ChemicalBook > CAS DataBase List > (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

Product Name
(3aR,4S,7aR)-Octahydro-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]-1H-indole-1-carboxylic acid methyl ester
CAS No.
543906-09-8
Chemical Name
(3aR,4S,7aR)-Octahydro-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]-1H-indole-1-carboxylic acid methyl ester
Synonyms
AFQ 056;GT0I9SV4F6;Mavoglurant;SureCN989279;CHEMBL3087515;UNII-GT0I9SV4F6;Mavoglurant, AFQ056;(3aR,4S,7aR)-Methyl 4-hydroxy-4-(2-M-tolylethynyl)-octahydroindole-1-carboxylate;methyl (3aR,4S,7aR)-4-hydroxy-4-(m-tolylethynyl)octahydro-1H-indole-1-carboxylate;UNII-GT0I9SV4F6; AFQ056; MAVOGLURANT; SURECN989279; GT0I9SV4F6; CHEMBL3087515; AFQ 056; AFQ-056
CBNumber
CB42510066
Molecular Formula
C19H23NO3
Formula Weight
313.39
MOL File
543906-09-8.mol
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(3aR,4S,7aR)-Octahydro-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]-1H-indole-1-carboxylic acid methyl ester Property

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)
pka
12.75±0.20(Predicted)
form 
Solid
color 
White to Off-White
InChI
InChI=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
InChIKey
ZFPZEYHRWGMJCV-ZHALLVOQSA-N
SMILES
N1(C(OC)=O)[C@@]2([H])[C@]([H])([C@](O)(C#CC3=CC=CC(C)=C3)CCC2)CC1
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML4054
Product name
AFQ056
Purity
≥98% (HPLC)
Packaging
1 unit
Price
$639
Updated
2025/07/31
TRC
Product number
M197920
Product name
Mavoglurant
Packaging
10mg
Price
$445
Updated
2021/12/16
ChemScene
Product number
CS-5245
Product name
Mavoglurant
Purity
99.99%
Packaging
5mg
Price
$420
Updated
2021/12/16
ChemScene
Product number
CS-5245
Product name
Mavoglurant
Purity
99.99%
Packaging
10mg
Price
$540
Updated
2021/12/16
ChemScene
Product number
CS-5245
Product name
Mavoglurant
Purity
99.99%
Packaging
50mg
Price
$1800
Updated
2021/12/16
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(3aR,4S,7aR)-Octahydro-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]-1H-indole-1-carboxylic acid methyl ester Chemical Properties,Usage,Production

Uses

Mavoglurant is a non-competitive metabotropic glutamate receptor 5 (mGlu5) receptor antagonist.

Biological Activity

Orally 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 pmol?mL-1/8400 pmol?g-1; Tmax≤0.08 h.

IC 50

mGluR5: 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

Raw materials

Preparation Products

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

China 53 India 1 United States 4 Global 58
WUHAN SUN-SHINE BIO-TECHNOLOGY Co., Ltd.
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17702719238 18971495150;
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021-58950125
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(86) 21-58955996
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MedChemexpress LLC
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543906-09-8, (3aR,4S,7aR)-Octahydro-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]-1H-indole-1-carboxylic acid methyl esterRelated Search:


  • (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
  • Mavoglurant
  • AFQ 056
  • Mavoglurant, AFQ056
  • UNII-GT0I9SV4F6; AFQ056; MAVOGLURANT; SURECN989279; GT0I9SV4F6; CHEMBL3087515; AFQ 056; AFQ-056
  • CHEMBL3087515
  • GT0I9SV4F6
  • SureCN989279
  • UNII-GT0I9SV4F6
  • 1H-Indole-1-carboxylic acid, octahydro-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]-, methyl ester, (3aR,4S,7aR)-
  • methyl (3aR,4S,7aR)-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]-3,3a,5,6,7,7a-hexahydro-2H-indole-1-carboxylate
  • methyl (3aR,4S,7aR)-4-hydroxy-4-(m-tolylethynyl)octahydro-1H-indole-1-carboxylate
  • 543906-09-8