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  • 2-溴麦角酸二乙基酰胺

    (8β)-2-Bromo-N,N-diethyl-6-methyl-9,10-didehydroergoline-8-carbox amide

化合物简介

2-Bromo-LSD, also known as BOL-148, is a derivative of lysergic acid invented by Albert Hofmann, as part of the original research from which the closely related compound LSD was also derived. 2-bromo-LSD was found to be inactive as a psychedelic and so was comparatively little researched for many years, although its similar behavior in the body made it useful for radiolabelling studies. It was found to bind to many of the same receptor targets as LSD, but acting as a neutral antagonist rather than an agonist. However its generally similar behavior to LSD in some respects has shown to be very useful in one specific area, the treatment of cluster headaches. These debilitating attacks have been known for some time to be amenable to treatment with certain hallucinogenic drugs such as LSD and psilocybin, but because of the illegal status of these drugs and the kind of mental changes they induce, research into their medical use has been slow and therapeutic application limited to very specific circumstances under strict supervision. It had been thought that this specific therapeutic action against cluster headaches was limited to hallucinogenic drugs of this type, and would always present a major barrier to their clinical use. However a serendipitous discovery found that 2-bromo-LSD is also able to produce this therapeutic effect, despite lacking the other effects of LSD. This has led to a resurgence of interest and research into 2-bromo-LSD and its possible medical uses. Some isolated incidents of hallucinogenic responses have been reported, but as with other non-hallucinogenic LSD analogues such as lisuride, this appears to be a rare side effect occurring only in individuals with an as yet unexplained susceptibility to this reaction.

基本信息

CAS:478-84-2
中文别名
英文别名:Bromolysergide;6-Bromo-3-pyridylmethyl bromide;2-bromo-lysergide;2-bromo-5-pyridylmethyl bromide;2-bromo-6-methyl-9,10-didehydro-ergoline-8-carboxylic acid diethylamide;2-Brom-lysergsaeurediethylamid;2-bromo-5-bromoethylpyridine;2-bromo-5-bromomethylpyridine;2-bromo-5R,8R-lysergic acid diethyl amide;
分子式:C20H24BrN3O
分子量:402.328
精确质量:401.11
Psa:39.34
Logp:3.6064

编号系统

UNII:JUA77QEU32

物化性质

密度:1.44g/cm3
沸点:580.7ºC at 760mmHg
闪点:305ºC
折射率:1.676
储存条件:库房通风低温干燥,与食品原料类分开存放
蒸汽压:1.77E-13mmHg at 25°C

安全信息

生产方法及用途

合成路线

  • 参考文献

    Stanovnik, Branko; Tisler, Miha; Jurgec, Milan; Rucman, Rudolf Heterocycles, 1981 , vol. 16, # 5 p. 741 - 745

上游原料

下游产品

图谱

13C NMR : Predict


1H NMR : Predict


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