You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2018-05-20 20:21:28 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
Thumb
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
2-(b-Methylaminoethyl)pyridineGenerator
2-(β-methylaminoethyl)pyridineGenerator
Betahistin stadaMeSH
Betahistine mesylateMeSH
Betahistine methanesulphonateMeSH
BetavertMeSH
By vertinMeSH
Dihydrobromide, betahistineMeSH
Ergha brand OF betahistine hydrochlorideMeSH
Mesylate, betahistineMeSH
SercMeSH
Solvay brand OF betahistine hydrochlorideMeSH
Stadapharm brand OF betahistine mesylateMeSH
VertigonMeSH
Betahistin alMeSH
Betahistin ratiopharmMeSH
Betahistine methanesulfonateMeSH
By-vertinMeSH
dexo Brand OF betahistine mesylateMeSH
Dihydrochloride, betahistineMeSH
Eurim brand OF betahistine hydrochlorideMeSH
Hennig brand OF betahistine mesylateMeSH
Medopharm brand OF betahistine mesylateMeSH
MelopatMeSH
Unimed brand OF betahistine hydrochlorideMeSH
AequamenMeSH
Altana pharma brand OF betahistine mesylateMeSH
Betahistine dihydrobromideMeSH
BetasercMeSH
Bouchara brand OF betahistine hydrochlorideMeSH
Fides ecopharma brand OF betahistine hydrochlorideMeSH
FidiumMeSH
Methanesulfonate, betahistineMeSH
Methanesulphonate, betahistineMeSH
RibrainMeSH
Ratiopharm brand OF betahistine mesylateMeSH
Aliud brand OF betahistine mesylateMeSH
Betahistin-ratiopharmMeSH
Betahistine bipharMeSH
Betahistine dihydrochlorideMeSH
Betahistine hydrochlorideMeSH
Byk gulden brand OF betahistine hydrochlorideMeSH
ExtovylMeSH
Gerard brand OF betahistine hydrochlorideMeSH
Hydrochloride, betahistineMeSH
LectilMeSH
MersilonMeSH
PT 9MeSH
PT-9MeSH
PT9MeSH
VasomotalMeSH
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
DescriptionThis compound 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-7632c62aa4558c2fb7ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0900000000-7f0e238dc7925ca025bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-1900000000-a73b4f9a37585a7631d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9400000000-bdcba572bab1c36614c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-5462e3c317b1d05012d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-4900000000-257c19b6692facdce66aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-d813ddb1dd9b7470131fView in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06698 details
UrineExpected but not Quantified Not 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
FoodDB 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
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 ]