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Home > Encyclopedia > Melamine

Melamine

Melamine structure

Melamine 

structure
  • CAS No:

    108-78-1

  • Formula:

    C3H6N6

  • Chemical Name:

    Melamine

  • Synonyms:

    1,3,5-Triazine-2,4,6-triamine;Melamine;s-Triazine,4,6-diamino-1,2-dihydro-2-imino-;Cyanuramide;Cyanurotriamide;Cyanurotriamine;2,4,6-Triamino-s-triazine;1,3,5-Triazine-2,4,6(1H,3H,5H)-triimine;Triaminotriazine;Isomelamine;2,4,6-Triaminotriazine;Teoharn;Theoharn;Virset 656-4;2,4,6-Triamino-1,3,5-triazine;s-Triazinetriamine;Pluragard C 133;Pluragard;Triamino-s-triazine;DG 002 (amine);DG 002;ZS 27;ADK Stab ZS 27;Mark ZS 27;Yukamelamine;Spinflam ML 94M;2,4,6-Triamino-1,2,3-triazine;PC 1;NSC 2130;Flammex MEL;Mitsui 2020A;Melamine 2020A;Melafine;Mel F 40;Melamine HM;Micromel 325;T 518;H 882;PMN 500;M 2659;Relugan XD;SM 1013;D-ACE 557;GPH-LD;JLS Melamine;A 11295;Aflammit PMN 500;AF-PMN 500;MEL AR;504-18-7;65544-34-5;67757-43-1;68379-55-5;70371-19-6;94977-27-2;130392-03-9;169314-62-9;1228929-27-8;1399841-69-0;1399841-71-4;1399841-73-6

  • Categories:

    Organic Chemistry  >  Nitrogen Compounds

Description

White Solid Melamine is a white crystalline solidChEBI: A trimer of cyanamide, with a 1,3,5-triazine skeleton. A white solid organic compound whose molecules consist of a sixmembered heterocyclic ring of alternate carbon and nitrogen atoms with three amino groups attached to the carbons. Condensation polymerization with methanal or other aldehydes produces melamine resins, which are important thermosetting plastics. melamine: A white crystalline compound.


Melamine appears as colorless to white monoclinic crystals or prisms or white powder. Sublimes when gently heated. (NTP, 1992)|DryPowder; DryPowder, Liquid; Liquid; WetSolid|Solid|COLOURLESS-TO-WHITE CRYSTALS.


Melamine appears as colorless to white monoclinic crystals or prisms or white powder. Sublimes when gently heated. (NTP, 1992)|Melamine is a trimer of cyanamide, with a 1,3,5-triazine skeleton. It has a role as a xenobiotic metabolite. It derives from a cyanamide. It is a conjugate base of a melamine(1+).

Melamine Basic Attributes

126.12000

126.12

203-615-4

N3GP2YSD88

1154

8152|2130

DTXSID6020802

Monoclinic prisms|Monoclinic colorless prisms or crystals|White, monoclinic crystals

2933610000

Characteristics

116.73000

-1.4

Melamine appears as colorless to white monoclinic crystals or prisms or white powder. Sublimes when gently heated. (NTP, 1992)

1.573 g/cm3 @ Temp: 14 °C

<250 °C

299.696ºC at 760 mmHg

135.052ºC

1.922

H2O: 3 g/L (20 ºC)

-20ºC

0.001mmHg at 25°C

4.34 (Air= 1)

LD50 orally in Rabbit: 3161 mg/kg LD50 dermal Rabbit > 1000 mg/kg

Henry's Law constant = 1.84X10-14 atm-cu m/mol at 25 °C (est)

pKa = 5.0

Heat of sublimation = -121 kJ/mol at 25 °C|Hydroxyl radical reaction rate constant = 6.6X10-13 cu cm/molec-sec at 25 °C (est)

Insoluble in water.

Amines, Phosphines, and Pyridines

MELAMINE is incompatible with strong oxidizing agents and strong acids (NTP, 1992). Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

greater than 500 °F (NTP, 1992)|>500 °C

-1967 kJ/mol at 25 °C

Dust explosion possible if in powder or granular form, mixed with air.

