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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
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 substance that triggers an immune response, causing allergic reactions. Its biological role is to stimulate the immune system, but it has no therapeutic applications. Key medical uses include diagnosing allergies and developing immunotherapies to desensitize patients to specific allergens, reducing the risk of severe reactions.DUKE
Anti-chilblainA vasodilator that stimulates blood vessel dilation, used to treat chilblains by improving blood flow to affected areas, reducing pain and inflammation, and promoting healing.DUKE
Anti Meniere's52217 An agent that alleviates symptoms of Meniere's disease, a disorder of the inner ear. It helps regulate fluid balance and reduce vertigo, tinnitus, and hearing loss, improving quality of life for affected individuals.DUKE
Anti-migraine52217 An agent that alleviates migraine symptoms, commonly used to treat and prevent migraine headaches by constricting blood vessels and blocking pain pathways, providing relief from severe headaches, nausea, and sensitivity to light and sound.DUKE
Bronchoconstrictor50141 An agent that narrows airway passages, used therapeutically to diagnose asthma or chronic obstructive pulmonary disease (COPD), and medically to treat conditions such as post-operative bronchospasm, or to reverse excessive bronchodilation.DUKE
Bronchostimulant52217 An agent that stimulates bronchial dilation, increasing airway patency. It plays a biological role in regulating respiratory function. Therapeutically, bronchostimulants are used to treat respiratory disorders, with key medical applications including asthma, chronic obstructive pulmonary disease (COPD), and bronchitis, providing relief from wheezing, coughing, and shortness of breath.DUKE
Cardiovascular38070 A system that transports blood, oxygen, and nutrients throughout the body, playing a crucial role in overall health. Therapeutically, cardiovascular agents manage conditions like hypertension, heart failure, and atherosclerosis, with key medical uses including regulating blood pressure, preventing blood clots, and improving cardiac function.DUKE
Gastrostimulant55324 An agent that stimulates digestive motility, increasing gastrointestinal movement and secretion. It enhances gut function, relieving symptoms of gastroparesis, constipation, and other motility disorders, commonly used in managing conditions like diabetes-related gastroparesis and postoperative ileus.DUKE
HistaminicA physiologically active amine that stimulates gastric secretion, causes capillary dilation, constricts bronchial smooth muscle, and lowers blood pressure. It plays a key role in allergic reactions, and its therapeutic applications include treating allergies, gastric disorders, and respiratory issues, with medical uses in antihistamines and gastric acid regulators.DUKE
HypotensiveAn agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.DUKE
IrritantAn agent that causes slight inflammation or discomfort, stimulating a biological response. Therapeutically, it can be used to increase blood flow or stimulate healing. Key medical uses include treating wounds, skin conditions, and respiratory issues, such as congestion, by inducing a mild inflammatory response to promote recovery.DUKE
MyostimulantAn agent that stimulates an increase in the rhythm and amplitude of smooth muscle movement, playing a biological role in enhancing muscle contraction. Therapeutically, it is used to treat gastrointestinal disorders, such as constipation, and other conditions characterized by reduced muscle activity, like urinary retention.DUKE
Radioprotective35232 An agent that shields cells from radiation damage, reducing oxidative stress and DNA harm. Its biological role is to mitigate radiation-induced injury, and it has therapeutic applications in cancer treatment, space exploration, and nuclear medicine, with key medical uses including protection of healthy tissues during radiation therapy.DUKE
SecretogogueA substance that stimulates secretion, playing a biological role in regulating hormone and enzyme release. Therapeutically, it has applications in treating conditions like hyposecretion and is used to manage digestive issues, respiratory problems, and endocrine disorders, promoting healthy secretion in various bodily systems.DUKE
SpasmogenicAn agent that induces spasms, causing sudden involuntary muscular contractions. It plays a biological role in stimulating muscle activity. Therapeutically, it has applications in diagnosing and treating muscle disorders. Key medical uses include assessing muscle function and treating conditions like muscle atrophy, with potential applications in physical therapy and rehabilitation.DUKE
Tachycardic38070 An agent that increases heart rate, playing a biological role in stress response and exercise. Therapeutically, it is used to manage bradycardia (abnormally slow heart rate) and cardiac arrest. Key medical uses include treating symptomatic bradycardia, Adams-Stokes syndrome, and asystole, helping to restore normal heart rhythm and maintain adequate blood circulation.DUKE
UlcerogenicAn agent that causes the production of ulcers, often used to study gastrointestinal disease mechanisms. Its biological role involves disrupting mucosal defense, leading to ulcer formation. Therapeutically, understanding ulcerogenic agents informs the development of anti-ulcer medications. Key medical uses include researching gastric ulcer pathogenesis and testing potential treatments for ulcer prevention and healing.DUKE
Vasodilator35620 An agent that widens blood vessels, reducing blood pressure and increasing blood flow. It plays a biological role in regulating cardiovascular function. Therapeutically, vasodilators are used to treat conditions such as hypertension, angina, and heart failure, improving oxygen delivery and reducing cardiac workload.DUKE
Neurotransmitter25512 A chemical messenger that transmits signals between neurons, regulating various physiological and psychological processes. Therapeutically, neurotransmitter modulators are used to treat conditions such as depression, anxiety, and Parkinson's disease, by altering neurotransmitter levels or activity to restore balance and alleviate symptoms.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).