Hexamethylenetetramine

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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 ?
(11) The recommendation is that an additional stain, PAS or Jones methenamine silver, be ordered up front for all cases on the nonneoplastic renal parenchymal section.
Caption: FIGURE 2: Grocott methenamine silver (GMS) stain of the same biopsy specimen as in Figure 1.
Silver methenamine staining was done on the samples and the samples were examined by an experienced microscopist.
(a) Brown-Hopps (tissue Gram stain), periodic acid--Schiff with diastase digestion, Grocott methenamine silver, acid-fast bacilli, and Fite.
Although the patient in our case was not known to have AIDS at the time of diagnosis, the microscopic findings of the granular, frothy, pink material and associated granulomatous feature prompted a test with Grocott methenamine silver stain.
Histopathological features exhibiting 2-4[micro]m spores with a clear halo was suggestive of histoplasmosis which was confirmed by Gommori's methenamine silver stain.
Histopathologic examination was conducted after the liver sections were stained with hematoxylin and eosin, periodic acid-Schiff, and Gomori methenamine silver.
We agree that Grocott methenamine silver, Congo red, and periodic acid-Schiff usually stain cellulose; however, modified cellulose, such as cellulose acetate may not stain with periodic acid-Schiff.
Histochemical studies (Gomori methenamine silver and acid-fast stains) showed no fungal elements or acid-fast bacilli.
Special stain for fungal elements Grocott's methenamine silver (GMS) (Figure 4) and Periodic Acid-Schiff (PAS) were positive for aspergillus and acid fast stain for tuberculosis was negative on the smears.
No bacterial or fungal agents were seen by light microscopy of specimens stained with hematoxylin and eosin, Giemsa, Warthin-Starry, Brown and Brenn, or Gomori methenamine silver stains or in a Wright-Giemsa-stained cytologic preparation of a joint aspirate.
Biopsy of the lateral wall of the nasal cavity and forehead was subjected to fungal stains: periodic acid-Schiff, Gomori methenamine silver, and Van Giesen stain.