Cannabis Compound Database: Showing Compound Card for Betahistine (CDB000576)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (1) Show 3 proteins XML

Record Information

Version

1.0

Created at

2020-03-19 00:44:36 UTC

Updated at

2020-12-07 19:07:32 UTC

CannabisDB ID

CDB000576

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Betahistine

Description

Betahistine belongs to the class of organic compounds known as aminoalkylpyridines. Aminoalkylpyridines are molecules that include a pyridine substituted by a 2-(methylamino)ethyl group at position 2. Betahistine is an antivertigo drug first used for treating vertigo associated with Meniere's disease. It is also commonly used for patients with balance disorders. Betahistine is only found in individuals that have used or taken this drug. Betahistine primarily acts as a histamine H1-agonist with 0.07 times the activity of histamine. Stimulating the H1-receptors in the inner ear causes a vasodilatory effect and increased permeability in the blood vessels which results in reduced endolymphatic pressure. Betahistine is believed to act by reducing the asymmetrical functioning of sensory vestibular organs as well as by increasing vestibulocochlear blood flow. Doing so aids in decreasing symptoms of vertigo and balance disorders. Betahistine also acts as a histamine H3-receptor antagonist which causes an increased output of histamine from histaminergic nerve endings which can further increase the direct H1-agonist activity. Furthermore, H3-receptor antagonism increases the levels of neurotransmitters such as serotonin in the brainstem, which inhibits the activity of vestibular nuclei, helping to restore proper balance and decrease in vertigo symptoms. Betahistine has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(beta-Methylaminoethyl)pyridine	ChEBI
2-[2-(Methylamino)ethyl]pyridine	ChEBI
[2-(2-Pyridyl)ethyl]methylamine	ChEBI
Betahistina	ChEBI
Betahistinum	ChEBI
N-Methyl-2-(2-pyridinyl)ethanamine	ChEBI
N-Methyl-2-pyridineethanamine	ChEBI
Vestibo	Kegg
2-(b-Methylaminoethyl)pyridine	Generator
2-(Β-methylaminoethyl)pyridine	Generator
Betahistin stada	HMDB
Betahistine mesylate	HMDB
Betahistine methanesulphonate	HMDB
Betavert	HMDB
By vertin	HMDB
Dihydrobromide, betahistine	HMDB
Ergha brand OF betahistine hydrochloride	HMDB
Mesylate, betahistine	HMDB
Serc	HMDB
Solvay brand OF betahistine hydrochloride	HMDB
Stadapharm brand OF betahistine mesylate	HMDB
Vertigon	HMDB
Betahistin al	HMDB
Betahistin ratiopharm	HMDB
Betahistine methanesulfonate	HMDB
By-vertin	HMDB
Dexo brand OF betahistine mesylate	HMDB
Dihydrochloride, betahistine	HMDB
Eurim brand OF betahistine hydrochloride	HMDB
Hennig brand OF betahistine mesylate	HMDB
Medopharm brand OF betahistine mesylate	HMDB
Melopat	HMDB
Unimed brand OF betahistine hydrochloride	HMDB
Aequamen	HMDB
Altana pharma brand OF betahistine mesylate	HMDB
Betahistine dihydrobromide	HMDB
Betaserc	HMDB
Bouchara brand OF betahistine hydrochloride	HMDB
Fides ecopharma brand OF betahistine hydrochloride	HMDB
Fidium	HMDB
Methanesulfonate, betahistine	HMDB
Methanesulphonate, betahistine	HMDB
Ribrain	HMDB
Ratiopharm brand OF betahistine mesylate	HMDB
Aliud brand OF betahistine mesylate	HMDB
Betahistin-ratiopharm	HMDB
Betahistine biphar	HMDB
Betahistine dihydrochloride	HMDB
Betahistine hydrochloride	HMDB
Byk gulden brand OF betahistine hydrochloride	HMDB
Extovyl	HMDB
Gerard brand OF betahistine hydrochloride	HMDB
Hydrochloride, betahistine	HMDB
Lectil	HMDB
Mersilon	HMDB
PT 9	HMDB
PT-9	HMDB
PT9	HMDB
Vasomotal	HMDB

Chemical Formula

C₈H₁₂N₂

Average Molecular Weight

136.19

Monoisotopic Molecular Weight

136.1

IUPAC Name

methyl[2-(pyridin-2-yl)ethyl]amine

Traditional Name

betahistine

CAS Registry Number

5638-76-6

SMILES

CNCCC1=CC=CC=N1

InChI Identifier

InChI=1S/C8H12N2/c1-9-7-5-8-4-2-3-6-10-8/h2-4,6,9H,5,7H2,1H3

InChI Key

UUQMNUMQCIQDMZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Aralkylamines

Alternative Parents

Substituents

Aralkylamine
Pyridine
Heteroaromatic compound
Azacycle
Organoheterocyclic compound
Secondary amine
Secondary aliphatic amine
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

secondary amino compound (CHEBI:35677 )
aminoalkylpyridine (CHEBI:35677 )

Ontology

Disposition

Biological location:

Biofluid and excreta:

Subcellular:

Role

Industrial application:

Drug

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.59	ALOGPS
logP	0.63	ChemAxon
logS	-0.44	ALOGPS
pKa (Strongest Basic)	9.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	24.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	41.33 m³·mol⁻¹	ChemAxon
Polarizability	15.85 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Betahistine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9200000000-7632c62aa4558c2fb7dd	Spectrum
Predicted GC-MS	Betahistine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - n/a 13V, positive	splash10-0006-9100000000-07342e47e4de2ed49a07	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-000i-0900000000-2383d4ee95382a0952b4	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-000i-1900000000-ca585604bb3faa20d632	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-000i-3900000000-20e6d7b7102f8bdf9f6d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-000l-6900000000-d6abf363e740f987060b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-000f-9700000000-6f1719ddcb978f3fb5dd	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-0006-9400000000-0db109b7fd166bbe90d1	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0006-9300000000-6f9e7848042fb2b00b42	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0006-9200000000-0fc13e19d4cc0935a41b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-0006-9100000000-4395f34d6dbb3a0be758	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-0006-9100000000-f6347495cdf25ea92871	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-0006-9000000000-b8660d839b89a1828fd9	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, positive	splash10-0006-9000000000-bb4d952e3112de0fa855	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, positive	splash10-0006-9000000000-5093f4a070434d834dbc	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 11V, positive	splash10-0006-9000000000-41f3edda74912fc48e09	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 9V, positive	splash10-0006-9100000000-ec255d8163bfe16ea693	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0900000000-7f0e238dc7925ca025bc	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-1900000000-a73b4f9a37585a7631d8	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9400000000-bdcba572bab1c36614c5	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-1900000000-5462e3c317b1d05012d9	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-4900000000-257c19b6692facdce66a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-d813ddb1dd9b7470131f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-1900000000-a399e016fa279418d20c	2021-10-11	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052f-9400000000-33e9b78ab853fa5c9d3a	2021-10-11	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-5c82222d49c9fd329ef9	2021-10-11	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Betahistine H1-Antihistamine Action		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Histamine H1 receptor	HRH1	3p25	P35367	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Histamine H3 receptor	HRH3	20q13.33	Q9Y5N1	details
Histamine H1 receptor	HRH1	3p25	P35367	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0015644

DrugBank ID

DB06698

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2276

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Betahistine

METLIN ID

Not Available

PubChem Compound

2366

PDB ID

Not Available

ChEBI ID

35677

References

General References

Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

Enzymes

Enzyme Details

1. 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

Showing Compound Card for Betahistine (CDB000576)

Structure for CDB000576 (Betahistine)

Enzymes