycardia and hypotension have also been observed in humans following acute oral exposure. Chronic (long-term) occupational exposure has been reported to cause chronic rhinitis with perforation of the nasal septum in workers. EPA has not classified calcium cyanamide with respect to potential carcinogenicity.

Cyanamide was found to be present in the wastewater from nitroguanidine processes after 271 days of operation of a continuous-flow columns. Concentrations in continuous-flow soil column effluent columns ranged from 0 to 1.7 mg/L(1).

Toxicity

Systemic absorption after taking alc causes nausea, headache, vertigo, fall in blood pressure, & transitory intense redness of face.|Rats fed ethanol (150 mL/L) for 3 mo & diet contaminated with calcium cyanamide showed 2-fold higher activity of low km acetaldehyde dehydrogenase in liver, higher rate of alc elimination & 2-3 times lower acetaldehyde levels in blood during alc elimination.|Blood pressure response after alc admin was studied in relation to blood acetaldehyde levels in rats pretreated with cyanamide. Cyanamide inhibited low-km aldehyde dehydrogenase in liver & caused & incr acetaldehyde level in blood.|Cyanamide reacted with amino & thiol groups to form guanidino & isothiouronium cmpd respectively under physiological conditions. Possible mode of action of cyanamide on alcohol metabolism are discussed.

LD50 Rat oral 125 mg/kg|LD50 Rat oral 280 mg/kg|LD50 Rat skin 84 mg/kg|LD50 Mouse ip 200 mg/kg|LD50 Rabbit skin 590 mg/kg

/BIRDS and MAMMALS/ A reproductive study ... showed no adverse effects in bobwhite quail up to 300 ppm in the feed.

Recently, cyanamide has been found in nature. Hairy vetch (Vicia villosa) produces free cyanamide from inorganic nitrate, obviously as an allelochemical to compete against neighboring plants. Cyanamide is regarded as a key intermediate within chemical evolution on earth billions of years ago. It is therefore not astonishing that cyanamide metabolism is common in nature(1).

Cyanamide's production and use as a key raw material for production of pesticides and pharmaceuticals(1) may result in its release to the environment through various waste streams; its use as a plant growth regulator to control broad-leaved weeds(2) will result in its direct release to the environment(SRC). It may also enter the environment in the wastewater effluent from nitroguanidine processes and by the abiotic breakdown of nitrosoguanidine(3).

TERRESTRIAL FATE: Based on a classification scheme(1), estimated Koc values of 4.7 and 7.3(SRC), determined from a structure estimation method(2) and a log Kow of -0.82(3) with a regression-derived equation(2), respectively, indicate that cyanamide is expected to have very high mobility in soil(SRC). Volatilization of cyanamide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.66X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, 3.75X10-3 mm Hg(3), and water solubility, 7.8X10+5 mg/L(3). In soil, cyanamide is converted to nitrogenous compounds which are rapidly taken up(3). In aqueous conditions, cyanamide decomposes by hydrolysis to urea and by dimerization to dicyanamide(4,5). Cyanamide does not absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis on sunlit soil or plant(SRC).|AQUATIC FATE: Based on a classification scheme(1), estimated Koc values of 4.7 and 7.3(SRC), determined from a structure estimation method(2) and a log Kow of -0.82(3) with a regression-derived equation(2), respectively, indicate that cyanamide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization of cyanamide from water surfaces is not expected(4) given an estimated Henry's Law constant of 2.66X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, 3.75X10-3 mm Hg(3), and water solubility, 7.8X10+5 mg/L(3). Cyanamide decomposes in water by hydrolysis to urea in acidic conditions and by dimerization to dicyanamide in alkaline conditions(5,6). Cyanamide does not absorb at wavelengths >290 nm(5) and therefore is not expected to be susceptible to direct photolysis on sunlit water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cyanamide, which has a vapor pressure of 3.75X10-3 mm Hg at 20 °C(2), will exist solely as a vapor in the ambient atmosphere. The rate constant for the vapor-phase reaction of cyanamide with photochemically-produced hydroxyl radicals can not be estimated; therefore, the half-life for this reaction in the atmosphere can not be estimated(SRC). Cyanamide does not absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Commercial aqueous solutions of cyanamide require the addition of stabilizers and buffers to prevent the cyanamide from dimerizing to dicyanamide or hydrolyzing to urea(1-2); hydrolysis to urea occurs in acidic conditions(1); dimerization to dicyanamide takes place most readily at pH 8-10(2). Cyanamide is stable to light(3); the UV spectrum of cyanamide shows only weak absorption below 230 nm, with no maximum observable above 208 nm(1), therefore, direct photolysis will not occur in sunlight. The rate constant for the vapor-phase reaction of cyanamide with photochemically-produced hydroxyl radicals can not be estimated(4,SRC), therefore, the half-life for this reaction in the atmosphere can not be estimated.

