Cannabis Compound Database: Showing Compound Card for Histamine (CDB005121)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (8) Show 17 proteins XML

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Record Information

Version

1.0

Created at

2020-04-17 19:11:25 UTC

Updated at

2022-12-13 23:36:22 UTC

CannabisDB ID

CDB005121

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Histamine

Description

Histamine, 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1H-Imidazole-4-ethanamine	ChEBI
2-(4-Imidazolyl)ethylamine	ChEBI
2-(1H-Imidazol-4-yl)ethanamine	HMDB
2-(1H-Imidazol-4-yl)ethylamine	HMDB
2-(1H-Imidazol-5-yl)ethanamine	HMDB
2-(1H-Imidazol-5-yl)ethylamine	HMDB
2-(4-Imidazolyl)ethanamine	HMDB
2-Imidazol-4-yl-ethylamine	HMDB
2-Imidazol-4-ylethylamine	HMDB
4-(2-Aminoethyl)-1H-imidazole	HMDB
4-(2-Aminoethyl)imidazole	HMDB
4-Imidazoleethylamine	HMDB
5-Imidazoleethylamine	HMDB
b-Imidazolyl-4-ethylamine	HMDB
beta-Aminoethylglyoxaline	HMDB
beta-Aminoethylimidazole	HMDB
beta-Aminothethylglyoxaline	HMDB
beta-Imidazolyl-4-ethylamine	HMDB
Eramin	HMDB
Ergamine	HMDB
Ergotidine	HMDB
HSM	HMDB
2-(3H-Imidazol-4-yl)ethylamine	HMDB
Imidazole-4-ethylamine	HMDB
Β-imidazolyl-4-ethylamine	HMDB
Histamine	HMDB

Chemical Formula

C₅H₉N₃

Average Molecular Weight

111.15

Monoisotopic Molecular Weight

111.0796

IUPAC Name

2-(1H-imidazol-4-yl)ethan-1-amine

Traditional Name

histamine

CAS Registry Number

51-45-6

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 Key

NTYJJOPFIAHURM-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.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

2-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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:18295 )
aralkylamino compound (CHEBI:18295 )
Biogenic amines (C00388 )
Histamine (C00388 )

Ontology

Physiological effect

Health effect:

Health condition:

Renal and urinary disorders:

Nephrotic syndrome

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Microbe:

Lactobacillus

Photobacterium:

Photobacterium phosphoreum

Environmental:

Wastewater

Neurotransmitter

Industrial application:

Food and nutrition

Pharmaceutical industry:

Pharmaceutical

Environmental role:

Water pollutant

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	86 °C	Not Available
Boiling Point	209.5 °C	Wikipedia
Water Solubility	Not Available	Not Available
logP	-0.70	SANGSTER (1993)

