3-[2-(甲基氨基)乙基]-1H-吲哚-4-醇 4-(磷酸二氢酯) | 21420-58-6

• 物质功能分类: 生物化工 - 抑制剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 3-[2-(甲基氨基)乙基]-1H-吲哚-4-醇 4-(磷酸二氢酯)
• 中文别名: 3-[2-(甲基氨基)乙基]-1H-吲哚-4-醇4-(磷酸二氢酯)
• 英文名称: baeocystin
• 英文别名: [3-(2-methylaminoethyl)-1H-indol-4-yl] dihydrogen phosphate；[3-[2-(methylamino)ethyl]-1H-indol-4-yl] dihydrogen phosphate
• CAS: 21420-58-6
• 化学式: C₁₁H₁₅N₂O₄P
• 分子量: 270.225
• InChiKey: WTPBXXCVZZZXKR-UHFFFAOYSA-N

物化性质

• 熔点：
  254-258 °C (decomp)
• 沸点：
  538.2±58.0 °C(Predicted)
• 密度：
  1.447±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（轻微、加热、超声处理）、水（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  94.6
• 氢给体数：
  4
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-[2-(甲基氨基)乙基]-1H-吲哚-4-醇 4-(磷酸二氢酯) 在 alkaline phosphatase 作用下， 生成 3-[2-(methylamino)ethyl]-1H-indol-4-ol
  参考文献：
  名称：

  10.1111/bph.16466

  摘要：

  Background and PurposeDemand for new antidepressants has resulted in a re‐evaluation of the therapeutic potential of psychedelic drugs. Several tryptamines found in psilocybin‐containing “magic” mushrooms share chemical similarities with psilocybin. Early work suggests they may share biological targets. However, few studies have explored their pharmacological and behavioural effects.Experimental ApproachWe compared baeocystin, norbaeocystin and aeruginascin with psilocybin to determine if they are metabolized by the same enzymes, similarly penetrate the blood–brain barrier, serve as ligands for similar receptors and modulate behaviour in rodents similarly. We also assessed the stability and optimal storage and handling conditions for each compound.Key ResultsIn vitro enzyme kinetics assays found that all compounds had nearly identical rates of dephosphorylation via alkaline phosphatase and metabolism by monoamine oxidase. Further, we found that only the dephosphorylated products of baeocystin and norbaeocystin crossed a blood–brain barrier mimetic to a similar degree as the dephosphorylated form of psilocybin, psilocin. The dephosphorylated form of norbaeocystin was found to activate the 5‐HT2A receptor with similar efficacy to psilocin and norpsilocin in in vitro cell imaging assays. Behaviourally, only psilocybin induced head twitch responses in rats, a marker of 5‐HT2A‐mediated psychedelic effects and hallucinogenic potential. However, like psilocybin, norbaeocystin improved outcomes in the forced swim test. All compounds caused minimal changes to metrics of renal and hepatic health, suggesting innocuous safety profiles.Conclusions and ImplicationsCollectively, this work suggests that other naturally occurring tryptamines, especially norbaeocystin, may share overlapping therapeutic potential with psilocybin, but without causing hallucinations.

  DOI：

  10.1111/bph.16466
• 作为产物：
  描述：

  4-羟基色胺 在 5’-三磷酸腺苷 作用下， 以 aq. buffer 为溶剂， 反应 8.0h， 生成 3-[2-(甲基氨基)乙基]-1H-吲哚-4-醇 4-(磷酸二氢酯)
  参考文献：
  名称：

  色氨酸合酶增强反应中裸盖菇素及其衍生物的生物催化生产

  摘要：

  裸盖菇素（4-磷酸氧基-N，N-二甲基色胺）是裸盖菇属真菌的主要生物碱，即所谓的“神奇蘑菇”。这种精神药物天然产品作为未来治疗抑郁症和焦虑症的药物的药学兴趣正在重新出现。在这里，我们通过将 TrpB（蘑菇Psilocybe cubensis的色氨酸合酶）添加到反应中，提出了一种增强的裸盖菇素生产酶促途径。我们利用其底物灵活性并展示了 4-羟基吲哚和l的裸盖菇素形成-丝氨酸，与以前的方法相比，它们是成本较低的底物。此外，我们通过相同的体外方法展示了 7-磷酸氧色胺（异降贝藻素）的酶促生产，这是裸盖菇生物碱降贝藻素（4-磷酸氧色胺）的一种非天然同类物，以及血清素（5-羟色胺）。

  DOI：

  10.1002/chem.201801047

文献信息

• Synthesis of Baeocystin, a natural Psilocybin Analogue
  作者：Rudolf Brenneisen、Stefan Borner、Nelly Peter-Oesch、Urs P. Schlunegger

  DOI：10.1002/ardp.19883210812

  日期：——

  Baeocystin (7) (4‐phosphoryloxy‐N‐methyltryptamine) has been synthesized starting from 2‐methyl‐3‐nitrophenol (1). The spectral data (UV, IR, 1H‐, 31P‐, 13C‐NMR, MS) are identical with those of 7 isolated from Psilocybe semilanceata.

