medicine: methenamine

methenamine description

Go to trade names and prices








Hexamine 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 °C.

Synthesis, structure, reactivity

Hexamine is prepared by the reaction of formaldehyde and ammonia. 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.

The molecule behaves like an amine base, undergoing protonation and N-alkylation.

Applications

The main 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.

Medicinal uses

Methenamine hippurate, a salt formed by the combination of hippuric acid and hexamine, is used to treat urinary tract infections. Since it is activated by the acids in urine, it is suitable only for infections of the lower urinary tract. It is also used in the treatment of obstructive post-renal disease, in combination with urine alkanization.

Combustion

Together with 1,3,5-trioxane, hexamine is a component of hexamine fuel tablets 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.

Standardized 0.149 g tablets of methenamine (hexamine) are used by fire-protection laboratories as a clean and reproducible fire source to test the flammability of carpets and rugs.

The explosives RDX and HMX can be derived from hexamine.

Reagent in organic chemistry

Hexamine is a versatile reagent in organic synthesis. It is used in the Duff reaction (formylation of arenes), the Sommelet reaction (converting benzyl halides to aldehydes), and in the Delepine reaction (synthesis of amines from alkyl halides).

Miscellaneous applications

Hexamine is used in rubber and textile adhesives, in paints and lacquers, in the photographic industry, in the production of as a corrosion inhibitor, as a protein modifier. It is also used in chemical analysis, as an anti-caking agent in the production of urea and in the production of deodorants and hair fixers, among many other uses.

Producers

Since 1990 the number of European producers has been significantly declining. The French SNPE factory closed in 1990; in 1993, the production of hexamine in Leuna, Germany ceased; in 1996, the Italian facility of Agrolinz closed down; in 2001, the UK producer Borden closed; in 2006, production at Chemko, Slovak Republic, was closed. Remaining producers include INEOS in Germany, Caldic in the Netherlands, and Hexion in Italy. In the US, Eli Lilly stopped producing methenamine tablets in 2002.

Trade names

Trade names and prices of methenamine

Name Information Price* Quantity
       
Dehydral Cream 15 grams (methenamine) $13 15 grams
Hiprex 1g 60 tablets (methenamine hippurate) $58 60 tablets
Mandelamine 500mg 100 tablets (methenamine) $42 100 tablets
Prosed DS 81.6/36.2/10.8/9/0.12mg 100 tablet (Benzoic Acid, Hyoscyamine Sulfate, Methenamine, Methylene Blue, Phenyl Salicylate) N/A
Uroquid Acid No2 100 tablet (methenamine/sodium phosphate) N/A

*) Prices related to some of online drugstores. There are only approximate prices. For some of drugs is needed a prescription.

Tags

Keywords related to methenamine

aloprim tarka microdermabrasion histapyrrodine pentolonium tartrate deferoxamine exelon cantil imolamine theoclear velcade eurax dtpa trizivir serevent frova etryptamine adrucil crescormon timentin etoxeridine lotrel ak pentolate valproic acid humulin vosol drospirenone menotropin ethmozine versed aniracetam fentonium bromide lorglumide sulfafurazole dispermox trandate ciclosporin cefcapene erypar thorazine depacon tacaryl lobeline ala scalp akne mycin filenadol cloroqualone eupatilin spiradoline rimiterol methadose sucraid


  • Related news


    Cranberry is not effective for the prevention or treatment of urinary
    18 Lastly, Lee et al. randomly assigned patients to one of the four groups using a factorial design, the groups being cranberry and Methenamine Hippurate (a ...
    Read full article

    Vyteris Initiates Phase II Clinical Trial of Infertility Treatment
    ovine triflutate for injection), PROSED DS (methenamine, phenyl salicylate, methylene blue, benzoic acid, hyoscyamine sulfate), and DESMOPRESSIN. ...
    Read full article

    formaldehyde -- Britannica Online Encyclopedia
    Formaldehyde and ammonia yield methenamine, or hexamethylenetetramine, which is used as Nitration of methenamine gives the explosive cyclonite, or RDX. ...
    Read full article

    Cystitis - Acute Bacterial Medications - Cystitis - Acute Bacterial
    Methenamine (such as Atrosept, Prosed, and Urised) or flavoxate (Urispas) reduce bladder spasms, which may occur with some UTIs. These drugs can have severe ...
    Read full article

    Company Profile Report
    Products:. Mandelamine (Methenamine Mandelate). Nitrofurantoins. Products:. Macrobid (Nitrofurantoin); Macrodantin (Nitrofurantoin) ...
    Read full article

    Put a "Pause" on Menopause-causing Urinary Tract Infections
    as it is the only over-the-counter urinary tract medication that contains methenamine, an antibacterial agent that attacks bacteria and helps prevent it ...
    Read full article

    Go With The "Flow"
    the progression of the infection with an extra ingredient -- methenamine -- that helps stop bacteria from adhering to the walls of the urinary tract. ...
    Read full article