Safety Information

III

UN 3263

1

R20/21; R44

S36/37

OS0700000

Xn

Stable. Incompatible with strong acids, strong oxidizing agents. Nonflammable.

P201, P202, P260, P261, P264, P270, P271, P272, P273, P280, P281, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P308+P313, P310, P312, P314, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P391, P403+P233, P405, P501

H302

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.

Strong oxidizers, strong acids.

Melamine is an indirect food additive for use only as a component of adhesives.

Organization for Economic Cooperation and Development; Screening Information Data Set for Melamine, CAS #108-78-1|European Chemicals Bureau; IUCLID Dataset, Melamine (CAS # 108-78-1)|Toxicology and Carcinogenesis Studies of Melamine in F344/N Rats and B6C3F1 Mice (Feed Studies) Technical Rpt Series 245 (1983) NIH Pub 83-2501 U.S. Department of Health and Human Services, National Toxicology Program, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709

Literature sources indicate that this compound is nonflammable. (NTP, 1992)|Combustible under specific conditions. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

|Warning|H361 (81.5%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]|P201, P202, P281, P308+P313, P405, and P501|Aggregated GHS information provided by 863 companies from 20 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H227: Combustible liquid [Warning Flammable liquids]|P210, P261, P264, P271, P272, P280, P302+P352, P304+P340, P312, P321, P332+P313, P333+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this chemical under ambient temperatures, and keep it away from oxidizing materials. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)|Wear protective gloves and clothing to prevent any reasonable probability of skin contact. Contact lenses should not be worn when working with this chemical. Wear dust-proof chemical goggles and face shield unless full face-piece respiratory protection is worn. Employees should wash immediately with soap when skin is wet or contaminated. Provide emergency showers and eyewash.

Powder, water spray, foam, carbon dioxide.|Melanine itself does not burn. Use any extinguishing agent suitable for surrounding fire. Poisonous gases including carbon monoxide, hydrogen cyanide, nitrogen oxides, and ammonia are produced in fire. If material or contaminated runoff enters waterways, notify downstream users of 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. If employees are expected to fight fires, they must be trained and equipped in OSHA 1910.156.

Evacuate persons not wearing protective equipment from area of spill or leak until clean-up is complete. Remove all ignition sources. Use HEPA vacuum or wet method to reduce dist during clean-up. Do not dry sweep. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Ventilate area after clean-up is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. 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. If employees are required to clean-up spills, they must be properly trained and equipped. OSHA 1910.120(q) may be applicable.|Sweep spilled substance into sealable containers; if appropriate, moisten first to prevent dusting. Carefully collect remainder, then remove to safe place (extra personal protection: P2 filter respirator for harmful particles).|DISSOLVED CYANURIC ACID, CYANURATES, & OTHER DERIVATIVES (0.2-3.0%) CONTAINED IN WASTE WATER FROM THE MFR OF CHLORINATED CYANURIC ACIDS ARE REMOVED BY SLURRYING WITH POWDERED OR GRANULATED ACTIVE CARBON FOR 0.5-3 HR & FILTRATION.|ACID WASTEWATERS FROM MFR OF CYANURIC ACID & ITS CHLORINATED DERIVATIVES WHICH CONTAIN CYANURIC ACID, MELAMINE, AMMELINE, & AMMELIDE & HAVE PH 0-6, ARE HEATED TO 245-270 °C UNDER EVOLVED PRESSURE, WHICH MAY BE 1-30 ATM & ARE HYDROLYZED COMPLETELY.

This material may be classified under tear gas substances. This compound requires a shipping label of: "Poison." It falls in DOT Hazard Class 6.1 and Packing Group II. Passenger aircraft or railcar shipment is forbidden and cargo aircraft is limited.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

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

NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.

PREVENT DISPERSION OF DUST!

Protective gloves.

Wear safety spectacles.

