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CAS NUMBER: 100-97-0
EC NUMBER: 202-905-8
MOLECULAR FORMULA: C6H12N4
MOLECULAR WEIGHT: 140.19
IUPAC NAME: 1,3,5,7-tetrazatricyclo[3.3.1.1^(3,7)]decane
Hexamethylenetetramine, also known as methenamine, hexamine, or urotropin
Hexamethylenetetramine is a heterocyclic organic compound with the formula (CH2)6N4.
This white crystalline compound is highly soluble in water and polar organic solvents.
Hexamethylenetetramine has a cage-like structure similar to adamantane.
Hexamethylenetetramine is useful in the synthesis of other organic compounds, including plastics, pharmaceuticals, and rubber additives.
Hexamethylenetetramine sublimes in vacuum at 280 °C.
Synthesis, structure, reactivity:
Hexamethylenetetramine was discovered by Aleksandr Butlerov in 1859.
Hexamethylenetetramine is prepared industrially by combining formaldehyde and ammonia.
The reaction can be conducted in gas phase and in solution.
The molecule has a tetrahedral cage-like structure, similar to adamantane.
Four vertices are occupied by nitrogen atoms, which are linked by methylene groups.
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.
Applications:
The dominant use of hexamethylenetetramine 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.
These products are used as:
-binders,
-in brake and clutch linings,
-abrasive products,
-non-woven textiles,
-formed parts produced by moulding processes,
-fireproof materials
Medical uses:
As the mandelic acid salt (methenamine mandelate) or the hippuric acid salt (methenamine hippurate), Hexamethylenetetramine is used for the treatment of urinary tract infection.
In an acidic environment, Hexamethylenetetramine is believed to act as an antimicrobial by converting to formaldehyde.
A systematic review of Hexamethylenetetramine's use for this purpose in adult women found there was insufficient evidence of benefit and further research is needed.
Hexamethylenetetramine acts as an over-the-counter antiperspirant due to the astringent property of formaldehyde.[8]
Histological stains:
Hexamethylenetetramine silver stains are used for staining in histology, including the following types:
-Grocott's Hexamethylenetetramine silver stain, used widely as a screen for fungal organisms.
-Jones' stain, a Hexamethylenetetramine silver-Periodic acid-Schiff that stains for basement membrane, availing to view the "spiked" Glomerular basement membrane associated with membranous glomerulonephritis.
Solid fuel:
Together with 1,3,5-trioxane, hexamethylenetetramine is a component of Hexamethylenetetramine fuel tablets used by campers, hobbyists, the military and relief organizations for heating camping food or military rations.
Hexamethylenetetramine 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 Hexamethylenetetramine (hexamine) are used by fire-protection laboratories as a clean and reproducible fire source to test the flammability of carpets and rugs.
Food additive:
Hexamethylenetetramine or Hexamethylenetetramine is also used as a food additive as a preservative (INS number 239).
Hexamethylenetetramine 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:
Hexamethylenetetramine is a versatile reagent in organic synthesis.
Hexamethylenetetramine 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).
Explosives:
Hexamethylenetetramine is the base component to produce RDX and, consequently, C-4 as well as Octogen, Hexamethylenetetramine dinitrate, Hexamethylenetetramine diperchlorate and HMTD.
Historical uses:
Hexamethylenetetramine was first introduced into the medical setting in 1899 as a urinary antiseptic.
However, Hexamethylenetetramine 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 hexamethylenetetramine'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, hexamethylenetetramine was found to be almost completely inactive.
Hexamethylenetetramine 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.
Producers:
Since 1990 the number of European producers has been declining.
The French SNPE factory closed in 1990; in 1993, the production of hexamethylenetetramine in Leuna, Germany ceased; in 1996, the Italian facility of Agrolinz closed down; in 2001, the UK producer Borden closed; in 2006, production at Chemko, Slovak Republic, was closed.
Remaining producers include INEOS in Germany, Caldic in the Netherlands, and Hexion in Italy.
In the US, Eli Lilly and Company stopped producing methenamine tablets in 2002.
In Australia, Hexamethylenetetramine Tablets for fuel are made by Thales Australia Ltd.
In México, Hexamethylenetetramine is produced by Abiya.
Hexamethylenetetramine is a urinary tract antiseptic that is used as suppressive therapy for chronic or recurrent urinary tract infections.
