Metenamine (CED0031870)

Record Information
Version1.0
Creation Date2014-09-11 05:18:28 UTC
Update Date2026-05-14 18:25:13 UTC
Accession NumberCHEM003790
Identification
Common NameMetenamine
ClassSmall Molecule
Description
Metenamine is an exogenous organic compound with the formula C6H12N4 and an average molecular weight of 140.19 g/mol. It exists as a solid at room temperature. Metenamine belongs to the 1,3,5-triazinanes, a subclass of triazinanes within the organic compounds. This compound serves as an industrial preservative and an industrial adhesion/cohesion promoter. It is utilized in healthcare, pharmaceuticals, and veterinary products as an antibacterial and urological agent, and it is used in agriculture and land management as a pesticide. In food preservation, it is used to prevent the "late blowing" of hard cheese by inhibiting the growth of unwanted bacteria, acting through the release of formaldehyde under acidic conditions. Its use in this capacity is declining and limited; as of 2002, European use was limited to Provolone, a type of Italian cheese. Metenamine is found in or released from 48 recorded sources. These include electrical and electronic equipment such as amplifiers, antennas, auxiliary devices, coils, and colour television systems. It is present in food, food processing, and cookware, including food contact materials, food preservation, the preparation of wine or sparkling wine, the preparation of wort, and fermentation processes for beer. In household cleaning and consumer products, it is found in bleaching agents, perfumes within detergents and soaps, cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. In building and construction, it is found in ceilings, fencing, ladders, roofs, stairs, and ramps. Recorded exposure routes for the compound include oral, inhalation, topical, touch, and extracorporeal.
Contaminant Type
  • Amine
  • Food Additive
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Organic Compound
  • Pesticide
  • Preservative
  • Synthetic Compound
Chemical Structure
Synonyms
ValueSource
1,3,5,7-Tetraazatricyclo[3.3.1.1(3,7)]decaneChEBI
HexamethylenamineChEBI
Hexamethylene tetramineChEBI
HexamethylentetraminChEBI
HexamethylentetraminumChEBI
HexamineChEBI
HexaminumChEBI
HMTChEBI
HMTAChEBI
MetenaminaChEBI
MethenamineChEBI
MethenaminumChEBI
UritoneChEBI
UrotropinChEBI
1,3,5,7-TetraazaadamantaneHMDB
1,3,5,7-Tetraazatricyclo (3.3.1.1(3,7))decaneHMDB
1,3,5,7-Tetraazatricyclo(3.3.1.13,7)decaneHMDB
1,3,5,7-Tetraazatricyclo(3.3.1.13,7)decane hydroiodideHMDB
1,3,5,7-Tetraazatricyclo[3.3.1.13,7 ]decaneHMDB
1,3,5,7-Tetraazatricyclo[3.3.1.1~3,7~]decaneHMDB
Aceto HMTHMDB
AminoformHMDB
AminoformaldehydeHMDB
AmmoformHMDB
AmmonioformaldehydeHMDB
AntihydralHMDB
CarinHMDB
CystaminHMDB
CystogenHMDB
DuirexolHMDB
e239HMDB
Ekagom HHMDB
EsametilentetraminaHMDB
Formaldehyde-ammonia 6:4HMDB
FormamineHMDB
ForminHMDB
Formin (heterocycle)HMDB
Formin (the heterocyclic compound)HMDB
Grasselerator 102HMDB
H.m.t.HMDB
Herax utsHMDB
HeterinHMDB
HEXHMDB
HexaHMDB
Hexa (vulcanization accelerator)HMDB
Hexa-flo-pulverHMDB
HexaformHMDB
HexaloidsHMDB
HexamethylamineHMDB
HexamethyleneamineHMDB
HexamethylenetetraamineHMDB
HexamethylenetetramineHMDB
Hexamethylenetetramine (aliphatic)HMDB
Hexamethylenetetramine, 8ciHMDB
Hexamethylenetetramine, acsHMDB
Hexamethylenetetramine-palladium chloride adductHMDB
HexamethylenetetraminumHMDB
HexamethylentetramineHMDB
Hexamine (heterocycle)HMDB
Hexamine silverHMDB
HexasanHMDB
HexilmethylenamineHMDB
MandelamineHMDB
MethaminHMDB
MethenaminHMDB
Methenamine silverHMDB
MetramineHMDB
NaphthamineHMDB
Natasol fast orange GR saltHMDB
Nocceler HHMDB
Preparation afHMDB
ResotropinHMDB
S 4 (Heterocycle)HMDB
Sanceler HHMDB
Silver methenamineHMDB
TetraazaadamantaneHMDB
UraminHMDB
UratrineHMDB
UrisolHMDB
Uro-phosphateHMDB
UrodeineHMDB
UrotropineHMDB
VesaloinHMDB
VesalvineHMDB
Vulkacit H 30HMDB
Vulkacit H30HMDB
XametrinHMDB
