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【结 构 式】 
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【药物名称】Bufotenine 【化学名称】3-[2-(Dimethylamino)ethyl]-1H-indol-5-ol 【CA登记号】487-93-4 【 分 子 式 】C12H16N2O 【 分 子 量 】204.27412 |
【开发单位】 【药理作用】 |
合成路线1
This compound can be obtained in two differents ways: 1) By oxidation of 2-(2,5-dihydroxyphenyl)-4-dimethylaminobutylamine (I) to give bufotenine in a 45% yield. 2) By alkylation of 2,5-dimethoxybenzyl cyanide (II) with beta-dimethylaminoethyl chloride (A) using sodamide. The product (III) is hydrogenated over Raney-Ni inducing partial cyclization and then demethylation with hydrogen bromide and oxidized with potassium ferricyanide in the cold to yield bufotenine.
| 【1】 Jackson, A.H.; Harley-Mason, J.; A new synthesis of bufotenine. Chem Ind 1952, 954. |
| 【2】 Amoros-Marin, L.; Carlin, R.B.; 2,4,6-Tri-p-chlorophenylpyridine. A by-product of a Fischer indole transformation. J Am Chem Soc 1959, 81, 730-733. |
| 【3】 Wallis, D.I.; Nash. H.L.; Bufotenine. Drugs Fut 1981, 6, 11, 671. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 39015 | 2-(2,5-dimethoxyphenyl)acetonitrile | 18086-24-3 | C10H11NO2 | 详情 | 详情 |
| (I) | 39014 | 2-[1-(aminomethyl)-3-(dimethylamino)propyl]-1,4-benzenediol | C12H20N2O2 | 详情 | 详情 | |
| (II) | 11907 | Dimethylaminoethyl chloride; 2-Dimethylaminoethyl chloride; 2-Chloro-N,N-dimethyl-1-ethanamine; N-(2-Chloroethyl)-N,N-dimethylamine | 107-99-3 | C4H10ClN | 详情 | 详情 |
| (III) | 39016 | 2-(2,5-dimethoxyphenyl)-4-(dimethylamino)butanenitrile | C14H20N2O2 | 详情 | 详情 | |
| (IV) | 39017 | N-[4-amino-3-(2,5-dimethoxyphenyl)butyl]-N,N-dimethylamine; 2-(2,5-dimethoxyphenyl)-N(4),N(4)-dimethyl-1,4-butanediamine | C14H24N2O2 | 详情 | 详情 |
Extended Information