1026016-84-1

Basic information

• Product Name: 2H-BENZO[A]QUINOLIZIN-2-ONE, 1,3,4,6,7,11B-HEXAHYDRO-9,10-DIMETHOXY-3-(2-METHYLPROPYL)-, (3S,11BS)-
• Synonyms: 2H-BENZO[A]QUINOLIZIN-2-ONE, 1,3,4,6,7,11B-HEXAHYDRO-9,10-DIMETHOXY-3-(2-METHYLPROPYL)-, (3S,11BS)-;2H-Benzo[a]quinolizin-2-one, 1,3,4,6,7,11b-hexahyd;(3S,11bS)-1,3,4,6,7,11b-Hexahydro-9,10-diMethoxy-3-(2-Methylpropyl)-2H-benzo[a]quinolizin-2-one;(3S,11bS);(3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one
• CAS NO: 1026016-84-1
• Molecular Formula: C19H27NO3
• Molecular Weight: 317.42258
• Mol File: 1026016-84-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Dichloromethane (Slightly), Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 2H-BENZO[A]QUINOLIZIN-2-ONE, 1,3,4,6,7,11B-HEXAHYDRO-9,10-DIMETHOXY-3-(2-METHYLPROPYL)-, (3S,11BS)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-BENZO[A]QUINOLIZIN-2-ONE, 1,3,4,6,7,11B-HEXAHYDRO-9,10-DIMETHOXY-3-(2-METHYLPROPYL)-, (3S,11BS)-(1026016-84-1)
• EPA Substance Registry System: 2H-BENZO[A]QUINOLIZIN-2-ONE, 1,3,4,6,7,11B-HEXAHYDRO-9,10-DIMETHOXY-3-(2-METHYLPROPYL)-, (3S,11BS)-(1026016-84-1)

Safety Data

• Hazardous Substances Data: 1026016-84-1(Hazardous Substances Data)

Usage

Uses

(-)-Tetrabenazine is a potent inhibitors of vascular monoamine transporter 2 (VMAT2) and may be applicable towards the treatment of chorea associated with Huntington’s disease.

Definition

ChEBI: A 9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one in which both stereocentres have S configuration.

Upstream product

• 58-46-8 (3R^*,11bR^*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one 
• 1223399-61-8 C₁₀H₁₆O₄S*C₁₉H₂₇NO₃ 
• 3144-16-9 (1S)-10-camphorsulfonic acid 
• 718635-93-9 tetrabenazine 

Downstream Products

• 862377-29-5 S,R,R-DHTBZ 
• 924854-62-6 (2R,3S,11bS)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-ol 
• 862377-33-1 RU 346 

Relevant articles and documents

Preparation method of benzoquinolizine derivative

The invention relates to a preparation method of a benzoquinolizine derivative, belongs to the technical field of medicinal chemistry, and particularly relates to a chiral resolution method of tetrabenazine. (3R, 11bR)-tetrabenazine or (3S, 11bS)-tetrabenazine with high optical purity is simply, conveniently and effectively prepared by taking tetrabenazine racemate as a raw material through the steps of salifying with chiral acid, pulping, dissociating and the like. Compared with the prior art, the method has the advantages of mild reaction conditions in each step, high yield, simplicity and convenience in operation, stable process and suitability for large-scale industrial production.

Preparation and characterization of tetrabenazine enantiomers against vesicular monoamine transporter 2

As a clinical medication for the treatment of hyperkinetic movement disorders, in conditions such as Huntington's disease, tetrabenazine (TBZ) has always been used in its racemic form. To establish whether or not its beneficial therapeutic actions are enantiospecific, a practical total synthetic route was developed to yield each enantiomeric form to allow their chemical and pharmacological characterization. We briefly summarize the total synthesis of TBZ and report a detailed procedure for resolution of TBZ into its enantiomers, (+)-TBZ and (-)-TBZ. This allowed determination of the optical rotation and absolute configurations of each TBZ enantiomer, based on X-ray crystallographic analysis, together with characterization of their inhibitory action at the vesicular monoamine transporter 2, where (+)-TBZ proved 3-fold more active than (-)-TBZ.

SUBSTITUTED 3-ISOBUTYL-9, 10-DIMETHOXY-1,3,4,6,7,11B-HEXAHYDRO-2H-PYRIDO[2,1-A] ISOQUINOLIN-2-OL COMPOUNDS AND METHODS RELATING THERETO

Substituted 3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-ol compounds are disclosed that are inhibitors of the vesicular monoamine transporter 2 (VMAT2). The compounds of this invention have the structure (I): wherein R1 is as defined herein, including stereoisomers and pharmaceutically acceptable salts and solvates thereof. Also disclosed are compositions containing a compound of this invention in combination with a pharmaceutically acceptable carrier, as well as methods relating to the use in a subject in need thereof.