1,2,3,4,10,10-hexachloro-1,4,4a,5,8,8a-hexahydro-endo,endo-1,4:5,8-dimethanonaphthalene | 1184248-23-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 1,2,3,4,10,10-hexachloro-1,4,4a,5,8,8a-hexahydro-endo,endo-1,4:5,8-dimethanonaphthalene
• 英文别名: Isodrin；Aldrin；compound 711；(1α,4α,4aβ,5β,8β8aβ)-1,2,3,4,10,10-hexachloro-1,4,4a,5,8,8a-hexahydro-1,4:5,8-dimethanonaphthalene；Aldrite；(1R,2S,3S,6R,7R,8S)-1,8,9,10,11,11-hexachlorotetracyclo[6.2.1.13,6.02,7]dodeca-4,9-diene
• CAS: 1184248-23-4
• 化学式: C₁₂H₈Cl₆
• 分子量: 364.914
• InChiKey: QBYJBZPUGVGKQQ-SEIHLVFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

代谢

当异狄林与来自切除的菜豆幼苗（Phaseolus vulgaris）根部的匀浆一起孵化时...观察到与狄林酮（delta-酮狄林）相对应的色谱化合物。第二种代谢物以非常小的量存在，观察到但未鉴定。没有发现狄林。

When isodrin was incubated with homogenates from excised roots of bean seedlings (phaseolus vulgaris) ... cmpd corresponding chromatographically to endrin ketone (delta-keto endrin) was observed. A second metabolite, present in very small amt, observed, but not identified. No endrin was found.

来源:Hazardous Substances Data Bank (HSDB)

代谢

... 异狄氏剂 ... 通过兔肝微粒体转化为狄氏剂。显然，这个酶系统不再对产物狄氏剂进行进一步代谢。

... Isodrin ... is converted to endrin by rabbit liver microsomes. Apparently no further metabolism of the product endrin occurs with this enzyme system.

来源:Hazardous Substances Data Bank (HSDB)

代谢

已证明在易感型和抗性家蝇品系中，异狄氏剂向恩氏剂的转化... 易感和抗性蝇在局部施用异狄氏剂和恩氏剂后，体内含有少量（施用剂量的3-4%）水溶性物质，这种物质似乎与半笼状酮衍生物相同.../这是/已知的恩氏剂重排产物。

Conversion of isodrin to endrin ... has been demonstrated in both susceptible & resistant strains of houseflies. ... Susceptible & resistant flies topically treated with isodrin & endrin contained small ... amt (3-4% of applied dose) of water sol substance that appeared to be identical to the semi-caged keto derivative ... /which is/ known rearrangement product of endrin.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在将14C标记的异狄林（1毫克/株）施用到幼嫩白菜叶片后，4周内在植物和土壤中回收了44%的施用放射性，10周后回收了37%。10周后，只有异狄林的转化产物作为残留物被检测到。在将14C异狄林施用到土壤中（0.19 ppm）后，胡萝卜在4周后仅含有3.1%的施用放射性，12周后含有4.0%。在这两个实验中，恩德林和 delta-酮恩德林被识别为异狄林的转化产物。

After application of (14)C labeled isodrin (1 mg/plant) to leaves of young white cabbage, 44% of the applied radioactivity was recovered in the plants & soil after 4 wk, & 37% after 10 wk. After 10 wk only conversion products of isodrin were detectable as residues. After application of (14)C isodrin to soil (0.19 ppm), carrots contained only 3.1% of the applied radioactivity after 4 wk & 4.0% after 12 wk. In both experiments, endrin and delta ketoendrin were identified as conversion products of isodrin.

来源:Hazardous Substances Data Bank (HSDB)

代谢

它通过口服吸收并主要分布到脂肪和皮肤中。主要的生物转化产物是对映体2-羟基艾氏剂和相应的硫酸盐，以及葡萄糖苷酸代谢物。对映体和同分异构体12-羟基艾氏剂以及12-酮艾氏剂是艾氏剂的主要有毒代谢物。艾氏剂及其代谢物通过尿液和粪便排出体外。

It is absorbed orally and distributed primarily to the fat and skin. The major biotransformation product is anti-l 2-hydroxyendrin and the corresponding sulfate, as well as glucuronide metabolites. Anti- and syn-12-hydroxyendrin and 12-ketoendrin are the main toxic metabolites of endrin. It and its metabolites are excreted in urine and feces. (L112)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

它拮抗神经递质γ-氨基丁酸（GABA）在GABA-A受体上的作用，有效地阻断了GABA诱导的氯离子摄取，导致中枢神经系统的过度兴奋性。它还抑制了对钙跨膜转运至关重要的Na+ K+ ATPase和Ca2+ Mg2+ ATPase。这导致细胞内自由钙离子的积累，促进储存囊泡中神经递质的释放，随后相邻神经元的去极化，以及刺激在整个中枢神经系统中的传播。它还导致肝细胞中脂质过氧化增加、膜流动性降低和DNA损伤，但确切机制尚不清楚。（T10，L112）

It antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. It also inhibits Na+ K+ ATPase and Ca2+ and Mg2+ ATPase which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. It also causes increased lipid peroxidation, decreased membrane fluidity, and DNA damage in hepatocytes, but the exact mechanism is unknown. (T10, L112)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

