Showing metabocard for 1-Methylhistamine (BMDB0000898)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:38:16 UTC
Update Date2020-05-21 16:28:38 UTC
BMDB IDBMDB0000898
Secondary Accession Numbers
  • BMDB00898
Metabolite Identification
Common Name1-Methylhistamine
Description1-1-1-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. 1-1-1-methylhistamine is possibly soluble (in water) and a very strong basic compound (based on its pKa). 1-1-1-methylhistamine exists in all living organisms, ranging from bacteria to humans. 1-1-1-methylhistamine participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and 1-1-methylhistamine can be biosynthesized from S-adenosylmethionine and histamine through its interaction with the enzyme histamine N-methyltransferase. In addition, 1-1-1-methylhistamine can be converted into methylimidazole acetaldehyde through the action of the enzyme amine oxidase [flavin-containing] a. In cattle, 1-1-methylhistamine is involved in the metabolic pathway called the histidine metabolism pathway. 1-1-1-methylhistamine is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
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
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Bone Marrow
  • Brain
  • Leukocyte
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Bone MarrowExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LeukocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000898
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
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)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Histamine N-methyltransferase
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:
Q58DV7
Molecular weight:
33646.0
Reactions
S-Adenosylmethionine + Histamine → S-Adenosylhomocysteine + 1-Methylhistaminedetails
Enzyme Details
2. Amine oxidase [flavin-containing] A
General function:
Amino acid transport and metabolism
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:
P21398
Molecular weight:
59758.0
Reactions
1-Methylhistamine + Water + Oxygen → Methylimidazole acetaldehyde + Ammonia + Hydrogen peroxidedetails