| Common Name |
Betahistine
| Description |
Betahistine is only found in individuals that have used or taken this drug. It is an antivertigo drug first used for treating vertigo assosicated with Menieres 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. Stimliating the H1-receptors in the inner ear causes a vasodilatory effect and increased permeability in the blood vessels which reslits in reduced endolymphatic pressure. Betahistine is believed to act by reducing the asymmetrical functioning of sensory vestibliar organs as well as by increasing vestibliocochlear 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 vestibliar nuclei, helping to restore proper balance and decrease in vertigo symptoms.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
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 methanesliphonateMeSH
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 methaneslifonateMeSH
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
Methaneslifonate, betahistineMeSH
Methanesliphonate, betahistineMeSH
RibrainMeSH
Ratiopharm brand OF betahistine mesylateMeSH
Aliud brand OF betahistine mesylateMeSH
Betahistin-ratiopharmMeSH
Betahistine bipharMeSH
Betahistine dihydrochlorideMeSH
Betahistine hydrochlorideMeSH
Byk gliden brand OF betahistine hydrochlorideMeSH
ExtovylMeSH
Gerard brand OF betahistine hydrochlorideMeSH
Hydrochloride, betahistineMeSH
LectilMeSH
MersilonMeSH
PT 9MeSH
PT-9MeSH
PT9MeSH
VasomotalMeSH
| Chemical Formlia |
C8H12N2
| Average Molecliar Weight |
136.1943
| Monoisotopic Molecliar Weight |
136.100048394
| 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 |
This compound belongs to the class of chemical entities known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organic nitrogen compounds
| Sub Class |
Organonitrogen compounds
| Direct Parent |
Aralkylamines
| Alternative Parents |
Pyridines and derivatives
Heteroaromatic compounds
Dialkylamines
Azacyclic compounds
Organopnictogen compounds
Hydrocarbon derivatives
| Substituents |
Aralkylamine
Pyridine
Heteroaromatic compound
Azacycle
Organoheterocyclic compound
Secondary amine
Secondary aliphatic amine
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound
| Molecliar Framework |
Aromatic heteromonocyclic compounds
| External Descriptors |
secondary amino compound (CHEBI:35677 )
aminoalkylpyridine (CHEBI:35677 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Drug
| Biofunction |
Antivertigo Agents
| Application |
Pharmaceutical
| Cellliar locations |
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility49.3 mg/mLALOGPS
logP0.59ALOGPS
logP0.63ChemAxon
logS-0.44ALOGPS
pKa (Strongest Basic)9.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area24.92 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity41.33 m3·mol-1ChemAxon
Polarizability15.85 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Membrane
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06698
21059682
details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06698
21059682
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
DB06698
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite 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
| NuGOwiki Link |
HMDB15644
| Metagene Link |
HMDB15644
| METLIN ID |
Not Available
| PubChem Compound |
2366
| PDB ID |
Not Available
| ChEBI ID |
35677
Product: Allylthiourea
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- 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
- Barak N: Betahistine: whats new on the agenda? Expert Opin Investig Drugs. 2008 May;17(5):795-804. doi: 10.1517/13543784.17.5.795 . [PubMed:18447604 ]
- 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 ]
- 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
- Barak N: Betahistine: whats new on the agenda? Expert Opin Investig Drugs. 2008 May;17(5):795-804. doi: 10.1517/13543784.17.5.795 . [PubMed:18447604 ]
- 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 ]
PMID: 12023528