Concentrations from 0.4 to 1.4 ppm of melamine were detected in the extract of tableware manufactured from thermosetting resins(1).

Toxicity

IDENTIFICATION: Melamine is a monoclinic prismatic substance that is slightly soluble in water and ethanol. It is insoluble in diethyl ether. Melamine forms synthetic resins with formaldehyde. It is used in the manufacture of melamine resins, laminates, surface coating resins, plastic molding compounds, textile resins, bonding resins, gypsum melamine resin mixtures, orthopedic casts, rubber additives and paper products. HUMAN EXPOSURE: Occupational exposure to melamine may occur during its production and use in manufacture of synthetic resins with formaldehyde. ANIMAL STUDIES: Melamine was tested for its carcinogenicity by oral diet in mice and rats and for initiating activity by skin application in mice. No neoplasm related to treatment was observed after oral administration in mice. Male rats fed diets containing melamine developed transitional cell tumors in the urinary bladder, with one exception; all tumor bearing animals had bladder stones probably containing melamine. The incidence of urinary bladder hyperplasia associated with toxicity in male mice treated with melamine in the diet was observed. Groups of 20 male Fisher 344 rats, six weeks old were fed diets containing melamine with a purity of 99.4% with or without 10% NaCl for a total of 36 weeks and were sacrificed at week 40. Urinary bladder carcinomas were observed in all dose groups given melamine alone and melamine with NaCl. No carcinomas were observed in the melamine and NaCl groups. The incidences of papillomas were significantly decreased by NaCl. In contrast to the incidence of papillomas in the group given high dose melamine alone and in rats receiving high dose melamine and NaCl respectively, developed papillomas. Papillomas developed in rats receiving lower dose melamine alone. The occurrence of tumors correlated with calculus (melamine uric acid salt) formation and papillomatosis. Male and female Fisher 344 rats and B6C3F1 mice were fed melamine in the diet for 103 weeks. Twenty percent of the males at high dose and only 2% at the low dose and none of the controls had bladder stones. Seven of the eight urinary bladders with transitional cell carcinomas and three of the remaining 41 bladders without neoplasms had stones. There was statistically significant correlation between the bladder stones and bladder tumors. Fifty percent of a single oral dose of melamine was recovered in the urine of rats within 6 hr. After administration of a single dose of (14)-C-melamine to adult Fisher 344/N rats, 90% of the dose was excreted in the urine within the first 24 hr. Most of the radiolabel was concentrated in the kidney and bladder and negligible amounts were detected in exhaled air and feces. The radiolabelled material found in the plasma and urine indicated that melamine was not metabolized in rats. Melamine induced lambda prophage in Escherichia coli (WP2s-lambda) but did not induce reverse mutation in Salmonella typhimurium in presence or absence of an exogenous metabolic activation system . Sex linked recessive lethal mutations were not induced in Drosophila melanogaster. Melamine did not induce gene linked mutation in Salmonella typhimurium or sister chromatid exchange in Chinese hamster cells in vitro or micronuclei in mouse bone marrow in vivo. Melamine by oral administration has produced urinary bladder and ureteral carcinomas in male rats but only urinary hyperplasia in male mice. The occurrence of urinary tumors in male rats correlated strictly with calculus formation and exposure to higher doses. The dose dependence was confirmed by other studies in male rats in which concomitant administration of sodium chloride to increase urinary output resulted in a decreased tumor yield.

