Basic information
- CAS
5579-84-0- Standard SMILES
CNCCc1ccccn1.Cl.Cl- InChIKey
XVDFMHARQUBJRE-UHFFFAOYSA-N- Molecular formula
- C8H14Cl2N2
- Average molar mass
- 209.11 g/mol
- Monoisotopic mass
- 208.0534038
Overview
Betahistine Hydrochloride is the hydrochloride salt form of betahistine, a histamine analog with weak histamine H1 agonistic and more potent histamine H3 antagonistic properties. Upon intranasal administration, betahistine binds to histamine H1 and H3 receptors and exerts its agonistic and antagonistic actions locally and centrally. This promotes cochlear, vestibular and cerebral blood flow, decreases neuronal firing in the vestibular nuclei and increases histamine synthesis and release in the brain which facilitates vestibular compensation. Increased blood flow around the inner ear reduces the amount of fluid in the inner ear and may alleviate vertigo, tinnitus, and hearing loss.
Names & identifiers
- Preferred name
- Betahistine Hydrochloride
- IUPAC
- N-methyl-2-pyridin-2-ylethanamine;dihydrochloride
- English name
- Betahistine dihydrochloride
- Molecular formula
- C8H14Cl2N2
- Molecular weight
- 209.12
Names & synonyms
Betahistine hydrochlorideBetahistine HClSercBetaserc2-Pyridineethanamine, N-methyl-, dihydrochloride2-(2-(Methylamino)ethyl)pyridine dihydrochloride49K58SMZ7UNSC-757397DTXSID102043552-[2-(Methylamino)ethyl]pyridine dihydrochlorideSerc-8Serc-16
Show more names
Betahistine Di HClPT-9SinMenierBetahistineHClBETASTINE DI HCLBetahistine 2 hcl
RefChem:567992DTXCID10126846226-966-5Betahistine dihydrochloride5579-84-0Betahistine 2HClMicroserAntivom
Database identifiers
- CAS
5579-84-0- PubChem CID
- 68643
- DTXSID
DTXSID10204355- ChEMBL
CHEMBL1446813- UNII
- 49K58SMZ7U
- EC Number
- 226-966-5
Properties
Computed structural properties
- Topological polar surface area
- 24.9 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 83.3
Physicochemical properties
- Melting point
- 150 · 150-154 °C
- storage temp.
- 2 · 2-8°C
- solubility
- Very soluble in water, soluble in ethanol (96 per cent), practically insoluble in 2propanol.
- form
- powder
- color
- Pale Yellow
- Stability
- Hygroscopic
- InChI
- InChI=1S/C8H12N2.2ClH/c1-9-7-5-8-4-2-3-6-10-8;;/h2-4,6,9H,5,7H2,1H3;2*1H
- InChIKey
- XVDFMHARQUBJRE-UHFFFAOYSA-N
- SMILES
- C1(CCNC)=NC=CC=C1.Cl.Cl
- CAS DataBase Reference
- 5579 · 5579-84-0(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 49 K58SMZ7U · 49K58SMZ7U
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Protein binding
- 0 · 0-5%
- Excreted unchanged in urine
- 85 · 85-90%
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 1.8% (1 of 55) of reports.
Warning
H315 (94.5%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 55 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Other Safety InformationIMAP assessments - 2-Pyridineethanamine, N-methyl-, dihydrochloride: Environment tier I assessment
Hazard Classes and CategoriesSkin Irrit. 2 (94.5%)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- rtecs
- UT2969000
- hs_code
- 29333990
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H413-H319-H315-H335
- Precautionary statements
- P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Drugs used to cause dilation of the blood vessels.
Drugs that bind to and activate histamine receptors. Although they have been suggested for a variety of clinical applications histamine agonists have so far been more widely used in research than therapeutically.
Applications
DescriptionBetahistine dihydrochloride (BH.2HCl) is an orally active histamine analog which has been used to control vertigo, lack of hearing and tinnitus related to Ménière’s disease. The mechanism of BH.2HCl is to reduce the pressure of the membranous labyrinth that results in enhancement of the microvasculature circulation and improves the signs of Ménière’s disease. Peroral administration undergoes extensive first-pass metabolism and gastric irritation in patients with peptic ulcer. In treatment of vertigo, a uniform and constant supply of drug is required in order to maintain steady-state concentration of the drug in the body. Unfortunately, BH.2HCl possesses a short half-life of about 3–4 h and requires frequent administration of the drug,12–15 thereby making it an ideal candidate for controlled release preparations.
UsesBetahistine is belongs to a group of medications used to treat vertigo associated with Ménière's disease. Vertigo is a condition that causes sufferers to have a sensation of rotation or movement of themselves or their surroundings. Ménière's disease is a disorder of the inner ear that causes vertigo in addition to symptoms such as ringing in the ears, headache, and loss of hearing.Betahistine is used to reduce the number of episodes of vertigo associated with Ménière's disease. It is believed to work by decreasing the pressure in the ear. This pressure is believed to contribute to the sense of dizziness, nausea, and ringing in the ears and hearing loss that people with Ménière's disease experience.
Usestherapeutic for thrombocytopenia, effective against idiopathic thrombocytopenic purpura and cirrhosis due to hepatitis C.
General DescriptionPharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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