Citation: Zhang Yu Yao, Hao Zhang, Huan Ming Sheng, Xiao Ming Wu, Hong Bin Sun. An unexpected Hoffmann elimination during the alkylation of dihydrotetrabenazine[J]. Chinese Chemical Letters, ;2010, 21(11): 1334-1337. doi: 10.1016/j.cclet.2010.06.022 shu

An unexpected Hoffmann elimination during the alkylation of dihydrotetrabenazine

Center for Drug Discovery, College of Pharmacy, China Pharmaceutical University, Nanjing 210009, China

Received Date: 23 March 2010

Fund Project: This work is partially supported by the "111 Project" from the Ministry of Education of China and the State Administration of Foreign Expert Affairs of China (No.111-2-07).

Dihydrotetrabenazine (DTBZ) is the major pharmacologically active form of tetrabenazine (TBZ), which was approved by FDA for the treatment of chorea associated with Huntington's disease (HD). An unexpected Hoffmann elimination was observed during the treatment of DTBZ with sodium hydrogen and alkyl halides, leading to the formation of both eliminated products (major) and hydroxyl-alkylated products (minor).
- Tetrabenazine,
- Dihydrotetrabenazine,
- Alkylation,
- Hoffmann elimination
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