The major pet food recall associated with acute renal failure in dogs and cats focused initially on melamine as the suspect toxicant. In the course of the investigation, cyanuric acid was identified in addition to melamine in the offending food. The purpose of this study was to characterize the toxicity potential of melamine, cyanuric acid, and a combination of melamine and cyanuric acid in cats. In this pilot study, melamine was added to the diet of 2 cats at 0.5% and 1%, respectively. Cyanuric acid was added to the diet of 1 cat at increasing doses of 0.2%, 0.5%, and 1% over the course of 10 days. Melamine and cyanuric acid were administered together at 0%, 0.2%, 0.5%, and 1% to 1 cat per dose group. No effect on renal function was observed in cats fed with melamine or cyanuric acid alone. Cats dosed with a combination were euthanized at 48 hours after dosing because of acute renal failure. Urine and touch impressions of kidneys from all cats dosed with the combination revealed the presence of fan-shaped, birefringent crystals. Histopathologic findings were limited to the kidneys and included crystals primarily within tubules of the distal nephron, severe renal interstitial edema, and hemorrhage at the corticomedullary junction. The kidneys contained estimated melamine concentrations of 496 to 734 mg/kg wet weight and estimated cyanuric acid concentrations of 487 to 690 mg/kg wet weight. The results demonstrate that the combination of melamine and cyanuric acid is responsible for acute renal failure in cats.

LD50 Mouse ip 112 mg/kg bw|LD50 Rabbit dermal >1000 mg/kg bw|LD50 Mouse (male) gavage 3.3 g/kg|LD50 Mouse (female) gavage 7.0 g/kg|For more Non-Human Toxicity Values (Complete) data for MELAMINE (9 total), please visit the HSDB record page.

/AQUATIC SPECIES/ EXPOSURE OF BIOMPHALARIA GLABRATA FOR 45 DAYS TO SUBLETHAL CONCN (500, 1000 & 2000 MG/L) OF MELAMINE IN WATER CAUSED A CONCN-DEPENDENT DECREASE IN REPRODUCTIVE ABILITY.|/AQUATIC SPECIES/ MELAMINE AT 500 & 1000 MG/L LOWERED THE RATE OF SALMO GAIRDNERI EGG HATCHABILITY & AT 125 & 250 MG/L IT INCREASED THE INCIDENCE OF MALFORMATION IN EXPOSED LARVAE.

A carcinogenesis bioassay of melamine (>95% pure), a chemical intermediate in the manufacture of amino resins and plastics, was conducted by feeding diets containing 2,250 or 4,500 ppm melamine to groups of 50 male F344/N rats and 50 B6C3F1 mice of each sex for 103 weeks. Groups of 49 male rats, 50 female rats, 49 male mice, and 50 female mice served as controls. Mean body weights of dosed rats of each sex were lower than those of the controls after week 20. Survival of high-dose male rats was significantly lower (P<0.05) than that of the controls. Survival of all other dosed rat groups was comparable with that of the respective controls. Transitional-cell carcinomas in the urinary bladder of male rats occurred with a statistically significant positive trend (P<0.002; controls, 0/45; low-dose, 0/50; high-dose, 8/49, 16%) and the incidence in the high-dose group was significantly higher (P<0.016) than that in the controls. A transitional-cell papilloma was observed in the urinary bladder of an additional high-dose male rat. These tumors were not observed in statistically significant proportions in female rats. Seven of the eight high-dose male rats with the transitional-cell carcinomas also had bladder stones. An association (P<0.001) was found between bladder stones and bladder tumors in male rats. Chronic inflammation, distinguishable from the nephropathy observed in aging F344/N rats, was significantly increased (P<0.01) in the kidney of dosed female rats (controls, 4/50, 8%; low-dose, 17/50, 34%; high-dose, 41/50, 82%) and is attributed to the administration of melamine. The mean body weight of high-dose male mice was lower than that of controls after week 50 of the study. The mean body weights of dosed and control female mice were comparable throughout the study. Survival of high dose male mice was significantly less (P<0.02) than that of the controls. Survival of all other dosed groups was similar to that of the respective controls. Acute and chronic inflammation and epithelial hyperplasia of the urinary bladder were found in increased incidence in dosed male mice. The incidence of bladder stones in dosed male mice was increased relative to controls (control, 2/45, 4%; low dose, 40/47, 85%; high-dose, 41/45, 93%); however, there was no evidence of bladder tumor development in this species. Also, four high-dose female mice had bladder stones without any tumors. Under the conditions of this bioassay, melamine was carcinogenic for male F344/N rats, causing transitional-cell carcinomas in the urinary bladder. With one exception, urinary bladder stones were observed in male rats that had transitional-cell carcinomas. Melamine was not carcinogenic for female F344/ N rats or for B6C3F1 mice of either sex.