An estimated BCF of 3.2 was calculated in fish for cyanamide(SRC), using a log Kow of -0.80(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

Using a structure estimation method based on molecular connectivity indices(1), the Koc of cyanamide can be estimated to be 4.7(SRC). The Koc of cyanamide can also be estimated as 7.3(SRC), using a log Kow of -0.82(2) and a regression-derived equation(1). According to a classification scheme(3), these estimated Koc values suggest that cyanamide is expected to have very high mobility in soil.

The Henry's Law constant for cyanamide is estimated as 2.66X10-10 atm-cu m/mole(SRC) derived from its vapor pressure, 3.75X10-3 mm Hg(1), and water solubility, 7.8X10+5 mg/L(1). This Henry's Law constant indicates that cyanamide is expected to be essentially nonvolatile from water surfaces(2). Cyanamide's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC).

According to the 2006 TSCA Inventory Update Report, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use og cyanamide is 100-999; the data may be greatly underestimated(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 2564 workers (272 of these were female) were potentially exposed to cyanamide in the US(1). The NOES Survey does not include farm workers. Occupational exposure to cyanamide may occur through dermal contact with this compound at workplaces where cyanamide is produced or used(SRC).

Drug Information

Cyanamide (carbimide or calcium carbimide) has been used to treat chronic alcoholism for more than 45 years.

A pharmacokinetic and dynamic study of cyanamide, an inhibitor of aldehyde dehydrogenase (ALDH) used as an adjuvant in the aversive therapy of chronic alcoholism, has been carried out in man after oral administrations. ... Blood ALDH activity were estimated after oral administration of 0.3, 1 and 1.5 mg/kg of cyanamide. One i.v. administration of 1 mg/kg was performed in order to determine the absolute bioavailability and the main pharmacokinetic parameters. Elimination half life and total plasma clearance values were 51.7 8.8 min and 14.4 2.7 mL/kg/min respectively. After oral administrations of 0.3, 1 and 1.5 mg/kg a rapid absorption rate was estimated with a Tmax values range of 10.5 to 15.5 min. The extent of absorption was not complete, oral bioavailability being 53%, 70% and 81% respectively. The presence of a first pass-effect is suggested. The inhibitory activity of cyanamide on blood ALDH reached the maximum value 4 hr after its administration and decreased progressively throughout six days period. The cyanamide plasma levels time course did not correlated with the pharmacodynamic time course responses.

Cyanide was detected as a product of cyanamide oxidation by bovine liver catalase in vitro under conditions that also produced an active aldehyde dehydrogenase (AlDH) inhibitor. Cyanide formation was directly related to both cyanamide and catalase concentrations and was also dependent on incubation time. The apparent Km for this reaction was 172 microM. Cyanide formation was blocked by ethanol, a known substrate for catalase Compound I. The toxic effects of cyanamide in the dog, a species with limited capacity to conjugate cyanamide by N-acetylation, may be causally related to enhancement of this catalase-mediated pathway for cyanamide metabolism.|The main urinary metabolite of hydrogen cyanamide (cyanamide) in rat and man is acetylcyanamide (n-acetylcyanamide). An analytical method was developed to determine acetylcyanamide in the urine with a limit of quantification of <10 ug/l (mean recovery 96.1% using spikes of 20 ug/l; relative standard deviation < 4%. This methodology is based upon ion chromatography using column-switch techniques and UV detection. It could be demonstrated that in rats an average of 45.6% of oral applied cyanamide (10 mg/kg) was excreted in the urine as acetylcyanamide. In male human volunteers a mean of 40% of oral admin cyanamide (mean dose 0.25 mg/kg body weight) was excreted via the urine as acetylcyanamide. The same group of volunteers participated in skin absorption study with dermal application of the above cyanamide dose onto a skin surface area of 32 sq cm. Within an application period of 6 hr an average cyanamide quantity of 2.3 mg, was available for skin absorption. A mean portion of 7.7% of this quantity was found as acetylcyanamide in the urine of the participants. Findings from literature state that cyanamide is metabolized in vitro to cyanide. According to examinations performed in vivo, however, such a metabolic pathway seems to be irrelevant for man. In comparisons with the control values there was no significant incr of both the cyanide concn in the blood and the thiocyanate concentrations in the urine of the above volunteers after the described oral cyanamide admin.

