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Record Information
Version2.0
Creation Date2014-09-11 05:18:28 UTC
Update Date2014-12-24 20:26:57 UTC
Accession NumberT3D4834
Identification
Common NameMetenamine
ClassSmall Molecule
DescriptionMetenamine 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.
Compound Type
  • Amine
  • Food Additive
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Organic Compound
  • Preservative
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
1,3,5,7-Tetraazaadamantane
1,3,5,7-Tetraazatricyclo (3.3.1.1(3,7))decane
1,3,5,7-Tetraazatricyclo(3.3.1.13,7)decane
1,3,5,7-Tetraazatricyclo(3.3.1.13,7)decane hydroiodide
1,3,5,7-Tetraazatricyclo(3.3.1.137)decane
1,3,5,7-Tetraazatricyclo[3.3.1.1(3,7)]decane
1,3,5,7-Tetraazatricyclo[3.3.1.13,7 ]decane
1,3,5,7-Tetraazatricyclo[3.3.1.1~3,7~]decane
Aceto HMT
Aminoform
Aminoformaldehyde
Ammoform
Ammonioformaldehyde
Antihydral
Carin
Cystamin
Cystogen
Duirexol
E239
Ekagom h
Esametilentetramina
Formaldehyde-ammonia 6:4
Formamine
Formin
Formin (heterocycle)
Formin (the heterocyclic compound)
Grasselerator 102
H.m.t.
Herax UTS
Heterin
HEX
Hexa
Hexa (vulcanization accelerator)
Hexa-flo-pulver
Hexaform
Hexaloids
Hexamethylamine
Hexamethylenamine
Hexamethylene tetramine
Hexamethyleneamine
Hexamethylenetetraamine
Hexamethylenetetramine
Hexamethylenetetramine (aliphatic)
Hexamethylenetetramine, 8CI
Hexamethylenetetramine, acs
Hexamethylenetetramine-palladium chloride adduct
Hexamethylenetetraminum
Hexamethylentetramin
Hexamethylentetramine
Hexamethylentetraminum
Hexamine
Hexamine (heterocycle)
Hexamine silver
Hexaminum
Hexasan
Hexilmethylenamine
HMT
HMTA
Mandelamine
Metenamina
Methamin
Methenamin
Methenamine
Methenamine silver
Methenaminum
Metramine
Naphthamine
Natasol fast orange GR salt
Nocceler H
Preparation af
Resotropin
S 4 (Heterocycle)
Sanceler h
Silver methenamine
Tetraazaadamantane
Uramin
Uratrine
Urisol
Uritone
Uro-phosphate
Urodeine
Urotropin
Urotropine
Vesaloin
Vesalvine
Vulkacit H 30
Vulkacit H30
Xametrin
[16]-Adamazane, INN
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 KeyInChIKey=VKYKSIONXSXAKP-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
LogPNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-0900000000-37095c7b831e11e5eee22017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0900000000-05c8e1598973350604432017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01ox-2900000000-86fe33e31cc8f7108c142017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01ti-9300000000-7eb44254c8cc65c09acd2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9000000000-fd4edf8f48f9c42bca0c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004l-9000000000-371b89c99afba49318482017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-fdd6b719cb07e41024422016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-fdd6b719cb07e41024422016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0900000000-fdd6b719cb07e41024422016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-4c20ce3a6256ce9cf8692016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-4c20ce3a6256ce9cf8692016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0900000000-4c20ce3a6256ce9cf8692016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-df90583457c2770605002021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-df90583457c2770605002021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0900000000-df90583457c2770605002021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-96b1ccc7b2dbac963a642021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-96b1ccc7b2dbac963a642021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0900000000-96b1ccc7b2dbac963a642021-09-22View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9300000000-e762ea01823717c4bda92014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB29598
PubChem Compound ID4101
ChEMBL IDCHEMBL1201270
ChemSpider ID3959
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI ID6824
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D4834.pdf
General References
  1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Transcriptional activator activity, rna polymerase ii distal enhancer sequence-specific binding
Specific Function:
Transcription activator that binds to antioxidant response (ARE) elements in the promoter regions of target genes. Important for the coordinated up-regulation of genes in response to oxidative stress. May be involved in the transcriptional activation of genes of the beta-globin cluster by mediating enhancer activity of hypersensitive site 2 of the beta-globin locus control region.
Gene Name:
NFE2L2
Uniprot ID:
Q16236
Molecular Weight:
67825.9 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC501.45 uMATG_NRF2_ARE_CISAttagene
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]