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ChemicalBook CAS DataBase List Tetrabenazine
58-46-8

Tetrabenazine synthesis

1synthesis methods
Tetrabenazine is a drug for the symptomatic treatment of hyperkinetic movement disorder. On August 15, 2008 the U.S. Food and Drug Administration (FDA) approved the use of tetrabenazine to treat chorea associated with Huntington's disease (HD), the first in the US. The precise mechanism of action of tetrabenazine is unknown. The antichorea effect is believed to be related to its effect as a reversible depletory of monoamines (such as dopamine, serotonin, norepinephrine and histamine)from nerve terminals) Tetrabenazine reversibly inhibits VMAT-2 resulting in decreased of monamines into synaptic vesicles
Synthetic Routes
  • ROUTE 1

    • 202112070939519906.jpg

    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. Organic Letters. Volume 13. Issue 24. Pages 6500-6503. 2011.

  • ROUTE 2

    • 202112078690936483.jpg

    Chen, Weijie; Seidel, Daniel. Redox-Annulation of Cyclic Amines and β-Ketoaldehydes. Organic Letters. Volume 18. Issue 5. Pages 1024-1027. 2016.

  • ROUTE 3

    • 202112072483806444.jpg

    Gano, Kyle W. Preparation of pyrido[2,1-a]isoquinoline derivatives for treating hyperkinetic disorders. Assignee Neurocrine Biosciences, Inc., USA. WO 2008058261. (2008).

  • ROUTE 4

    • 202112070507685373.jpg

    Orgren, Lindsey R.; Maverick, Emily E.; Marvin, Christopher C. Synthesis of (±)-Tetrabenazine by Visible Light Photoredox Catalysis. Journal of Organic Chemistry. Volume 80. Issue 24. Pages 12635-12640. 2015.

  • ROUTE 5

    • 202112077525999591.jpg

    Ray, Purna Chandra; Pawar, Yogesh Dadaji; Singare, Dnyaneshwar Tukaram; Deshpande, Tushar Nandkumar; Singh, Girij Pal. Novel Process for Preparation of Tetrabenazine and Deutetrabenazine. Organic Process Research & Development. Volume 22. Issue 4. Pages 520-526. 2018.

  • ROUTE 6

    • 202112073004859810.jpg

    Liu, Chunyi; Chen, Zhengping; Li, Xiaomin; Tang, Jie. A Concise Synthesis of Tetrabenazine and Its Crystal Structure. Molecular Crystals and Liquid Crystals. Volume 557. Issue 1. Pages 39-49. 2012.

  • ROUTE 7

    • 202112074631838337.jpg

    Despande, Tushar Nandkumar; Singare, Dnyaneshwar Tukaram; Pawar, Yogesh Dadaji; Chavan, Yuvraj Atmaram; Ray, Purna Chandra; Singh, Girij Pal. Novel process for the preparation of tetrabenazine and deutetrabenazine. Assignee Lupin Limited, India. WO 2017182916. (2017).

  • ROUTE 8

    • 202112076015846664.jpg

    Rhee, Sung-Whi; Ryan, Kenneth J.; Tanga, Mary J. Synthesis of 3H-labeled Tetrabenazine (TBZ). Journal of Labelled Compounds and Radiopharmaceuticals. Volume 54. Issue 7. Pages 367-370. 2011.

  • ROUTE 9

    • 202112074930957870.jpg

    Wu, Yen-Ku; Rawal, Viresh H. Rapid construction of tetrahydropyridine scaffolds via formal imino Diels-Alder reactions of Schiff bases and Nazarov reagents. Organic & Biomolecular Chemistry. Volume 17. Issue 39. Pages 8827-8831. 2019.

  • ROUTE 10

    • 202112075836003756.jpg

    Niu, Yongtao; Li, Zhengyu. Synthesis method of tetrabenazine and its intermediate for treatment of Huntington disease. Assignee Beijing Hengrui Kangda Pharmaceutical Science & Technology Development Co., Ltd., Peop. Rep. China. CN 107698582. (2018).

202112070939519906.jpg

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. Organic Letters. Volume 13. Issue 24. Pages 6500-6503. 2011.

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