Betahistine hydrochloride

Base Information

• Chemical Name: Betahistine hydrochloride
• CAS No.: 5579-84-0
• Molecular Formula: C8H12N2^.2ClH
• Molecular Weight: 209.119
• Hs Code.: 29333990
• NSC Number: 757397
• DSSTox Substance ID: DTXSID00165582
• NCI Thesaurus Code: C73794
• ChEMBL ID: CHEMBL1464589
• Mol file: 5579-84-0.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 hydrochloride

Chemical Property:

• Appearance/Colour: white to light yellow crystalline powder
• Vapor Pressure: 0.187mmHg at 25°C
• Melting Point: 150-154 °C
• Boiling Point: 210.9 °C at 760 mmHg
• Flash Point: 96.7 °C
• PSA: 24.92000
• Density: 0.967 g/cm3
• LogP: 2.83840
• Storage Temp.: 2-8°C
• Solubility.: Very soluble in water, soluble in ethanol (96 per cent), practically insoluble in 2propanol.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 172.0767261
• Heavy Atom Count: 11
• Complexity: 83.3

Purity/Quality:

99% ^*data from raw suppliers

Betahistine dihydrochloride ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CNCCC1=CC=CC=N1.Cl
• Recent ClinicalTrials: Effects of Betahistine Hydrochloride in Overweight Women
• Description: Betahistine 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.
• Uses: Betahistine 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. therapeutic for thrombocytopenia, effective against idiopathic thrombocytopenic purpura and cirrhosis due to hepatitis C.
• Clinical Use: Treatment of vertigo, tinnitus and hearing loss associated with Ménière’s syndrome
• Drug interactions: Potentially hazardous interactions with other drugs None known

Technology Process of Betahistine hydrochloride

There total 3 articles about Betahistine hydrochloride 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:

betahistine (5638-76-6) → [3H]-Betahistine dihydrochloride (5579-84-0,15430-48-5)

Guidance literature:

With hydrogenchloride; In isopropyl alcohol; pH=2;

DOI:10.1016/j.tetlet.2016.01.107

Reference yield:

α-picoline (109-06-8) → [3H]-Betahistine dihydrochloride (5579-84-0,15430-48-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 20 h / 125 °C / 3040.2 Torr / Inert atmosphere

2: sodium hydroxide / 2 h / 95 - 100 °C

3: hydrogenchloride / water / 95 - 105 °C

4: hydrogenchloride / water; isopropyl alcohol / 0 - 10 °C / pH 2

With hydrogenchloride; sodium hydroxide; In water; isopropyl alcohol;

Reference yield:

2-(2-Hydroxyethyl)pyridine (103-74-2) → [3H]-Betahistine dihydrochloride (5579-84-0,15430-48-5)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydroxide / 2 h / 95 - 100 °C

2: hydrogenchloride / water / 95 - 105 °C

3: hydrogenchloride / water; isopropyl alcohol / 0 - 10 °C / pH 2

With hydrogenchloride; sodium hydroxide; In water; isopropyl alcohol;

upstream raw materials:

betahistine

α-picoline

2-(2-Hydroxyethyl)pyridine

Downstream raw materials:

C₁₉H₂₄N₂O

Refernces

• 1、 Ghasemi, Mohammad Hadi,Kowsari, Elaheh,Shafiee, Abbas. "Aza-Michael-type addition reaction catalysed by a supported ionic liquid phase incorporating an anionic heteropoly acid". supporting information. p. 1150 - 1153. Retrieved 2016/03/09.