Hexamethylenetetramine

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Related to methenamine: methylamine, methenamine mandelate, methenamine silver stain

Hexamethylenetetramine

 

hexamine, or urotropine, colorless crystals with a sweet taste that carbonize at 280° C and sublime in vacuum above 230° C. Hexamethylenetetramine is highly soluble in water and carbon disulfide, moderately in alcohol and chloroform, and slightly in ether and benzene.

Hexamethylenetetramine is prepared by condensing ammonia with formaldehyde: 4NH3 + 6CH2O⇌(CH2)6N4 + 6H2O.

This reaction is reversible and under certain conditions the equilibrium may be shifted toward the left, which makes it possible to use hexamethylenetetramine as a convenient formaldehyde source (for example, in the production of ureaformaldehyde resins). Hexamethylenetetramine is also used in the production of the powerful explosive hexogen, in analytical chemistry (for example, in the preparation of buffer solutions), and as a smokeless solid fuel (so-called solid alcohol). Hexamethylenetetramine is a medicinal preparation of the antiseptic variety. Its antimicrobial action is due to formaldehyde formation from the decomposition of hexamethylenetetramine in acid media. Hexamethylenetetramine is used internally in powders, tablets, and solutions, as well as intravenously in infectious diseases, particularly for urinary tract infections. It was first synthesized by A. M. Butlerov in 1860.

References in periodicals archive ?
jiroveci was done using Grocott's Gomori methenamine silver staining (GMS) (12) and direct fluorescent antibody staining (DFA) (13) using commercial kit (Meriflour, France) and by amplification of the major surface glycoprotein (MSG) gene by conventional polymerase chain reaction (PCR) (14).
Methenamine therapy and urine acidification with ascorbic acid and cranberry juice.
After undergoing 10 wash cycles with detergent, the samples are again dried in preparation for the methenamine pill test.
Fungal profiles are well highlighted by PAS and methenamine silver staining, on which they appear magenta-pink and black, respectively.
Allergic contact dermatitis from methenamine in an antiperspirant spray.
Interface changes are typically lacking, and special stains for fungi (Gomori-Grocott methenamine silver stain, periodic acid-Schiff) and tissue cultures will demonstrate organisms.
Periodic acid-Schiff and Gomori's methenamine silver stains were negative for fungi, but the overall appearance was compatible with a fungal infection.
Urinary germicides include cinoxacin (Cinobac) [C], methenamine [C], nalidixic acid (NegGram) [C], and nitrofurantoin (Macrodantin) [B].
The cyst form may be visualised using the Gomori methenamine silver, toluidine blue O, cresyl echt violet or calcofluor white stains; trophic forms are visualised by modified Papanicolaou, Gram-Weigert or Wright-Giemsa stains.
Methenamine silver (GMS) stains were performed, retrospectively, on antemortem liver biopsy, and no fungi were identified.
She took pyridoxine, oxazepam, methenamine, paracetamol, furosemide, and tamoxifen on a regular basis.
But methenamine is not aggressively promoted, and when Dr.