Hexamine = Hexamethylenetetramine = Methenamine = Urotropin
Hexamethylenetetramine, also known as methenamine, hexamine, or urotropin, is a heterocyclic organic compound with the formula (CH2)6N4.
This white crystalline compound is highly soluble in water and polar organic solvents.
Hexamine has a cage-like structure similar to adamantane.
Hexamine is useful in the synthesis of other organic compounds, including plastics, pharmaceuticals, and rubber additives.
Hexamine sublimes in vacuum at 280 °C.
Synthesis, structure, reactivity
Hexamine was discovered by Aleksandr Butlerov in 1859.
Hexamine is prepared industrially by combining formaldehyde and ammonia.
The reaction can be conducted in gas phase and in solution.
The molecule has a symmetric tetrahedral cage-like structure, similar to adamantane, whose four "corners" are nitrogen atoms and "edges" are methylene bridges.
Although the molecular shape defines a cage, no void space is available at the interior for binding other atoms or molecules, unlike crown ethers or larger cryptand structures.
The molecule behaves like an amine base, undergoing protonation and N-alkylation (e.g. Quaternium-15).
The dominant use of Hexamine is in the production of powdery or liquid preparations of phenolic resins and phenolic resin moulding compounds, where it is added as a hardening component.
Hexamines are used as binders, e.g. in brake and clutch linings, abrasive products, non-woven textiles, formed parts produced by moulding processes, and fireproof materials.
Hexamine has been proposed that hexamethylenetetramine could work as a molecular building block for self-assembled molecular crystals.
As the mandelic acid salt (generic methenamine mandelate, USP)
Hexamine is used for the treatment of urinary tract infection.
A systematic review of its use for this purpose in adult women found there was no good evidence of benefit
Hexamine silver stains are used for staining in histology, including the following types:
Grocott's methenamine silver stain, used widely as a screen for fungal organisms.
Jones' stain, a methenamine silver-Periodic acid-Schiff that stains for basement membrane, availing to view the "spiked" Glomerular basement membrane associated with membranous glomerulonephritis.
Together with 1,3,5-trioxane, hexamethylenetetramine is a component of hexamine fuel tablets used by campers, hobbyists, the military and relief organizations for heating camping food or military rations.
Hexamine burns smokelessly, has a high energy density of 30.0 megajoules per kilogram (MJ/kg), does not liquify while burning, and leaves no ashes, although its fumes are toxic.
Standardized 0.149 g tablets of methenamine (hexamine) are used by fire-protection laboratories as a clean and reproducible fire source to test the flammability of carpets and rugs.
Hexamethylene tetramine or hexamine is also used as a food additive as a preservative (INS number 239).
Hexamine is approved for usage for this purpose in the EU, where it is listed under E number E239, however it is not approved in the USA, Russia, Australia, or New Zealand.
Reagent in organic chemistry
Hexamine is a versatile reagent in organic synthesis.
Hexamine is used in the Duff reaction (formylation of arenes), the Sommelet reaction (converting benzyl halides to aldehydes), and in the Delepine reaction (synthesis of amines from alkyl halides).
Hexamine is the base component to produce RDX and, consequently, C-4as well as Octogen, hexamine dinitrate, hexamine diperchlorate and HMTD.
Hexamine was first introduced into the medical setting in 1899 as a urinary antiseptic.
However, Hexamine was only used in cases of acidic urine, whereas boric acid was used to treat urinary tract infections with alkaline urine.
Scientist De Eds found that there was a direct correlation between the acidity of Hexamine's environment and the rate of its decomposition.
Therefore, its effectiveness as a drug depended greatly on the acidity of the urine rather than the amount of the drug administered.
In an alkaline environment, Hexamine was found to be almost completely inactive.
Hexamine was also used as a method of treatment for soldiers exposed to phosgene in World War I.
Subsequent studies have shown that large doses of hexamethylenetetramine provide some protection if taken before phosgene exposure but none if taken afterwards.
Chemical formula C6H12N4
Molar mass 140.186 g/mol
Appearance White crystalline solid
Odor Fishy, ammonia like
Density 1.33 g/cm3 (at 20 °C)
Melting point 280 °C (536 °F; 553 K) (sublimes)
Solubility in water 85.3 g/100 mL
Hexamine is a heterocyclic organic compound with antibiotic activity.