Melamine's production and use in the manufacture of melamine resins, organic synthesis, and leather tanning(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5(SRC), determined from a log Kow of -1.37(2) and a regression-derived equation(3), indicates that melamine is expected to have very high mobility in soil(SRC). Volatilization of melamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.8X10-14 atm-cu m/mole(SRC), derived from its vapor pressure, 3.59X10-10 mm Hg(4), and water solubility, 3.23 mg/L(5). Melamine is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). No biodegradation using a standard 5-day BOD test(6) suggests that biodegradation may not be an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5(SRC), determined from a log Kow of -1.37(2) and a regression-derived equation(3), indicates that melamine is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.84X10-14 atm-cu m/mole(SRC), derived from its vapor pressure, 3.59X10-10 mm Hg(4), and water solubility, 3.23X10+3 mg/L(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is(SRC). No biodegradation using a standard 5-day BOD test was observed(8), suggesting that biodegradation may not be an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), melamine, which has a vapor pressure of 3.59X10-10 mm Hg at 20 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase melamine may be removed from the air by wet or dry deposition(SRC).

Melamine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). Melamine is hydrolyzed by mineral acid or inorganic alkali(2).

3.80|An estimated BCF of 3 was calculated in fish for melamine(SRC), using a log Kow of -1.37(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(SRC).

The Koc of melamine is estimated as 50(SRC), using a log Kow of -1.37(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that melamine is expected to have very high mobility in soil. Aromatic amines may bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(4,5), suggesting that mobility may be much lower in some soils(SRC). Adsorption of melamine to suspended clay sediment was reported from pH 1 to 6.5, with a maximum absorption of 500X10-6 mols/g at pH 4.0(6).

The Henry's Law constant for melamine is estimated as atm-cu m/mole(SRC) derived from its vapor pressure, 3.59X10-10 mm Hg(1), and water solubility, 3.23X10+3 mg/L mg/L(2). This Henry's Law constant indicates that melamine is expected to be essentially nonvolatile from water surfaces(3). Melamine is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

On March 15, 2007, the Food and Drug Administration (FDA) learned that certain pet foods were sickening and killing cats and dogs. FDA found contaminants in vegetable proteins imported into the United States from China and used as ingredients in pet food(1). Melamine was found in wheat gluten imported from China and used in pet food made by Menu Foods, which recalled 60 million cans and pouches of dog and cat food in mid-March of 2007. A portion of the tainted pet food was used to produce farm animal feed and fish feed. FDA and the U.S. Department of Agriculture discovered that some animals that ate the tainted feed had been processed into human food. All tainted pet food, animal and fish feed, and vegetable proteins continue to be recalled and destroyed (2007)(1).

MELAMINE ITSELF DOES NOT SEEM TO BE IMPORTANT INDUSTRIAL HAZARD EXCEPT IF DECOMP BY HEAT. ...SKIN SHOULD BE KEPT FREE FROM UNREACTED RESINS...|NIOSH (NOES Survey 1981-1983) has statistically estimated that 43,104 workers (6,239 of these are female) are potentially exposed to melamine in the US(1). Occupational exposure to melamine may occur through inhalation and dermal contact with this compound at workplaces where melamine is produced or used. Monitoring data indicate that the general population may be exposed to melamine via ingestion of contaminated food(SRC).

