(+)-Tetrabenazine

Base Information

• Chemical Name: (+)-Tetrabenazine
• CAS No.: 1026016-83-0
• Molecular Formula: C19H27NO3
• Molecular Weight: 317.42
• UNII: 69ENL3U6BF
• DSSTox Substance ID: DTXSID101117156
• Nikkaji Number: J2.727.068I
• Wikidata: Q27132977
• Pharos Ligand ID: 44CJ21UJTQZT
• Metabolomics Workbench ID: 63097
• ChEMBL ID: CHEMBL61636
• Mol file: 1026016-83-0.mol

Synonyms:(+)-Tetrabenazine;1026016-83-0;(3R,11Br)-Tetrabenazine;Tetrabenazine (+)-;Tetrabenazine, (+)-;(+)-Tbz;(3R,11bR)-Tbz;Tetrabenazine R,R-form [MI];(3R,11bR)-3-isobutyl-9,10-dimethoxy-3,4,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-2(11bH)-one;UNII-69ENL3U6BF;69ENL3U6BF;CHEMBL61636;CHEBI:64029;(3R,11bR)-9,10-dimethoxy-3-(2-methylpropyl)-1,3,4,6,7,11b-hexahydrobenzo[a]quinolizin-2-one;(+)-Ro 1-9569;(3R,11bR)-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo(a)quinolizin-2-one;2H-Benzo(a)quinolizin-2-one, 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-, (3R,11bR)-;(-)-tetrabenazine;(3R,11bR)-3-Isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-pyrido[2,1-a]isoquinolin-2-one;(3R,11bR)-9,10-dimethoxy-3-(2-methylpropyl)-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one;(3R,11bR)-9,10-dimethoxy-3-(2-methylpropyl)-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-one;(3R,11bR)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one;(R,R)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-one;(3R,11bR)-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-one;Tetrabenazine ((+)-);SCHEMBL340173;HY-B0590B;DTXSID101117156;BDBM50048891;AKOS025290764;CS-5827;Tetrabenazine, >=98% (HPLC), solid;AC-22623;AS-74541;D97714;P10603;EN300-7433031;A896752;BRD-K24125544-001-01-3;Q27132977;(3R,11bR)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one

Chemical Property of (+)-Tetrabenazine

Chemical Property:

• Melting Point: 108-110 °C
• Boiling Point: 448.9 °C at 760 mmHg
• PKA: 6.46±0.40(Predicted)
• Flash Point: 225.3 °C
• PSA: 38.77000
• Density: 1.12g/cm³
• LogP: 3.17600
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Chloroform (Slightly), Dichloromethane (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 317.19909372
• Heavy Atom Count: 23
• Complexity: 425

Purity/Quality:

99% ^*data from raw suppliers

(3R,11bR)-Tetrabenazine ^*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=C3C2CC1=O)OC)OC
• Isomeric SMILES: CC(C)C[C@@H]1CN2CCC3=CC(=C(C=C3[C@H]2CC1=O)OC)OC
• Uses: (3R,11bR)-Tetrabenazine is an isomer of Tetrabenazine (T284000), a dopamine depleting agent, an antidyskinetic and antipsychotic.

Technology Process of (+)-Tetrabenazine

There total 31 articles about (+)-Tetrabenazine 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: 90.75%

(3R,11bR)-3-isobutyl-9,10-dimethoxy-2-oxo-1,2,3,4,5,6,7,11b-octahydropyrido[2,1-a]isoquinolin-5-ium (2S,3S)-3-carboxy-2,3-bis((4-methylbenzoyl)oxy)propanoate → ((3R,11bR)-3-isobutyl-9.10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one) (1026016-83-0,1381929-92-5)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; water; at 0 ℃; for 17h;

Reference yield: 82.2%

tetrabenazine (718635-93-9,1381929-92-5) → ((3R,11bR)-3-isobutyl-9.10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one) (1026016-83-0,1381929-92-5)

Guidance literature:

With camphor-10-sulfonic acid; In ethyl acetate; for 52h; Solvent; Reflux;

Reference yield: 72.0%

(2R,3R,11bR)-dihydrotetrabenazine → ((3R,11bR)-3-isobutyl-9.10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one) (1026016-83-0,1381929-92-5)

Guidance literature:

(2R,3R,11bR)-dihydrotetrabenazine; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -60 ℃; for 2h; Inert atmosphere;

With triethylamine; In dichloromethane; at -60 - 20 ℃;

DOI:10.1080/00397910902788125

upstream raw materials:

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

(R)-tert-butyl 6,7-dimethoxy-1-(5-methyl-3-methylene-2-oxohexyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

(3R,11bR)-tetrabenazine D-camphorsulfonate

(R)-10-camphorsulfonic acid

Downstream raw materials:

(+)-β-DHTBZ

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

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

(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)

Refernces

• 1、 Rishel, Michael J.,Amarasinghe, Kande K. D.,Dinn, Sean R.,Johnson, Bruce F.. "Asymmetric synthesis of tetrabenazine and dihydrotetrabenazine". . p. 4001 - 4004. Retrieved 2009.
• 2、 -. "Preparation method of benzoquinolizine derivative". Paragraph 0035; 0037; 0039. . Retrieved 2020/07/06.
• 3、 -. "CRYSTALLINE VALBENAZINE FREE BASE". Page/Page column 18. . Retrieved 2018/08/03.