(+)-alpha-Dihydrotetrabenazine

Base Information

• Chemical Name: (+)-alpha-Dihydrotetrabenazine
• CAS No.: 85081-18-1
• Molecular Formula: C₁₉H₂₉NO₃
• Molecular Weight: 319.444
• European Community (EC) Number: 948-387-3,809-846-2
• UNII: IFRYDMLSGE,OHZ3DQX6Q3
• ChEMBL ID: CHEMBL576222
• DSSTox Substance ID: DTXSID30561896
• Nikkaji Number: J664.543G
• Wikidata: Q27216116
• Mol file: 85081-18-1.mol

Synonyms:85081-18-1;NBI-98782;(+)-ALPHA-DIHYDROTETRABENAZINE;IFRYDMLSGE;(+)-Dihydrotetrabenazine;(+)-Dtbz;2H-Benzo[a]quinolizin-2-ol, 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-, (2R,3R,11bR)-;UNII-IFRYDMLSGE;(+)-dihydrotetrabenzaine;alpha-dihydrotetrabenazine;OHZ3DQX6Q3;(2R,3R,11bR)-9,10-dimethoxy-3-(2-methylpropyl)-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-ol;Tetrabenazine metabolite M6;(+)-(2R,3R,11bR)-Dihydrotetrabenazine;CHEMBL576222;Dihydrotetrabenazine, (+)-alpha-;SD-946;171598-74-6;Trans (2,3)-Dihydrotetrabenazine;trans (2,3)-Dihydro Tetrabenazine;2H-Benzo(a)quinolizin-2-ol, 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-, (2R,3R,11bR)-rel-;2R,3R,11bR)-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo(a)quinolizin-2-ol;Rel-(2R,3R,11bR)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo(a)quinolizin-2-ol;alpha-Htbn;MFCD08061467;(2R,3R,11BR)-1,3,4,6,7,11B-HEXAHYDRO-9,10-DIMETHOXY-3-(2-METHYLPROPYL)-2H-BENZO(A)QUINOLIZIN-2-OL;(2R,3R,11bR)-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benZo[a]quinoliZin-2-ol;[2R-(2a,3b,11bb)]-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-ol;(+/-)-alpha-Htbn;.ALPHA.-HTBN;UNII-OHZ3DQX6Q3;SCHEMBL871659;WEQLWGNDNRARGE-DJIMGWMZSA-;DTXSID30561896;(+/-)-.ALPHA.-HTBN;CHEBI:125495;WEQLWGNDNRARGE-DJIMGWMZSA-N;AC9494;BDBM50301021;AKOS015851828;CS-1899;AC-22624;HY-15793;WS-01865;DIHYDROTETRABENAZINE, (+)-.ALPHA.-;A915039;(+)-DTBZ;(+)--Dihydrotetrabenazine;(+)--DHTBZ;BRD-K15241725-001-01-0;Q27216116;(2R,3R,11bR)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-ol;(2R,3R,11bR)-9,10-Dimethoxy-3-(2-methylpropyl)-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-ol;InChI=1/C19H29NO3/c1-12(2)7-14-11-20-6-5-13-8-18(22-3)19(23-4)9-15(13)16(20)10-17(14)21/h8-9,12,14,16-17,21H,5-7,10-11H2,1-4H3/t14-,16-,17-/m1/s1

Chemical Property of (+)-alpha-Dihydrotetrabenazine

Chemical Property:

• Melting Point: 106-108 °C(Solv: hexane (110-54-3))
• Boiling Point: 457.8±45.0 °C(Predicted)
• PKA: 14.75±0.40(Predicted)
• PSA: 41.93000
• Density: 1.13
• 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

(+)-α-Dihydrotetrabenazine ^*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
• Isomeric SMILES: CC(C)C[C@@H]1CN2CCC3=CC(=C(C=C3[C@H]2C[C@H]1O)OC)OC
• Recent EU Clinical Trials: Randomized, double-blind, placebo controlled clinical trial of (+)-α-dihydrotetrabenazine in patients with moderate to severe tardive dyskinesia.
• Uses: (+)-α-Dihydrotetrabenazine is a potent inhibitor of vascular monoamine transporter 2 (VMAT2) and an agent of significant interest for therapeutic and molecular imaging applications.

Technology Process of (+)-alpha-Dihydrotetrabenazine

There total 17 articles about (+)-alpha-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: 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;

Reference yield: 67.0%

(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) → 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 0.5 - 6.5h; 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、 Son, Young Wook,Kwon, Tae Hui,Lee, Jae Kyun,Pae, Ae Nim,Lee, Jae Yeol,Cho, Yong Seo,Min, Sun-Joon. "A concise synthesis of tetrabenazine: An intramolecular aza-prins-type cyclization via oxidative c-h activation". . p. 6500 - 6503. Retrieved 2012/02/02.
• 2、 -. "USE OF 3,1IB-CIS-DIHYDROTETRABENAZINE FOR THE TREATMENT OF SYMPTONS OF HUNTINGTON' S DISEASE". Page/Page column 25; 26; 31. . Retrieved 2008/06/13.