... Elimination half life and total plasma clearance values were 51.7 8.8 min and 14.4 2.7 mL/kg/min respectively. ...

Dicyandiamide ... /is/ the main impurity in cyanamide.|Cyanamide, especially in solution, always contains the dimer.

Exposure Routes: inhalation, skin absorption, ingestion, skin and/or eye contact Symptoms: Irritation eyes, skin, respiratory system; eye, skin burns; miosis, salivation, lacrimation (discharge of tears), twitching; Antabuse-like effects Target Organs: Eyes, skin, respiratory system, central nervous system (NIOSH, 2016)

Eye: If this chemical contacts the eyes, immediately wash the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately. Contact lenses should not be worn when working with this chemical. Skin: If this chemical contacts the skin, immediately flush the contaminated skin with water. If this chemical penetrates the clothing, immediately remove the clothing and flush the skin with water. Get medical attention promptly. Breathing: If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform mouth-to-mouth resuscitation. Keep the affected person warm and at rest. Get medical attention as soon as possible. Swallow: If this chemical has been swallowed, get medical attention immediately. (NIOSH, 2016)|(See procedures)


Fresh air, rest. Seek medical attention if you feel unwell.


Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Skin decontamination. Skin contamination with either the calcium salt or the free form should be removed by washing with soap and water. Flush eyes with copious amounts of clean water. If skin or eye irritation persists, medical attention should be obtained promptly. /Calcium cyanamide/|Gastrointestinal decontamination. If large doses have been ingested within an hour of exposure, gastrointestinal decontamination should be considered. If dosage was small or treatment is delayed, oral administration of activated charcoal and sorbitol probably represents reasonable management. /Calcium cyanamide/|Hypotension or Antabuse-type reactions should be treated by placing the patient in the Trendelenburg position, giving intravenous fluids, including plasma or blood, if needed, and, if necessary, vasopressor drugs parenterally. /Calcium cyanamide/

