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“神奇蘑菇”主要致幻成分裸盖菇素和脱磷酸裸盖菇素的简洁大规模合成。

Concise large-scale synthesis of psilocin and psilocybin, principal hallucinogenic constituents of "magic mushroom".

作者信息

Shirota Osamu, Hakamata Wataru, Goda Yukihiro

机构信息

Division of Pharmacognosy, Phytochemistry and Narcotics, and Division of Organic Chemistry, National Institute of Health Sciences, 1-18-1 Kamiyoga, Setagaya-ku, Tokyo 158-8501, Japan.

出版信息

J Nat Prod. 2003 Jun;66(6):885-7. doi: 10.1021/np030059u.

DOI:10.1021/np030059u
PMID:12828485
Abstract

The concise large-scale syntheses of psilocin (1) and psilocybin (2), the principal hallucinogenic constituents of "magic mushroom", were achieved without chromatographic purification. The key step in the synthesis of 2 was the isolation of the dibenzyl-protected intermediate (7) as a zwitterionic derivative (8), which was completely identified by means of 2D NMR analyses.

摘要

实现了对裸盖菇素(1)和裸盖菇碱(2)这两种“神奇蘑菇”主要致幻成分的简洁大规模合成,且无需色谱纯化。合成2的关键步骤是将二苄基保护的中间体(7)分离为两性离子衍生物(8),通过二维核磁共振分析对其进行了完全鉴定。

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Concise large-scale synthesis of psilocin and psilocybin, principal hallucinogenic constituents of "magic mushroom".“神奇蘑菇”主要致幻成分裸盖菇素和脱磷酸裸盖菇素的简洁大规模合成。
J Nat Prod. 2003 Jun;66(6):885-7. doi: 10.1021/np030059u.
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Morphological and chemical analysis of magic mushrooms in Japan.日本神奇蘑菇的形态学和化学分析。
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The determination of psilocin and psilocybin in hallucinogenic mushrooms by HPLC utilizing a dual reagent acidic potassium permanganate and tris(2,2'-bipyridyl)ruthenium(II) chemiluminescence detection system.利用酸性高锰酸钾和三(2,2'-联吡啶)钌(II)双试剂化学发光检测系统,通过高效液相色谱法测定致幻蘑菇中的裸盖菇素和脱磷酸裸盖菇素。
J Forensic Sci. 2006 Jan;51(1):45-51. doi: 10.1111/j.1556-4029.2005.00033.x.
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DARK Classics in Chemical Neuroscience: Psilocybin.《化学神经科学中的经典作品:裸盖菇素》
ACS Chem Neurosci. 2018 Oct 17;9(10):2438-2447. doi: 10.1021/acschemneuro.8b00186. Epub 2018 Jul 16.
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Hallucinogenic mushrooms on the German market - simple instructions for examination and identification.德国市场上的致幻蘑菇——检验与识别简易指南
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Liquid chromatography-mass spectrometric and liquid chromatography-tandem mass spectrometric determination of hallucinogenic indoles psilocin and psilocybin in "magic mushroom" samples.液相色谱-质谱联用和液相色谱-串联质谱法测定“神奇蘑菇”样品中的致幻吲哚类物质裸盖菇素和脱磷酸裸盖菇素。
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Fungal hallucinogens psilocin, ibotenic acid, and muscimol: analytical methods and biologic activities.真菌致幻剂裸盖菇素、鹅膏蕈氨酸和麦斯卡林:分析方法和生物活性。
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Detection of psilocin in body fluids.体液中裸盖菇素的检测。
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Potential therapeutic effects of psilocybin/psilocin are minimized while possible adverse reactions are overrated.裸盖菇素/脱磷酸裸盖菇素的潜在治疗效果被最小化,而可能的不良反应却被高估了。
Ther Drug Monit. 2014 Feb;36(1):131-2. doi: 10.1097/FTD.0000000000000028.

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