Hexamethylenetetramine has not been linked to serum enzyme elevations or to instances of clinically apparent acute liver injury.
Hexamethylenetetramine is a heterocyclic organic compound with antibiotic activity.
In the body Hexamethylenetetramine is converted to formaldehyde, a nonspecific bactericidal agent.
Hexamethylenetetramine is typically used long-term to treat chronic urinary tract infections and to prevent the recurrence of infections.
Hexamethylenetetramine is a heterocyclic organic compound with a cage-like structure similar to adamantane.
In salt form Hexamethylenetetramine is used for the treatment of urinary tract infection (Example: methenamine hippurate which is the hippuric acid salt of methenamine).
Hexamethylenetetramine appears as odorless white crystalline powder or colorless lustrous crystals.
Hexamethylenetetramine Sublimes in a vacuum at about 505° F with some decomposition.
Mechanism of Action:
Hexamethylenetetramine does not have antibacterial properties in an alkaline environment (pH≥6); however, in a more acidic environment (pH<6), methenamine is hydrolyzed to formaldehyde.
Formaldehyde is considered to be highly bactericidal.
Formaldehyde has nonspecific antibacterial activity and works by denaturing proteins and nucleic acid of bacteria.
Certain bacteria such as Proteus sp. can alkalize urine, inhibiting the beneficial activity of formaldehyde.
The key role of the salt component of the drug, for example hippuric acid, is to maintain the acidic state of the urine.
GENERAL USES OF THE COMPOUND:
Industry Uses:
-Adhesives and sealant chemicals
-Automotive parts ingredient (brake pads)
-Corrosion inhibitors and anti-scaling agents
-Curing Accelerator
-Explosive Materials
-Finishing agents
-Intermediates
-Ion exchange agents
-Making phenolic resins
-Overlays
-Plating agents and surface treating agents
-Process regulators
-Processing aids, not otherwise listed
-Processing aids, specific to petroleum production
-Propellants and blowing agents
Consumer Uses:
-Adhesives and sealants
-Agricultural products (non-pesticidal)
-Automotive Sound Insulation Material
-Automotive care products
-Building/construction materials not covered elsewhere
-Explosive materials
-Fuels and related products
-Metal products not covered elsewhere
-Plastic and rubber products not covered elsewhere
-Rubber Tires
Methods of Manufacturing:
Formaldehyde and ammonia can be converted into hexamethylenetetramine in the gas phase, in aqueous solution, or in a suspension in an inert solvent, although the most important of these procedures is that carried out in water.
The usual process gives a pure product in yields near 90% and includes an economical drying step.
Hexamethylenetetramine is readily prepared by treating aqueous formaldehyde with ammonia followed by evaporation and crystallization of the solid product.
The reaction is fast and essentially quantitative.
Industry Processing Sectors:
-Adhesive manufacturing
-All other chemical product and preparation manufacturing
-Computer and electronic product manufacturing
-Custom compounding of purchased resin
-Electrical equipment, appliance, and component manufacturing
-Explosives manufacturing
-Fabricated metal product manufacturing
-Lightbulb manufacturing
-Mining (except oil and gas) and support activities
-Miscellaneous manufacturing
-Nonmetallic mineral product manufacturing (includes clay, glass, cement, concrete, lime, gypsum, and other nonmetallic mineral product manufacturing.
-Oil and gas drilling, extraction, and support activities
-Pesticide, fertilizer, and other agricultural chemical manufacturing
-Petrochemical manufacturing
-Plastic material and resin manufacturing
-Rubber product manufacturing
-Services
-Soap, cleaning compound, and toilet preparation manufacturing
-Textiles, apparel, and leather manufacturing
-Transportation equipment manufacturing
-Wholesale and retail trade
Hexamethylenetetramine, also known as methenamine, is a white crystalline heterocyclic organic compound that is highly soluble in water and polar organic solvents.
Hexamethylenetetramine's chemical formula is (CH2)6N4.
The flammable solid has a cage-like structure similar to adamantine.
Hexamethylenetetramine is used in the synthesis of other chemical compounds such as plastics, pharmaceuticals, and rubber additives.
Hexamethylenetetramine 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.
Hexamethylenetetramine is 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.
Hexamethylenetetramine is also used in the medical profession for the treatment of urinary tract infections.
Because Hexamethylenetetramine 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, hexamethylenetetramine is a component of Hexamethylenetetramine 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.
