5638-76-6 Usage
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
Different sources of media describe the Uses of 5638-76-6 differently. You can refer to the following data:
1. 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was FDA approved for Meniere's disease in the US market for a short period of time in the 1970s, but approval was then rescinded due to lack of evidence supporting its efficacy.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.
2. 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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 5638-76-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,6,3 and 8 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 5638-76:
(6*5)+(5*6)+(4*3)+(3*8)+(2*7)+(1*6)=116
116 % 10 = 6
So 5638-76-6 is a valid CAS Registry Number.
InChI:InChI=1S/C8H12N2/c1-9-7-5-8-4-2-3-6-10-8/h2-4,6,9H,5,7H2,1H3
5638-76-6Relevant articles and documents
Preparation method of betahistine
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Paragraph 0046-0052; 0067-0176;, (2021/09/29)
The invention discloses a preparation method of betahistine. The preparation method comprises the following steps: in the continuous flow reactor, 2 - vinylpyridine and methylamine salt solution are reacted to obtain the betahistine, and the preparation method is sufficient. Therein, 2 - vinylpyridine is not diluted or diluted with solvent and fed. The residence time of the reaction is not less 0.6 min. The reaction temperature is 100 - 250 °C. prepared by the method of the invention, the conversion rate of the raw material is high, the selectivity and yield of the product are high, the solvent residue is low, and the reaction time is short.
Selective synthesis of mono- and di-methylated amines using methanol and sodium azide as C1 and N1 sources
Chakrabarti, Kaushik,Mishra, Anju,Panja, Dibyajyoti,Paul, Bhaskar,Kundu, Sabuj
supporting information, p. 3339 - 3345 (2018/07/29)
A Ru(ii) complex mediated synthesis of various N,N-dimethyl and N-monomethyl amines from organic azides using methanol as a methylating agent is reported. This methodology was successfully applied for a one-pot reaction of bromide derivatives and sodium azide in methanol. Notably, by controlling the reaction time several N-monomethylated and N,N-dimethylated amines were synthesized selectively. The practical applicability of this tandem process was revealed by preparative scale reactions with different organic azides and synthesis of an anti-vertigo drug betahistine. Several kinetic experiments and DFT studies were carried out to understand the mechanism of this transformation.
The catalytic effect of anion-exchanged supported ionic liquid on aza-Michael-type addition
Ghasemi, Mohammad Hadi,Kowsari, Elaheh
, p. 3691 - 3709 (2017/06/20)
Abstract: An effective synthesis of anion-exchanged supported ionic liquids using diatomaceous earth as solid support and its catalytic effect on the aza-Michael-type addition is described. Anionic polytungstophosphate and bisulfate ion are used in the anion-exchange step in catalyst design. In addition, the aza-Michael-type addition of various amines to 2- and 4-vinyl pyridine was examined in this article. The catalytic system can be separated from the reaction mixture and recycled in subsequent reactions. The structure of anion-exchanged supported ionic liquid on diatomaceous earth was studied by XRD, FT-IR, SEM, TGA and BET techniques. The structure of organic products was determined by 1HNMR, 13CNMR, FTIR, CHN and MASS spectroscopy. Graphical Abstract: [Figure not available: see fulltext.].
