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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:17 UTC
HMDB IDHMDB0000898
Secondary Accession Numbers
  • HMDB0000976
  • HMDB00898
  • HMDB00976
Metabolite Identification
Common Name1-Methylhistamine
Description1-Methylhistamine, also known as H137, 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. 1-Methylhistamine exists in all living organisms, ranging from bacteria to humans. Within humans, 1-methylhistamine participates in a number of enzymatic reactions. In particular, S-adenosylhomocysteine and 1-methylhistamine can be biosynthesized from S-adenosylmethionine and histamine; which is mediated by the enzyme histamine N-methyltransferase. In addition, 1-methylhistamine can be converted into methylimidazole acetaldehyde through its interaction with the enzyme amine oxidase [flavin-containing] a. In humans, 1-methylhistamine is involved in histidine metabolism. 1-Methylhistamine is a potentially toxic compound.
Structure
Data?1676999717
Synonyms
ValueSource
1-Methyl-1H-imidazole-4-ethanamineChEBI
1-Methyl-4-(2-aminoethyl)imidazoleChEBI
3-MethylhistamineChEBI
4-(1-Aminoethyl)-1-methyl-1H-imidazoleChEBI
MethylhistamineChEBI
N-MethylhistamineChEBI
N(1)-MethylhistamineChEBI
Ntau-methylhistamineChEBI
tele-MethylhistamineChEBI
tele-Methylhistamine dihydrochlorideHMDB
1-Methyl-4-(beta-aminoethyl)imidazoleHMDB
1,4-MethylhistamineHMDB
N-tele MethylhistamineHMDB
1-Methyl-4-(b-aminoethyl)imidazoleHMDB
1-Methyl-4-histamineHMDB
2-(1-Methyl-1H-imidazol-4-yl)ethanamineHMDB
2-(1-Methyl-1H-imidazol-4-yl)ethylamineHMDB
4-(2-Aminoethyl)-1-methyl-imidazoleHMDB
4-(2-Aminoethyl)-1-methylimidazoleHMDB
H137HMDB
N( 1)-MethylhistamineHMDB
N(T)-MethylhistamineHMDB
N-tele-MethylhistamineHMDB
N-Telle-methylhistamineHMDB
N1-MethylhistamineHMDB
NT-MethylhistamineHMDB
Chemical FormulaC6H11N3
Average Molecular Weight125.1716
Monoisotopic Molecular Weight125.095297367
IUPAC Name2-(1-methyl-1H-imidazol-4-yl)ethan-1-amine
Traditional Namemethylhistamine
CAS Registry Number501-75-7
SMILES
CN1C=NC(CCN)=C1
InChI Identifier
InChI=1S/C6H11N3/c1-9-4-6(2-3-7)8-5-9/h4-5H,2-3,7H2,1H3
InChI KeyFHQDWPCFSJMNCT-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 Descriptors
Ontology
Physiological effect
Disposition
Biological locationSource
Process
Role
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]+Baker122.55530932474
[M+H]+MetCCS_train_pos121.30230932474
[M+H]+Not Available121.9http://allccs.zhulab.cn/database/detail?ID=AllCCS00000535
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.12 g/LALOGPS
logP-0.57ALOGPS
logP-0.48ChemAxon
logS-1.4ALOGPS
pKa (Strongest Basic)9.57ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.84 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity36.56 m³·mol⁻¹ChemAxon
Polarizability14.24 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]+126.15631661259
DarkChem[M+H]+126.15631661259
DarkChem[M-H]-123.86931661259
DarkChem[M-H]-123.86931661259
AllCCS[M+H]+127.18832859911
AllCCS[M-H]-127.17232859911
DeepCCS[M+H]+122.34830932474
DeepCCS[M-H]-119.10130932474
DeepCCS[M-2H]-155.74530932474
DeepCCS[M+Na]+130.91730932474
AllCCS[M+H]+127.232859911
AllCCS[M+H-H2O]+122.532859911
AllCCS[M+NH4]+131.532859911
AllCCS[M+Na]+132.832859911
AllCCS[M-H]-127.232859911
AllCCS[M+Na-2H]-129.432859911
AllCCS[M+HCOO]-131.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-MethylhistamineCN1C=NC(CCN)=C12150.0Standard polar33892256
1-MethylhistamineCN1C=NC(CCN)=C11375.0Standard non polar33892256
1-MethylhistamineCN1C=NC(CCN)=C11277.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-Methylhistamine,1TMS,isomer #1CN1C=NC(CCN[Si](C)(C)C)=C11513.1Semi standard non polar33892256
1-Methylhistamine,1TMS,isomer #1CN1C=NC(CCN[Si](C)(C)C)=C11559.5Standard non polar33892256
1-Methylhistamine,1TMS,isomer #1CN1C=NC(CCN[Si](C)(C)C)=C11930.0Standard polar33892256