Hexamethylenetetramine is a heterocyclic organic compound with a chemical name Hexamethylenetetramine.
Hexamethylenetetramine is also called Methenamine or Hexamethylenetetramine or Urotropin.
Hexamethylenetetramine acts as an anti-infective agent which is most commonly used to treat urinary tract infections.
Hexamethylenetetramine's anti-infective action is derived from the slow release of formaldehyde (CH2O) by hydrolysis at acidic pH of 0.2 molars.
Hexamethylenetetramine is an odourless colourless lustrous crystal or white crystalline powder which is hygroscopic.
*Hexamethylenetetramine is used in the production of liquid or powdery preparations of phenolic resins.
*Hexamethylenetetramine is used as binders in clutch and brake linings.
*Hexamethylenetetramine is used in the form of spray and cream to treat concomitant odour and excessive sweating.
*Hexamethylenetetramine is used in Grocott’s methenamine silver stain.
*Hexamethylenetetramine is used as a solid fuel.
*Hexamethylenetetramine is used as a food preservative.
*Hexamethylenetetramine is used as a primary ingredient in making RDX.
*Hexamethylenetetramine is used to prevent vulcanized rubber.
*Hexamethylenetetramine is used as a corrosion inhibitor for steel.
Hexamethylenetetramine (HMTA) is a water soluble, heterocyclic organic compound with a cage-like structure resembling adamantane.
Hexamethylenetetramine is commonly used in treating urinary tract infection.
Application:
Hexamethylenetetramine (HMTA) may be used as:
Raw material in the synthesis of blue emitting boron carbon oxynitride (BCNO) phosphors and Zinc oxide (ZnO) nanorods.
Catalyst in the synthesis of 2-amino-4H-pyran derivatives.
Surfactant in the synthesis of HMTA capped transition metals doped ZnS nanoparticles.
Precipitant and template in the synthesis of Ni(OH)2.
Applications of Hexamethylenetetramine:
The dominant use of Hexamethylenetetramine can be in the production of liquid or powdery preparations of phenolic resins.
The molding 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 molding processes,
-fireproof materials.
Hexamethylenetetramine has been proposed that the Hexamethylenetetramine powder could work as a molecular building block for the self-assembled molecular crystals.
Medical Uses of Hexamethylenetetramine:
The mandelic acid salt is used for urinary tract infection treatments, and it decomposes at an acidic pH to produce ammonia, and formaldehyde, which is bactericidal, which the mandelic acid adds to this effect.
The use of this compound was temporarily reduced in the late 1990s, because of the adverse effects, specifically because of the chemically-induced hemorrhagic cystitis in the case of overdose.
Hexamethylenetetramine is considered to be suitable for the long-term prophylactic urinary tract infection treatments.
Hexamethylenetetramine should not be used in chronic kidney disease presence.
Hexamethylenetetramine is used in the treatment of concomitant odor and excessive sweating.
Since the mandelic acid salt (which is a generic methenamine mandelate, USP) is used for urinary tract infection treatments, it decomposes at an acidic pH to produce ammonia, and formaldehyde is bactericidal; which the mandelic acid adds to this effect.
Typically, urinary acidity is ensured by co-administering ammonium chloride or vitamin C (otherwise an ascorbic acid).
This compound's usage had temporarily been reduced in the late 1990s because of the adverse effects, specifically chemically-induced hemorrhagic cystitis in the case of overdose.
However, currently, its use has been re-approved due to the prevalence of antibiotic resistance to drugs, which are more commonly used.
Hexamethylenetetramine is especially suitable for long-term prophylactic urinary tract infection treatments because the bacteria do not develop resistance to formaldehyde.
Also, Hexamethylenetetramine should not be used in chronic kidney disease presence.
In the form of spray and creams, Hexamethylenetetramine is successfully used for the treatment of concomitant odor and excessive sweating with the medical citation.
Solid Fuel:
Together with 1,3,5-trioxane, the Hexamethylenetetramine fuel tablets component is used by hobbyists, campers, the relief, and military organizations to heat camp food or military rations.
Hexamethylenetetramine also burns smokeless, and it holds a high energy density of 30.0 megajoules per kilogram (MJ/kg), which does not liquify while burning, and does not leave ashes, although it has toxic fumes.
Fire-protection laboratories use the standardized Hexamethylenetetramine tablets of 0.149 g as a clean and reproducible fire source to test the flammability of rugs and carpets.
