File:Hexamine.svg · Wikimedia Commons · See Wikimedia Commons
methenamine
Sign in to saveAlso known as Hexamethylene tetramine, hexamine, HMTA, HMT, hexamethylenamine, hexamethylenetetramine, 1,3,5,7-tetraazatricyclo[3.3.1.1(3,7)]decane
Hexamethylenetetramine (HMTA), also known as 1,3,5,7-tetraazaadamantane, is a heterocyclic organic compound with diverse applications. It has the chemical formula (CH2)6N4 and is a white crystalline compound that is highly soluble in water and polar organic solvents. It is useful in the synthesis of other organic compounds, including plastics, pharmaceuticals, explosives, and rubber additives. The compound is also used medically for certain conditions. It sublimes in vacuum at 280°C. It has a tetrahedral cage-like structure similar to adamantane. The four vertices are occupied by nitrogen atom
Chemical data
- Formula
- C6H12N4
- Molecular weight
- 140.19 g/mol
- IUPAC name
- 1,3,5,7-tetrazatricyclo[3.3.1.13,7]decane
- SMILES
- C1N2CN3CN1CN(C2)C3
- InChIKey
- VKYKSIONXSXAKP-UHFFFAOYSA-N
- XLogP
- 0.3
- Polar surface area
- 13 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
2,364 papers- Methenamine for urinary tract infection prophylaxis: A systematic review.Pharmacotherapy · 2024
- Methenamine hippurate compared with antibiotic prophylaxis to prevent recurrent urinary tract infections in women: the ALTAR non-inferiority RCT.Health technology assessment (Winchester, England) · 2022
- Methenamine hippurate as prophylaxis for recurrent urinary tract infections in older women-a triple-blind, randomised, placebo-controlled, phase IV trial (ImpresU).Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases · 2025
- Use of Methenamine for Urinary Tract Infection Prophylaxis: Systematic Review of Recent Evidence.International urogynecology journal · 2024
- Effectiveness of methenamine hippurate in preventing urinary tract infections: an updated systematic review, meta-analysis and trial sequential analysis of randomized controlled trials.BMC urology · 2025
via PubMed
Wikidata facts
- Mass
- 140.106
- Image
- Urotropin.JPG
Show 5 more facts
- Commons category
- Hexamine
- canonical SMILES
- C1N2CN3CN1CN(C2)C3
- chemical formula
- C₆H₁₂N₄
- World Health Organisation international non-proprietary name
- methenamine
- time of discovery or invention
- 1859-00-00
via Wikidata · CC0
~7 min read
Article
13 sectionsContents
- Synthesis, structure, reactivity
- Applications
- Medical uses
- Histological stains
- Solid fuel
- Food additive
- Reagent in organic chemistry
- Explosives
- Pyrotechnics
- Historical uses
- Producers
- Occurrence
- References
Hexamethylenetetramine (HMTA), also known as 1,3,5,7-tetraazaadamantane, is a heterocyclic organic compound with diverse applications. It has the chemical formula (CH2)6N4 and is a white crystalline compound that is highly soluble in water and polar organic solvents. It is useful in the synthesis of other organic compounds, including plastics, pharmaceuticals, explosives, and rubber additives. The compound is also used medically for certain conditions. It sublimes in vacuum at 280°C. It has a tetrahedral cage-like structure similar to adamantane. The four vertices are occupied by nitrogen atoms, which are linked by methylene groups. Although the molecular shape defines a cage, no void space is available at the interior.
==Synthesis, structure, reactivity== Hexamethylenetetramine was discovered by Aleksandr Butlerov in 1859. It is prepared industrially by combining formaldehyde and ammonia: 350px