/SIGNS AND SYMPTOMS/ Hydrogen cyanamide is highly toxic, and adverse health effects from contact include severe irritation and ulceration of the eyes, skin, and respiratory tract. The substance also inhibits aldehyde dehydrogenase and can produce acetaldehyde syndrome (e.g., vomiting, parasympathetic hyperactivity, dyspnea, hypotension, and confusion) when exposure coincides with alcohol use. After Dormex ... , a pesticide product containing hydrogen cyanamide (49% by weight), was introduced in Italy in 2000, a total of 23 cases of acute illness associated with exposure to this chemical were identified in early 2001. This led to a temporary suspension of sales and usage of Dormex on February 23, 2002, and strengthening of protective measures, as specified on the pesticide label when sales were resumed on June 20, 2003.|/SIGNS AND SYMPTOMS/ Short term exposure: cyanamide is caustic and severely irritates the eyes, skin, and respiratory tracts, and may affect the liver. Ingestion or inhalation may cause transitory intense redness of the face, headache, vertio, increased respiration, tachycardia, and hypotension. The adverse effects of cyanamide are potentiated by the ingestion of alcohol (beer, wine, or liquor) within 1-2 days before or after exposure. Cyanamide is a highly reactive chemical and is a dangerous explosion hazard. Long term exposure: Repeated or prolonged contact may cause skin sensitization and allergy. Exposure may cause liver and nervous system damage.|/CASE REPORTS/ Cyanamide, an aversive agent widely used in Japan, is known to induce various degrees of hepatic lesion with ground-glass inclusion bodies. When cyanamide-treated alcoholics relapse into drinking, more severe inflammation develops in the liver. However, it is controversial whether progressive hepatic lesions develop in complete abstainers as a result of long-term cyanamide treatment. Case 1: A 53-year-old male alcoholic received cyanamide treatment for 4.5 months and completely abstained without cyanamide treatment for 6 years. A liver biopsy shortly after abstinence showed extensive pericellular fibrosis, but a biopsy after 6 years showed very mild fibrosis. Case 2: A 43-year-old male alcoholic remained completely abstinent with cyanamide treatment for 5 years and complained of general fatigue. His serum transaminases were slightly elevated and hepatic hyperechogenicity was observed on ultrasonography. Only mild pericellular fibrosis was present in the liver biopsy specimen obtained shortly after abstinence, but after 5 years the second liver biopsy showed that thin septum-like fibrosis that formed portal-to-portal and portal-to-central linkage had developed and ground-glass hepatocytes had emerged extensively. Case 3: A 29-year-old female alcoholic complained of general fatigue and a slight fever after 1.5 years of abstinence with cyanamide treatment. Slight elevation of serum transaminases and hepatic hyperechogenicity were observed. The liver biopsy showed extensive ground-glass hepatocytes and thin septum-like fibrosis that formed portal-to-portal linkage. Case 4: A 61-year-old male alcoholic who remained completely abstinent while taking cyanamide for 3 years showed slight elevation of serum transaminases. Liver biopsy showed extensive ground-glass hepatocytes and extension of thin septum-like fibers from portal tract to the lobule. Ultrasonography revealed hepatic hyperechogenicity. In some abstainers who take cyanamide for several years, thin septum-like liver fibrosis progresses along with the emergence of ground-glass hepatocytes. Hepatic hyperechogenicity on ultrasonography and slight elevation of serum transaminases might erroneously lead to a diagnosis of hepatic steatosis without liver histology.|/CASE REPORTS/ Drug-induced hypersensitivity syndrome (DIHS), characterized by serious adverse systemic reactions in addition to skin rash, has unknown pathogenesis. ... A 46-year-old Japanese man is described in whom a generalized eruption developed about 1 month after taking cyanamide, a drug for alcoholism. This was associated with the following manifestations: high fever, lymphadenopathy, facial edema, marked leukocytosis with eosinophilia and atypical lymphocytes, lymphocytopenia, liver and renal dysfunction, and low IgG level. He was treated with 8 mg betamethasone daily and his condition improved, but he needed low-dose corticosteroid for almost 1 year because of several episodes of recurrence. Human herpesviris (HHV-6, HHV-7), herpes simplex virus (HSV), and cytomegalovirus (CMV) specific IgG titers showed more than a four-fold rise sequentially. Significant numbers of copies of HHV-6 and HHV-7 DNA were detected in the peripheral white blood cells by real-time polymerase chain reaction (PCR). HHV-6 and CMV DNA were detected in the serum by nested PCR. A patch test for cyanamide was positive. The diagnosis of DIHS due to cyanamide, which has never been reported as a causal drug of DIHS, accompanied by reactivation of not only HHV-6, but also HHV-7, CMV, and HSV, was made. Disturbance of the immune system was suggested by the persistent low level of IgG, and consecutive viral reactivation may have participated in the prolonged course in this case.|For more Human Toxicity Excerpts (Complete) data for Cyanamide (14 total), please visit the HSDB record page.

Abstem

The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.|inhalation, skin absorption, ingestion, skin and/or eye contact

irritation eyes, skin, respiratory system; eye, skin burns; miosis, salivation, lacrimation (discharge of tears), twitching; Antabuse-like effects


Cough. Shortness of breath.


MAY BE ABSORBED! Redness. Pain.


Redness. Pain.

Eyes, skin, respiratory system, central nervous system

Cyanamide Use and Manufacturing

Methods of Manufacturing

Prepared commercially by continuous carbonation of calcium cyanamide in water according to the equations: 2CaNCN + 2H2O = Ca(HNCN)2 + Ca(OH)2; Ca(HNCN)2 + CO2 + H2O = 2H2NCN + CaCO3.|Cyanamide is manufactured from calcium cyanamide by continuous carbonation in an aqueous medium. In the continuous cyanamide process, the amount of calcium cyanamide and water added is equivalent to the aqueous cyanamide removed.

