desmethyl nereistoxin | 19216-99-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: desmethyl nereistoxin
• 英文别名: 4-methylamino-1,2-dithiolane；N-methyl-1,2-dithiolan-4-amine；N-methyldithiolan-4-amine
• CAS: 19216-99-0
• 化学式: C₄H₉NS₂
• mdl: MFCD02731105
• 分子量: 135.254
• InChiKey: WWGIXOHGNPTFQE-UHFFFAOYSA-N

物化性质

• 沸点：
  207.9±29.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  desmethyl nereistoxin 以 氯仿 为溶剂， 反应 3.0h， 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Povalyaeva, O.S.; Rodionov, V.Ya.; Suvorov, N.M., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 773 - 782

  摘要：

  DOI：
• 作为产物：
  描述：

  N-methyl-1,3-di(benzylthio)-2-propylamine hydrochloride 在 氧气 、 lithium 作用下， 生成 1,2-二苯乙烷 、 desmethyl nereistoxin
  参考文献：
  名称：

  Povalyaeva, O.S.; Rodionov, V.Ya.; Suvorov, N.M., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 773 - 782

  摘要：

  DOI：

文献信息

• Nereistoxin and Cartap Neurotoxicity Attributable to Direct Block of the Insect Nicotinic Receptor/Channel
  作者：Seog-Jong Lee、Motohiro Tomizawa、John E. Casida

  DOI：10.1021/jf021149s

  日期：2003.4.1

  Nereistoxin (NTX) (4-dimethylamino-1,2-dithiolane) is the naturally occurring prototype for cartap [the bis(thiocarbamate) derivative of the NTX dithiol], which is generally regarded as a proinsecticide reverting to NTX. The aim of this study is to define the target site(s) for dithiolanes and dithiol esters. The affinity of [H-3]NTX was not suitable for binding assays with honeybee (Apis mellifera) head membranes. However, NTX and cartap are equally potent, direct-acting, and competitive displacers of [H-3]thienylcyclohexylpiperidine binding at the noncompetitive blocker (NCB) site of the Apis nicotinic acetylcholine receptor (nAChR)/channel. NTX also binds at the Apis [H-3]imidacloprid agonist site, but cartap does not. As candidate metabolic pathways, sequential N-desmethylation and S-oxidation of NTX progressively reduce its potency at the NCB site and toxicity to houseflies. A P450 inhibitor reduces the toxicity of NTX and enhances it with cartap. Surprisingly, cartap is not just a pro-NTX but instead directly induces inhibitory neurotoxicity by blocking the nAChR/channel, whereas NTX may have dual NCB and agonist targets.
• Povalyaeva, O.S.; Rodionov, V.Ya.; Suvorov, N.M., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 773 - 782
  作者：Povalyaeva, O.S.、Rodionov, V.Ya.、Suvorov, N.M.

  DOI：——

  日期：——