Introduction

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. It has a cage-like structure similar to adamantane. It is useful in the synthesis of other organic compounds, including plastics, pharmaceuticals, and rubber additives. It sublimes in vacuum at 280 °C.

Hexamethylenetetramine 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.

As the mandelic acid salt (methenamine mandelate) or the hippuric acid salt (methenamine hippurate),[5] it is used for the treatment of urinary tract infection. In an acidic environment, methenamine is believed to act as an antimicrobial by converting to formaldehyde.[5][6] A systematic review of its use for this purpose in adult women found there was insufficient evidence of benefit and further research is needed. A UK study showed that methenamine is as effective as daily low-dose antibiotics at preventing UTIs among women who experience recurrent UTIs. As methenamine is an antiseptic, it may avoid the issue of antibiotic resistance.
Methenamine acts as an over-the-counter antiperspirant due to the astringent property of formaldehyde.

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.