Food Additive:
Hexamethylenetetramine can also be used as a food additive as a preservative (with the INS number 239).
In the EU, Hexamethylenetetramine is approved for usage for this purpose, listed under E number E239.
However, Hexamethylenetetramine is not approved in other countries such as the USA, Australia, Russia, New Zealand.
Reagent in Organic Chemistry:
Hexamethylenetetramine compound is a versatile reagent in organic synthesis.
Hexamethylenetetramine can be used in the Duff reaction (which is the formylation of arenes), in the Delepine reaction (amine synthesis from alkyl halides), and in the Sommelet reaction (by converting benzyl halides to aldehydes).
Explosives:
Hexamethylenetetramine is a base component for making RDX and, consequently, C-4 and Octogen, Hexamethylenetetramine the piper chlorate, Hexamethylenetetramine dinitrate, and HMTD.
Hexamethylenetetramine, also known as Hexamethylenetetramine, Methenamine or C6H12N4, is produced by combining formaldehyde and ammonia.
Hexamethylenetetramine appears as an odourless white crystalline powder or a colourless lustrous crystal that is both highly soluble in water and highly flammable.
Hexamethylenetetramine is used in the production of;
-explosive compounds,
-phenolic resins,
-adhesives,
-dyes,
-shrink proof fabrics,
-motor oils/lubricants,
-antiseptics,
-fire starters and pharmaceuticals.
Medically, Hexamethylenetetramine is used to treat urinary tract infections.
Hexamethylenetetramine's use was temporarily reduced in the 1990s due to the adverse effects when taken in excess, but has since been re-approved due to the fact that bacteria are unable to develop a resistance to formaldehyde.
PHYSICAL PROPERTIES:
-Molecular Weight: 140.19
-Exact Mass: 140.106196400
-Monoisotopic Mass: 140.106196400
-Topological Polar Surface Area: 13 Ų
-Physical Description: Colourless or white crystalline powder
-Color: Colorless
-Form: crystalline powder
-Odor: Odorless
-Boiling Point: Sublimes
-Melting Point: Sublimes at about 260 °C without melting and with partial decomposition
-Flash Point: 250 °C
-Solubility: >21 [ug/mL]
-Density: 1.33 g/cm³
-Vapor Density: 4.9
-Vapor Pressure: 6.1X10-4 mm Hg
-log Kow: -2.18
-Stability/Shelf Life: Stable under recommended storage conditions.
The dominant use of Hexamethylenetetramine can be in the production of liquid or powdery preparations of phenolic resins.
The molding 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 molding processes, and fireproof materials.
Hexamethylenetetramine has been proposed that the Hexamethylenetetramine powder could work as a molecular building block for the self-assembled molecular crystals.
Hexamethylenetetramine is a heterocyclic organic compound that has the chemical formula C6H12N4.
Hexamethylenetetramine is also known as Hexamethylenetetramine, Methenamine, or Urotropin.
Hexamethylenetetramine acts as an anti-infective agent, the most commonly used element to treat urinary tract infections.
This compound acts as an anti-infective agent, which is the most commonly used element to treat urinary tract infections.
The anti-infective action of Hexamethylenetetramine is derived from the slow release of formaldehyde (CH2O) by the process of hydrolysis at an acidic pH of 0.2 molars.
Also, Hexamethylenetetramine is a colorless, odorless, and lustrous crystal or white hygroscopic crystalline powder.
CHEMICAL PROPERTIES:
-Heavy Atom Count: 10
-Formal Charge: 0
-Complexity: 84.8
-Isotope Atom Count: 0
-Defined Atom Stereocenter Count: 0
-Undefined Atom Stereocenter Count: 0
-Defined Bond Stereocenter Count: 0
-Undefined Bond Stereocenter Count: 0
-Covalently-Bonded Unit Count: 1
-Compound Is Canonicalized: Yes
-XLogP3-AA: 0.3
-Hydrogen Bond Donor Count: 0
-Hydrogen Bond Acceptor Count: 4
-Rotatable Bond Count: 0
-Autoignition Temperature: 390 °C
-Decomposition: When heated to decomposition it emits toxic fumes of formaldehyde and /nitrogen oxides/.
