102771-26-6

Basic information

• Product Name: GYKI 52466 HYDROCHLORIDE
• Synonyms: gyki52466;4-(8-METHYL-9H-1,3-DIOXOLO[4,5-H][2,3]BENZODIAZEPIN-5-YL)-BENZENAMINE HYDROCHLORIDE;GYKI 52466 HYDROCHLORIDE;4-(8-Methyl-(9H)-1,3-dioxolo[4.5-h][2.3]benzodiazepine-5-yl)benzenaminehydrochloride;GYKI52466HCl;1-(4-Aminophenyl)-4-methyl-7,8-(methylenedioxy)-5H-2,3-benzodiazepine;4-(8-Methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine-5-yl)aniline;1-(p-Aminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine hydrochloride
• CAS NO: 102771-26-6
• Molecular Formula: C₁₇H₁₅N₃O₂
• Molecular Weight: 329.78
• Product Categories: Amines, Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 102771-26-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 472.8°C at 760 mmHg
• Flash Point: 239.7°C
• Appearance: yellow/solid
• Density: 1.39
• Vapor Pressure: 4.15E-09mmHg at 25°C
• Storage Temp.: Desiccate at RT
• Solubility: DMSO: 0.39 mg/mL
• PKA: 8.14±0.20(Predicted)
• CAS DataBase Reference: GYKI 52466 HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: GYKI 52466 HYDROCHLORIDE(102771-26-6)
• EPA Substance Registry System: GYKI 52466 HYDROCHLORIDE(102771-26-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-26-36
• WGK Germany: 3
• Hazardous Substances Data: 102771-26-6(Hazardous Substances Data)

Usage

Description

GYKI 52466 HYDROCHLORIDE is a non-competitive AMPA receptor antagonist, which is a type of drug that acts on the AMPA receptors in the brain. It has been identified for its therapeutic potential in the treatment of cocaine addiction.

Uses

Used in Pharmaceutical Industry:
GYKI 52466 HYDROCHLORIDE is used as a therapeutic agent for the treatment of cocaine addiction. It works by blocking the excessive stimulation of AMPA receptors in the brain, which is associated with the rewarding effects of cocaine use. This action helps to reduce the cravings and the reinforcing effects of cocaine, making it a promising candidate for addiction treatment.

Biological Activity

Selective non-competitive AMPA receptor antagonist (IC 50 values are 10-20, ~ 450 and >> 50 μ M for AMPA- , kainate- and NMDA-induced responses respectively). Skeletal muscle relaxant and orally-active anticonvulsant. Has anti-proliferative effects in transformed cells. Also available as part of the AMPA Receptor Tocriset? . Also available as part of the Kainate Receptor Tocriset? .

InChI:InChI=1/C17H15N3O2.ClH/c1-10-6-12-7-15-16(22-9-21-15)8-14(12)17(20-19-10)11-2-4-13(18)5-3-11;/h2-5,7-8H,6,9,18H2,1H3;1H

Upstream product

• 102771-27-7 5-(4-nitrophenyl)-8-methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine 
• 94-59-7 1-allyl-3,4-methylenedioxybenzene 
• 6974-61-4 β-oxy-α-(3',4'-methylenedioxyphenyl)propane 
• 4676-39-5 1-(1,3-benzodioxol-5-yl)-2-propanone 
• 433716-67-7 2-(4-nitrobenzoyl)-4,5-methylenedioxyphenylacetone 
• 7440-05-3 palladium 

Downstream Products

• 114460-08-1 GYKI 52895 
• 143692-25-5 1-(4-Methylcarbamoylaminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine 

Relevant articles and documents

A simple and efficient synthesis of GYKI 52466 and GYKI 52895

The synthesis of 1-(4-aminophenyl)-4-methyl-7,8-methylene-dioxy-5H-2,3-benzodiazepine (GYKI 52466, 1), the prototype of a series of noncompetitive AMPA receptor antagonists, and its 3,4-dihydroderivative (GYKI 52895, 2) is described. The title compounds have been prepared starting from safrole through a quite effective procedure.