1065193-59-0

Basic information

• Product Name: (+)-9-deMe-DTBZ
• Synonyms: (2R,3R,11bR)-1,3,4,6,7,11b-Hexahydro-10-methoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizine-2,9-diol;(+)-9-O-Desmethyl-a-dihydrotetrabenazine;(2R,3R,11bR)-3-isobutyl-10-methoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline-2,9-diol
• CAS NO: 1065193-59-0
• Molecular Formula: C₁₈H₂₇NO₃
• Molecular Weight: 305.41188
• Product Categories: Heterocycles, Derivatives, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 1065193-59-0.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly, Heated), Methanol (Slightly, Sonicated)
• CAS DataBase Reference: (+)-9-deMe-DTBZ(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-9-deMe-DTBZ(1065193-59-0)
• EPA Substance Registry System: (+)-9-deMe-DTBZ(1065193-59-0)

Safety Data

• Hazardous Substances Data: 1065193-59-0(Hazardous Substances Data)

Usage

Description

(+)-9-deMe-DTBZ, a desmethyl derivative of Tetrabenzine (T284000), is a dopamine depleting agent with potential applications in the treatment of various conditions related to dopamine dysregulation. It possesses antidyskinetic and antipsychotic properties, making it a promising candidate for pharmaceutical development.

Uses

Used in Pharmaceutical Industry:
(+)-9-deMe-DTBZ is used as an antidyskinetic agent for the treatment of dyskinesias, which are involuntary muscle movements often associated with conditions like Huntington's disease. Its dopamine depleting action helps alleviate the symptoms and improve the quality of life for patients.
(+)-9-deMe-DTBZ is also used as an antipsychotic agent for the management of psychotic disorders, such as schizophrenia. Its ability to modulate dopamine levels in the brain contributes to the reduction of psychotic symptoms and provides a potential alternative or adjunct to conventional antipsychotic medications.

Upstream product

• 1141448-87-4 (2R,3R,11bR)-9-(benzyloxy)-3-isobutyl-10-methoxy-2,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-ol 
• 7744-58-3 9-(benzyloxy)-3-isobutyl-10-methoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one 
• 110-12-3 5-Methyl-2-hexanone 
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• 91342-74-4 3-[(dimethylamino)methyl]-5-methylhexan-2-one 
• 68360-20-3 N-formyl-3-benzyloxy-4-methoxyphenethylamine 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 
• 63909-29-5 (E)-2-(benzyloxy)-1-methoxy-4-(2-nitrovinyl)benzene 
• 36455-21-7 3-benzyloxy-4-methoxyphenylethylamine 
• 68360-22-5 6-(benzyloxy)-7-methoxy-3,4-dihydroisoquinoline 
• 1069-62-1 trimethyl[2-(2-methylpropyl)-3-oxobutyl]azanium iodide 

Relevant articles and documents

The synthesis of precursor of FP- (+) DTBZ

A synthetic route to the precursor of FP- (+) DTBZ was disclosed, in which 3-hydroxy-4-methoxybenzaldehyde was employed as a starting material. In the method, the benzyl-protecting protocol and the in-situ Diels-Alder reaction made the procedure more practical because of the mild conditions for selectively deprotection and the accelerated reaction process.

Deuterated 18F-9-O-hexadeutero-3-fluoropropoxyl-(+)-dihydrotetrabenazine (D6-FP-(+)-DTBZ): A vesicular monoamine transporter 2 (VMAT2) imaging agent

Introduction Vesicular monoamine transporters 2 (VMAT2) in the brain serve as transporter for packaging monoamine in vesicles for normal CNS neurotransmission. Several VMAT2 imaging agents, [11C]-(+)-DTBZ, dihydrotetrabenazine and [18F]FP-(+)-DTBZ (9-O-fluoropropyl-(+)-dihydro tetrabenazine, a.k.a. [18F]AV-133), are useful for studying the changes in brain function related to monoamine transmission by in vivo imaging. Deuterated analogs have been reported targeting VMAT2 binding sites. Methods A novel deuterated [18F]9-O-hexaduterofluoropropyl-(+)-dihydrotetrabenazine, [18F]D6-FP-(+)-DTBZ, [18F]1, was prepared as a VMAT2 imaging agent. This 18F agent which targeted VMAT2 was evaluated by in vitro binding, in vivo biodistribution and microPET imaging studies in rodents. Results The one step radiolabeling reaction led to the desired [18F]D6-FP-(+)-DTBZ, [18F]1, which showed excellent binding affinity to VMAT2 (Ki = 0.32 ± 0.07 nM) comparable to that of FP-(+)-DTBZ (Ki = 0.33 ± 0.02 nM) using [18F]FP-(+)-DTBZ and rat striatum membrane homogenates. In vivo biodistribution in normal rats showed that 1, exhibited excellent brain uptake and comparable high ratio of striatum to cerebellum (target/background) ratio at 1 h after injection (ratio of 6.05 ± 0.43 vs 5.66 ± 0.72 for [18F]FP-(+)-DTBZ vs [18F]1, respectively). MicroPET imaging studies in rats further confirm that the striatum with high VMAT2 concentration was clearly delineated in normal rat brain after iv injection of [18F]1. We observed minor changes of metabolism in rat plasma between these two agents; however, the changes showed little effect on regional brain uptake and retention. Conclusions The results reported here lend support for using [18F]D6-FP-(+)-DTBZ, [18F]1, as in vivo PET imaging agent for VMAT2 binding in the brain.