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Record Information
Version3.6
Creation Date2006-02-22 11:40:36 UTC
Update Date2016-05-13 19:53:52 UTC
HMDB IDHMDB01861
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Methylhistamine
DescriptionN tau-methylhistamine is one of the histamine metabolites. N tau-methylhistamine in plasma and urine is a good parameter for histamine release, and the determination of this histamine metabolite is generally less hampered by possible artifacts (due to basophil disrupture, a very short half-life time or bacterial production) than determinations of histamine itself. (PMID 2409780 ).
Structure
Thumb
Synonyms
ValueSource
L-Histamine deriv. 1HMDB
N(T)-MethylhistamineHMDB
N(Tau)-methylhistamineHMDB
N-Tau-methylhistamineHMDB
Tau-methylhistamineHMDB
Chemical FormulaC6H11N3
Average Molecular Weight125.1716
Monoisotopic Molecular Weight125.095297367
IUPAC Name2-(1-methyl-1H-imidazol-5-yl)ethan-1-amine
Traditional Name3-methylhistamine
CAS Registry Number644-42-8
SMILES
CN1C=NC=C1CCN
InChI Identifier
InChI=1S/C6H11N3/c1-9-5-8-4-6(9)2-3-7/h4-5H,2-3,7H2,1H3
InChI KeyInChIKey=CPAGZVLINCPJEH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassAmines
Sub ClassAralkylamines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • N-substituted imidazole
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary aliphatic amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.85 mg/mLALOGPS
logP-0.83ALOGPS
logP-0.82ChemAxon
logS-1.4ALOGPS
pKa (Strongest Basic)9.78ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.84 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.13 m3·mol-1ChemAxon
Polarizability13.92 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-056s-2900000000-c9f454504e6359b0b0beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0002-9200000000-8ce6c84f30341c8124e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00lr-9000000000-dbef26b4250bbde784a8View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.011 +/- 0.03 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified0.13 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022715
KNApSAcK IDNot Available
Chemspider ID62725
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01861
Metagene LinkHMDB01861
METLIN ID6355
PubChem Compound69520
PDB IDNot Available
ChEBI ID114444
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Keyzer JJ, Breukelman H, Wolthers BG, Richardson FJ, de Monchy JG: Measurement of N tau-methylhistamine concentrations in plasma and urine as a parameter for histamine release during anaphylactoid reactions. Agents Actions. 1985 Apr;16(3-4):76-9. [2409780 ]
  2. Murray S, Wellings R, Taylor IK, Fuller RW, Taylor GW: Gas chromatographic-mass spectrometric assay to measure urinary N tau-methylhistamine excretion in man. J Chromatogr. 1991 Jul 5;567(2):289-98. [1939463 ]
  3. Mita H, Yasueda H, Shida T: Simultaneous determination of histamine and N tau-methylhistamine in human plasma and urine by gas chromatography--mass spectrometry. J Chromatogr. 1980 Nov 14;221(1):1-7. [7451611 ]