Drug Information

... A single oral dose of 0.025 mCi (0.38 mg) [14C]melamine /was administered/ to adult male Fischer 344 rats. Within the first 24 hr, 90% of the administered dose was excreted in the urine. Negligible radioactivity appeared in breath and feces. There was little difference in blood, liver or plasma concentrations of 14C, suggesting that melamine distributes in body water. The only organs showing radioactivity levels much higher than plasma were the kidney and bladder. The bladder level was by far the highest, a finding probably due either to back diffusion from urine or to contamination of bladder tissue with urine. Virtually no residual radioactivity was observed in tissues examined at 24 hr or later. The elimination-phase half-life calculated from plasma data, 2.7 hr, was in good agreement with the urinary-excretion half-life of 3.0 hr. The renal clearance of melamine was 2.5 mL/min.|... Following oral administration of 250 mg/kg melamine to rats, 50% of the mother compound was excreted with the urine within 6 hrs. ... Crystals found in the urine were composed of dimelamine monophosphate, amounting to nearly 20% of the administered dose. After feeding melamine to dogs, 60 - 86.5% of the mother compound was recovered in the urine within 24 hrs. ...|Doses of 2.4 g/kg cause diuresis & elimination of fine crystals of dimelamine monophosphate in urine.|After administration of a single oral dose of 0.38 mg (14)C-melamine to adult male Fischer 344/N rats, 90% of the administered dose was excreted in the urine within the first 24 hours. Negligible radioactivity was detected in exhaled air and feces; and radioactivity was concentrated in the kidney and bladder. Virtually no residual radioactivity was observed in tissue after 24 hours or more. Chromatography of the radioactivity found in plasma or urine indicated that melamine is not metabolized in rats.

Toxicokinetic studies in rats given 14C-labelled cyromazine as single and repeated oral doses showed that the active substance is rapidly and almost completely absorbed from the gastrointestinal tract and distributed to all organs and tissues. ... Cyromazine was incompletely metabolized, essentially by methylation, hydroxylation or Ndealkylation. The major component present was cyromazine, which accounted for 71-72% of the radiolabel; a further 7% was attributable to melamine, 8-11% to hydroxy-cyromazine and methylcyromazine.|... A single oral dose of 0.025 mCi (0.38 mg) [14C]melamine /was administered/ to adult male Fischer 344 rats. ... Radioactivity in plasma or urine co-chromatographed with that of the dosing solution, indicating that melamine is not metabolized in the male Fischer 344 rat.|Crystalluria was due to excretion of dimelamine-monophosphate crystals.

... A single oral dose of 0.025 mCi (0.38 mg) [14C]melamine /was administered/ to adult male Fischer 344 rats. ... The elimination-phase half-life calculated from plasma data, 2.7 hr, was in good agreement with the urinary-excretion half-life of 3.0 hr. ...

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes and mucous membranes. It may also cause irritation of the upper respiratory tract. Other symptoms may include urinary bladder stones, diuresis and crystalluria. Dermatitis has been reported. Kidney injury may occur. ACUTE/CHRONIC HAZARDS: This compound is toxic by ingestion. It may be harmful by inhalation or skin absorption. It is an irritant of the skin, eyes, mucous membranes and upper respiratory tract. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide and nitrogen oxides. It also emits highly toxic fumes of cyanides. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)


Fresh air, rest.


Rinse and then wash skin with water and soap.


Rinse with plenty of water for several minutes (remove contact lenses if easily possible).

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/HUMAN EXPOSURE STUDIES/ HUMAN SUBJECTS WERE GIVEN PATCH TESTS WITH MELAMINE. NO EVIDENCE OF EITHER PRIMARY IRRITATION OR SENSITIZATION WAS FOUND.|/SIGNS AND SYMPTOMS/ SUMMARY TOXICITY STATEMENT: ACUTE... MODERATE VIA ORAL ROUTE. MODERATE= MAY CAUSE REVERSIBLE OR IRREVERSIBLE CHANGES TO EXPOSED TISSUE, NOT PERMANENT INJURY OR DEATH; CAN CAUSE CONSIDERABLE DISCOMFORT.|/CASE REPORTS/ DERMATITIS HAS BEEN REPORTED FROM MFR OF MELAMINE FORMALDEHYDE RESINS & GLUES. IT IS PROBABLE THAT THESE CASES WERE CHIEFLY DUE TO FORMALDEHYDE OR INTERMEDIATE REACTION PRODUCTS OF FORMALDEHYDE & MELAMINE.

