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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-02-22 11:40:36 UTC
Update Date2021-09-07 16:45:31 UTC
HMDB IDHMDB0001861
Secondary Accession Numbers
  • HMDB01861
Metabolite Identification
Common Name3-Methylhistamine
Description3-Methylhistamine belongs to the class of organic compounds known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group. 3-Methylhistamine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 3-methylhistamine a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on 3-Methylhistamine.
Structure
Data?1582752213
Synonyms
ValueSource
L-Histamine deriv. 1HMDB
N(T)-MethylhistamineHMDB
N(Tau)-methylhistamineHMDB
N-Tau-methylhistamineHMDB, MeSH
Tau-methylhistamineHMDB, MeSH
3-Methylhistamine dihydrochlorideMeSH, HMDB
3-MethylhistamineMeSH
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 KeyCPAGZVLINCPJEH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct Parent2-arylethylamines
Alternative Parents
Substituents
  • 2-arylethylamine
  • Aralkylamine
  • N-substituted imidazole
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Baker126.53330932474
[M+H]+MetCCS_train_pos123.75230932474
[M+H]+Not Available124.4http://allccs.zhulab.cn/database/detail?ID=AllCCS00000539
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.85 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.13 m³·mol⁻¹ChemAxon
Polarizability13.92 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+124.25631661259
DarkChem[M-H]-120.55831661259
AllCCS[M+H]+126.85932859911
AllCCS[M-H]-125.90132859911
DeepCCS[M+H]+124.46530932474
DeepCCS[M-H]-121.88230932474
DeepCCS[M-2H]-158.30730932474
DeepCCS[M+Na]+133.29530932474
AllCCS[M+H]+126.932859911
AllCCS[M+H-H2O]+122.232859911
AllCCS[M+NH4]+131.232859911
AllCCS[M+Na]+132.532859911
AllCCS[M-H]-125.932859911
AllCCS[M+Na-2H]-128.132859911
AllCCS[M+HCOO]-130.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-MethylhistamineCN1C=NC=C1CCN2167.4Standard polar33892256
3-MethylhistamineCN1C=NC=C1CCN1436.1Standard non polar33892256
3-MethylhistamineCN1C=NC=C1CCN1372.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Methylhistamine,1TMS,isomer #1CN1C=NC=C1CCN[Si](C)(C)C1496.1Semi standard non polar33892256
3-Methylhistamine,1TMS,isomer #1CN1C=NC=C1CCN[Si](C)(C)C1561.9Standard non polar33892256
3-Methylhistamine,1TMS,isomer #1CN1C=NC=C1CCN[Si](C)(C)C1878.7Standard polar33892256
3-Methylhistamine,2TMS,isomer #1CN1C=NC=C1CCN([Si](C)(C)C)[Si](C)(C)C1742.7Semi standard non polar33892256
3-Methylhistamine,2TMS,isomer #1CN1C=NC=C1CCN([Si](C)(C)C)[Si](C)(C)C1777.3Standard non polar33892256
3-Methylhistamine,2TMS,isomer #1CN1C=NC=C1CCN([Si](C)(C)C)[Si](C)(C)C1849.8Standard polar33892256
3-Methylhistamine,1TBDMS,isomer #1CN1C=NC=C1CCN[Si](C)(C)C(C)(C)C1739.9Semi standard non polar33892256
3-Methylhistamine,1TBDMS,isomer #1CN1C=NC=C1CCN[Si](C)(C)C(C)(C)C1801.0Standard non polar33892256
3-Methylhistamine,1TBDMS,isomer #1CN1C=NC=C1CCN[Si](C)(C)C(C)(C)C1996.9Standard polar33892256
3-Methylhistamine,2TBDMS,isomer #1CN1C=NC=C1CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2131.8Semi standard non polar33892256
3-Methylhistamine,2TBDMS,isomer #1CN1C=NC=C1CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2202.8Standard non polar33892256
3-Methylhistamine,2TBDMS,isomer #1CN1C=NC=C1CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2028.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylhistamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-9200000000-052f704135f11d74ed402017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylhistamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylhistamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistamine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-056s-2900000000-c9f454504e6359b0b0be2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistamine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0002-9200000000-8ce6c84f30341c8124e92012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistamine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-00lr-9000000000-dbef26b4250bbde784a82012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistamine , positive-QTOFsplash10-004i-0900000000-05db0a907f55fd5697b32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistamine 35V, Positive-QTOFsplash10-004i-0900000000-6bb37dbd89e15ed1ff0b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistamine 10V, Positive-QTOFsplash10-004i-1900000000-054aff5c788523f9fb692021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistamine 35V, Positive-QTOFsplash10-004i-0900000000-b1a73061bf275ded0bb62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistamine 35V, Positive-QTOFsplash10-004i-0900000000-7f98177798dededd8b8a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistamine 40V, Positive-QTOFsplash10-0fr2-9000000000-d746354f237ae0d5c8ca2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistamine 20V, Positive-QTOFsplash10-0002-9200000000-515b613508cc660733202021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistamine 40V, Positive-QTOFsplash10-0002-9000000000-d86d2dcd3ee01a3bb1d12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistamine 10V, Positive-QTOFsplash10-004i-1900000000-0e1bd2d92202d959dd582021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistamine 20V, Positive-QTOFsplash10-0002-9200000000-f506556ec8dce3bed55d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylhistamine 10V, Positive-QTOFsplash10-056r-0900000000-70a4f63c7c70678531b62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylhistamine 20V, Positive-QTOFsplash10-0a4i-3900000000-bb58b80ce0d729f81a6c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylhistamine 40V, Positive-QTOFsplash10-014i-9000000000-863d517768f138904f022017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylhistamine 10V, Negative-QTOFsplash10-00di-1900000000-a6d65a6f86b3c40f46262017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylhistamine 20V, Negative-QTOFsplash10-00di-3900000000-58dfa354fec01badb28b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylhistamine 40V, Negative-QTOFsplash10-0a6r-9100000000-601c15d8230e0983d2e92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylhistamine 10V, Positive-QTOFsplash10-056r-2900000000-ab3814c48d66a74e01172021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylhistamine 20V, Positive-QTOFsplash10-0a59-8900000000-f5a1919f413b6efc109d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylhistamine 40V, Positive-QTOFsplash10-05o3-9000000000-0b568a6f55699dc3d8772021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylhistamine 10V, Negative-QTOFsplash10-00di-3900000000-14f3c97f00ccfa6fa4462021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylhistamine 20V, Negative-QTOFsplash10-0603-9500000000-084b1cab57e4da1aac122021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylhistamine 40V, Negative-QTOFsplash10-06r6-9000000000-56ef0c724afe8a89402b2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
Phenol Explorer Compound IDNot Available
FooDB IDFDB022715
KNApSAcK IDNot Available
Chemspider ID62725
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethylhistamine
METLIN ID6355
PubChem Compound69520
PDB IDNot Available
ChEBI ID114444
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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. [PubMed: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. [PubMed: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. [PubMed:7451611 ]