norbaeocystin | 21420-59-7

• 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
• 英文名称: norbaeocystin
• 英文别名: 3-(2-aminoethyl)-1H-indol-4-yl dihydrogen phosphate；[3-(2-aminoethyl)-1H-indol-4-yl] dihydrogen phosphate
• CAS: 21420-59-7
• 化学式: C₁₀H₁₃N₂O₄P
• 分子量: 256.198
• InChiKey: IKQGYCWFBVEAKF-UHFFFAOYSA-N

物化性质

• 沸点：
  556.5±58.0 °C(Predicted)
• 密度：
  1.552±0.06 g/cm3(Predicted)
• 溶解度：
  PBS (pH 7.2)：微溶

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  109
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  norbaeocystin 在 alkaline phosphatase 作用下， 生成 4-羟基色胺
  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 4.0h， 生成 norbaeocystin
  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

• Scalable Hybrid Synthetic/Biocatalytic Route to Psilocybin
  作者：Janis Fricke、Robert Kargbo、Lars Regestein、Claudius Lenz、Gundela Peschel、Miriam A. Rosenbaum、Alexander Sherwood、Dirk Hoffmeister

  DOI：10.1002/chem.202000134

  日期：2020.7.2

  disorder. The psilocybin supply for pharmaceutical purposes is met by synthetic chemistry. We replaced the problematic phosphorylation step during synthesis with the mushroom kinase PsiK. This enzyme was biochemically characterized and used to produce one gram of psilocybin from psilocin within 20 minutes. We also describe a pilot‐scale protocol for recombinant PsiK that yielded 150 mg enzyme in active

  Psilocybin是Psilocybe蘑菇的主要吲哚生物碱，目前正在作为抗治疗性抑郁症和重性抑郁症的药物进行临床试验。用于合成目的的psilocybin供应可以通过合成化学来满足。我们在合成过程中用蘑菇激酶PsiK取代了有问题的磷酸化步骤。对该酶进行了生化表征，并用于在20分钟内从psilocin产生1克psilocybin。我们还描述了重组PsiK的中试规模的协议，该协议可产生150 mg活性和可溶形式的酶。我们的工作巩固了色胺盐化学的简便性与酶催化的特异性和选择性，并有助于以潜在合理的成本获得重要药物。
• 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。
• Methods and compositions comprising psychoactive compounds from psychoactive organisms
  申请人：PSILO SCIENTIFIC LTD

  公开号：US11331357B2

  公开（公告）日：2022-05-17

  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。
• Extraction of psychoactive compounds from psilocybin fungus
  申请人：PSILO SCIENTIFIC LTD

  公开号：US11382942B2

  公开（公告）日：2022-07-12

  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。