Methenamine

Methanamine, C6H12N4, also called hexamine for commercial uses, is a heterocyclic organic compound. It can be prepared by the reaction of formaldehyde and ammonia. It is a white crystalline and is moderately soluble in water.

Effects
Methenamine can affect you if it is breathed in. Symptoms that can occur if the chemical is inhaled can be coughing, if it gets on the skin or eyes it can cause redness and pain, and if it is ingested then it can cause abdominal pain, nausea, and vomiting. It may also cause mutations, be sure to handle with extreme care and caution. It may irritate the nose and throat which can cause coughing and wheezing. Methenamine may cause nausea, vomiting, and abdominal pain along with skin allergy, itching, and skin rash. It is highly flammable and may cause sensitization by inhalation and skin contact. Side effects upset stomach, vomiting, diarrhea, stomach cramps, loss of appetite, skin rash, hives, itching (allergic reaction)

Uses
Methenamine has several uses. This chemical is used in these types of products; shampoo and conditioner. It is used in adhesives, coating, sealants, and leather preservatives, it is also used as an anticorrosion agent, antibiotic, dye fixative, chemical stabilizer, and curing agent for formaldehyde resins and rubber. It is used as a drug taken by mouth in the form of a tablet or a liquid, to prevent recurrent urinary tract infections and used as a hardener for epoxy resins of the bisphenol A type. It is used as a formaldehyde releaser for photographic film development. Methenamine is used as an antibiotic that eliminates bacteria that causes urinary tract infections. It is hydrolyzed in the acidic pH of urine to form formaldehyde. Formaldehyde is an effective antiseptic against bacteria and fungi //in vitro//. However, is has not shown to be effective for treatment of urinary tract infections, so methenamine may really not be effective in treating urinary tract infections. Nevertheless, it is used on a long term basis to treat chronic infections and to prevent the recurrence of infections. It is also used topically to treat hyperhidrosis. Some of it's brand names (for medications) are Hiprex, Mandelamine, and Urex. It is used in fuel tablets for heating camping food or military rations used by campers, the military and relief organizations. They burn smokelessly, have a high energy density, does not liquify when burning and does not leave behind any ashes. It is also used as a preservative in cheeses. Some of its other uses include rubber and textile adhesives, in paints and lacquers, as a corrosion inhibitor, as a protein modifier, and as a reagent in chemical analysis. It is used in the production of powdery or liquid preparations of phenolic resins and phenolic resin moulding compounds as a hardening component. These products are used as binders (brake and clutch linings, abrasive products, non-woven textiles, and fireproof materials). It is also used in the production of explosives and the production of deodorants and hair fixers.
 * ~ Properties ||
 * [|Molecular formula] || C6H12N4 ||
 * [|Molar mass] || 140.186 g/mol ||
 * [|Density] || 1.33 g/cm³ (at 20 °C) ||
 * [|Boiling point] || 280 °C ( [|sublimes] ) ||
 * [|Solubility] in [|water] || 85.3 g/100 mL ||

Synthesis, structure, reactivity
Hexamethylenetetramine is prepared by the [|reaction] of [|formaldehyde] and [|ammonia]. [|[4]] The reaction can be conducted in gas-phase and in solution. The molecule has a symmetric [|tetrahedral] cage-like structure, similar to [|adamantane], whose four "corners" are [|nitrogen] atoms and "edges" are [|methylene] groups. Although the molecular shape defines a cage, no void space is available at the interior for binding other atoms or molecules, unlike [|crown ethers] or larger [|cryptand] structures. The molecule behaves like an amine base, undergoing protonation and //N//- [|alkylation].

Medical uses
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.