In the body Hexamine is converted to formaldehyde, a nonspecific bactericidal agent.
Hexamine is typically used long-term to treat chronic urinary tract infections and to prevent the recurrence of infections.
Hexamine is a urinary tract antiseptic that is used as suppressive therapy for chronic or recurrent urinary tract infections.
Hexamine has not been linked to serum enzyme elevations or to instances of clinically apparent acute liver injury.
Hexamine is a heterocyclic organic compound with a cage-like structure similar to adamantane.
In salt form it is used for the treatment of urinary tract infection (Example: Hexamine hippurate which is the hippuric acid salt of methenamine).
Hexamine is used in the rubber industry to prevent vulcanized rubber from blocking and as a accelerator, as a curing agent for thermosetting resins (particularly phenyl-formaldehyde and urea-formaldehyde resins; in foundry mold castings as part of binder resins, in the production of nitrilotriacetic acid; in the manufacture of adhesives and coatings; in firelogs and briquettes for camping; and in flame-retardent materials. Because of its unique ability to hydrolyze to formaldehyde and ammonia under acidic conditions, Hexamine is also used in pharmaceuticals, for intestinal infection, and as a preservative in the food industry.
Adhesives and sealant chemicals
Automotive parts ingredient (brake pads)
Corrosion inhibitors and anti-scaling agents
Ion exchange agents
Making phenolic resins
Plating agents and surface treating agents
Processing aids, not otherwise listed
Processing aids, specific to petroleum production
Propellants and blowing agents
Adhesives and sealants
Agricultural products (non-pesticidal)
Automotive Sound Insulation Material
Automotive care products
Building/construction materials not covered elsewhere
Fuels and related products
Metal products not covered elsewhere
Plastic and rubber products not covered elsewhere
What is Hexamine?
C6H12N4 is a heterocyclic organic compound with a chemical name Hexamine.
It is also called Methenamine or Hexamethylenetetramine or Urotropin.
It acts as an anti-infective agent which is most commonly used to treat urinary tract infections.
Hexamine is anti-infective action is derived from the slow release of formaldehyde (CH2O) by hydrolysis at acidic pH of 0.2 molars.
Hexamine is an odourless colourless lustrous crystal or white crystalline powder which is hygroscopic.
C6H12N4 Uses (Hexamine)
Hexamine is used in the production of liquid or powdery preparations of phenolic resins.
Hexamine is used as binders in clutch and brake linings.
Hexamine is used in the form of spray and cream to treat concomitant odour and excessive sweating.
Hexamine is used in Grocott’s methenamine silver stain.
Hexamine is used as a solid fuel.
Hexamine is used as a food preservative.
Hexamine is used as a primary ingredient in making RDX.
Hexamine is used to prevent vulcanized rubber.
Hexamine is used as a corrosion inhibitor for steel.
Hexamine is also known as hexamethylenetetramine, aminoform, crystamine, methenamine or formin.
Hexamine was first prepared in 1859 by Butlerov of Russia.
Hexamine is a white, crystalline powder with a slight amine odor.
Hexamine is soluble in water, alcohol, and chloroform, but it is insoluble in ether.
However the aqueous solutions exhibit inverse solubility, i.e., less hexamine dissolves as the temperature increases. The hydrate, can be crystallized from the aqueous solution at temperatures below 14°C.
Hexamine is used as a formylation agent in the synthesis and as a precipitating agent.
Hexamine is also used in the production of phenolic resins and its moulding compounds, which finds application as binders in fire proof materials, brake and clutch linings.
Hexamine is involved in the preparation of 5-tert-butyl-2-hydroxy-isophthalaldehyde.
Hexamine is useful for the treatment of urinary tract infection.
Further, Hexamine is used in the Duff reaction, Sommelet reaction and in the Delepine reaction.
Hexamine or methenamine is a heterocyclic organic compound with the formula C6H12N4.
This white crystalline compound is highly soluble in water and polar organic solvents.
Hexamine has a cage-like structure similar to adamantane.
Hexamine is useful in the synthesis of other chemical compounds, e.g., plastics, pharmaceuticals, rubber additives.
Hexamine sublimes in vacuum at 280 °C.
