Record Information
Version1.0
Creation Date2016-09-30 22:37:48 UTC
Update Date2020-06-04 20:46:48 UTC
BMDB IDBMDB0000870
Secondary Accession Numbers
  • BMDB00870
Metabolite Identification
Common NameHistamine
DescriptionHistamine, also known as eramin or ceplene, 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. Histamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Histamine exists in all living species, ranging from bacteria to humans. Histamine participates in a number of enzymatic reactions, within cattle. In particular, Histamine can be converted into histamine; which is mediated by the enzyme histamine H2 receptor. In addition, Histamine can be converted into histamine; which is mediated by the enzyme histamine H2 receptor. In cattle, histamine is involved in the metabolic pathway called the intracellular signalling through histamine H2 receptor and histamine pathway. Histamine is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
1H-Imidazole-4-ethanamineChEBI
2-(4-Imidazolyl)ethylamineChEBI
2-(1H-Imidazol-4-yl)ethanamineHMDB
2-(1H-Imidazol-4-yl)ethylamineHMDB
2-(1H-Imidazol-5-yl)ethanamineHMDB
2-(1H-Imidazol-5-yl)ethylamineHMDB
2-(4-Imidazolyl)ethanamineHMDB
2-Imidazol-4-yl-ethylamineHMDB
2-Imidazol-4-ylethylamineHMDB
4-(2-Aminoethyl)-1H-imidazoleHMDB
4-(2-Aminoethyl)imidazoleHMDB
4-ImidazoleethylamineHMDB
5-ImidazoleethylamineHMDB
b-Imidazolyl-4-ethylamineHMDB
beta-AminoethylglyoxalineHMDB
beta-AminoethylimidazoleHMDB
beta-AminothethylglyoxalineHMDB
beta-Imidazolyl-4-ethylamineHMDB
EraminHMDB
ErgamineHMDB
ErgotidineHMDB
HSMHMDB
2-(3H-Imidazol-4-yl)ethylamineHMDB
Imidazole-4-ethylamineHMDB
Β-imidazolyl-4-ethylamineHMDB
HistamineHMDB
Chemical FormulaC5H9N3
Average Molecular Weight111.1451
Monoisotopic Molecular Weight111.079647303
IUPAC Name2-(1H-imidazol-4-yl)ethan-1-amine
Traditional Namehistamine
CAS Registry Number51-45-6
SMILES
NCCC1=CNC=N1
InChI Identifier
InChI=1S/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8)
InChI KeyNTYJJOPFIAHURM-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
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Myelin sheath
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point86 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.7SANGSTER (1993)
Predicted Properties
PropertyValueSource
logP-0.69ALOGPS
logP-0.7ChemAxon
logS0.18ALOGPS
pKa (Strongest Acidic)14.46ChemAxon
pKa (Strongest Basic)9.58ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area54.7 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity31.66 m³·mol⁻¹ChemAxon
Polarizability12.08 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Myelin sheath
Biospecimen Locations
  • Adipose Tissue
  • Adrenal Medulla
  • Bladder
  • Brain
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Leukocyte
  • Liver
  • Longissimus Thoracis Muscle
  • Milk
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate Tissue
  • Ruminal Fluid
  • Semimembranosus Muscle
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Adrenal MedullaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BladderExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LeukocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected and Quantified25 +/- 16 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Longissimus Thoracis MuscleDetected and Quantified17 +/- 4 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
MilkDetected and Quantified5.938 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified4.229 uMNot SpecifiedNot Specified
Normal
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PancreasExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified5.07 +/- 6.37 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified5.07 +/- 6.37 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified57 +/- 43 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Semimembranosus MuscleDetected and Quantified23 +/- 6 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000870
DrugBank IDDB05381
Phenol Explorer Compound IDNot Available
FooDB IDFDB012596
KNApSAcK IDC00001414
Chemspider ID753
KEGG Compound IDC00388
BioCyc IDHISTAMINE
BiGG ID1810403
Wikipedia LinkHistamine
METLIN ID68
PubChem Compound774
PDB IDNot Available
ChEBI ID18295
References
Synthesis ReferencePyman, Frank L. 2-Thiol-4(5)-b-aminoethylglyoxaline (2-thiolhistamine). Journal of the Chemical Society (1930), 98-100.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Aurand LW, Moore PA, Jones EE: Effect of histamine on bovine milk fatty acids. J Anim Sci. 1980 May;50(5):783-92. [PubMed:7190139 ]

Enzymes

General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity (By similarity).
Gene Name:
AOC3
Uniprot ID:
Q9TTK6
Molecular weight:
84500.0
Reactions
Histamine + Water + Oxygen → Imidazole-4-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:
Q58DV7
Molecular weight:
33646.0
Reactions
S-Adenosylmethionine + Histamine → S-Adenosylhomocysteine + 1-Methylhistaminedetails
General function:
Amino acid transport and metabolism
Specific function:
Catalyzes the biosynthesis of histamine from histidine.
Gene Name:
HDC
Uniprot ID:
Q5EA83
Molecular weight:
73912.0
Reactions
L-Histidine → Histamine + Carbon dioxidedetails
General function:
Carbohydrate transport and metabolism
Specific function:
Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles. Requisite for vesicular amine storage prior to secretion via exocytosis.
Gene Name:
SLC18A2
Uniprot ID:
Q27963
Molecular weight:
55756.0
General function:
Involved in histamine receptor activity
Specific function:
Not Available
Gene Name:
HRH1
Uniprot ID:
A5D795
Molecular weight:
55989.0
General function:
Involved in histamine receptor activity
Specific function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system.
Gene Name:
HRH1
Uniprot ID:
P30546
Molecular weight:
55957.0