1-Methylhistamine,2TMS,isomer #1CN1C=NC(CCN([Si](C)(C)C)[Si](C)(C)C)=C11793.8Semi standard non polar33892256
1-Methylhistamine,2TMS,isomer #1CN1C=NC(CCN([Si](C)(C)C)[Si](C)(C)C)=C11764.3Standard non polar33892256
1-Methylhistamine,2TMS,isomer #1CN1C=NC(CCN([Si](C)(C)C)[Si](C)(C)C)=C11892.4Standard polar33892256
1-Methylhistamine,1TBDMS,isomer #1CN1C=NC(CCN[Si](C)(C)C(C)(C)C)=C11743.8Semi standard non polar33892256
1-Methylhistamine,1TBDMS,isomer #1CN1C=NC(CCN[Si](C)(C)C(C)(C)C)=C11791.7Standard non polar33892256
1-Methylhistamine,1TBDMS,isomer #1CN1C=NC(CCN[Si](C)(C)C(C)(C)C)=C12045.2Standard polar33892256
1-Methylhistamine,2TBDMS,isomer #1CN1C=NC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C12147.2Semi standard non polar33892256
1-Methylhistamine,2TBDMS,isomer #1CN1C=NC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C12184.9Standard non polar33892256
1-Methylhistamine,2TBDMS,isomer #1CN1C=NC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C12060.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 1-Methylhistamine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0fki-3900000000-8197b65f233a917f6f5d2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Methylhistamine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00dr-3900000000-4a05dead99e371226a6c2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Methylhistamine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9700000000-b8108f1cb31c26ab942f2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Methylhistamine GC-MS (2 TMS)splash10-0fe0-5900000000-c04c884eec0846197eb82014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Methylhistamine EI-B (Non-derivatized)splash10-00di-2910000000-3458f7def44a74d73f7b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Methylhistamine GC-EI-TOF (Non-derivatized)splash10-0fki-3900000000-8197b65f233a917f6f5d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Methylhistamine GC-EI-TOF (Non-derivatized)splash10-00dr-3900000000-4a05dead99e371226a6c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Methylhistamine GC-EI-TOF (Non-derivatized)splash10-00di-9700000000-b8108f1cb31c26ab942f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Methylhistamine GC-MS (Non-derivatized)splash10-0fe0-5900000000-c04c884eec0846197eb82017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Methylhistamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-9200000000-f6dbf3d86200b3f6be5f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-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 - 1-Methylhistamine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0a4i-0900000000-b77c6433a2a8bdb852dd2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Methylhistamine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0aor-9600000000-a2a8c75c945ca81ded8a2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Methylhistamine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-001i-9200000000-fa9fad79e09f38a3450d2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Methylhistamine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-004i-0900000000-b9f4341a558b04495c542012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Methylhistamine LC-ESI-QTOF , positive-QTOFsplash10-004i-0900000000-b9f4341a558b04495c542017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methylhistamine 10V, Positive-QTOFsplash10-056r-0900000000-b9f2ff9fde6f1a170d382017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methylhistamine 20V, Positive-QTOFsplash10-0a4i-1900000000-0ad300b172fcdc68e1042017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methylhistamine 40V, Positive-QTOFsplash10-0le9-9000000000-fe751072b0ecf7a0d5bf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methylhistamine 10V, Negative-QTOFsplash10-00di-0900000000-c7b86cf59142756c4f912017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methylhistamine 