Hexamine is prepared industrially by reacting formaldehyde and ammonia. The reaction can be conducted in gas phase and in solution.
One of the major uses of Hexamine is in the manufacture of dinitrosopentamethylene-tetramine, a blowing agent for rubber.
Hexamine is used as a catalyst in the manufacture of Bakelite phenol formaldehyde molding powders.
Hexamine is used as a basic raw material in slurry explosives.
Hexamine has many other applications in the manufacture of plastics, paints, foundry resins, textiles, plywood, laminated sheets, cement, fertilizers, pesticides, solid fuel tablets etc.
Unstabilized Hexamine is used in adhesives, coatings and sealing compounds, in the preservation of hides, as cross-linking agent for hardening phenol-formaldehyde resins and vulcanizing rubber, as corrosion inhibitor for steel, as dye fixative, as fuel tablets for camping stoves, as stabilizer for lubricating and insulating oils, for manufacture of explosives, chemical detection of metals and as an urinary antiseptic.
Stabilized Hexamine is used in process industry, as per the requirements of specific customers.
Hexamine is a formaldehyde derivative.
Hexamine is a white granular material made from ammonia and formaldehyde.
Hexamine is highly soluble in water and polar organic solvents.
Hexamine is used in the production of other chemical compounds, e.g., plastics, pharmaceuticals, rubber additives.
Hexamine provides range of benefits for producers like, efficient cross-linking (with no water release) and as formaldehyde donor when used in aqueous acidic environment.
Curing agent for industrial phenolic resins (Novolac Resins)
Rubber and lacquer film as cross-linking or vulcanizing agent
Medicine and food industry
As dry fuel - Fuel tablets
Chemical intermediate/chemical synthesis
Antiseptic agent for livestock
Preservative & anti-microbial effect
Synthetic resin industry
In adhesives, coatings and sealing compounds; in the preservation of hides; as cross-linking agent for hardening phenol formaldehyde resins & vulcanizing rubber; as corrosion inhibitor for steal; as dye fixative; as fuel tablets for camping stoves; as stabilizer for lubricating and insulating oils; for manufacture of explosives; chemical detection of metals; as an urinary antiseptic.
Properties of Hexamine - C6H12N4
Let us look at some important properties of the hexamine compound.
The chemical formula for hexamine can be given as C6H12N4,
The density of Hexamine is 1.33 g/cm3,
The molecular weight of C6H12N4 is 140.186 g/mol,
The Boiling point of Hexamine can be given as "Sublimes,"
The Melting point of Hexamine can be given as 280°C,
The odor of this compound is Fishy (Ammonia like).
Applications of Hexamine
The dominant use of hexamine can be in the production of liquid or powdery preparations of phenolic resins.
The moulding compounds of phenolic resin are added as a hardening component. Where, we can use these products like binders, for example, in clutch and brake linings, non-woven textiles, abrasive products, formed parts produced by the moulding processes, and fireproof materials.
Hexamine has been proposed that the hexamine powder could work as a molecular building block for the self-assembled molecular crystals.
Hexamine, also known as methenamine, is a white crystalline heterocyclic organic compound that is highly solubi.in water and polar organic solvents.
Hexamine is chemical formula is (CH2)6N4. The flammable solid has a cage-like structure similar to adamantine.
Hexamine is used in the synthesis of other chemical compounds such as plastics, pharmaceuticals, and rubber additives.
Hexamine is dominantly used in the production of powdery or liquid preparations of phenolic resins and phenolic resin molding compounds where it is added as a hardening component. Hexamines are used as binders in the manufacture of brake and clutch linings, abrasive products, non-woven textiles, formed parts produced by molding processes, and fireproof materials.
Hexamine is also used in the medical profession for the treatment of urinary tract infections.
Because it is smokeless when burned, has a high energy density of 30.0 megajoules per kilogram (MJ/kg), does not liquify while burning, and leaves no ashes, Hexamine is a component of hexamine fuel tablets used by campers, hobbyists, the military and relief organizations for heating camping food as well as military rations.
The crystalline compound is also used as a reagent in organic chemistry, a food additive as a preservative, and as the base component in the manufacture of certain explosives.