  Baeocystin (7)（4-磷酰氧基-N-甲基色胺）已从 2-甲基-3-硝基苯酚 (1) 开始合成。光谱数据（UV、IR、1H-、31P-、13C-NMR、MS）与从半披针松中分离出的 7 种的光谱数据相同。
• Aeruginascin, a Trimethylammonium Analogue of Psilocybin from the Hallucinogenic Mushroom<i>Inocybe aeruginascens</i>
  作者：Niels Jensen、Jochen Gartz、Hartmut Laatsch

  DOI：10.1055/s-2006-931576

  日期：2006.4

  The hallucinogenic mushroom Inocybe aeruginascens contains several typical Psilocybe alkaloids including psilocybin. We have now elucidated the structure of a further indole derivative named aeruginascin as the quaternary ammonium compound N,N,N-trimethyl-4-phosphoryloxytryptamine. Aeruginascin is closely related to the frog skin toxin bufotenidine (5-HTQ), a potent 5-HT3 receptor agonist, and has been found exclusively in Inocybe aeruginascens so far.

  致幻蘑菇Inocybe aeruginascens含有多种典型的裸盖菇碱，包括裸盖菇碱。我们现在已经阐明了另一种名为aeruginascin的吲哚衍生物的结构，它是一种季铵化合物，即N,N,N-三甲基-4-磷酰氧基色胺。Aeruginascin与蛙皮毒素bufotenidine（5-HTQ）密切相关，是一种强效5-HT3受体激动剂，迄今为止仅在Inocybe aeruginascens中发现。
• [EN] CRYSTALLINE NORPSILOCIN COMPOUNDS<br/>[FR] COMPOSÉS DE NORPSILOCINE CRISTALLINS
  申请人：CAAMTECH INC

  公开号：WO2021188812A1

  公开（公告）日：2021-09-23

  The disclosure relates to norpsilocin compounds, compositions containing those crystalline compounds, and methods of treatment using them. The norpsilocin compounds include crystalline 4-hydroxy-N-methyltryptamine ("crystalline 4-HO-NMT" or "crystalline norpsilocin freebase"), crystalline 4-hydroxy-N-methyltryptammonium fumarate ("crystalline norpsilocin fumarate"), and 4-hydroxy-N-methyltryptammonium fumarate ("norpsilocin fumarate") and their compositions and uses.

  本公开涉及norpsilocin化合物、含有这些晶体化合物的组合物以及使用它们的治疗方法。Norpsilocin化合物包括结晶的4-羟基-N-甲基色胺（“结晶4-HO-NMT”或“结晶norpsilocin游离基”）、结晶的4-羟基-N-甲基色胺富马酸盐（“结晶norpsilocin富马酸盐”）和4-羟基-N-甲基色胺富马酸盐（“norpsilocin富马酸盐”）及其组合物和用途。
• Compositions and methods comprising a psilocybin derivative
  申请人：CaaMTech, LLC

  公开号：US10933073B2

  公开（公告）日：2021-03-02

  This disclosure pertains to new compositions and methods comprising a psilocybin derivative. In one embodiment, the compositions disclosed herein are used for a method of regulating a neurotransmitter receptor, e.g., a serotonin receptor. In one embodiment, the compositions disclosed herein comprise purified compounds, e.g., a purified psilocybin derivative, a purified cannabinoid, or purified terpene.

  本公开涉及包含迷迭香衍生物的新组合物和方法。在一个实施方案中，本文公开的组合物用于调节神经递质受体（如血清素受体）的方法。在一个实施方案中，本文公开的组合物包含纯化的化合物，例如纯化的迷幻素衍生物、纯化的大麻素或纯化的萜烯。
• Psychoactive alkaloid extraction and composition with controlled dephosphorylation
  申请人：PSILO SCIENTIFIC LTD

  公开号：US11298388B2

  公开（公告）日：2022-04-12

  This invention relates to the extraction of psychoactive compounds from organisms for use in medicine. Extraction is carried out with a strong acid or strong base to either promote or inhibit dephosphorylation. The extract in the slurry form is standardized with added excipient so that when it is dried the powdered composition has a specified total psychoactive alkaloid concentration, with a known ratio of phosphorylated to dephosphorylated psychoactive alkaloids.

  本发明涉及从生物体中提取精神活性化合物用于医药。萃取时使用强酸或强碱，以促进或抑制去磷酸化作用。浆状提取物用添加的赋形剂进行标准化，使其干燥后的粉末状组合物具有特定的精神活性生物碱总浓度，以及已知的磷酸化和去磷酸化精神活性生物碱的比例。