Record Information
Version1.0
Creation date2010-04-08 22:10:15 UTC
Update date2019-11-26 03:07:10 UTC
Primary IDFDB012596
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHistamine
DescriptionAn amine derived by enzymatic decarboxylation of histidine. It is a powerful stimulant of gastric secretion, a constrictor of bronchial smooth muscle, a vasodilator, and also a centrally acting neurotransmitter.; Histamine is a biogenic amine involved in local immune responses as well as regulating physiological function in the gut and acting as a neurotransmitter. Histamine triggers the inflammatory response. As part of an immune response to foreign pathogens, histamine is produced by basophils and by mast cells found in nearby connective tissues. Histamine increases the permeability of the capillaries to white blood cells and other proteins, in order to allow them to engage foreign invaders in the affected tissues. It is found in virtually all animal body cells.[citation needed]; Histamine is derived from the decarboxylation of the amino acid histidine, a reaction catalyzed by the enzyme L-histidine decarboxylase. It is a hydrophilic vasoactive amine.
CAS Number51-45-6
Structure
Thumb
Synonyms
SynonymSource
β-aminoethylglyoxalinebiospider
β-aminoethylimidazolebiospider
β-Imidazolyl-4-ethylaminebiospider
1H-Imidazole-4-ethanamineChEBI
1H-Imidazole-4-ethanamine, 9CIdb_source
2-(4-Imidazolyl)ethylamineChEBI
4-(2-Aminoethyl)-1H-imidazoledb_source
Ergaminedb_source
Histaminumbiospider
Histaminum hydrochloricumbiospider
Histaminum muriaticumbiospider
Scombrotoxindb_source
Predicted Properties
PropertyValueSource
Water Solubility165 g/LALOGPS
logP-0.88ALOGPS
logP-1ChemAxon
logS0.17ALOGPS
pKa (Strongest Acidic)13.5ChemAxon
pKa (Strongest Basic)9.79ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area54.7 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity32.23 m³·mol⁻¹ChemAxon
Polarizability11.99 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H18N6
IUPAC namebis(2-(1H-imidazol-5-yl)ethan-1-amine)
InChI IdentifierInChI=1S/2C5H9N3/c2*6-2-1-5-3-7-4-8-5/h2*3-4H,1-2,6H2,(H,7,8)
InChI KeyCLIIFKDZHSLNHY-UHFFFAOYSA-N
Isomeric SMILESNCCC1=CN=CN1.NCCC1=CNC=N1
Average Molecular Weight222.2901
Monoisotopic Molecular Weight222.159294606
Classification
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 FrameworkNot Available
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 54.03%; H 8.16%; N 37.81%DFC
Melting PointMp 86°DFC
Boiling PointBp0.8 167°DFC
Experimental Water SolubilityNot Available
Experimental logP-0.70SANGSTER (1993)
Experimental pKapKa2 9.7 (25°, 0.1M KCl)DFC
Isoelectric pointNot Available
Charge+1
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID753
ChEMBL IDCHEMBL90
KEGG Compound IDC00388
Pubchem Compound ID774
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB60263
CRC / DFC (Dictionary of Food Compounds) IDHJF38-X:HJF38-X
EAFUS IDNot Available
Dr. Duke IDHISTAMINE
BIGG ID1810403
KNApSAcK IDC00001414
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
anti chilblainDUKE
anti Meniere's52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti migraine52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
bronchoconstrictor50141 A drug which causes a narrowing of the lumen of a bronchus or bronchiole.DUKE
bronchostimulant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
cardiovascular38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
gastrostimulant55324 A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion.DUKE
histaminicDUKE
hypotensiveDUKE
irritantDUKE
myostimulantDUKE
radioprotective35232 Any pharmaceutical compound containing a radioisotope.DUKE
secretogogueDUKE
spasmogenicDUKE
tachycardic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
ulcerogenicDUKE
vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
neurotransmitter25512 An endogenous compound that is used to transmit information across the synapse between a neuron and another cell.CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).