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Betahistine

CAS No.
5638-76-6
Chemical Name:
Betahistine
Synonyms
Y-G 14-d3;PT 9 base;Serc base;Vasomotal;β-Histine;BETAHISTINE;NSC 42617-d3;AKOS BBS-00002883;Sinmenier (free base);2-(METHYLAMINOETHYL)PYRIDINE
CBNumber:
CB4489793
Molecular Formula:
C8H12N2
Molecular Weight:
136.19
MDL Number:
MFCD00006362
MOL File:
5638-76-6.mol
Last updated:2023-05-18 11:31:13

Betahistine Properties

Boiling point 113-114 °C30 mm Hg(lit.)
Density 0.984 g/mL at 25 °C(lit.)
vapor pressure 17.7Pa at 25℃
refractive index n20/D 1.518(lit.)
Flash point 206 °F
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility Chloroform (Slightly), DMSO (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)
form Oil
pka pKa 3.46 (Uncertain)
color Light Yellow to Yellow
Water Solubility 1000g/L at 25℃
Merck 13,1181
LogP 0.68
CAS DataBase Reference 5638-76-6(CAS DataBase Reference)
FDA UNII X32KK4201D
ATC code N07CA01
EPA Substance Registry System 2-Pyridineethanamine, N-methyl- (5638-76-6)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P264-P271-P280-P302+P352-P305+P351+P338
Hazard Codes  Xi,C
Risk Statements  36/37/38
Safety Statements  26-37/39
WGK Germany  2
RTECS  UT5552000
Hazard Note  Corrosive
HS Code  2933399990
NFPA 704
1
3 0

Betahistine price More Price(22)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich M28804 2-(2-Methylaminoethyl)pyridine 97% 5638-76-6 5g $62.4 2024-03-01 Buy
Sigma-Aldrich M28804 2-(2-Methylaminoethyl)pyridine 97% 5638-76-6 25g $298.2 2024-03-01 Buy
TRC B324005 Betahistine 5638-76-6 1g $145 2021-12-16 Buy
Oakwood 065480 N-Methyl-N-(2-pyridin-2-ylethyl)amine 95% 5638-76-6 250mg $20 2021-12-16 Buy
Matrix Scientific 081894 N-Methyl-N-(2-pyridin-2-ylethyl)amine 97% 5638-76-6 1g $37 2021-12-16 Buy
Product number Packaging Price Buy
M28804 5g $62.4 Buy
M28804 25g $298.2 Buy
B324005 1g $145 Buy
065480 250mg $20 Buy
081894 1g $37 Buy

Betahistine Chemical Properties,Uses,Production

Description

Betahistine is an analogue of histamine with weak agonist properties at histamine H1 receptors and more potent antagonistic effects at histamine H3 receptors.
This drug is broadly used worldwide, except for the USA, since it has not been approved by the US Food and Drug Administration. Betahistine is a structural analog of histamine that acts as a weak partial postsynaptic histamine H1 receptor agonist and presynaptic H3 receptor antagonist, with no effect on postsynaptic H2 receptors (Gbahou et al, 2010). The mechanism of action of the drug appears to depend mainly on its action on H3 receptors mediated by two metabolites, aminoethylpyridine and hydroxyethylpyridine (Bertich et al, 2014).

Uses

Anti - Vertigo/Anti-Nauseants/Antiemetics

Uses

Betahistine is a vasodilator, a mild H1 histamine agonist, and a potent H3 histamine antagonist. The mechanism of action in Meniere's disease is unknown, but theories include reducing the endolymphatic pressure through improved circulation in the stria vascularis or inhibiting activity in the vestibular nuclei. It has been found to be a safe drug with a very low side effect profile. Betahistine was FDA approved for Meniere's disease in the US market for a short period of time in the 1970s, but approval was then rescinded due to lack of evidence supporting its efficacy. However, based on clinical experience and several observational studies, it is still widely used elsewhere in the world.

Definition

ChEBI: Betahistine is an aminoalkylpyridine that is pyridine substituted by a 2-(methylamino)ethyl group at position 2. It acts as a histamine agonist and a vasodilator, and is thought to improve the microcirculation of the labyrinth, resulting in reduced endolymphatic pressure. It is used (generally as the hydrochloride or mesylate salt) to reduce the symptoms of vertigo, tinnitus, and hearing loss associated with Meniere's disease. It has a role as a vasodilator agent and a H1-receptor agonist. It is an aminoalkylpyridine and a secondary amino compound.

Indications

Betahistine is indicated in treatment of Meniere's disease (vertigo, hearing loss and tinnitus); it is not effective in preventing vertigo attacks.

brand name

Serc (Unimed).

