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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:09:32 UTC
HMDB IDHMDB00898
Secondary Accession Numbers
  • HMDB00976
Metabolite Identification
Common Name1-Methylhistamine
Description1-Methylhistamine is a histamine metabolite. It is a product of histamine 1-methyltransferase [EC 2.1.1.8] in the pathway histidine metabolism (KEGG).
Structure
Thumb
Synonyms
  1. 1-Methyl-1H-imidazole-4-ethanamine
  2. 1-Methyl-4-(2-aminoethyl)imidazole
  3. 1-Methyl-4-(b-aminoethyl)imidazole
  4. 1-Methyl-4-(beta-aminoethyl)imidazole
  5. 1-Methyl-4-histamine
  6. 1-Methylhistamine
  7. 2-(1-Methyl-1H-imidazol-4-yl)ethanamine
  8. 2-(1-Methyl-1H-imidazol-4-yl)ethylamine
  9. 4-(2-Aminoethyl)-1-methyl-Imidazole
  10. 4-(2-Aminoethyl)-1-methylimidazole
  11. H137
  12. Methylhistamine
  13. N( 1)-Methylhistamine
  14. N(T)-Methylhistamine
  15. N-Methylhistamine
  16. N-Tele-Methylhistamine
  17. N-Telle-methylhistamine
  18. N1-Methylhistamine
  19. NT-methylhistamine
  20. Ntau-Methylhistamine
  21. Tele-methylhistamine
Chemical FormulaC6H11N3
Average Molecular Weight125.1716
Monoisotopic Molecular Weight125.095297367
IUPAC Name2-(1-methyl-1H-imidazol-4-yl)ethan-1-amine
Traditional Nametele-methylhistamine
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
KingdomOrganic Compounds
Super ClassAromatic Heteromonocyclic Compounds
ClassAzoles
Sub ClassImidazoles
Other Descriptors
  • imidazoles(ChEBI)
Substituents
  • Primary Aliphatic Amine (Alkylamine)
Direct ParentImidazoles
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Histidine metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 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 Area43.84ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity36.56ChemAxon
Polarizability14.24ChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Bone Marrow
  • Brain
  • Mast Cell
Pathways
NameSMPDB LinkKEGG Link
Histidine MetabolismSMP00044map00340
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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 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
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
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
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
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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022306
KNApSAcK IDNot Available
Chemspider ID3488
KEGG Compound IDC05127
BioCyc IDN-METHYL-HISTAMINE
BiGG ID45171
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00898
Metagene LinkHMDB00898
METLIN ID5854
PubChem Compound3614
PDB IDNot Available
ChEBI ID29009
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
  9. Brumsen C, Papapoulos SE, Lentjes EG, Kluin PM, Hamdy NA: A potential role for the mast cell in the pathogenesis of idiopathic osteoporosis in men. Bone. 2002 Nov;31(5):556-61. Pubmed: 12477568
  10. Rozniecki JJ, Hauser SL, Stein M, Lincoln R, Theoharides TC: Elevated mast cell tryptase in cerebrospinal fluid of multiple sclerosis patients. Ann Neurol. 1995 Jan;37(1):63-6. Pubmed: 7818259
  11. Alakarppa K, Tupala E, Mantere T, Sarkioja T, Rasanen P, Tarhanen J, Tiihonen J, Tuomisto L: Effect of alcohol abuse on human brain histamine and tele-methylhistamine. Inflamm Res. 2002 Apr;51 Suppl 1:S40-1. Pubmed: 12013402
  12. 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
  13. van Toorenenbergen AW, Oranje AP: Comparison of serum tryptase and urine N-methylhistamine in patients with suspected mastocytosis. Clin Chim Acta. 2005 Sep;359(1-2):72-7. Pubmed: 15913591
  14. Droogendijk HJ, Kluin-Nelemans HJ, van Doormaal JJ, Oranje AP, van de Loosdrecht AA, van Daele PL: Imatinib mesylate in the treatment of systemic mastocytosis: a phase II trial. Cancer. 2006 Jul 15;107(2):345-51. Pubmed: 16779792
  15. Oranje AP, Mulder PG, Heide R, Tank B, Riezebos P, van Toorenenbergen AW: Urinary N-methylhistamine as an indicator of bone marrow involvement in mastocytosis. Clin Exp Dermatol. 2002 Sep;27(6):502-6. Pubmed: 12372095
  16. Rinne JO, Anichtchik OV, Eriksson KS, Kaslin J, Tuomisto L, Kalimo H, Roytta M, Panula P: Increased brain histamine levels in Parkinson's disease but not in multiple system atrophy. J Neurochem. 2002 Jun;81(5):954-60. Pubmed: 12065607
  17. Fitzpatrick MF, Mackay T, Walters C, Tai PC, Church MK, Holgate ST, Douglas NJ: Circulating histamine and eosinophil cationic protein levels in nocturnal asthma. Clin Sci (Lond). 1992 Aug;83(2):227-32. Pubmed: 1327639
  18. Butterfield JH, Tefferi A, Kozuh GF: Successful treatment of systemic mastocytosis with high-dose interferon-alfa: long-term follow-up of a case. Leuk Res. 2005 Feb;29(2):131-4. Pubmed: 15607359
  19. Winterkamp S, Weidenhiller M, Wilken V, Donhauser N, Schultis HW, Buchwald F, Hahn EG, Raithel M: Standardised evaluation of urinary excretion of N-tele-methylhistamine in different periods of age in a healthy population. Inflamm Res. 2003 Apr;52 Suppl 1:S57-8. Pubmed: 12755411
  20. Coruzzi G, Morini G, Adami M, Grandi D: Role of histamine H3 receptors in the regulation of gastric functions. J Physiol Pharmacol. 2001 Dec;52(4 Pt 1):539-53. Pubmed: 11787757

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