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【结 构 式】 
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【药物名称】8-OH-DPAT HBr 【化学名称】8-Hydroxy-2-(di-N-propylamino)tetralin hydrobromide 【CA登记号】87394-87-4, 80300-08-9 (free base) 【 分 子 式 】C16H26BrNO 【 分 子 量 】328.29572 |
【开发单位】Uppsala University (Originator) 【药理作用】PHARMACOLOGICAL TOOLS, 5-HT1A Receptor Agonists |
合成路线1
8-OH-DPAT is conveniently prepared from 8-methoxy-2-tetralone (I) (1-3). Reductive amination of (I) gives 8-methoxy-2-(n-propylamino)tetralin (II). Subsequent N-acylation using propionyl chloride followed by LiAlH4 reduction yields 8-methoxy-2-(di-n-propylamino)tetralin (III). The title compound is obtained as the hydrobromide after O-demethylation of (III) in aqueous HBr.
| 【1】 Hjorth, S.; Arvidsson, L.E.; Lindberg, P.; Wikstrom, H.; Nilsson, J.L.G.; Hacksell, U.; Carlsson, A.; 8-Hydroxy-2-(di-n-propylamino)tetralin, a new centrally acting 5-hydroxytryptamine receptor agonist. J Med Chem 1981, 24, 8, 921-923. |
| 【2】 Carlsson, A.; Lindberg, P.; Hacksell, U.; Svensson, K.; Hjorth, S.; Wikström, H.; Nilsson, J.L.G.; Johansson, A.M.; Sanchez, D.; Arvidsson, L.E.; 8-Hydroxy-2-(alkylamino)tetralins and related compounds as central 5-hydroxytyptamine receptor agonist. J Med Chem 1984, 27, 1, 45-51. |
| 【3】 Arvidsson, L.-E.; 8-OH-DPAT Hydrobromide. Drugs Fut 1985, 10, 11, 916. |
| 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) | 23923 | 1-propanamine | 107-10-8 | C3H9N | 详情 | 详情 |
| (I) | 29783 | 8-methoxy-3,4-dihydro-2(1H)-naphthalenone | 5309-19-3 | C11H12O2 | 详情 | 详情 |
| (II) | 29784 | 8-methoxy-N-propyl-1,2,3,4-tetrahydro-2-naphthalenamine; N-(8-methoxy-1,2,3,4-tetrahydro-2-naphthalenyl)-N-propylamine | C14H21NO | 详情 | 详情 | |
| (III) | 29785 | 8-methoxy-N,N-dipropyl-1,2,3,4-tetrahydro-2-naphthalenamine; N-(8-methoxy-1,2,3,4-tetrahydro-2-naphthalenyl)-N,N-dipropylamine | C17H27NO | 详情 | 详情 |
Extended Information