Mechanism of action

The precise mechanism of betahistine's actions is unclear; it has antagonistic actions on histamine H3 receptors, and is a weak agonist at H receptors. In animal studies, it inhibits generation of spikes in vestibular nuclei. Its vasodilator activity (similar to histamine's) presumably improves blood flow in the inner ear and brainstem.

Pharmacokinetics

After oral administration, betahistine is rapidly and completely absorbed, rapidly metabolised (to one major metabolite, 2-pyridylacetic acid) and 90% excreted within 24 hours. Plasma and urinary half-lives are about 3.5 hours.

Side effects

Common adverse reactions include headache, nausea and dyspepsia. More rarely, hypersensitivity reactions (rash, pruritis, bronchospasm) and hypotension may occur.

Drug interactions

Co-administration of betahistine and monoamine oxidase inhibitors type B reduces metabolism of betahistine. Theoretically, interactions might occur with concurrent antihistamines; however, no significant problems have been reported.

Dosage forms

Betahistine is provided as scored tablets, 16 mg. Dose is 8-16 mg taken three times daily. It should be taken with food to minimise risk of GIT upsets. Patients are warned that it may take several weeks for beneficial effects to be noticed.

Precautions

Betahistine should be used with caution in individuals with asthma, urticaria, phaeochromocytoma or hypersensitivity to any components of tablets. Betahistine is contraindicated in people with active or history of peptic ulcer. Betahistine is classified in Pregnancy Safety Category B2: insufficient data available; it is contraindicated in pregnancy and lactation, and in children under 18.

100-69-6
593-51-1
5638-76-6
Synthesis of Betahistine from 2-Vinylpyridine and Methylamine hydrochloride
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View Lastest Price from Betahistine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2-(2-METHYLAMINOETHYL)PYRIDINE USP/EP/BP pictures 2021-08-13 2-(2-METHYLAMINOETHYL)PYRIDINE USP/EP/BP
5638-76-6
US $1.10 / g 1g 99.9% 100 Tons min Dideu Industries Group Limited
2-[2-(Methylamino)ethyl]pyridine  pictures 2020-05-12 2-[2-(Methylamino)ethyl]pyridine
5638-76-6
US $1.00 / KG 1KG 99% 20T Shaanxi Dideu Medichem Co. Ltd
2-(2-METHYLAMINOETHYL)PYRIDINE pictures 2019-12-23 2-(2-METHYLAMINOETHYL)PYRIDINE
5638-76-6
US $1.00 / g 100g 99% G/KG/T Career Henan Chemical Co
N-Methyl-N-(2-pyridin-2-ylethyl)amine METHYL-(2-PYRIDIN-2-YL-ETHYL)-AMINE BETAHISTINE AKOS BBS-00002883 2'-(2-N-METHYLAMINO ETHYL)PYRIDINE 2-(2-METHYLAMINOETHYL)PYRIDINE 2-[B-(METHYLAMINO)ETHYL]PYRIDINE 2-(METHYLAMINOETHYL)PYRIDINE N-METHYL-N-[2-(2-PYRIDYL)ETHYL]AMINE (2-(2-pyridyl)ethyl)methylamine [2-(2-Pyridyl)ethyl]methylamine 2-(2-(methylamino)ethyl)-pyridin 2-(beta-Methylaminoethyl)pyridine 2-Pyridineethanamine, N-methyl- N-Methyl-2-(2-pyridinyl)ethanamine 2-[-(Methyl-d3)aminoethyl]pyridine 2-[2-(Methyl-d3)aminoethyl]pyridine N-(Methyl-d3)-2-pyridineethanamine N-(Methyl-d3)-N-[2-(pyridin-2-yl)ethyl]amine NSC 42617-d3 Y-G 14-d3 n-methyl-2-pyridineethanamin n-methyl-2-pyridineethanamine N-Methyl-2-pyridineethylamine N-Methyl-N-beta-(2-pyridyl)ethylamine PT 9 base Pyridine, 2-[2-(methylamino)ethyl]- Serc base Sinmenier (free base) Vasomotal N-Methyl-2-(2-pyridyl)ethylamine β-Histine 2-(2-Methylaminoethyl)pyridine ,97% n-Methyl-n-[2-(2-pyridyl)amine, 97+% 2-(2-Methylaminoethyl)pyridine ,95% 2-(2-METHYLAMINOETHYL)PYRIDINE USP/EP/BP 5638-76-6 C8H9D3N2 AMINE C7 and C8 Building Blocks Heterocyclic Building Blocks Pyridines C7 and C8 Heterocyclic Building Blocks Pyridines Aromatics Heterocycles Isotope Labeled Compounds