Showing Compound Card for Histamine (CDB005121)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (8) Show 17 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:11:25 UTC
Updated at2022-12-13 23:36:22 UTC
CannabisDB IDCDB005121
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameHistamine
DescriptionHistamine, also known as histaminum or eramin, 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 is a very strong basic compound (based on its pKa). Histamine exists in all living species, ranging from bacteria to humans. This can lead to three clinical responses:sneezing due to histamine-associated sensory neural stimulationhyper-secretion from glandular tissuenasal congestion due to vascular engorgement associated with vasodilation and increased capillary permeability Sleep-wake regulation Histamine is a neurotransmitter that is released from histaminergic neurons which project out of the mammalian hypothalamus. Within humans, histamine participates in a number of enzymatic reactions. In particular, histamine can be converted into histamine; which is catalyzed by the enzyme histamine H2 receptor. In addition, histamine can be converted into histamine; which is catalyzed by the enzyme histamine H2 receptor. In humans, histamine is involved in intracellular signalling through histamine H2 receptor and histamine. Histamine is a potentially toxic compound. Histamine is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight111.15
Monoisotopic Molecular Weight111.0796
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Environmental role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point86 °CNot Available
Boiling Point209.5 °CWikipedia
Water SolubilityNot AvailableNot Available
logP-0.70SANGSTER (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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-9d57c893be8c75ce81782014-09-20View Spectrum
GC-MSHistamine, 3 TMS, GC-MS Spectrumsplash10-0f79-5910000000-9946e1707fcaf5562f88Spectrum
GC-MSHistamine, non-derivatized, GC-MS Spectrumsplash10-00di-2910000000-8c243055df15d6ce8116Spectrum
GC-MSHistamine, 3 TMS, GC-MS Spectrumsplash10-00di-9710000000-bf79b524c104e1cc94baSpectrum
GC-MSHistamine, 2 TMS, GC-MS Spectrumsplash10-0udi-2900000000-a40a3d0aed04ccfe9365Spectrum
GC-MSHistamine, 3 TMS, GC-MS Spectrumsplash10-00dr-3910000000-44d8fb649d4e75eba66cSpectrum
GC-MSHistamine, non-derivatized, GC-MS Spectrumsplash10-0f79-5910000000-9946e1707fcaf5562f88Spectrum
GC-MSHistamine, non-derivatized, GC-MS Spectrumsplash10-00di-2910000000-8c243055df15d6ce8116Spectrum
GC-MSHistamine, non-derivatized, GC-MS Spectrumsplash10-00di-9710000000-bf79b524c104e1cc94baSpectrum
GC-MSHistamine, non-derivatized, GC-MS Spectrumsplash10-0udi-2900000000-a40a3d0aed04ccfe9365Spectrum
GC-MSHistamine, non-derivatized, GC-MS Spectrumsplash10-00dr-3910000000-44d8fb649d4e75eba66cSpectrum
GC-MSHistamine, non-derivatized, GC-MS Spectrumsplash10-0udi-2900000000-a40a3d0aed04ccfe9365Spectrum
GC-MSHistamine, non-derivatized, GC-MS Spectrumsplash10-00dr-3910000000-44d8fb649d4e75eba66cSpectrum
Predicted GC-MSHistamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-9100000000-3de6a14d8a45af6c9d66Spectrum
Predicted GC-MSHistamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01ot-9600000000-06c58d75770dfd76aeab2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kf-9000000000-0135b8f0628e592abc222012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000x-9000000000-6fccc177582b320a48ae2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-03di-1900000000-6cda8885da689473fb422012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0002-9100000000-37450d9969c24ad44ad72012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0002-9000000000-e9e368926d3146437e132012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-015a-9000000000-f51ad8a82595956009382012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00lu-9000000000-3e02d5b58a7c9f77ec532012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03di-0900000000-046407320168835599f02012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-03di-3900000000-29ccabc0b6f5396168f22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-1900000000-6cda8885da689473fb422017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-9100000000-37450d9969c24ad44ad72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-9000000000-e9e368926d3146437e132017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-015a-9000000000-f51ad8a82595956009382017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00lu-9000000000-77394d92ed9170d75b982017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0900000000-046407320168835599f02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-01ot-9400000000-a19fc5e555afd53dafe72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-982b635075f56f26d2162021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0frx-9000000000-262a5d1ecfe104fb57712021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-9700000000-b06ddb1eb7ed3ddf4f692015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9200000000-a93565f24c40eddb6cf42015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9000000000-71d70766bb4f9d3b13a02015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2900000000-2705dc2d177edbc4faa42015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-6900000000-9e9ebaae6f68b4c2d89d2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-9d4fe74f18b21423615d2015-04-25View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 50.18 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Aromatic-L-amino-acid decarboxylaseDDC7p12.2P20711 details
Amiloride-sensitive amine oxidase [copper-containing]ABP17q36.1P19801 details
Retina-specific copper amine oxidaseAOC217q21O75106 details
Histamine N-methyltransferaseHNMT2q22.1P50135 details
Histidine decarboxylaseHDC15q21-q22P19113 details
Histamine H2 receptorHRH25q35.2P25021 details
Synaptic vesicular amine transporterSLC18A210q25Q05940 details
Histamine H1 receptorHRH13p25P35367 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Amiloride-sensitive amine oxidase [copper-containing]ABP17q36.1P19801 details
Retina-specific copper amine oxidaseAOC217q21O75106 details
Zinc finger protein 219ZNF21914q11Q9P2Y4 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Amiloride-sensitive amine oxidase [copper-containing]ABP17q36.1P19801 details
Histamine H2 receptorHRH25q35.2P25021 details
Histamine H3 receptorHRH320q13.33Q9Y5N1 details
Histamine H1 receptorHRH13p25P35367 details
Histamine H4 receptorHRH418q11.2Q9H3N8 details
Zinc finger protein 219ZNF21914q11Q9P2Y4 details
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.000577 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.000297 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.000904 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.000557 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.000165 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.000256 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0000870
DrugBank IDDB05381
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012596
KNApSAcK IDC00001414
Chemspider ID753
KEGG Compound IDC00388
BioCyc IDHISTAMINE
BiGG ID1810403
Wikipedia LinkHistamine
METLIN ID68
PubChem Compound774
PDB IDNot Available
ChEBI ID18295
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 17 proteins in total.