[16]-Adamazane, innHMDB
Methenamine, silverHMDB
Silver, hexamineHMDB
Silver, methenamineHMDB
Chemical FormulaC6H12N4
Average Molecular Mass140.186 g/mol
Monoisotopic Mass140.106 g/mol
CAS Registry Number100-97-0
IUPAC Name1,3,5,7-tetraazatricyclo[3.3.1.1^{3,7}]decane
Traditional Name1,3,5,7-tetraazatricyclo[3.3.1.1^{3,7}]decane
SMILESC1N2CN3CN1CN(C2)C3
InChI IdentifierInChI=1S/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2
InChI KeyVKYKSIONXSXAKP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,3,5-triazinanes. These are triazinanes having three nitrogen ring atoms at the 1-, 3-, and 5- positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTriazinanes
Sub Class1,3,5-triazinanes
Direct Parent1,3,5-triazinanes
Alternative Parents
Substituents
  • 1,3,5-triazinane
  • Azacycle
  • Aminal
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point> 250 °C
Boiling PointNot Available
Solubility449 mg/mL at 12 °C
Predicted Properties
PropertyValueSource
Water Solubility766 g/LALOGPS
logP-1.4ALOGPS
logP0.39ChemAxon
logS0.74ALOGPS
pKa (Strongest Basic)5.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.96 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity37 m³·mol⁻¹ChemAxon
Polarizability14.25 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-0900000000-37095c7b831e11e5eee2Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0900000000-05c8e159897335060443Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01ox-2900000000-86fe33e31cc8f7108c14Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01ti-9300000000-7eb44254c8cc65c09acdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9000000000-fd4edf8f48f9c42bca0cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004l-9000000000-371b89c99afba4931848Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0900000000-fdd6b719cb07e4102442Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0900000000-fdd6b719cb07e4102442Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0900000000-fdd6b719cb07e4102442Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0900000000-4c20ce3a6256ce9cf869Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0900000000-4c20ce3a6256ce9cf869Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0900000000-4c20ce3a6256ce9cf869Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0900000000-df90583457c277060500Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0900000000-df90583457c277060500Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0900000000-df90583457c277060500Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0900000000-96b1ccc7b2dbac963a64Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0900000000-96b1ccc7b2dbac963a64Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0900000000-96b1ccc7b2dbac963a64Not AvailableView Spectrum
MSMS Spectrumsplash10-0006-9300000000-e762ea01823717c4bda9Not AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2749.0Log mg/kg[1500:4900]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
7PesticidesAgriculture & land managementNot Available
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
326UrologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
347AntibacterialsHealthcare, pharmaceuticals & veterinary productsNot Available
494Food contact materialsFood, food processing & cookwareNot Available
495CeilingsBuilding & ConstructionNot Available
496FencingBuilding & ConstructionNot Available
498LaddersBuilding & ConstructionNot Available
499RoofsBuilding & ConstructionNot Available
500Stairs And RampsBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
508CoilsElectrical & Electronic EquipmentNot Available
509Colour Television SystemsElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
513Cores Yokes Or ArmaturesElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
533Sparking PlugsElectrical & Electronic EquipmentNot Available
534Still Video CamerasElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
