ChemicalBook > Product Catalog >Biochemical Engineering >Biochemical Reagents >Agonist Inhibitors >(3aR,4S,7aR)-Octahydro-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]-1H-indole-1-carboxylic acid methyl ester

(3aR,4S,7aR)-Octahydro-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]-1H-indole-1-carboxylic acid methyl ester

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(3aR,4S,7aR)-Octahydro-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]-1H-indole-1-carboxylic acid methyl ester Basic information
Product Name:(3aR,4S,7aR)-Octahydro-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]-1H-indole-1-carboxylic acid methyl ester
Synonyms:(3aR,4S,7aR)-Octahydro-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]-1H-indole-1-carboxylic acid methyl ester;(3aR,4S,7aR)-Methyl 4-hydroxy-4-(2-M-tolylethynyl)-octahydroindole-1-carboxylate;AFQ 056;Mavoglurant, AFQ056;UNII-GT0I9SV4F6; AFQ056; MAVOGLURANT; SURECN989279; GT0I9SV4F6; CHEMBL3087515; AFQ 056; AFQ-056;CHEMBL3087515;GT0I9SV4F6;SureCN989279
CAS:543906-09-8
MF:C19H23NO3
MW:313.39
EINECS:
Product Categories:
Mol File:543906-09-8.mol
(3aR,4S,7aR)-Octahydro-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]-1H-indole-1-carboxylic acid methyl ester Structure
(3aR,4S,7aR)-Octahydro-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]-1H-indole-1-carboxylic acid methyl ester Chemical Properties
Melting point 119 - 121°C
Boiling point 476.3±45.0 °C(Predicted)
density 1.21
storage temp. 2-8°C
solubility DMSO (Slightly), Methanol (Slightly)
pka12.75±0.20(Predicted)
form Solid
color White to Off-White
InChIInChI=1S/C19H23NO3/c1-14-5-3-6-15(13-14)8-11-19(22)10-4-7-17-16(19)9-12-20(17)18(21)23-2/h3,5-6,13,16-17,22H,4,7,9-10,12H2,1-2H3/t16-,17-,19-/m1/s1
InChIKeyZFPZEYHRWGMJCV-ZHALLVOQSA-N
SMILESN1(C(OC)=O)[C@@]2([H])[C@]([H])([C@](O)(C#CC3=CC=CC(C)=C3)CCC2)CC1
Safety Information
WGK Germany WGK 3
Storage Class11 - Combustible Solids
MSDS Information
(3aR,4S,7aR)-Octahydro-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]-1H-indole-1-carboxylic acid methyl ester Usage And Synthesis
UsesMavoglurant is a non-competitive metabotropic glutamate receptor 5 (mGlu5) receptor antagonist.
Biological ActivityOrally active, potent and selective mGluR5 antagonist.

AFQ056 (Mavoglurant) is an orally active, potent and selective antagonist of metabotropic glutamate receptor 5 (mGluR5). AFQ056 was investigated for treatment of fragile X syndrome and for Parkinsonμs disease.
in vivo

Mavoglurant (0.1-10 mg/kg; a single p.o.) inhibits the stress-induced hyperthermia (SIH) in a dose-dependent manner in mice[1].
Mavoglurant (9.4 mg/kg; a single p.o.) exhibits moderate oral bioavailability (32%), terminal half-life (2.9 h) and Cmax (plasma; brain) (950 pmol/mL; 3500 pmol/g)[1].
Mavoglurant (3.1 mg/kg; a single i.v.) exhibits terminal half-life (0.69 h), Cmax (plasma; brain) (3330 pmol/mL; 8400 pmol/g) and Tmax (≤0.08 h)[1].

Animal Model:Male OF1/IC mice[1]
Dosage:0.1, 1, 10 mg/kg
Administration:A single p.o. administration
Result:Attenuated the stress-induced hyperthermia.
Was comparable to the positive control Chlordiazepoxide.
Animal Model:Male Sprague-Dawley rats (175-250 g)[1]
Dosage:3.1 mg/kg for i.v.; 9.4 mg/kg for p.o. (Pharmacokinetic Analysis)
Administration:A single i.v. or p.o. administration
Result:P.o.: F=32%; T1/2=2.9 h; Tmax≤0.25 h.
I.v.: T1/2=0.69 h; Cmax (plasma/brain)=3330 pmolmL-1/8400 pmolg-1; Tmax≤0.08 h.
IC 50mGluR5: 30 nM (IC50)
(3aR,4S,7aR)-Octahydro-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]-1H-indole-1-carboxylic acid methyl ester Preparation Products And Raw materials
Tag:(3aR,4S,7aR)-Octahydro-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]-1H-indole-1-carboxylic acid methyl ester(543906-09-8) Related Product Information
(3aR,4S,7aR)-Octahydro-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]-1H-indole-1-carboxylic acid tert-butyl ester (3aR,4S,7aR)-Octahydro-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]-1H-indole-1-carboxylic acid methyl ester Mavoglurant (racemate) NA LY 341495 Ro 67-7476