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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:41:59 UTC
HMDB IDHMDB0015644
Secondary Accession Numbers
  • HMDB15644
Metabolite Identification
Common NameBetahistine
DescriptionBetahistine is only found in individuals that have used or taken this drug. It is an antivertigo drug first used for treating vertigo assosicated with Meniere's disease. It is also commonly used for patients with balance disorders.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.
Structure
Data?1582753319
Synonyms
ValueSource
2-(beta-Methylaminoethyl)pyridineChEBI
2-[2-(Methylamino)ethyl]pyridineChEBI
[2-(2-Pyridyl)ethyl]methylamineChEBI
BetahistinaChEBI
BetahistinumChEBI
N-Methyl-2-(2-pyridinyl)ethanamineChEBI
N-Methyl-2-pyridineethanamineChEBI
VestiboKegg
2-(b-Methylaminoethyl)pyridineGenerator
2-(Β-methylaminoethyl)pyridineGenerator
Betahistin stadaHMDB
Betahistine mesylateHMDB
Betahistine methanesulphonateHMDB
BetavertHMDB
By vertinHMDB
Dihydrobromide, betahistineHMDB
Ergha brand OF betahistine hydrochlorideHMDB
Mesylate, betahistineHMDB
SercHMDB
Solvay brand OF betahistine hydrochlorideHMDB
Stadapharm brand OF betahistine mesylateHMDB
VertigonHMDB
Betahistin alHMDB
Betahistin ratiopharmHMDB
Betahistine methanesulfonateHMDB
By-vertinHMDB
Dexo brand OF betahistine mesylateHMDB
Dihydrochloride, betahistineHMDB
Eurim brand OF betahistine hydrochlorideHMDB
Hennig brand OF betahistine mesylateHMDB
Medopharm brand OF betahistine mesylateHMDB
MelopatHMDB
Unimed brand OF betahistine hydrochlorideHMDB
AequamenHMDB
Altana pharma brand OF betahistine mesylateHMDB
Betahistine dihydrobromideHMDB
BetasercHMDB
Bouchara brand OF betahistine hydrochlorideHMDB
Fides ecopharma brand OF betahistine hydrochlorideHMDB
FidiumHMDB
Methanesulfonate, betahistineHMDB
Methanesulphonate, betahistineHMDB
RibrainHMDB
Ratiopharm brand OF betahistine mesylateHMDB
Aliud brand OF betahistine mesylateHMDB
Betahistin-ratiopharmHMDB
Betahistine bipharHMDB
Betahistine dihydrochlorideHMDB
Betahistine hydrochlorideHMDB
Byk gulden brand OF betahistine hydrochlorideHMDB
ExtovylHMDB
Gerard brand OF betahistine hydrochlorideHMDB
Hydrochloride, betahistineHMDB
LectilHMDB
MersilonHMDB
PT 9HMDB
PT-9HMDB
PT9HMDB
VasomotalHMDB
Chemical FormulaC8H12N2
Average Molecular Weight136.1943
Monoisotopic Molecular Weight136.100048394
IUPAC Namemethyl[2-(pyridin-2-yl)ethyl]amine
Traditional Namebetahistine
CAS Registry Number5638-76-6
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 KeyUUQMNUMQCIQDMZ-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.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Pyridine
  • Heteroaromatic compound
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Secondary aliphatic amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility49.3 g/LALOGPS
logP0.59ALOGPS
logP0.63ChemAxon
logS-0.44ALOGPS
pKa (Strongest Basic)9.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area24.92 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity41.33 m³·mol⁻¹ChemAxon
Polarizability15.85 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-7632c62aa4558c2fb7ddSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 13V, positivesplash10-0006-9100000000-07342e47e4de2ed49a07Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-000i-0900000000-2383d4ee95382a0952b4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-000i-1900000000-ca585604bb3faa20d632Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-000i-3900000000-20e6d7b7102f8bdf9f6dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-000l-6900000000-d6abf363e740f987060bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-000f-9700000000-6f1719ddcb978f3fb5ddSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0006-9400000000-0db109b7fd166bbe90d1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0006-9300000000-6f9e7848042fb2b00b42Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0006-9200000000-0fc13e19d4cc0935a41bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0006-9100000000-4395f34d6dbb3a0be758Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0006-9100000000-f6347495cdf25ea92871Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-0006-9000000000-b8660d839b89a1828fd9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-0006-9000000000-bb4d952e3112de0fa855Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-0006-9000000000-5093f4a070434d834dbcSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-0006-9000000000-41f3edda74912fc48e09Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 9V, positivesplash10-0006-9100000000-ec255d8163bfe16ea693Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0900000000-7f0e238dc7925ca025bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-1900000000-a73b4f9a37585a7631d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9400000000-bdcba572bab1c36614c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-5462e3c317b1d05012d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-4900000000-257c19b6692facdce66aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-d813ddb1dd9b7470131fSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06698 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06698 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06698
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2276
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBetahistine
METLIN IDNot Available
PubChem Compound2366
PDB IDNot Available
ChEBI ID35677
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Health Canada [Link]

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The H3 subclass of histamine receptors could mediate the histamine signals in CNS and peripheral nervous system. Signals through the inhibition of adenylate cyclase and displays high constitutive activity (spontaneous activity in the absence of agonist). Agonist stimulation of isoform 3 niether modified adenylate cyclase activity nor induced intracellular calcium mobilization
Gene Name:
HRH3
Uniprot ID:
Q9Y5N1
Molecular weight:
48670.8
References
  1. Barak N: Betahistine: what's new on the agenda? Expert Opin Investig Drugs. 2008 May;17(5):795-804. doi: 10.1517/13543784.17.5.795 . [PubMed:18447604 ]
  2. Lacour M, Sterkers O: Histamine and betahistine in the treatment of vertigo: elucidation of mechanisms of action. CNS Drugs. 2001;15(11):853-70. [PubMed:11700150 ]
  3. Gbahou F, Davenas E, Morisset S, Arrang JM: Effects of betahistine at histamine H3 receptors: mixed inverse agonism/agonism in vitro and partial inverse agonism in vivo. J Pharmacol Exp Ther. 2010 Sep 1;334(3):945-54. doi: 10.1124/jpet.110.168633. Epub 2010 Jun 8. [PubMed:20530654 ]
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
References
  1. Barak N: Betahistine: what's new on the agenda? Expert Opin Investig Drugs. 2008 May;17(5):795-804. doi: 10.1517/13543784.17.5.795 . [PubMed:18447604 ]
  2. Lacour M, Sterkers O: Histamine and betahistine in the treatment of vertigo: elucidation of mechanisms of action. CNS Drugs. 2001;15(11):853-70. [PubMed:11700150 ]