新石房蛤毒素 | 64296-20-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 新石房蛤毒素
• 英文名称: neosaxitoxin
• 英文别名: neoSTX；[(3aS,4R,10aS)-2-amino-5,10,10-trihydroxy-6-imino-3a,4,8,9-tetrahydro-1H-pyrrolo[1,2-c]purin-4-yl]methyl carbamate
• CAS: 64296-20-4
• 化学式: C₁₀H₁₇N₇O₅
• 分子量: 315.289
• InChiKey: PPEKGEBBBBNZKS-HGRQIUPRSA-N

物化性质

• 沸点：
  684.3±65.0 °C(Predicted)
• 密度：
  2.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  194
• 氢给体数：
  7
• 氢受体数：
  7

安全信息

• 危险品标志：
  T+
• 安全说明：
  S36/37/39,S45
• 危险类别码：
  R26/27/28
• 危险品运输编号：
  UN 3172 6.1/PG 1

制备方法与用途

类别

有毒物质

毒性分级

剧毒

急性毒性

腹腔-小鼠 LD50: 0.0092 毫克/公斤

可燃性危险特性

可燃; 火场分解有毒氮氧化物烟雾

储运特性

库房低温, 通风, 干燥; 与食品原料分开存放

灭火剂

水, 二氧化碳, 干粉, 砂土

反应信息

• 作为产物：
  描述：

  gonyautoxin VI 在 盐酸 作用下， 反应 0.08h， 生成 新石房蛤毒素
  参考文献：
  名称：

  Studies on paralytic shellfish poisoning in tropical waters. Part IV. Structures of two paralytic shellfish toxins, gonyautoxins V and VI, isolated from a tropical dinoflagellate, Pyrodinium bahamense var. compressa.

  摘要：

  从一种名为巴哈马热鞭毛藻（pyrodinium bahamense var. compressa）的热带鞭毛藻中分离出的两种麻痹性贝类毒素——戈尼亚毒素V和戈尼亚毒素VI，分别被鉴定为含有磺酰胺基氨基甲酰基部分的石房蛤毒素和新型石房蛤毒素的衍生物。

  DOI：

  10.1271/bbb1961.46.1861

文献信息

• Preparative scale conversion of gonyautoxins to neosaxitoxin
  申请人：THE CAWTHRON INSTITUTE TRUST BOARD

  公开号：US10822344B2

  公开（公告）日：2020-11-03

  A method of preparing neosaxitoxin in quantities of a purity sufficient to allow the compound to be used as an active pharmaceutical ingredient (API) is described. The method includes the reductive desulfonation of an unresolved mixture of gonyautoxin 1 (GTX1) and gonyautoxin 4 (GTX4).

  本文介绍了一种制备新沙西托星的方法，其纯度足以使该化合物用作活性药物成分（API）。该方法包括对贡戈毒素 1（GTX1）和贡戈毒素 4（GTX4）的未还原混合物进行还原脱硫。
• Journal of the Chemical Society, Chemical Communications. 1981, 7, 314-315
  作者：

  DOI：——

  日期：——
• Identification of thioether intermediates in the reductive transformation of gonyautoxins into saxitoxins by thiols
  作者：Shigeru Sato、Ryuichi Sakai、Masaaki Kodama

  DOI：10.1016/s0960-894x(00)00332-2

  日期：2000.8

  O-Sulfate group of gonyautoxin I and IV is transformed into methylene to form neosaxitoxin by thiols such as glutathione, a common cellular scavenger, in mild conditions. We isolated the intermediate of this conversion and propose that this reaction proceeds through formation of thiohemiketal, 1,2 shift to form stable thioether intermediate, and then redox exchange at sulfur atom to form the final product, (C) 2000 Elsevier Science Ltd. All rights reserved.
• PREPARATIVE SCALE CONVERSION OF GONYAUTOXINS TO NEOSAXITOXIN
  申请人：The Cawthron Institute Trust Board

  公开号：EP3853231A1

  公开（公告）日：2021-07-28
• METHODS FOR PURIFYING PHYCOTOXINS, PHARMACEUTICAL COMPOSITIONS CONTAINING PURIFIED PHYCOTOXINS, AND METHODS OF USE THEREOF
  申请人：PROTEUS S.A.

  公开号：US20150099878A1

  公开（公告）日：2015-04-09

  Phycotoxins are purified from a mixture of phycotoxins produced in a continuous process. Cyanobacteria are produced in a continuous culture, then lyzed, the cells pelleted and extracted, and the extract purified using an organic solvent-aqueous mixture and repeated passage through a diatomaceous earth column. The column is washed with acetic acid, then the neosaxitoxin extracted with an alcohol-water mixture. The eluate is passed through activated charcoal columns, which are washed with distilled water to remove the retained pigments and impurities, the further purified by HPLC. In one embodiment, the process produces only neosaxitoxin and saxitoxin. In another embodiment, the process produces only GTX2/3.