Predicted Properties

Property	Value	Source
logP	-0.69	ALOGPS
logP	-0.7	ChemAxon
logS	0.18	ALOGPS
pKa (Strongest Acidic)	14.46	ChemAxon
pKa (Strongest Basic)	9.58	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	54.7 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	31.66 m³·mol⁻¹	ChemAxon
Polarizability	12.08 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-9d57c893be8c75ce8178	2014-09-20	View Spectrum
GC-MS	Histamine, 3 TMS, GC-MS Spectrum	splash10-0f79-5910000000-9946e1707fcaf5562f88	Spectrum
GC-MS	Histamine, non-derivatized, GC-MS Spectrum	splash10-00di-2910000000-8c243055df15d6ce8116	Spectrum
GC-MS	Histamine, 3 TMS, GC-MS Spectrum	splash10-00di-9710000000-bf79b524c104e1cc94ba	Spectrum
GC-MS	Histamine, 2 TMS, GC-MS Spectrum	splash10-0udi-2900000000-a40a3d0aed04ccfe9365	Spectrum
GC-MS	Histamine, 3 TMS, GC-MS Spectrum	splash10-00dr-3910000000-44d8fb649d4e75eba66c	Spectrum
GC-MS	Histamine, non-derivatized, GC-MS Spectrum	splash10-0f79-5910000000-9946e1707fcaf5562f88	Spectrum
GC-MS	Histamine, non-derivatized, GC-MS Spectrum	splash10-00di-2910000000-8c243055df15d6ce8116	Spectrum
GC-MS	Histamine, non-derivatized, GC-MS Spectrum	splash10-00di-9710000000-bf79b524c104e1cc94ba	Spectrum
GC-MS	Histamine, non-derivatized, GC-MS Spectrum	splash10-0udi-2900000000-a40a3d0aed04ccfe9365	Spectrum
GC-MS	Histamine, non-derivatized, GC-MS Spectrum	splash10-00dr-3910000000-44d8fb649d4e75eba66c	Spectrum
GC-MS	Histamine, non-derivatized, GC-MS Spectrum	splash10-0udi-2900000000-a40a3d0aed04ccfe9365	Spectrum
GC-MS	Histamine, non-derivatized, GC-MS Spectrum	splash10-00dr-3910000000-44d8fb649d4e75eba66c	Spectrum
Predicted GC-MS	Histamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-9100000000-3de6a14d8a45af6c9d66	Spectrum
Predicted GC-MS	Histamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-01ot-9600000000-06c58d75770dfd76aeab	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00kf-9000000000-0135b8f0628e592abc22	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000x-9000000000-6fccc177582b320a48ae	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-03di-1900000000-6cda8885da689473fb42	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0002-9100000000-37450d9969c24ad44ad7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0002-9000000000-e9e368926d3146437e13	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-015a-9000000000-f51ad8a8259595600938	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-00lu-9000000000-3e02d5b58a7c9f77ec53	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-03di-0900000000-046407320168835599f0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-03di-3900000000-29ccabc0b6f5396168f2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03di-1900000000-6cda8885da689473fb42	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-9100000000-37450d9969c24ad44ad7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-9000000000-e9e368926d3146437e13	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-015a-9000000000-f51ad8a8259595600938	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00lu-9000000000-77394d92ed9170d75b98	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03di-0900000000-046407320168835599f0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-01ot-9400000000-a19fc5e555afd53dafe7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-982b635075f56f26d216	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0frx-9000000000-262a5d1ecfe104fb5771	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dj-9700000000-b06ddb1eb7ed3ddf4f69	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9200000000-a93565f24c40eddb6cf4	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uxr-9000000000-71d70766bb4f9d3b13a0	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-2900000000-2705dc2d177edbc4faa4	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-6900000000-9e9ebaae6f68b4c2d89d	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-9d4fe74f18b21423615d	2015-04-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50.18 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Histidine Metabolism
Histidinemia		Not Available
Gastric Acid Production		Not Available
Esomeprazole Action Pathway		Not Available
Omeprazole Action Pathway		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Aromatic-L-amino-acid decarboxylase	DDC	7p12.2	P20711	details
Amiloride-sensitive amine oxidase [copper-containing]	ABP1	7q36.1	P19801	details
Retina-specific copper amine oxidase	AOC2	17q21	O75106	details
Histamine N-methyltransferase	HNMT	2q22.1	P50135	details
Histidine decarboxylase	HDC	15q21-q22	P19113	details
Histamine H2 receptor	HRH2	5q35.2	P25021	details
Synaptic vesicular amine transporter	SLC18A2	10q25	Q05940	details
Histamine H1 receptor	HRH1	3p25	P35367	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Amiloride-sensitive amine oxidase [copper-containing]	ABP1	7q36.1	P19801	details
Retina-specific copper amine oxidase	AOC2	17q21	O75106	details
Zinc finger protein 219	ZNF219	14q11	Q9P2Y4	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Amiloride-sensitive amine oxidase [copper-containing]	ABP1	7q36.1	P19801	details
Histamine H2 receptor	HRH2	5q35.2	P25021	details
Histamine H3 receptor	HRH3	20q13.33	Q9Y5N1	details
Histamine H1 receptor	HRH1	3p25	P35367	details
Histamine H4 receptor	HRH4	18q11.2	Q9H3N8	details
Zinc finger protein 219	ZNF219	14q11	Q9P2Y4	details

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Alien Dawg	Detected and Quantified	0.000577 mg/g dry wt	David S. Wishart,...	details
Gabriola	Detected and Quantified	0.000297 mg/g dry wt	David S. Wishart,...	details
Island Honey	Detected and Quantified	0.000904 mg/g dry wt	David S. Wishart,...	details
Quadra	Detected and Quantified	0.000557 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	0.000165 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream	Detected and Quantified	0.000256 mg/g dry wt	David S. Wishart,...	details

External Links

HMDB ID

HMDB0000870

DrugBank ID

DB05381

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

774

PDB ID

Not Available

ChEBI ID

18295

References

General References

Not 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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Showing Compound Card for Histamine (CDB005121)

Structure for CDB005121 (Histamine)

Enzymes