924854-60-4

Basic information

• Product Name: 2H-Benzo[a]quinolizin-2-ol, 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-, (2S,3R,11bR)-
• Synonyms: 2H-Benzo[a]quinolizin-2-ol, 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-, (2S,3R,11bR)-;(2S,3R,11bR)-3-isobutyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-ol;(2S,3R,11bR);-3-Isobutyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-ol
• CAS NO: 924854-60-4
• Molecular Formula: C19H29NO3
• Molecular Weight: 319.44
• Product Categories: Impurities & Metabolites
• Mol File: 924854-60-4.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 457.8±45.0 °C(Predicted)
• Appearance: /
• Density: 1.13±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 14.75±0.40(Predicted)
• CAS DataBase Reference: 2H-Benzo[a]quinolizin-2-ol, 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-, (2S,3R,11bR)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Benzo[a]quinolizin-2-ol, 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-, (2S,3R,11bR)-(924854-60-4)
• EPA Substance Registry System: 2H-Benzo[a]quinolizin-2-ol, 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-, (2S,3R,11bR)-(924854-60-4)

Safety Data

• Hazardous Substances Data: 924854-60-4(Hazardous Substances Data)

Usage

Uses

(+)-β-Dihydrotetrabenazine is a potent inhibitor of vascular monoamine transporter 2 (VMAT2) and an agent of significant interest for therapeutic and molecular imaging applications.

InChI:InChI=1S/C19H29NO3/c1-12(2)7-14-11-20-6-5-13-8-18(22-3)19(23-4)9-15(13)16(20)10-17(14)21/h8-9,12,14,16-17,21H,5-7,10-11H2,1-4H3/t14-,16-,17+/m1/s1

Upstream product

• 718635-93-9 tetrabenazine 
• 58-46-8 (3R^*,11bR^*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one 
• 1148116-71-5 C₁₀H₁₆O₄S*C₁₉H₂₉NO₃ 
• 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) 
• 718635-93-9 (3RS,11bRS)-tetrabenazine 
• 1091627-85-8 C₂₄H₃₇NO₅ 
• 1091627-89-2 (R)-tert-butyl 6,7-dimethoxy-1-(5-methyl-3-methylene-2-oxohexyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 

Downstream Products

• 862377-27-3 (2S,3S,11bR)-1,3,4,6,7,11b-hexahydro-9,10-methoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-ol 
• 862377-31-9 (2R,3S,11bR)-1,3,4,6,7,11b-hexahydro-9,10-methoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-ol 

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.

FLUORINATED DIHYDROTETRABENAZINE ETHER IMAGING AGENTS AND PROBES

The present invention provides novel fluorinated ether compounds having structure I wherein R1 is a C2-C10 fluorinated aliphatic radical; R2 is a C1-C10 aliphatic radical, or a C3/sub

Asymmetric synthesis of tetrabenazine and dihydrotetrabenazine

(Chemical Equation Presented) The enantioselective synthesis of (+)-tetrabenazine (TBZ) and (+)-dihydrotetrabenazine (DTBZ), agents of significant interest for therapeutic and molecular imaging applications, has been completed in 21% (TBZ) and 16% (DTBZ)