国际癌症研究机构致癌物：狄氏剂，以及代谢成狄氏剂的艾氏剂

IARC Carcinogenic Agent:Dieldrin, and aldrin metabolized to dieldrin

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构（IARC）致癌物分类：2A组：可能对人类致癌

IARC Carcinogenic Classes:Group 2A: Probably carcinogenic to humans

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构专著：第5卷：(1974年)一些有机氯农药 增补第7卷：致癌性的整体评估：对国际癌症研究机构专著第1至42卷的更新，1987年；440页；ISBN 92-832-1411-0（已绝版） 第117卷：(2019年)五氯苯酚及其一些相关化合物

IARC Monographs:Volume 5: (1974) Some Organochlorine Pesticides Volume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987; 440 pages; ISBN 92-832-1411-0 (out of print) Volume 117: (2019) Pentachlorophenol and Some Related Compounds

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

无致癌性迹象（未被国际癌症研究机构列名）。

No indication of carcinogenicity (not listed by IARC). (L135)

来源:Toxin and Toxin Target Database (T3DB)

吸收、分配和排泄

从哺乳动物研究中发现，与阿德灵和狄尔德林相比，异德灵和恩德灵中未氯化降冰片烯核的倒置使这个环在体内暴露于酶促羟基化，大大增加了这些化合物从哺乳动物组织中消除的速率，这与它们在昆虫组织中的行为形成对比。

... From mammalian studies that the inversion of the unchlorinated norbornene nucleus in isodrin and endrin (as compared with aldrin and dieldrin) exposes this ring to enzymatic hydroxylation in vivo and greatly incr the rate of elimination of these cmpd from mammalian tissues, in contrast to their behavior in insect tissues.

来源:Hazardous Substances Data Bank (HSDB)

反应信息

• 作为反应物：
  描述：

  1,2,3,4,10,10-hexachloro-1,4,4a,5,8,8a-hexahydro-endo,endo-1,4:5,8-dimethanonaphthalene 在 碘 作用下， 以 四氯化碳 为溶剂， 生成 1,8,9,10,11,11-Hexachlor-hexacyclo[6.2.1.1^3.6.0^2.7.0^4.10.0^5.9]dodecan
  参考文献：
  名称：

  Thermal and base-catalyzed isomerizations of birdcage and half-cage compounds

  摘要：

  DOI：

  10.1021/jo00422a022
• 作为产物：
  描述：

  环戊二烯 、 alkaline earth salt of/the/ methylsulfuric acid 生成 1,2,3,4,10,10-hexachloro-1,4,4a,5,8,8a-hexahydro-endo,endo-1,4:5,8-dimethanonaphthalene
  参考文献：
  名称：

  Polycyclic insecticidal compounds

  摘要：

  公开号：

  US02717851A1

文献信息

• Electronic ID database and detection method for pesticide compounds in edible Agro-products based on GC-Q-Orbitrap
  申请人：CHINESE ACADEMY OF INSPECTION AND QUARANTINE

  公开号：US11181512B2

  公开（公告）日：2021-11-23

  Disclosed is an electronic ID database and detection method for pesticide compounds in edible agro-products based on GC-Q-Orbitrap. The electronic ID database includes a collection of various pesticide compounds electronic ID information and is sorted according to retention time in the electronic ID. The electronic ID contains pesticide compounds information, retention time, mass spectrum, fragment ions information and intelligent matching value. The detection method includes sample pretreatment procedures, setting GC-Q-Orbitrap operating conditions and screening procedures for pesticide residues in samples, wherein setting GC-Q-Orbitrap operating conditions includes setting suitable chromatography and mass spectrometry conditions. In pesticide residue screening procedures, firstly, the retention time is used to find out pesticide compounds in electronic ID database. If there is a match, the corresponding electronic ID information is extracted. Then the intelligent matching value is compared, if it is less than threshold value, the result is recorded and displayed, and the screening is completed.

  本发明公开了一种基于 GC-Q-Orbitrap 的食用农产品中农药化合物电子 ID 数据库和检测方法。电子标识数据库包括各种农药化合物电子标识信息的集合，并根据电子标识中的保留时间进行排序。电子 ID 包含农药化合物信息、保留时间、质谱、碎片离子信息和智能匹配值。检测方法包括样品前处理程序、GC-Q-Orbitrap 操作条件设置和样品中农药残留筛选程序，其中 GC-Q-Orbitrap 操作条件设置包括设置合适的色谱和质谱条件。在农药残留筛选程序中，首先利用保留时间在电子 ID 数据库中查找农药化合物。如果匹配，则提取相应的电子 ID 信息。然后比较智能匹配值，如果小于阈值，则记录并显示结果，完成筛选。
• 946. Cyclisations and rearrangements in the isodrin–aldrin series
  作者：C. W. Bird、R. C. Cookson、E. Crundwell

  DOI：10.1039/jr9610004809

  日期：——
• Skeletal Rearrangements in Reactions of Isodrin and Endrin
  作者：S. B. Soloway、A. M. Damiana、J. W. Sims、H. Bluestone、R. E. Lidov

  DOI：10.1021/ja01505a024

  日期：1960.10
• Cookson; Crundwell, Chemistry and industry, 1958, p. 1004
  作者：Cookson、Crundwell

  DOI：——

  日期：——
• Methods and compositions for increasing the efficacy of biologically-active ingredients
  申请人：Windsor Brian J.

  公开号：US20060276339A1

  公开（公告）日：2006-12-07

  The invention provides methods and compositions for modulating the sensitivity of cells to cytotoxic compounds and other active agents. In accordance with the invention, compositions are provided comprising combinations of ectophosphatase inhibitors and active agents. Active agents include antibiotics, fungicides, herbicides, insecticides, chemotherapeutic agents, and plant growth regulators. By increasing the efficacy of active agents, the invention allows use of compositions with lowered concentrations of active ingredients.