-Heat of Combustion: -13,300 Btu/lb = -7400 cal/g = -310X10+5 J/kg
-pH: pH of 0.2 molar aqueous solution: 8.4
-Index of refraction: 1.5911 at 25 °C
-pKa: 4.89
-Collision Cross Section: 126.8 Ų
SYNONYMS:
methenamine
Hexamethylenetetramine
Hexamine
Urotropine
Aminoform
Urotropin
Hexamethylenamine
1,3,5,7-Tetraazaadamantane
Methenamin
Hexamethylenetetraamine
Hexamethylene tetramine
Formamine
Uritone
Aminoformaldehyde
Ammonioformaldehyde
Ammoform
Antihydral
Cystamin
Cystogen
Duirexol
Hexaform
Hexaloids
Metramine
Resotropin
Uratrine
Urodeine
Xametrin
Formin
Heterin
Hexasan
Uramin
Preparation AF
Hexamethyleneamine
Hexilmethylenamine
Hexa-Flo-Pulver
Ekagom H
methenaminum
Aceto HMT
Herax UTS
Hexamethylentetramin
Metenamina
Hexaminum
Formin (heterocycle)
Nocceler H
Sanceler H
Hexamine (heterocycle)
Vulkacit H 30
Hexamethylentetraminum
1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decane
Hexamethylentetramine
Hexasan (VAN)
Mandelamine
S 4 (heterocycle)
Hexamethylenetetraminum
Uro-phosphate
1,3,5,7-tetraazatricyclo[3.3.1.1~3,7~]decane
Esametilentetramina
Metenamine
Methamin
VesaloinHexa (vulcanization accelerator)
1,3,5,7-Tetraazatricyclo (3.3.1.1(3,7))decane
Hexamine (JAN)
Hexamine (TN)
Hexamethylenetetramine (aliphatic)
Methenamine (USP/INN)
1,3,5,7-Tetraazatricyclo(3.3.1.13,7)decane
1,3,5,7-Tetraazatricyclo(3.3.1.1(sup 37))decane
1,3,5,7-tetrazatricyclo[3.3.1.13,7]decane
Formin (the heterocyclic compound)
1,3,5,7-tetraazatricyclo[3.3.1.1^{3,7}]decane
1,3,5,7-Tetraazatricyclo(3.3.1.1(sup 3,7))decane
Hexamine Silver
Hexamethylenetetramine-palladium chloride adduct
Methenamine Silver
Silver Methenamine
1,3,5,7-Tetraazatricyclo[3.3.1.1(3,7)]decane
Methenamine [USAN:INN]
Sanceler HT
Metenamina [INN-Spanish]
Methenaminum [INN-Latin]
Heksa K
Hexamine Superfine
Nocceler H-PO
Sanceler HT-PO
Hexa B
1,3,5,7-Tetraazatricyclo(3.3.1.13,7)decane hydroiodide
Esametilentetramina [Italian]
Hexamethylentetramin [German]
Cohedur H 30
hexamethylene-tetramine
Rhenogran HEXA 80
Thixon 715B
1,3,5,7-Tetraazotricyclo[3.3.1.13,7]decane
Methenamine [USP:INN]
1,3,5,7-tetraazatricyclo[3.3.1.1<3,7>]decane
1,3,5,7-Tetraazatricyclo[3.3.1.1{3,7}]decane
1,3,5,7-Tetraazatricyclo[3.3.1.1(sup 3,7)]decane
Hexamethylamine
Naphthamine
Vesalvine
Urisol
Carin
Prestwick_79
Vulkacit H30
1,3,5,7-Tetraazatricyclo[3.3.1.13,7 ]decane
Grasselerator 102
Cystex (Salt/Mix)
hexam-ethylenetetraamine
hexamethylene tetraamine
Methenamine (Mandelamine)
Formaldehyde-ammonia 6:4
[16]-Adamazane, INN
Uro-phosphate (Salt/Mix)
1,5,7-Tetraazaadamantane
Hexamethylentetramin(german)
Hexamethylenetetramine, 8CI
1,3,5,7-tetraazatricyclo[3.3.1.1?,?]decane
Pharmakon1600-01500394
Urotropine 100 microg/mL in Methanol
1,5,7-Tetraazatricyclo[3.3.1.13,7]decane
1,3,5,7-tetraaza-tricyclo[3.3.1.13,7]decane
1,3,5,7-tetraazatricyclo-[3.3.1.13,7]decane
1,3,5,7-tetraazatricyclo[3,3,1,13,7]decane
1,5:3,7-Dimethano-1,3,5,7-tetraazacyclooctane