540X Ray TubesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
585Canoes And KayaksMarine, shipping & aquacultureNot Available
589Life BuoysMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
625Racing SportsRecreation & sports surfacesNot Available
630ToysRecreation & sports surfacesNot Available
631Anthraquinone DyesTextiles, leather & furnishingsNot Available
632ApparelTextiles, leather & furnishingsNot Available
634BucklesTextiles, leather & furnishingsNot Available
635ButtonsTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
639Degreasing LeatherTextiles, leather & furnishingsNot Available
641Foam DyeingTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
651Purses Money Bags WalletsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
655Slide FastenersTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
661UmbrellasTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)7784.38
Muscarinic acetylcholine receptor M1 structureClick to view 3D structureMuscarinic acetylcholine receptor M1P11229HumansPredicted (SEA)7784.38
Click to view 3D structureFarnesyltransferase, putativeQ4CXF7Trypanosoma cruzi (strain CL Brener)Predicted (SEA)5396.9
Click to view 3D structureSigma non-opioid intracellular receptor 1Q9R0C9Rattus norvegicusPredicted (SEA)7782.98
Muscarinic acetylcholine receptor M2 structureClick to view 3D structureMuscarinic acetylcholine receptor M2P08172HumansPredicted (SEA)7784.3
Neuronal acetylcholine receptor subunit alpha-7 structureClick to view 3D structureNeuronal acetylcholine receptor subunit alpha-7P36544HumansPredicted (SEA)7780.95
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)7784.53
Replicase polyprotein 1ab structureClick to view 3D structureReplicase polyprotein 1abP0DTD1SARS-CoV-2Predicted (SEA)7784.3
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)7783.99
Monoglyceride lipase structureClick to view 3D structureMonoglyceride lipaseQ99685HumansPredicted (SEA)7781.57
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)7784.14
5-hydroxytryptamine receptor 6 structureClick to view 3D structure5-hydroxytryptamine receptor 6P50406HumansPredicted (SEA)7784.14
Click to view 3D structureSodium-dependent dopamine transporterP23977Rattus norvegicusPredicted (SEA)7783.68
Muscarinic acetylcholine receptor M5 structureClick to view 3D structureMuscarinic acetylcholine receptor M5P08912HumansPredicted (SEA)7784.3
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)7784.46
Click to view 3D structureMuscarinic acetylcholine receptor M1P08482Rattus norvegicusPredicted (SEA)7783.83
Click to view 3D structureCholine trimethylamine-lyaseQ30W70Desulfovibrio alaskensisPredicted (SEA)2331.35
5-hydroxytryptamine receptor 7 structureClick to view 3D structure5-hydroxytryptamine receptor 7P34969HumansPredicted (SEA)7784.3
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)7784.38
5-hydroxytryptamine receptor 1D structureClick to view 3D structure5-hydroxytryptamine receptor 1DP28221HumansPredicted (SEA)7784.14
Alpha-2C adrenergic receptor structureClick to view 3D structureAlpha-2C adrenergic receptorP18825HumansPredicted (SEA)7784.38
Click to view 3D structureSodium-dependent serotonin transporterP31652Rattus norvegicusPredicted (SEA)7784.07
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)7784.53
Click to view 3D structureNeuronal acetylcholine receptor subunit alpha-7Q05941Rattus norvegicusPredicted (SEA)7779.47
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)7784.61
Concentrations
Not Available
External Links
DrugBank IDDB06799
HMDB IDHMDB0029598
FooDB IDFDB000762
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMethenamine
Chemspider ID3959
ChEBI ID6824
PubChem Compound ID4101
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=13186006
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22365691
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24641608
4. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.