Adhesives and Sealants
Agricultural Products (non-pesticidal)
Automotive Care Products
Building/Construction Materials not covered elsewhere
Plastic and Rubber Products not covered elsewhere
Hexamine is a heterocyclic organic compound which is soluble in water and in most ogranic solvents.
The main use of Hexamine is in the production of powdery or liquid preparations of phenolic (phenolic formaldehyde) resins and phenolic resin molding compound, where it is added as a hardening component.
Hexamines are used as binders, e.g., in brake and clutch linings, abrasive products, no-woven textiles, fire proof materials.
Phenolic formaldehyde resins include synthetic thermosetting resins got by the reaction of phenol (an organic compound) and formaldehyde
Medicinal uses: Medical professionals use hexamine as an antibiotic to treat urinary tract infections. The specific medication used is called methenamine hippurate, which is formed by the combination of hexamine and hippuric acid.
In acidic urine, methenamine hydrolyzes into ammonia and formaldehyde, a non-specific antibiotic. As this reaction is activated by acid in the urine, methenamine is often ineffective as an antibiotic in those whose urine is not acidic.
In fire-protection laboratories: Hexamine tablets are used by fire-protection laboratories as a clean and reproducible fire source to test the flammability of carpets and rugs.
As a chemical agent in organic chemistry: Organic chemists use hexamine as a chemical agent in several chemical reactions which are quite complex and is often used for teaching purposes. Very often they are used for purposes of chemical analysis to determine the identity of an unknown solute (particles that are dissolved into a solution) in a solution.
Other uses: Hexamine is also used in rubber and textile adhesives, in paints and lacquers, in the photographic industry, in the production of deodorants and hair fixers.
Hexamine is suppliers of microbial preservatives in the food industry, multi-industry products used in industry, industry and textile manufacturing industry.
About this substance
Hexamine is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 000 tonnes per annum.
Hexamine is used by consumers, in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.
Hexamine is used in the following products: washing & cleaning products, fuels and cosmetics and personal care products.
Other release to the environment of Hexamine is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners), indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters) and outdoor use.
Article service life
Other release to the environment of Hexamine is likely to occur from: outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials) and indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment).
Hexamine can be found in products with material based on: rubber (e.g. tyres, shoes, toys) and plastic (e.g. food packaging and storage, toys, mobile phones).
Widespread uses by professional workers
Hexamine is used in the following products: fuels, pH regulators and water treatment products, laboratory chemicals and polymers.
Hexamine is used in the following areas: health services and scientific research and development.
Other release to the environment of Hexamine is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners), outdoor use and indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters).
Formulation or re-packing
Hexamine is used in the following products: adhesives and sealants and polymers.
Release to the environment of this substance can occur from industrial use: formulation of mixtures and formulation in materials.
Uses at industrial sites
Hexamine is used in the following products: fillers, putties, plasters, modelling clay, adhesives and sealants, fuels, pH regulators and water treatment products, laboratory chemicals and polymers.
Hexamine has an industrial use resulting in manufacture of another substance (use of intermediates).
Hexamine is used in the following areas: scientific research and development.
Hexamine is used for the manufacture of: metals, fabricated metal products, electrical, electronic and optical equipment and machinery and vehicles.
Release to the environment of Hexamine can occur from industrial use: as processing aid, as processing aid, in the production of articles, as an intermediate step in further manufacturing of another substance (use of intermediates), in processing aids at industrial sites and for thermoplastic manufacture.
Hexamine has an adamantane structure with high degree of symmetry and the characteristics of tertiary amines. Each of the four nitrogen atoms has a pair of unshared electron with being able to form coordination compound with many kinds of inorganic compounds.
Hexamine can have heating reaction with strong inorganic acid to generate formaldehyde and ammonium salts.
In the presence of zinc powder, Hexamine can have reaction with hydrochloric acid to generate the hydrochloride salt of trimethylamine and ammonium chloride.
Hexamine can also be subject to nitrification and generate RDX.
Hexamine can also have reaction with nitrous acid to form N'N'-Dinitroso pentamethylene tetramine.
Hexamine can have reaction with hydrogen peroxide and hydrogen cyanide.
Hexamine can also have reaction with sulfur and sulfur compounds or react with the alkali metal salts, alkaline earth metal, and rare earth metal salts to form a complex.
