718635-93-9

Basic information

• Product Name: TETRABENAZINE
• Synonyms: 2H-Benzo[a]quinolizin-2-one, 1,3,4,6,7,11b-hexahydro-9,10-diMethoxy-3-(2-Methylpropyl)-;3-Isobutyl-9,10-dimethoxy-3,4,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-2(11bH)-one;Tetrabenazine (Racemate)
• CAS NO: 718635-93-9
• Molecular Formula: C₁₉H₂₇NO₃
• Molecular Weight: 317.42258
• Mol File: 718635-93-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 125 °C
• Boiling Point: 448.9±45.0 °C(Predicted)
• Appearance: /
• Density: 1.12±0.1 g/cm3(Predicted)
• PKA: 6.46±0.40(Predicted)
• CAS DataBase Reference: TETRABENAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: TETRABENAZINE(718635-93-9)
• EPA Substance Registry System: TETRABENAZINE(718635-93-9)

Safety Data

• Hazardous Substances Data: 718635-93-9(Hazardous Substances Data)

Usage

Description

Tetrabenazine, also known as TBZ, is a synthetic benzoquinone derivative with dopamine-depleting properties. It is a reversible and selective monoamine-depleting agent that works by inhibiting the vesicular monoamine transporter type 2 (VMAT2), leading to the depletion of dopamine in the synaptic cleft. This mechanism of action makes it a potential therapeutic agent for various conditions characterized by hyperdopaminergic activity.
Source:
Tetrabenazine was first synthesized in the 1960s and has been used in the medical field since then.
Production Methods:
Tetrabenazine is produced through a series of chemical reactions involving the synthesis of benzoquinone derivatives.

Uses

Used in Neurological Disorders:
Tetrabenazine is used as a dopamine-depleting medication for the treatment of chorea in Huntington's disease. It helps to alleviate the involuntary movements and motor symptoms associated with the condition by reducing the levels of dopamine in the brain.
Used in Other Hyperdopaminergic Conditions:
Although primarily used for Huntington's disease, Tetrabenazine has also shown potential in the treatment of other hyperdopaminergic conditions, such as tardive dyskinesia, Tourette syndrome, and some cases of dystonia. Its ability to deplete dopamine makes it a candidate for managing symptoms related to excessive dopamine activity in these disorders.

Upstream product

• 14301-36-1 N-[2-(3,4-dimethoxyphenyl)ethyl]formamide 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 1745-07-9 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 67-56-1 methanol 
• 89929-27-1 2-Oxo-3-isobutyl-9,10-dihydroxy-1,2,3,4,6,7-hexahydro-11bH-benzochinolizin 
• 20232-39-7 3,4-dihydro-6,7-dimethoxyisoquinoline hydrochloride 
• 110-12-3 5-Methyl-2-hexanone 
• 91342-74-4 3-[(dimethylamino)methyl]-5-methylhexan-2-one 
• 3382-18-1 6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 1069-62-1 trimethyl[2-(2-methylpropyl)-3-oxobutyl]azanium iodide 

Downstream Products

• 1639208-54-0 (2R,3R,11bR)-3-isobutyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-yl (S)-2-amino-3-methylbutanoate di(4-methylbenzenesulfonate) 
• 1026016-84-1 (3S,11bS)-tetrabenazine 
• 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) 
• 924854-60-4 (+)-β-DHTBZ 
• 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 
• 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 
• 1223399-61-8 C₁₀H₁₆O₄S*C₁₉H₂₇NO₃ 
• 1223399-57-2 (3R,11bR)-tetrabenazine D-camphorsulfonate 
• 3466-75-9 2β-hydroxy-3-isobutyl-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine 
• 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 
• 3466-75-9 Dihydrotetrabenazine 
• 100322-43-8 3-isobutyl-9,10-dimethoxy-3,4,6,7-tetrahydro-2H-benzo[a]quinolizine-2-one 

Relevant articles and documents

PROCESSES FOR THE SYNTHESIS OF VALBENAZINE

The present application relates to processes for making (2R,3R,11bR)-3-isobutyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-yl (S)-2-amino-3-methylbutanoate di(4-methylbenzenesulfonate), which is an inhibitor of vesicular monoamine transporter 2 (VMAT2) useful in the treatment of hyperkinetic movement disorders such as tardive dyskinesia (TD).

Synthetic method for tetrabenazine and intermediate of tetrabenazine

The invention discloses a simple and effective method for synthesizing tetrabenazine (cis-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-3-isobutyl-2H-benzo[a]quinolizin-2-one) and an intermediate of the tetrabenazine. The method comprises the following steps: firstly, paraformaldehyde, dimethylamine hydrochloride and 5-methyl-2-hexanone are taken as raw materials to synthesize a key intermediate 3-dimethylaminomethyl-5-methyl-2-hexanone; secondly, a crude product is effectively optimized by using simple chemical purification operation to obtain a key intermediate with higher purity; and finally, water is taken as a solvent, under the action of a catalyst, the purified key intermediate and 6,7-dimethoxy-3,4-dihydroisoquinoline hydrochloride are subjected to condensation to obtain a tetrabenazine crude product, and recrystallization is performed to obtain the tetrabenazine product, wherein the HPLC purity is greater than 99.5%. According to the method provided by the invention, the key intermediate with higher purity can be obtained by the simple chemical raw materials through synthesis and purification, and therefore the tetrabenazine product with good purity is further obtained; and the raw materials used in the method are easy to obtain, the operation is simple, special equipment is not needed, the yield is higher, and the obtained tetrabenazine has higher purity.

NOVEL PROCESS FOR PREPARATION OF TETRABENAZINE AND DEUTETRABENAZINE

The present invention provides process for preparation of dihydroxy benzoquinoline compound (III) comprising reacting dihydroxy isoquinoline compound (IV) or a salt thereof with (2-acetyl-4-methyl-pentyl)-trimethyl-ammonium iodide (V) and further 5 converting it to tetrabenazine (I) and deutetrabenazine (II).