Human Metabolome Database Version 3.5

Showing metabocard for 1-Methylhistamine (HMDB00898)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:32 -0700
HMDB ID HMDB00898
Secondary Accession Numbers
  • HMDB00976
Metabolite Identification
Common Name 1-Methylhistamine
Description 1-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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C6H11N3
Average Molecular Weight 125.1716
Monoisotopic Molecular Weight 125.095297367
IUPAC Name 2-(1-methyl-1H-imidazol-4-yl)ethan-1-amine
Traditional IUPAC Name tele-methylhistamine
CAS Registry Number 501-75-7
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 Key FHQDWPCFSJMNCT-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteromonocyclic Compounds
Class Azoles
Sub Class Imidazoles
Other Descriptors
  • imidazoles(ChEBI)
Substituents
  • Primary Aliphatic Amine (Alkylamine)
Direct Parent Imidazoles
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Histidine metabolism
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
LogP -0.57 ALOGPS
LogP -0.48 ChemAxon
LogS -1.39 ALOGPS
pKa (strongest basic) 9.57 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 43.84 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 36.56 ChemAxon
Polarizability 14.24 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Bone Marrow
  • Brain
  • Mast Cell
Pathways
Name SMPDB Link KEGG Link
Histidine Metabolism SMP00044 map00340 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.00034 (0.00021-0.00047) uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.002 +/- 0.0005 (0.0015 - 0.0025) uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.005 +/- 0.0006 (0.003-0.006) uM Children (1-13 year old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.007 +/- 0.0005 (0.006 - 0.008) uM Children (1-13 year old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.002209 +/- 0.000463 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.00214 +/- 0.0001 uM Not Specified Not Specified Normal
Urine Detected and Quantified
0.13 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.098 (0.032-0.18) umol/mmol creatinine Adult (>18 years old) Both Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
0.065 (0.32- 0.98) umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.00078 (0.00055-0.00100) uM Adult (>18 years old) Both Dermal fibroproliferative disorder (hypertrophic scarring)
Cerebrospinal Fluid (CSF) Detected and Quantified 0.002431 +/- 0.000461 uM Adult (>18 years old) Not Specified sporadic narcolepsy-cataplexy
Cerebrospinal Fluid (CSF) Detected and Quantified 0.00276 +/- 0.00013 uM Adult (>18 years old) Not Specified Alzheimer's disease
Urine Detected and Quantified 0.73 umol/mmol creatinine Adult (>18 years old) Both Mastocytosis
Associated Disorders and Diseases
Disease References
Dermal fibroproliferative disorder
  • 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 Link_out
      Mastocytosis
      • 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 Link_out
          Associated OMIM IDs
          DrugBank ID Not Available
          DrugBank Metabolite ID Not Available
          Phenol Explorer Compound ID Not Available
          Phenol Explorer Metabolite ID Not Available
          FoodDB ID FDB022306
          KNApSAcK ID Not Available
          Chemspider ID 3488 Link_out
          KEGG Compound ID C05127 Link_out
          BioCyc ID N-METHYL-HISTAMINE Link_out
          BiGG ID 45171 Link_out
          Wikipedia Link Not Available
          NuGOwiki Link HMDB00898 Link_out
          Metagene Link HMDB00898 Link_out
          METLIN ID 5854 Link_out
          PubChem Compound 3614 Link_out
          PDB ID Not Available
          ChEBI ID 29009 Link_out
          References
          Synthesis Reference Rothschild, 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. 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 Link_out
          2. 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 Link_out
          3. Ito C: The role of the central histaminergic system on schizophrenia. Drug News Perspect. 2004 Jul-Aug;17(6):383-7. Pubmed: 15334189 Link_out
          4. 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 Link_out
          5. 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 Link_out
          6. 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 Link_out
          7. 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 Link_out
          8. 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 Link_out
          9. 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 Link_out
          10. 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 Link_out
          11. 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 Link_out
          12. 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 Link_out
          13. 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 Link_out
          14. 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 Link_out
          15. 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 Link_out
          16. 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 Link_out
          17. 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 Link_out
          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 Link_out
          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 Link_out
          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 Link_out

          Enzymes
          Name: Amine oxidase [flavin-containing] B
          Reactions:
          1-Methylhistamine + Water + Oxygen unknown Methylimidazole acetaldehyde + Ammonia + Hydrogen peroxide details
          Gene Name: MAOB
          Uniprot ID: P27338 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Amine oxidase [flavin-containing] A
          Reactions:
          1-Methylhistamine + Water + Oxygen unknown Methylimidazole acetaldehyde + Ammonia + Hydrogen peroxide details
          Gene Name: MAOA
          Uniprot ID: P21397 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Histamine N-methyltransferase
          Reactions:
          S-Adenosylmethionine + Histamine unknown S-Adenosylhomocysteine + 1-Methylhistamine details
          Gene Name: HNMT
          Uniprot ID: P50135 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA