862377-31-9

Basic information

• Product Name: (2R,3S,11bR)-1,3,4,6,7,11b-hexahydro-9,10-methoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-ol
• CAS NO: 862377-31-9
• Molecular Weight: 319.444
• Mol File: 862377-31-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 457.8±45.0 °C(Predicted)
• Density: 1.13±0.1 g/cm3(Predicted)
• CAS DataBase Reference: (2R,3S,11bR)-1,3,4,6,7,11b-hexahydro-9,10-methoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,11bR)-1,3,4,6,7,11b-hexahydro-9,10-methoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-ol(862377-31-9)
• EPA Substance Registry System: (2R,3S,11bR)-1,3,4,6,7,11b-hexahydro-9,10-methoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-ol(862377-31-9)

Safety Data

• Hazardous Substances Data: 862377-31-9(Hazardous Substances Data)

Usage

Uses

(2R,3S,11bR)-Dihydrotetrabenazine is an enantiomer of?(2S,3R,11bS)-Dihydrotetrabenazine (D454920). Tetrabenazine?and dihydrotetrabenazines are potent inhibitors of?vesicular monoamine transporter 2?(VMAT2). Furthermore, the derivatives of these compounds are potential drug candidates for treating various diseases such as?Huntington’s disease and other hyperkinetic disorders.

Upstream product

• 924854-60-4 (+)-β-DHTBZ 
• 58-46-8 (3R^*,11bR^*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one 
• 718635-93-9 (3RS,11bRS)-tetrabenazine 
• 1300639-86-4 (8aS,9aR,10aR)-5,8,8a,9a,10,10a-hexahydro-2,3-dimethoxy-8a-(2-methylpropyl)-6H-benz[a]oxireno[g]quinolizine 
• 920265-21-0 (11bR)-1,6,7,11b-tetrahydro-9,10-dimethoxy-3-(2-methylpropyl)-4H-benzo[a]quinolizine 
• 1026016-83-0 ((3R,11bR)-3-isobutyl-9.10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one) 
• 920265-22-1 C₁₉H₂₇NO₃ 
• 862287-33-0 C₁₉H₂₇NO₃ 
• 862287-34-1 C₂₉H₃₆F₃NO₅ 

Relevant articles and documents

Preparation and evaluation of tetrabenazine enantiomers and all eight stereoisomers of dihydrotetrabenazine as VMAT2 inhibitors

Tetrabenazine (TBZ) ((±)-1) and dihydrotetrabenazines (DHTBZ) are potent inhibitors of VMAT2. Herein, a practical chemical resolution of (±)-1 and stereoselective synthesis of all eight DHTBZ stereoisomers are described. The result of VMAT2 binding assay revealed that (+)-1 (Ki = 4.47 nM) was 8000-fold more potent than (-)-1 (Ki = 36,400 nM). Among all eight DHTBZ stereoisomers, (2R,3R,11bR)-DHTBZ ((+)-2: Ki = 3.96 nM) showed the greatest affinity for VMAT2. The (3R,11bR)-configuration appeared to play a key role for VMAT2 binding. In summary, (+)-1, (+)-2, and their derivatives warrant further studies in order to develop more potent and safer drugs for the treatment of chorea associated with Huntington's disease and other hyperkinetic disorders.

3 , llB-CIS-DIHYDROTETRABENAZINE FOR THE TREATMENT OF A PROLIFERATIVE DISEASE OR AN INFLAMMATION

The invention provides the use of a compound for the manufacture of a medicament for the prophylaxis or treatment of a proliferative disease or an inflammatory disease, the compound being 3,1lb-cis-dihydrotetrabenazine or a pharmaceutically acceptable sal