resiniferatoxin | 57444-62-9

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: resiniferatoxin
• 英文别名: [(1R,2R,6R,10S,11R,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl 2-(4-hydroxy-3-methoxyphenyl)acetate
• CAS: 57444-62-9
• 化学式: C₃₇H₄₀O₉
• 分子量: 628.719
• InChiKey: DSDNAKHZNJAGHN-IHCAYWNCSA-N

物化性质

• 沸点：
  768.7±60.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)
• 溶解度：
  在DMSO中水中的溶解度为至100mM，在乙醇中水中的溶解度为至50mM

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  46
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  9

ADMET

毒理性

• 毒性总结

树脂毒素（Resiniferatoxin）激活了一部分初级传入感觉神经元的香草酸受体，这些神经元参与痛觉传递（生理性疼痛的传递）。RTX导致感觉神经元的质膜上出现一种新型的离子通道，即瞬时受体电位香草酸1通道，使其对阳离子，尤其是钙离子的通透性增加。这引发了一种强烈的刺激效应，随后是脱敏和镇痛作用。

Resiniferatoxin activates the vanilloid receptor in a subpopulation of primary afferent sensory neurons involved in nociception (the transmission of physiological pain). RTX causes a novel ion channel in the plasma membrane of sensory neurons, the transient receptor potential vanilloid 1, to become permeable to cations, most particularly the calcium cation. This evokes a powerful irritant effect followed by desensitization and analgesia. (L1244)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

树脂毒素是一种神经毒素，作用于参与痛觉感知的传入感觉神经。它引起强烈的刺激作用，随后是脱敏和镇痛。

Resiniferatoxin is a neurotoxin that targets afferent sensory neurons involved in nociception. It evokes a powerful irritant effect followed by desensitization and analgesia. (L1244)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服（摄入）（L1817）；皮肤（L1817）

Oral (ingestion) (L1817) ; dermal (L1817)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

树脂毒素（Resiniferatoxin）引起强烈的刺激性效应，随后是脱敏和镇痛。

Resiniferatoxin evokes a powerful irritant effect followed by desensitization and analgesia. (L1244)

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 危险等级：
  6.1(a)
• 危险类别码：
  R35,R25
• 危险品运输编号：
  UN 2928 6.1/PG 2
• WGK Germany：
  3
• RTECS号：
  CY1633700
• 包装等级：
  II
• 危险类别：
  6.1(a)

反应信息

• 作为反应物：
  描述：

  resiniferatoxin 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以60%的产率得到9,13,14-orthophenylacetyl-3β-hydroxyresiniferonyl 20-(4-hydroxy-3-methoxyphenylacetate)
  参考文献：
  名称：

  Similarities and Differences in the Structure−Activity Relationships of Capsaicin and Resiniferatoxin Analogues

  摘要：

  Structure-activity relationships in analogues of the irritant natural product capsaicin have previously been rationalized by subdivision of the molecule into three structural regions (A, B, and C). The hypothesis that resiniferatoxin (RTX), which is a high-potency ligand for the same receptor and which has superficial structural similarities with capsaicin, could be analogously subdivided has been investigated. The effects of making parallel changes in the two structural series have been studied in a cellular functional assay which is predictive of analgesic activity. Parallel structural changes in the two series lead to markedly different consequences on biological activity; the 3- and 4-position aryl substituents (corresponding to the capsaicin 'A-region') which are strictly required for activity in capsaicin analogues are not important in RTX analogues. The homovanillyl C-20 ester group in RTX (corresponding to the capsaicin 'B-region') is more potent than the corresponding amide, in contrast to the capsaicin analogues. Structural variations to the diterpene moiety suggest that the functionalized 5-membered diterpene ring of RTX is an important structural determinant for high potency. Modeling studies indicate that the 3D position of the alpha-hydroxy ketone moiety in the 5-membered ring is markedly different in the phorbol (inactive) analogues and RTX (active) series. This difference appears to be due to the influence of the strained ortho ester group in RTX, which acts as a local conformational constraint. The reduced activity of an analogue substituted in this region and the inactivity of a simplified analogue in which this unit is entirely removed support this conclusion.

  DOI：

  10.1021/jm960139d
• 作为产物：
  描述：

  在 吡啶 、 三乙烯二胺 、 2,6-二甲基吡啶 、 盐酸 、 4-二甲氨基吡啶 、 2,2'-联吡啶 、 selenium(IV) oxide 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 2-氮杂金刚烷-N-氧自由基 、 cerium(III) chloride heptahydrate 、 四丁基氟化铵 、 三正丁基氢锡 、 lead(IV) tetraacetate 、 sodium hexamethyldisilazane 、 乙酸酐 、 L-Selectride 、 sodium hydride 、 二异丁基氢化铝 、 碳酸氢钠 、