·
CAS Number 100-97-0
·
Empirical Formula (Hill Notation) C6H12N4
·
Molecular Weight 140.19
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Beilstein Registry Number 2018
·
EC Number 202-905-8
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MDL number MFCD00006895
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PubChem Substance ID 24864723
Hexamethylenetetramine or methenamine is
a heterocyclic
organic compound with the formula (CH2)6N4.
This white crystallinecompound is
highly soluble in water and polar organic solvents. It has a cage-like
structure similar to adamantane.
Detailed description
It
is useful in the synthesis of other chemical compounds, e.g., plastics,
pharmaceuticals, rubber additives. It sublimes in vacuum at 280 °C.
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, e.g. in brake and clutch
linings, abrasive products, non-woven textiles, formed parts produced by
moulding processes, and fireproof materials.[5]
It has been proposed that hexamethylenetetramine
could work as a molecular building block for self-assembled molecular crystals.[6][7]
Medical uses
As the mandelic acid salt (generic methenamine
mandelate, USP[8]) it is used for the treatment of
urinary tract infection. It decomposes at an acidic pH to form formaldehyde and ammonia, and the
formaldehyde is bactericidal; the mandelic acid adds to this effect. Urinary
acidity is typically ensured by co-administering vitamin C (ascorbic acid) or ammonium chloride. Its use had
temporarily been reduced in the late 1990s, due to adverse effects,
particularly chemically-induced hemorrhagic cystitis in overdose,[9] but its use
has now been re-approved because of the prevalence of antibiotic resistance to more commonly used drugs. This drug is particularly
suitable for long-term prophylactic treatment of urinary tract infection,
because bacteria do not develop resistance to formaldehyde. It should not be
used in the presence of renal insufficiency. Methenamine in the form of cream
and spray is successfully used for treatment of excessive sweating and
concomitant odour.
Histological stains
Methenamine 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.
Solid fuel
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. It burns
smokelessly, has a high energy density of
30.0 megajoules per kilogram (MJ/kg), does
not liquify while burning, and leaves no ashes.
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.[10]
Food additive
Hexamethylene tetramine or hexamine is also used as
a food additive as a
preservative (INS number 239). It 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. It 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, hexamine dinitrate and HMTD.
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