In acidic medium, Hexamine can react with alcohol. It can also react with organic acid to form salt.
Hexamine can also react with halides, phenols and amides as well as some natural products such as protein and fiber.
Hexamine is irritating to the skin and can cause dermatitis.
Hexamine is a therapeutic drug for treating the bacterial urinary tract infections.
Hexamine itself has no antibacterial effect.
After oral absorption, Hexamine can be secreted out by renal with being broken down into ammonia and formaldehyde in acidic urine with the later one being able to effectively inhibit the G-bacteria, especially having a strong antibacterial effect on Escherichia coli, Enterobacter aerogenes and Pseudomonas aeruginosa.
Hexamine can be used for treating urinary tract infections caused by susceptible strains.
When Hexamine is subject to oral administration, the patients should also take vitamin C or ammonium chloride at the same time in order to acidify the urine
Hexamine is white hygroscopic crystalline powder or shiny colorless rhombic crystals.
Hexamine is almost odorless with sweet and bitter taste.
Hexamine is soluble in water and chloroform but less soluble in carbon tetrachloride, acetone, benzene and ether and insoluble in petroleum ether.
Hexamine can be used as the curing agent for resins and plastics, the vulcanization accelerator of rubber (accelerator H) and textiles shrink-proof agent.
Hexamine can also be used for making antibacterial drug, explosives and so on.
As medicine, after oral administration, Hexamine can be decomposed when coming across acidic urine to generate formaldehyde and exerts its antibacterial effect used for treating mild urinary tract infection;
Hexamine can be externally used for treating ringworm, antiperspirants, and treatment of underarm odor. Its being mixed with caustic soda and sodium phenol can be used as the phosgene absorber of gas masks.
Hexamine can be used as a kind of anti-microbial agents.
Hexamine can be used as anti-shrinking textile finishing agent, bleaching agents of sodium chlorite and the buffer of waterproofing agents CR.
Hexamine is mainly used as the curing agent of plastic and resin, the catalyst and foaming agent of aminoplast, rubber vulcanization accelerator (accelerator H), and the shrink-proof agents of textiles.
Hexamine is the raw material for organic synthesis and can be used for the production of chloramphenicol in the pharmaceutical industry.
Hexamine can be used as the disinfectant of urinary system with itself having no antibacterial effect and being effective in treating gram-negative bacteria.
Hexamine is 20% solution can be used for the treatment of underarm odor, sweaty feet, tinea and so on.
Hexamine is being mixed with caustic soda and sodium phenol can be used as the phosgene absorber of gas masks.
Hexamine can also be used for the manufacture of pesticides.
Hexamine can react with fuming nitric acid to obtain highly explosive cyclonite, briefly referred as RDX.
Hexamine can be used as the reagent and chromatography reagents for determination of bismuth, indium, manganese, cobalt, thorium, platinum, producing magnesium, lithium, copper, uranium, beryllium, tellurium, bromide, and iodide.
In the liver function tests,Hexamine can be used for formulating thymol turbidity, test and measurement of object such as bismuth, iron, manganese, cobalt, thorium, platinum and magnesium as well as the determination and identification of lithium, iron cyanide, iron bromide and iodide.
Hexamine can also be used for the determination of copper, uranium, beryllium, tellurium etc.
Moreover, Hexamine can be used as gas chromatography fixed solution (maximum usage temperature of 180 ℃ with the solvent being chloroform).
Hexamine is a tetraamine compound with a structure analogous to adamantane.
Hexamine is used in synthesis as a formylation agent and is employed in preparing specialized materials.
Methenamin p.a. (R)
Stabilised Hexamine, HMT
Urotropine technical stabilized
1,3,5,7-Tetraazatricyclo[184.108.40.206,7]decan [German] [ACD/IUPAC Name]
1,3,5,7-Tetraazatricyclo[220.127.116.11,7]decane [ACD/Index Name] [ACD/IUPAC Name]
1,3,5,7-Tétraazatricyclo[18.104.22.168,7]décane [French] [ACD/IUPAC Name]
metenamina [Spanish] [INN]
methenamine [INN] [USAN] [USP]
Méthénamine [French] [INN]
methenaminum [Latin] [INN]
MFCD00006895 [MDL number]