Betahistine

Base Information

• Chemical Name: Betahistine
• CAS No.: 5638-76-6
• Molecular Formula: C8H12N2
• Molecular Weight: 136.197
• Hs Code.: 2933399090
• European Community (EC) Number: 227-086-4
• NSC Number: 42617
• UNII: X32KK4201D
• DSSTox Substance ID: DTXSID3022665
• Nikkaji Number: J8.042J
• Wikipedia: Betahistine
• Wikidata: Q368995
• NCI Thesaurus Code: C83554
• Pharos Ligand ID: JSTBVXS1B5JX
• Metabolomics Workbench ID: 43679
• ChEMBL ID: CHEMBL24441
• Mol file: 5638-76-6.mol

Synonyms:Aequamen;Betahistin AL;Betahistin ratiopharm;Betahistin Stada;Betahistin-ratiopharm;Betahistine;Betahistine Biphar;Betahistine Dihydrobromide;Betahistine Dihydrochloride;Betahistine Hydrochloride;Betahistine Mesylate;Betahistine Methanesulfonate;Betahistine Methanesulphonate;Betaserc;Betavert;By Vertin;By-Vertin;Dihydrobromide, Betahistine;Dihydrochloride, Betahistine;Extovyl;Fidium;Hydrochloride, Betahistine;Lectil;Melopat;Mersilon;Mesylate, Betahistine;Methanesulfonate, Betahistine;Methanesulphonate, Betahistine;PT 9;PT-9;PT9;Ribrain;Serc;Vasomotal;Vertigon

Chemical Property of Betahistine

Chemical Property:

• Appearance/Colour: Pale yellow.
• Vapor Pressure: 17.7Pa at 25℃
• Refractive Index: n20/D 1.518(lit.)
• Boiling Point: 210.9 °C at 760 mmHg
• PKA: pKa 3.46 (Uncertain)
• Flash Point: 96.7 °C
• PSA: 24.92000
• Density: 0.967 g/cm³
• LogP: 1.23440
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Chloroform (Slightly), DMSO (Sparingly), Ethyl Acetate (Slightly), Methanol (Sli
• Water Solubility.: 1000g/L at 25℃
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 136.100048391
• Heavy Atom Count: 10
• Complexity: 83.3

Purity/Quality:

99.9% ^*data from raw suppliers

Betahistine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,C
• Hazard Codes: Xi,C
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNCCC1=CC=CC=N1
• Recent ClinicalTrials: Effects of Betahistine Hydrochloride in Overweight Women
• Recent EU Clinical Trials: A Multicenter, Three- arm, Double- blind, Double dummy, Parallel-group, placebo controlled Study for efficacy and safety evaluation of prolonged release formulation of Betahistine PR 48 mg once daily in comparison with conventional release formulation of Betahistine IR 24 mg, twice daily in treatment of adult patients with Menière's disease.
• Recent NIPH Clinical Trials: Effect of betahistine in treating in patients with peripheral vestibular disease
• 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: 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. Anti - Vertigo/Anti-Nauseants/Antiemetics
• Indications: Betahistine is indicated in treatment of Meniere's disease (vertigo, hearing loss and tinnitus); it is not effective in preventing vertigo attacks.
• 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.

Technology Process of Betahistine

There total 19 articles about Betahistine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

2-vinylpyridine (100-69-6,25014-15-7,27476-03-5,329041-71-6) + methylamine hydrochloride (593-51-1) → betahistine (5638-76-6)

Guidance literature:

In water; at 170 ℃; under 7500.75 Torr; Temperature; Pressure; Solvent;

Reference yield: 91.0%

2-vinylpyridine (100-69-6,25014-15-7,27476-03-5,329041-71-6) + methylamine (74-89-5) → betahistine (5638-76-6)

Guidance literature:

With NPs-Fe₃O₄-DE-bmim3PW; In dichloromethane; water; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2016.01.107

Reference yield: 84.0%

2-vinylpyridine (100-69-6,25014-15-7,27476-03-5,329041-71-6) + methylamine acetate (6998-30-7) → betahistine (5638-76-6)

Guidance literature:

In water; toluene; at 170 ℃; under 7500.75 Torr;

upstream raw materials:

2-vinylpyridine

methylamine hydrochloride

2-(2-Hydroxyethyl)pyridine

methylamine acetate

Downstream raw materials:

(2R)-2-benzyl-3-<<(2-pyridin-2-ylethyl)methylamino>carbonyl>propionic acid

2-benzyl-3-<<(2-pyridin-2-ylethyl)methylamino>sulfonyl>propionic acid

(S)-3-Methyl-2-[3-methyl-3-(2-pyridin-2-yl-ethyl)-ureido]-butyric acid 4-nitro-phenyl ester

4-amino-N-methyl-N-(2-pyridin-2-ylethyl)benzamide

Refernces

• 1、 Sun, Maolin,Yang, Jingxin,Fu, Youtian,Liang, Chaoming,Li, Hong,Yan, Guoming,Yin, Chao,Yu, Wei,Ma, Yueyue,Cheng, Ruihua,Ye, Jinxing. "Continuous Flow Process for the Synthesis of Betahistine via Aza-Michael-Type Reaction in Water". supporting information. p. 1160 - 1166. Retrieved 2021/05/06.
• 2、 Chakrabarti, Kaushik,Mishra, Anju,Panja, Dibyajyoti,Paul, Bhaskar,Kundu, Sabuj. "Selective synthesis of mono- and di-methylated amines using methanol and sodium azide as C1 and N1 sources". . p. 3339 - 3345. Retrieved 2018/07/29.