1,3,5-triazine-2,4,6-triamine

Melamine Use and Manufacturing

Methods of Manufacturing

Melamine is produced from urea by a high or low pressure process in either one or two stages. In the low pressure route, the reaction is carried out in the vapour phase generally using an alumina catalyst. Urea forms isocyanic acid, which is converted first to cyanamide and then to melamine. In the high pressure process, carried out in the liquid phase without a catalyst, urea forms cyanuric acid which is reacted with ammonia to form melamine. Carbon dioxide and ammonia by-products are recycled to urea.|1) by heating urea and ammonia; the resulting mixture of isocyanic acid and ammonia reacts over a solid catalyst at about 400 °C to form melamine, 2) from cyanamide, dicyanamide or cyanuric chloride|Melamine can be synthesized from urea at 390 - 410 °C: ... The overall reaction is endothermic, requiring 649 kJ per mole of melamine starting with molten urea at 135 °C. The processes themselves may be subdivided into two categories: 1. noncatalytic, high-pressure (> or = to 8 MPa) processes, and 2. catalytic, low-pressure processes (ca 1 MPa). Each type includes three stages: synthesis; melamine recovery and purification; and off-gas treatment.

Uses

Melamine (CAS NO.108-78-1) is combined with formaldehyde to produce melamine resin, which is a very durable thermosetting plastic used in Formica, and melamine foam, a polymeric cleaning product and so on.聽Melamine also enters the fabrication of melamine poly-sulfonate used as superplasticizer for making high-resistance concrete.聽Melamine Iis also used as fertilizer for crops during the '50s and '60s because of its high nitrogen content (2/3).聽Melamine derivatives of arsenical drugs are potentially important聽for the treatment of African trypanosomiasis. Sometime,聽Melamine is illegally added to food products in order to increase the apparent protein content.


Adhesives and sealant chemicals


Adhesives and sealants

Production

100,000,000 - 250,000,000 lb|1990/1991 97,000 TONS/ANNUALLY|(1974) 5.49X10+10 GRAMS (EST)|(1983) 8.17X10+10 g|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#4121]|For more U.S. Production (Complete) data for MELAMINE (7 total), please visit the HSDB record page.

Over 95% of global output is used to make thermosetting resins for use in laminates, protective coatings, moulding compounds, textile finishes and paper coatings with applications in the automotive, appliance, dinnerware, furniture, fabric and wood panelling industries. The rest is mostly consumed as melamine crystal or salts for flame retardant or moisture-resistan applications.|AS A COMONOMER IN THE PRODN OF AMINO RESINS IN THE FOLLOWING APPLICATIONS: 36% IN HIGH PRESSURE LAMINATES; 22.5% IN MOLDING COMPDS; 15.5% IN SURFACE COATINGS; 7% IN TEXTILE PRINTING; 8% IN PAPER TREATING; 11% IN MISC APPLICATIONS (1974)|26% FOR LAMINATES; 22% FOR COATINGS; 20% FOR MOLDING COMPOUNDS; 13% FOR PAPER COATINGS; 5% FOR ADHESIVES; 3% FOR TEXTILE TREATMENT RESINS; 7% OTHER (1985)|CHEMICAL PROFILE: Melamine. Surface coatings, 29%; laminates, 22%; exports, 14%; paper coatings, 13%; molding compounds, 6%; textile treatment resins, 5%; adhesives, 4%; flame retardants, 3%; miscellaneous uses (including tanning and pigment cross-linking agents), 4%.|CHEMICAL PROFILE: Melamine. Demand: 1987: 132 million lb; 1988: 135 million lb; 1992 /projected/: 149 million lb.