    Urine pH - Tests, Test Results & Diagnosis - NY Times Health Informati
    Drugs that can decrease urine pH include ammonium chloride, thiazide diuretics, and methenamine mandelate. Eat a normal, balanced diet for several days ...
    Read full article

    Searching for meaning: in an expanding universe of unstructured
    For example, one study may refer to the antibacterial methenamine, while another mentions a different antibacterial, nitrofurtoin; neither study mentions ...
    Read full article

    Elderly woman presents with painful, swollen left eye
    Pathology specimen with Gomori's methenamine silver stain showing branching septate hyphae. The otolaryngology and infectious disease services were ...
    Read full article

    Nodular glomerulosclerosis in a patient with metabolic syndrome
    Mesangial cells are of normal or reduced number and at the periphery of the nodules (periodic acidmethenamine silver staining; magnification 400). ...
    Read full article

    A novel classification for IgA nephropathy
    pathologists throughout the United Kingdom graded 20 renal biopsy sections of lupus nephritis stained by hematoxylin and eosin and methenamine silver. ...
    Read full article

    Ferring Pharmaceuticals announces trade name FIRMAGON (degarelix
    PROSED DS (methenamine, phenyl salicylate, methylene blue, benzoic acid, hyoscyamine sulfate), DESMOPRESSIN, and EUFLEXXA (1% sodium hyaluronate). ...
    Read full article

    Treatment of lower urinary tract disorders.(DRUGS, PREGNANCY, AND
    Methenamine, either as the mandelate or hippurate salt, is an old drug that is Methenamine is broken down in the urine (not in serum) to ammonia and the ...
    Read full article

    Ferring Pharmaceuticals and Resolve
    Ferring's line of orthopaedic and urology products includes EUFLEXXA(R) (1% sodium hyaluronic acid) and PROSED(R) DS (methenamine, phenyl salicylate, ...
    Read full article

    Old Remedy Works for Recurrent UTIs in Renal Transplant Recipients:
    BOSTON -- June 5, 2009 -- Methenamine salt plus vitamin C prophylaxis (PPX), an older remedy for urinary tract infections (UTIs), significantly reduced UTI ...
    Read full article

    GMP-17-positive T-lymphocytes in renal tubules predict progression in
    Biopsy sections were stained with hematoxylineosin, periodic acidSchiff, and silver methenamine. Glomerular, tubular, interstitial, and vascular ...
    Read full article

    Atropine, Hyoscyamine, Methenamine, Methylene Blue, Phenyl Salicylate
    Housecall, our weekly general-interest e-newsletter, keeps you up to date on a wide variety of health topics with timely, reliable, practical information, ...
    Read full article

    Ferring Pharmaceuticals Launches Phase IIIB Trial of Degarelix as
    ENDOMETRIN(R) (progesterone) Vaginal Insert, 100 mg, PROSED(R) DS (methenamine, phenyl salicylate, methylene blue, benzoic acid, hyoscyamine sulfate), ...
    Read full article

    Urinary Tract Infection - Children
    Methenamine (such as Atrosept, Prosed, and Urised) or flavoxate (Urispas) reduce bladder spasms, which may occur with some UTIs. These drugs can have severe ...
    Read full article

    Press Release: Dr. Paul Korner Promoted to Senior Vice President of
    PROSED(R) DS (methenamine, phenyl salicylate, methylene blue, benzoic acid, hyoscyamine sulfate), Degarelix for injection, and DESMOPRESSIN. ...
    Read full article

    Say 'I Do' to a Happy and Healthy Honeymoon
    The medicine contains the natural antiseptic methenamine that helps stop bacteria from adhering to the wall of the urinary tract, which prevents the ...
    Read full article

    Clinical Evidence Handbook
    We do not know whether single-dose, self-administered trimethoprim/sulfamethoxazole or continuous prophylaxis with methenamine hippurate are effective in ...
    Read full article

    Collapsing glomerulopathy: Many means to a similar end
    8 (Photomicrograph: silver methenamine stain; original magnification, 400.) Mutations in ACTN4, the gene encoding the actin filament cross-linking protein ...
    Read full article

    Vyteris Announces Agreement for Additional Funding
    ovine triflutate for injection), PROSED DS (methenamine, phenyl salicylate, methylene blue, benzoic acid, hyoscyamine sulfate), and DESMOPRESSIN. ...
    Read full article

    The clinical importance of bronchoalveolar lavage in allogeneic SCT
    The Grocott (methenamine silver) procedure was used to detect P. jiroveci and other fungal species. 19, 21 The viral and fungal cultures were most often ...
    Read full article

    Migratory pulmonary infiltrates
    Figure 3: (A) A renal biopsy specimen stained with silver methenamine showing proliferating epithelial cells in a crescent form within the glomerulus ...
    Read full article

    Subcutaneous mycosis and fungemia by Aureobasidium pullulans: a rare
    (b) Gomori methenamine silver-stained sections of a skin biopsy specimen. This is probably the first case report of A. pullulans fungemia after allogeneic ...
    Read full article