Uses

1.Cyanamide is an important intermediate of pesticide. It can also be used for production of antibacterial agent such as carbendazim, benzene benomyl, methyl mepanipyrim and mepanipyrim, Pirimicarb, pyrimidinoxy phosphorus, herbicide Chlorsulfuron, Metsulfuron methyl, Metsulfuron methyl ethyl, long ether tribenuron methyl and bensulfuron methyl and pyrazole ethyl, hexazinone, etc.
2. In the pharmaceutical industry, it is used as a raw material for the production of hydrochloric acid. It is also used for the production intermediates of 3-amino-5-hydroxyl-1,2,4-triazol in the dye industry. In addition, for organic synthesis and plastic raw materials, it can be used for production of cyanuric amide, dicyandiamide, cyanide methyl carbamate etc.
3.Cyanamide liquid is used for industrial raw materials, pharmaceutical intermediates, agricultural pesticides, fertilizer, plant growth regulator, food additives etc.
4. Used in the production of materials such as urine. In Europe, cyanamide is used as a fertilizer, weed killer, and defoliant. In North America, these applications have been practically discontinued. It is also used to produce cationic starch and calcium cyanide, dicyandiamide, and melamine. New uses include intermediates for pesticides; detergents; medicines such as antihistamines, hypertension, sedatives, and contraceptives; photography industry; additive for fuels and lubricants; paper preservative; and cement additive. Dormex is a common rest-breaking agent applied in spring to stimulate uniform opening of buds.
Cyanamide has been tested as an effective and welltolerated pharmacological adjunct to treat alcohol-dependent patients. It is a potent aldehyde dehydrogenase inhibitor, and alters cholinergic function in the frontal cortex and hippocampus of rats exposed to ethanol.


Intermediates

Production

According to the 2006 TSCA Inventory Update Report, the 2006 Production Volume for cyanamide (CAS 420-04-2) was 1 to <10 million lbs (aggregated Import + Manufacture).|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#3245]|Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Cyanamide. Aggregated National Production Volume: 1 to < 10 million lbs.

100% AS A CHEM INT (CAPTIVELY) FOR DICYANDIAMIDE IN MELAMINE MFR

Cyanamide is sold as anhydrous, aqueous 50%, and calcium cyanamide. Anhydrous and aqueous 50% cyanamide contain a buffering additive, usually 2% sodium biphosphate to stabilize the pH and prevent formation of dicyanamide and urea.|Emulsifiable concentrate|Cyanamide in 50% aqueous solution: cyanamide = 50%; dicyandiamide, urea, and related compounds max. 4%; Iron max. 300 mg/L; calcium max. 100 mg/L; stabilizer max. 2%.|Cyanamide, crystalline, min 98%; dicyandiamide max. 1%; water max.|For more Formulations/Preparations (Complete) data for Cyanamide (7 total), please visit the HSDB record page.

Pesticide, fertilizer, and other agricultural chemical manufacturing|Cyanamide: ACTIVE|CYANAMIDE IS A NAME APPLIED BOTH TO CARBODIIMIDE & TO CALCIUM DERIVATIVE, CALCIUM CYANAMIDE.

Cyanamide is determined by potentiometric titration with silver nitrate in ammoniacal medium. It can also be determined by precipitation as the silver salt in ammoniacal solution and back-titration of the excess of silver ions or by determination of nitrogen in the silver cyanamide precipitate. Cyanamide can also be determined by direct HPLC with UV detection at 200 nm.|Traces of cyanamide can be analyzed spectrophotometrically after derivatization with pentacyanoammineferrate(II). Due to its low UV absorption, direct HPLC determination is not generally suitable. However, after derivatization with 1,2-naphthoquinone-4-sulfonate or with acetic anhydride, it can be detected by HPLC.|Product by the Kjeldahl method or by argentometric determination. .... Residues (1) By colorimetric determination of a derivative. ... (2) By HPLC

Hazardous Air Pollutants (HAPs)|Agrochemicals -> Herbicides, Plant Growth Regulators|Fire Hazards -> Flammable - 3rd degree, Reactive - 1st degree|Environmental transformation -> Pesticides (parent, predecessor)

Cyanamide has known environmental transformation products that include Dicyandiamide.

Computed Properties

Molecular Weight:42.040
XLogP3:-0.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:42.021798072
Monoisotopic Mass:42.021798072
Topological Polar Surface Area:49.8
Heavy Atom Count:3
Complexity:29.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Downstream Products

Recommended Suppliers of Cyanamide

Scan the QR Code to Share

Feedback & Suggestions
Send Message

Thank you for your feedback. If you require further assistance, please contact us by email at info@echemi.com or call us at +86-532-55729510.