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Enzymes

Enzyme Details
1. Aromatic-L-amino-acid decarboxylase
General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:
DDC
Uniprot ID:
P20711
Molecular weight:
53893.755
Enzyme Details
2. Amiloride-sensitive amine oxidase [copper-containing]
General function:
Involved in copper ion binding
Specific function:
Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:
ABP1
Uniprot ID:
P19801
Molecular weight:
85377.1
Enzyme Details
3. Retina-specific copper amine oxidase
General function:
Involved in copper ion binding
Specific function:
Has a monoamine oxidase activity with substrate specificity for 2-phenylethylamine and tryptamine. May play a role in adipogenesis. May be a critical modulator of signal transmission in retina.
Gene Name:
AOC2
Uniprot ID:
O75106
Molecular weight:
80515.11
Enzyme Details
4. 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:
P50135
Molecular weight:
6045.9
Enzyme Details
5. Histidine decarboxylase
General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the biosynthesis of histamine from histidine.
Gene Name:
HDC
Uniprot ID:
P19113
Molecular weight:
74139.825
Enzyme Details
6. Histamine H2 receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The H2 subclass of histamine receptors mediates gastric acid secretion. Also appears to regulate gastrointestinal motility and intestinal secretion. Possible role in regulating cell growth and differentiation. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase and, through a separate G protein-dependent mechanism, the phosphoinositide/protein kinase (PKC) signaling pathway
Gene Name:
HRH2
Uniprot ID:
P25021
Molecular weight:
40097.7
Enzyme Details
7. Synaptic vesicular amine transporter
General function:
Involved in transmembrane transport
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:
Q05940
Molecular weight:
55712.1
Enzyme Details
8. Histamine H1 receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
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:
P35367
Molecular weight:
55783.6

Only showing the first 10 proteins. There are 17 proteins in total.

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