Betahistin
n-methyl-2-(pyridin-2-yl)ethan-1-amine · Y-G 14-d3 · PT 9 base · Serc base · Vasomotal · β-Histine · BETAHISTINE · NSC 42617-d3
Identifikatoren & physikalische Daten
| CAS No. | 5638-76-6 |
|---|---|
| Summenformel | C8H12N2 |
| Durchschnittliche Molmasse | 136,19 g/mol |
| Monoisotopische Masse | 136,10004838 g/mol |
| SMILES | CNCCc1ccccn1 |
| InChIKey | UUQMNUMQCIQDMZ-UHFFFAOYSA-N |
| PubChem CID | 2366 |
| ChEMBL | CHEMBL24441 |
| ChEBI | CHEBI:35677 |
| EC No. | 227-086-4 |
| DTXSID | DTXSID3022665 |
| Lokaler Name | Betahistin |
Chemische & physikalische Eigenschaften
| XLogP | 0,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 24,9 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 83,3 |
| Arzneimittel | Pharmaceuticals -> Used in SwitzerlandPharmaceuticals -> Listed in ZINC15 |
| LogP (Verteilungskoeffizient) | 0.68 |
| Siedepunkt | 210.9±15.0 °C113-114 °C30 mm Hg(lit.) |
| Schmelzpunkt | 150-144 |
| Physical Description | Solid |
| Dissociation Constants | 3.5, 9.7 |
| Collision Cross Section | 128.98 Ų [M+Na]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| Dichte | 0.984 g/mL at 25 °C(lit.) |
| Dampfdruck | 17.7Pa at 25℃ |
| Brechungsindex | n20/D 1.518(lit.) |
| Flammpunkt | 206 °F |
| Lagerbedingungen | Keep in dark place,Inert atmosphere,Room temperature |
| Löslichkeit | Chloroform (Slightly), DMSO (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)1000g/L at 25℃ |
| pKa (Säurekonstante) | pKa 3.46 (Uncertain) |
| Aggregatzustand | Oil |
| Farbe | Light Yellow to Yellow |
| Merck | 13,1181 |
| InChI | 1S/C8H12N2/c1-9-7-5-8-4-2-3-6-10-8/h2-4,6,9H,5,7H2,1H3 |
| InChIKey | UUQMNUMQCIQDMZ-UHFFFAOYSA-N |
| SMILES | CNCCc1ccccn1 |
| LogP (Verteilungskoeffizient) | 0.68 |
| CAS Datenbank | 5638-76-6(CAS DataBase Reference) |
| EPA chemische Informationen | 2-Pyridineethanamine, N-methyl- (5638-76-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, 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 47 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Status: Active Update: 01-10-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/18902 |
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| Drug Induced Liver Injury | Drug-Induced Liver Injury Severity and Toxicity (DILIst)betahistineDILI PositiveOralDOI:10.1016/j.drudis.2019.09.022 |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 2933399990 |
| RTECS-Nr. | UT5552000 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi,C |
| hazard_note | Corrosive |
| Sicherheitshinweise (S) | 26-37/39 |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrenklasse | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
Anwendungen & Verwendung
Beschreibung
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).
Verwenden
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.