20V, Negative-QTOFsplash10-00di-3900000000-0bed565bcfefeb389d2b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methylhistamine 40V, Negative-QTOFsplash10-0arv-9100000000-fc2c7dc356034fe098ae2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methylhistamine 10V, Positive-QTOFsplash10-0a4i-0900000000-317df42b1c6c53a3cd832021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methylhistamine 20V, Positive-QTOFsplash10-0a4i-6900000000-e29c16ae4d103e7eaa012021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methylhistamine 40V, Positive-QTOFsplash10-066u-9000000000-2d8cc6d1c8601ed4eed02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methylhistamine 10V, Negative-QTOFsplash10-00di-1900000000-c5c45bb41ea05838fa942021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methylhistamine 20V, Negative-QTOFsplash10-00di-5900000000-68ef55e857c894f923092021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methylhistamine 40V, Negative-QTOFsplash10-014i-9000000000-434d60e1525fedada46a2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C 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

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Bone Marrow
  • Brain
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00034 (0.00021-0.00047) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.002 +/- 0.0005 (0.0015 - 0.0025) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.005 +/- 0.0006 (0.003-0.006) uMChildren (1-13 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified1.12 +/- 0.22 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.007 +/- 0.0005 (0.006 - 0.008) uMChildren (1-13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.002209 +/- 0.000463 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00214 +/- 0.0001 uMNot SpecifiedNot SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified0.0117 +/- 0.0359 uMAdult (>18 years old)BothNormal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.0125 +/- 0.0348 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.0301 +/- 0.0193 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
UrineDetected and Quantified0.13 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.098 (0.032-0.18) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified0.065 (0.32-0.98) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00078 (0.00055-0.00100) uMAdult (>18 years old)BothDermal fibroproliferative disorder (hypertrophic scarring) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.002431 +/- 0.000461 uMAdult (>18 years old)Not Specifiedsporadic narcolepsy-cataplexy details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00276 +/- 0.00013 uMAdult (>18 years old)Not SpecifiedAlzheimer's disease details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00290 +/- 0.00027 uMAdult (>18 years old)BothSchizophrenia details
Cerebrospinal Fluid (CSF)Detected and Quantified2.90 +/- 0.27 uMAdult (>18 years old)Both
Schizophrenia
details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUnclassified IBD details
SalivaDetected and Quantified0.0203 +/- 0.0254 uMAdult (>18 years old)BothOral cavity disorders
    • Sugimoto et al. (...
details
UrineDetected and Quantified0.73 umol/mmol creatinineAdult (>18 years old)BothMastocytosis details
Associated Disorders and Diseases
Disease References
Dermal fibroproliferative disorder
  1. Tredget EE, Iwashina T, Scott PG, Ghahary A: Determination of plasma Ntau-methylhistamine in vivo by isotope dilution using benchtop gas chromatography-mass spectrometry. J Chromatogr B Biomed Sci Appl. 1997 Jun 20;694(1):1-9. [PubMed:9234842 ]
Alzheimer's disease
  1. Motawaj M, Peoc'h K, Callebert J, Arrang JM: CSF levels of the histamine metabolite tele-methylhistamine are only slightly decreased in Alzheimer's disease. J Alzheimers Dis. 2010;22(3):861-71. doi: 10.3233/JAD-2010-100381. [PubMed:20858978 ]
