Dihydrotetrabenazine

Base Information

• Chemical Name: Dihydrotetrabenazine
• CAS No.: 3466-75-9
• Molecular Formula: C19H29 N O3
• Molecular Weight: 319.4385
• Hs Code.: 2933990090
• European Community (EC) Number: 948-387-3
• DSSTox Substance ID: DTXSID90956148
• Nikkaji Number: J440.810A
• Wikipedia: Dihydrotetrabenazine
• Pharos Ligand ID: 44G8CHGFQGRX
• ChEMBL ID: CHEMBL4206824
• Mol file: 3466-75-9.mol

Synonyms:2-hydroxy-3-isobutyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzo(a)quinolizine;2-hydroxytetrabenazine;dihydrotetrabenazine;dihydrotetrabenazine, (2alpha,3beta,11bbeta)-isomer;TBZOH cpd

Chemical Property of Dihydrotetrabenazine

Chemical Property:

• Vapor Pressure: 3.56E-09mmHg at 25°C
• Boiling Point: 457.8 °C at 760 mmHg
• Flash Point: 230.7 °C
• PSA: 41.93000
• Density: 1.13 g/cm³
• LogP: 2.96780
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 319.21474379
• Heavy Atom Count: 23
• Complexity: 389

Purity/Quality:

98%min ^*data from raw suppliers

HydroxyTetrabenazine-MixtureofcisandtransIsomers ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC1CN2CCC3=CC(=C(C=C3C2CC1O)OC)OC
• Description: Dihydrotetrabenazine is an active metabolite of the vesicular monoamine transporter 2 (VMAT2) inhibitor tetrabenazine that is generated by hepatic carbonyl reductases. Dihydrotetrabenazine binds to mouse pons medulla, hypothalamus, and striatum (Kds = 2.72, 2.28, and 2.4 nM, respectively) and inhibits synaptic vesicular serotonin (5-HT) uptake (IC50s = 2.2, 2.8, and 2.3 nM, respectively). It also binds to human caudate nucleus, hippocampus, and substantia nigra pars compacta (Kds = 2.9, 2.5, and 2.8 nM, respectively). Dihydrotetrabenazine stereoisomers bind to VMAT2 in rat striatum.

Technology Process of Dihydrotetrabenazine

There total 30 articles about Dihydrotetrabenazine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

tetrabenazine (718635-93-9,1381929-92-5) → Dihydrotetrabenazine (3466-75-9)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 20 ℃; for 1h;

Reference yield: 80.0%

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one (58-46-8,1381929-92-5) → 2α-hydroxy-3-isobutyl-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine (3466-75-9,7744-53-8,7744-54-9,85081-18-1,113627-25-1)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 - 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol202792q

Reference yield: 80.0%

tetrabenazine (718635-93-9,1381929-92-5) → 2β-hydroxy-3-isobutyl-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine (3466-75-9,7744-53-8,7744-54-9,85081-18-1,113627-25-1)

Guidance literature:

With L-selectride; In tetrahydrofuran; ethanol; at 0 - 20 ℃; for 1h; Product distribution / selectivity;

upstream raw materials:

(3R^*,11bR^*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

4-methyl-2-(3-(trimethylsilyl)prop-1-ene-2-yl)pentyl-4-methylbenzenesulfonate

6,7-dimethoxy-2-(4-methyl-2-(3-(trimethylsilyl)prop-1-ene-2-yl)pentyl)-1,2,3,4-tetrahydroisoquinoline

methyl 4-methyl-2-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)pentanoate

Downstream raw materials:

C₂₉H₃₆F₃NO₅

C₂₉H₃₆F₃NO₅

C₂₉H₃₆F₃NO₅

C₂₉H₃₆F₃NO₅

Refernces

• 1、 -. "PROCESSES FOR THE SYNTHESIS OF VALBENAZINE". Page/Page column 66-67. . Retrieved 2021/03/19.
• 2、 -. "SYNTHETIC METHODS FOR PREPARATION OF (S)-(2R,3R,11bR)-3-ISOBUTYL-9,10-DIMETHOXY-2,3,4,6,7,11b-HEXAHYDRO-1H-PYRIDO[2,1-a]ISOQUINOLIN-2-YL 2-AMINO-3-METHYLBUTANOATE DI(4-METHYLBENZENESULFONATE)". Paragraph 0166; 0167. . Retrieved 2017/07/14.