Grade: min-99%

Adhesive manufacturing|1,3,5-Triazine-2,4,6-triamine: ACTIVE|IF MELAMINE IS REACTED WITH FORMALDEHYDE, TRIMETHYLOL MELAMINE... IS PRODUCED, FROM WHICH RESIN IS MADE BY POLYCONDENSATION. TRIMETHYLOLAMINE RESINS ARE USED IN PAPER & TEXTILE FINISHES, IN ADHESIVES & IN IMPREGNATION OF PLASTER OF PARIS BANDAGES TO SPEED UP CURING OF CAST.|MIXT OF PARTIALLY AMINOALKYLATED POLYACRYLAMIDE & UREA, THIOUREA, GUANIDINE, DICYANDIAMIDE, ANILINE, & MELAMINE WERE USED AS FLOCCULANTS FOR WASTEWATER SLUDGE TREATMENT. [NAGATSU H, CATIONIC POLYMER FLOCCULANTS FOR WASTE WATER TREATMENT; JAPAN KOKAI PATENT NO 77 61185 05/20/77 (KURITA WATER INDUSTRIES, LTD)]|SOX-CONTAINING GAS IS CONTACTED WITH AN AQ SUSPENSION OF MELAMINE CONTAINING AN OXIDATION INHIBITOR CAUSING THE FORMATION OF SOLID HYDRATED MELAMINE SULFITE & SOLID HYDRATE MELAMINE SULFATE. THE SOLIDS ARE SEPARATED & THE LIQ RECYCLED.|ALLIED CHEMICAL CORP CEASED PRODUCTION/OF MELAMINE/IN 1978|METHOD OF PURIFICATION; RECRYSTALLIZATION FROM WATER

A GAS-LIQUID CHROMATOGRAPHIC METHOD FOR DETERMINATION OF MELAMINE @ NANOGRAM LEVEL USING TRIFLUOROACETIC ACID AS SOLVENT & N-METHYL- N-TRIMETHYL SILYLTRIFLUORO- ACETAMIDE AS THE SILYLATION REAGENT IS DESCRIBED.|Absorption of s-Triazines by Montmorillonite As a Function of pH and Molecular Structure; A UV spectroscopic procedure to determine the amount of melamine adsorbed to clay sediments as a function of pH.|Melamine is difficult to characterize by traditional chemical methods. Purity specifications are usually based on differences obtained after subtracting determined impurity levels for moisture, ash, and alkali solubles. Instrumental analysis is possible using liquid chromatography and spectroscopic methods, although melamine tends to form complexes with the pH-control buffers used in liquid chromatography, leading to variability in the UV absorption observed at different pHs. Melamine can be precipitated for quantitative determination as the perchlorate or picrate salt|Method: AOAC 988.01; Procedure: liquid chromatographic method; Analyte: triamino-s-triazine; Matrix: fertilizer mixes; Detection Limit: not provided.

A triple quadrupole liquid chromatography tandem mass spectrometry method is presented for the quantitative determination and confirmation of melamine residues in catfish. Catfish tissue was extracted with 50:50 acetonitrile:water and 1 N hydrochloric acid and cleaned-up using Oasis MCX solid phase extraction cartridges. Extracts were analyzed by LC-MS-MS with HILIC chromatography and electrospray ionization in positive ion mode. The precursor ion for melamine is m/z 127. Two product ion transitions were monitored at m/z 85 and 68 for quantification and confirmation. Catfish tissue was fortified at 10, 25, 50, 100, and 500 ng/g (ppb). The average recovery of melamine from fortified samples (n = 17) was 76.3% with an RSD of 14.3%.|A METHOD IS DESCRIBED FOR DETERMINING THE URINE & BLOOD MELAMINE CONTENT, USING THE SENSITIVE & SPECIFIC REACTION OF FORMATION OF MELAMINE CYANURATE. THE METHOD CAN DETECT 0.01 MG/ML MELAMINE.

Environmental transformation -> Pesticide transformation products (metabolite, successor)

Melamine is a known environmental transformation product of Cyromazine.

Computed Properties

Molecular Weight:126.12
XLogP3:-1.4
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:6
Exact Mass:126.06539422
Monoisotopic Mass:126.06539422
Topological Polar Surface Area:117
Heavy Atom Count:9
Complexity:63.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Downstream Products

Price Analysis

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  • Data: 2026-07-24
  • Price: 6002.50Yuan/mt
  • Change: 0

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