1381929-92-5

Basic information

• Product Name: C₁₉H₂₇NO₃
• CAS NO: 1381929-92-5
• Molecular Weight: 317.428
• Mol File: 1381929-92-5.mol
• Article Data: 32

Chemical Properties

• CAS DataBase Reference: C₁₉H₂₇NO₃(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₉H₂₇NO₃(1381929-92-5)
• EPA Substance Registry System: C₁₉H₂₇NO₃(1381929-92-5)

Safety Data

• Hazardous Substances Data: 1381929-92-5(Hazardous Substances Data)

Usage

Description

C₁₉H₂₇NO₃, also known as trans-Tetrabenazine, is a chemical compound that is the trans isomer of Tetrabenazine. It is a dopamine depleting agent with properties that make it useful in various medical applications.

Uses

Used in Neurological Applications:
C₁₉H₂₇NO₃ is used as an antidyskinetic agent for the treatment of movement disorders, such as Huntington's disease. It works by depleting dopamine in the brain, which helps to reduce the severity of involuntary movements associated with these conditions.
Used in Psychiatry:
C₁₉H₂₇NO₃ is used as an antipsychotic medication to manage symptoms of certain psychiatric disorders. Its dopamine depleting action helps to alleviate symptoms like hallucinations, delusions, and agitation in patients.
Used in Drug Delivery Systems:
Similar to gallotannin, C₁₉H₂₇NO₃ can also be incorporated into drug delivery systems to enhance its efficacy and bioavailability. These systems may include various organic and metallic nanoparticles as carriers, aiming to improve the delivery and therapeutic outcomes of the compound in treating the targeted conditions.

Upstream product

• 3382-18-1 6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 1069-62-1 trimethyl[2-(2-methylpropyl)-3-oxobutyl]azanium iodide 
• 91342-74-4 3-[(dimethylamino)methyl]-5-methylhexan-2-one 
• 20232-39-7 3,4-dihydro-6,7-dimethoxyisoquinoline hydrochloride 
• 1187-87-7 5-methyl-3-methylidenehexan-2-one 
• 110-12-3 5-Methyl-2-hexanone 
• 58-46-8 (3R^*,11bR^*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one 
• 1745-07-9 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 51756-09-3 methyl 2-acetyl-4-methylpentanoate 
• 1091627-89-2 (R)-tert-butyl 6,7-dimethoxy-1-(5-methyl-3-methylene-2-oxohexyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 1091627-85-8 C₂₄H₃₇NO₅ 
• 718635-93-9 tetrabenazine 
• 244177-70-6 (4S,5R)-3-((2S,3R)-2-isobutyl-3-hydroxypent-4-enoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-on 
• 244177-76-2 (2S,3R)-3-(tert-butyldimethylsilanyloxy)-2-isobutylpent-4-enoic acid 

Downstream Products

• 862377-29-5 S,R,R-DHTBZ 
• 862377-33-1 RU 346 
• 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 
• 1147130-19-5 C₂₉H₄₁NO₄ 
• 1147130-24-2 C₂₈H₃₉NO₆S 
• 100322-43-8 3-isobutyl-9,10-dimethoxy-3,4,6,7-tetrahydro-2H-benzo[a]quinolizine-2-one 

Relevant articles and documents

Novel Process for Preparation of Tetrabenazine and Deutetrabenazine

A novel process for the synthesis of tetrabenazine (1) and deutetrabenazine (2), two well-known drugs used for the treatment of chorea associated with Huntington's disease, has been developed. All of the reaction parameters were optimized through a series of reactions and by using Design of Experiment techniques. The newly developed methods are industrially scalable and employ cheap, commercially available raw materials and hence are highly efficient. The added advantage is that the developed processes evade the use of genotoxic alkylating agents and therefore could be considered as safe and viable alternatives to the existing methods.

Synthesis of (±)-Tetrabenazine by Visible Light Photoredox Catalysis

(±)-Tetrabenazine was synthesized in six steps from commercially available compounds. The key cyclization substrate was assembled rapidly via Baylis-Hillman and aza-Michael reactions. Annulation of the final ring was achieved through visible light photocatalysis, wherein carbon-carbon bond formation was driven by the oxidation of a tertiary amine. Solvent played a critical role in the photoredox cyclization outcome, whereas methanol led to a mixed ketal, acetonitrile/water (10:1) gave direct cyclization to (±)-tetrabenazine and occurred more rapidly.

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).

Dynamic resolution method of tetrabenazine

The invention provides a dynamic resolution method of tetrabenazine, and belongs to the field of medicinal chemical industry. The method can be used for resolving tetrabenazine to obtain (3R,11bR)-tetrabenazine. The method comprises the following steps: mixing and reacting a resolving reagent is with tetrabenazine to obtain a desired configuration, performing separation, and then carrying out alkali dissociation to obtain the (3R,11bR)-tetrabenazine. The analytical method can effectively separate tetrabenazine, and has the advantages of high product purity, high yield, simplicity in operationand solvent recoverability.