Methenamine

Also Known As: Methenamine, Hexamethylenetetramine

Hexamethylenetetramine 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 chemical compounds, e.g. plastics, pharmaceuticals, rubber additives. It sublimes in a vacuum at 280 Â°C.

As the mandelic acid salt (generic methenamine mandelate tablets, USP [1]) it is used for the treatment of urinary tract infection: hexamethyltetramine ("methenamine") decomposes at an acid pH to 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 (notably chemically-induced hemorrhagic cystitis in overdose[2]), but its use has now been reapproved 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: however, it should not be used in the presence of renal insufficiency.

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