Schizophrenia
  1. Prell GD, Green JP, Kaufmann CA, Khandelwal JK, Morrishow AM, Kirch DG, Linnoila M, Wyatt RJ: Histamine metabolites in cerebrospinal fluid of patients with chronic schizophrenia: their relationships to levels of other aminergic transmitters and ratings of symptoms. Schizophr Res. 1995 Jan;14(2):93-104. [PubMed:7711000 ]
Crohn's disease
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Mastocytosis
  1. Martens-Lobenhoffer J, Neumann HJ: Determination of 1-methylhistamine and 1-methylimidazoleacetic acid in human urine as a tool for the diagnosis of mastocytosis. J Chromatogr B Biomed Sci Appl. 1999 Jan 8;721(1):135-40. [PubMed:10027644 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022306
KNApSAcK IDNot Available
Chemspider ID3488
KEGG Compound IDC05127
BioCyc IDN-METHYL-HISTAMINE
BiGG ID45171
Wikipedia LinkMethylhistamine
METLIN ID5854
PubChem Compound3614
PDB IDNot Available
ChEBI ID29009
Food Biomarker OntologyNot Available
VMH IDMHISTA
MarkerDB IDMDB00000278
Good Scents IDNot Available
References
Synthesis ReferenceRothschild, Zuleika; Schayer, Richard W. Synthesis and metabolism of a histamine metabolite, 1-methyl-4-(b-aminoethyl)imidazole. Biochimica et Biophysica Acta (1958), 30 23-7.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Ito C: The role of the central histaminergic system on schizophrenia. Drug News Perspect. 2004 Jul-Aug;17(6):383-7. [PubMed:15334189 ]
  2. Khandelwal JK, Hough LB, Morrishow AM, Green JP: Measurement of tele-methylhistamine and histamine in human cerebrospinal fluid, urine, and plasma. Agents Actions. 1982 Dec;12(5-6):583-90. [PubMed:7164933 ]
  3. Winterkamp S, Weidenhiller M, Otte P, Stolper J, Schwab D, Hahn EG, Raithel M: Urinary excretion of N-methylhistamine as a marker of disease activity in inflammatory bowel disease. Am J Gastroenterol. 2002 Dec;97(12):3071-7. [PubMed:12492192 ]
  4. Elmore BO, Bollinger JA, Dooley DM: Human kidney diamine oxidase: heterologous expression, purification, and characterization. J Biol Inorg Chem. 2002 Jun;7(6):565-79. Epub 2002 Feb 13. [PubMed:12072962 ]
  5. Robbins IM, Barst RJ, Rubin LJ, Gaine SP, Price PV, Morrow JD, Christman BW: Increased levels of prostaglandin D(2) suggest macrophage activation in patients with primary pulmonary hypertension. Chest. 2001 Nov;120(5):1639-44. [PubMed:11713147 ]
  6. O'Sullivan S, Roquet A, Dahlen B, Dahlen S, Kumlin M: Urinary excretion of inflammatory mediators during allergen-induced early and late phase asthmatic reactions. Clin Exp Allergy. 1998 Nov;28(11):1332-9. [PubMed:9824404 ]
  7. Martens-Lobenhoffer J, Neumann HJ: Determination of 1-methylhistamine and 1-methylimidazoleacetic acid in human urine as a tool for the diagnosis of mastocytosis. J Chromatogr B Biomed Sci Appl. 1999 Jan 8;721(1):135-40. [PubMed:10027644 ]
  8. Theoharides TC, Sant GR, el-Mansoury M, Letourneau R, Ucci AA Jr, Meares EM Jr: Activation of bladder mast cells in interstitial cystitis: a light and electron microscopic study. J Urol. 1995 Mar;153(3 Pt 1):629-36. [PubMed:7861501 ]
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Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
Reactions
1-Methylhistamine + Water + Oxygen → Methylimidazole acetaldehyde + Ammonia + Hydrogen peroxidedetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
Reactions
1-Methylhistamine + Water + Oxygen → Methylimidazole acetaldehyde + Ammonia + Hydrogen peroxidedetails
General function:
Involved in histamine N-methyltransferase activity
Specific function:
Inactivates histamine by N-methylation. Plays an important role in degrading histamine and in regulating the airway response to histamine.
Gene Name:
HNMT
Uniprot ID:
P50135
Molecular weight:
6045.9
Reactions
S-Adenosylmethionine + Histamine → S-Adenosylhomocysteine + 1-Methylhistaminedetails