Hexamine
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| {{{name|Hexamine}}} | |
|---|---|
| Image:Hexamine.png | |
| Chemical name | 1,3,5,7-tetraazatricyclo[3.3.1.13,7]decane}}} |
| Other names | methenamine urotropine hexamethylenetetramine uritone 1,3,5,7-tetraazaadamantane HMT |
| Chemical formula | C6H12N4}}} |
| Molecular mass | 140.19}}} g/mol |
| CAS number | 100-97-0}}}] |
| Density | ?}}} g/cm3 |
| Boiling point | 270}}} °C (sublimes) |
| SMILES | N1(CN3C2)CN(C3)CN2C1}}} |
| Disclaimer and references | |
Hexamine, also called methenamine (INN), is a heterocyclic organic compound that can be prepared by the reaction of formaldehyde and ammonia. It is crystalline and white in appearance. Particle size ranges from 80-800 micrometres. It is moderately soluble in water and well soluble in most organic solvents. It has a cage-like structure similar to adamantane.
It has two very different types of uses: as an antibiotic (commonly the hippurate salt, methenamine hippurate), and as a solid fuel tablet used for cooking while camping or hiking. The name methanmine is more common in its medicinal uses and hexamine is more common in commercial uses.
Medicinal and food uses
Methenamine hippurate is mainly used for the prophylaxis (prevention) of urinary tract infections, where it is hydrolysed in the acidic pH of the urine to form formaldehyde. Formaldehyde is an effective antiseptic against bacteria and fungi in vitro, but may not be effective in vivo - it has not been shown to be effective for the treatment of urinary tract infections. Furthermore, certain bacteria (including Proteus spp. and Pseudomonas spp. increase urinary pH, rendering methenamine ineffective. (Rossi, 2004) Methenamine can also be used to treat hyperhidrosis when applied topically. (Beers & Berkow, 1999)
As a food additive, hexamine is used as a preservative in cheeses. It has E number E239. In some countries, such as Russia, it is banned for this use.
Hexamine can be absorbed through the skin, and some people are allergic to it. This usually only manifests as a rash.
Industrial and commercial uses
Hexamine is used as a component with 1,3,5-trioxane in hexamine fuel tablets (often called Esbit). This solid fuel in tablet form is used by campers, hobbyists, the military and relief organizations for heating camping food or military rations. It burns smokelessly, has a high energy density, does not liquify while burning and leaves no ashes.
Another important area for use of hexamine is in the production of powdery or liquid preparations of phenolic resins and phenolic resin moulding compounds, where hexamine 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.
It is used in rubber and textile adhesives, in paints and lacquers, in the photographic industry, in the production of explosives such as RDX, as a corrosion inhibitor, as a protein modifier, as a reagent in chemical analysis, and in the production of deodorants and hair fixers, among many other uses. (Roempp, 1997; Ullmann, 1995)
References
- Beers MH, Berkow R, editors. The Merck Manual, 17th edition. Whitehouse Station (NJ): Merck Research Laboratories; 1999. ISBN 0911910-10-7
- Rossi S, editor. Australian Medicines Handbook 2004. Adelaide: Australian Medicines Handbook; 2004. ISBN 0-9578521-4-2.
- Merck Index, Twelfth Edition, 6036.
Image:Hexamethylenetetramine-pov-rod.pngbg:Уротропин de:Urotropin fr:Méthénamine lt:Heksaminas lv:Urotropīns nl:Hexamine ru:Гексаметилентетрамин
