Metenamine (CHEM003790)

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 belongs to the family of Aminals. These are organic compounds containing the aminal functional group. Metenamine is an antimicrobial food preservative, but is of limited use and usage is declining. It is used to prevent "late blowing" of hard cheese by inhibiting growth of unwanted bacteria. Presently (2002) its European use is limited to one type of Italian cheese, Provolone. It acts by releasing formaldehyde under acidic conditions.
Contaminant Sources
  • FooDB Chemicals
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Food Additive
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Organic Compound
  • Pesticide
  • Preservative
  • Synthetic Compound
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D 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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
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.