(1S,8R)-1,5,6,8,9,10,11,11-octachloro-4-oxatetracyclo[6.2.1.02,7.03,5]undec-9-ene | 27304-13-8

• 物质功能分类: 分析化学 - 标准品 - 标准物质
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (1S,8R)-1,5,6,8,9,10,11,11-octachloro-4-oxatetracyclo[6.2.1.02,7.03,5]undec-9-ene
• CAS: 27304-13-8
• 化学式: C₁₀H₄Cl₈O
• 分子量: 423.7
• InChiKey: VWGNQYSIWFHEQU-IBAUKUMTSA-N

物化性质

• 熔点：
  144°C
• 沸点：
  534.76°C (rough estimate)
• 密度：
  1.7939 (rough estimate)
• 溶解度：
  可溶于氯仿（少许）、乙酸乙酯（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

代谢

活体和体外大鼠研究表明，氯化萘的生物转化有两种途径，并显示出代谢物包括：顺式氯化萘、1,2-二氯氯化萘、氧化氯化萘、1-羟基-2-氯氯化萘、1-羟基-2-氯-2,3-环氧氯化萘、氯化萘氯醇和1,2-顺式-二羟基二氢氯化萘，以及七氯的代谢物。体外研究表明，大鼠和人类的肝脏几乎具有相同的降解氯化萘的能力，不同的是人类肝脏将反式-非氯转化为反式-氯化萘的能力较弱。

IN VIVO & IN VITRO STUDIES IN RATS HAVE REVEALED TWO ROUTES OF BIOTRANSFORMATION OF CHLORDANE & SHOWN THAT THE METABOLITES INCLUDE: TRANS-CHLORDANE, 1,2-DICHLOROCHLORDENE, OXYCHLORDANE, 1-HYDROXY-2-CHLOROCHLORDENE, 1-HYDROXY-2-CHLORO-2,3-EPOXY CHLORDENE, CHLORDENE CHLOROHYDRIN, & 1,2-TRANS-DIHYDROXY DIHYDROCHLORDENE, AS WELL AS METABOLITES OF HEPTACHLOR. IN VITRO STUDIES SHOWED THAT THE LIVER OF RAT & MAN HAVE ALMOST IDENTICAL CAPACITY TO DEGRADE CHLORDANE EXCEPT THAT HUMAN LIVER HAS LITTLE CAPACITY TO CONVERT TRANS-NONACHLOR TO TRANS-CHLORDANE.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在纯反式氯丹的饮食中15天后，无论雌雄大鼠，其体内积累的氧化氯丹含量都高于喂食顺式异构体时的含量。雌性大鼠的积累量高于雄性。此外，还形成了1-外-2-内-二氯桥烯，数据显示这是氧化氯丹途径的一个中间产物。

... AFTER 15 DAYS ON DIET CONTAINING PURE TRANS-CHLORDANE, RATS OF BOTH SEXES STORED MORE OXYCHLORDANE THAN WHEN FED CIS-ISOMER. ... STORAGE IN FEMALES WAS HIGHER THAN IN MALES. ... 1-EXO-2-ENDO-DICHLOROCHLORDENE WAS ALSO FORMED & DATA INDICATED THAT THIS WAS AN INTERMEDIATE IN OXYCHLORDANE PATHWAY.

来源:Hazardous Substances Data Bank (HSDB)

代谢

培养土壤中分离出的放线菌（诺卡氏菌种），能将纯顺式或反式氯丹代谢至少为8种可溶于溶剂的化合物，包括二氯氯丹、氧化氯丹、七氯、七氯内酯、氯丹氯醇和3-羟基-反式氯丹。氧化氯丹在代谢上是不活跃的，在菌丝体中作为终极残留物积累。

GROWING CULTURES OF ACTINOMYCETE (NOCARDIOPSIS SPECIES), WHICH HAD BEEN ISOLATED FROM THE SOIL, METABOLIZED PURE CIS- OR TRANS-CHLORDANE TO AT LEAST 8 SOLVENT-SOL SUBSTANCES INCL DICHLOROCHLORDANE, OXYCHLORDANE, HEPTACHLOR, HEPTACHLOR ENDO-EPOXIDE, CHLORDANE CHLOROHYDRIN, & 3-HYDROXY-TRANS-CHLORDANE. OXYCHLORDANE WAS METABOLICALLY INERT, & ACCUMULATED IN MYCELIUM AS A TERMINAL RESIDUE.

来源:Hazardous Substances Data Bank (HSDB)

代谢

热带淡水丽鱼，每种重300克，分别放入16升含有80微克顺式-(14)C-氯丹的水中，持续72小时。二氯氯丹、氧化氯丹、氯丹醇、二羟基七氯、二羟基二氢氯丹以及4种未识别的化合物占从鱼和水中共回收到的放射性碳的12.5%。其余部分为未改变的顺式氯丹。

TROPICAL FRESHWATER CICHILDS, CICHLASOMA SPECIES, WEIGHING 300 G EACH, WERE INDIVIDUALLY PLACED IN 16 L OF WATER WITH 80 UG OF CIS-(14)C-CHLORDANE FOR 72 HR. DICHLOROCHLORDENE, OXYCHLORDANE, CHLORDENE CHLOROHYDRIN, DIHYDROXY HEPTACHLOR, DIHYDROXYL DIHYDROCHLORDENE PLUS 4 UNIDENTIFIED COMPOUNDS ACCOUNTED FOR 12.5% OF RADIOCARBON RECOVERED FROM FISH & WATER. REMAINDER WAS UNCHANGED CIS-CHLORDANE.

来源:Hazardous Substances Data Bank (HSDB)

代谢

... 从单一环氧化合物、氧化氯丹或1-外-2-内-4,5,6,7,8,8-八氯-2,3-外环氧-2,3,3A,4,7,7A-六氢-4,7-甲烷茚中提取的反式和顺式氯丹 ... 最近才被识别为动物组织和牛奶中的主要终末残留物 ... 氧化氯丹 ... 比氯丹的任何一种同分异构体都要毒性更大 ...

... CIS- & TRANS-CHLORDANES FROM SINGLE EPOXIDE, OXYCHLORDANE, OR 1-EXO-2-ENDO-4,5,6,7,8,8-OCTACHLORO-2,3-EXOEPOXY-2,3,3A,4,7,7A-HEXAHYDRO-4,7- METHANOINDENE ... ONLY RECENTLY ... RECOGNIZED AS MAJOR TERMINAL RESIDUE IN ANIMAL TISSUES, AND MILK ... OXYCHLORDANE ... MORE TOXIC ... THAN EITHER OF CHLORDANE ISOMERS.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

治疗是对症和支持性的。油类不应作为泻药或皮肤清洁剂使用，因为它们会增加吸收。对于摄入，建议进行洗胃和使用活性炭和硫酸钠。如果发生皮肤接触，应去除受污染的衣物，并用肥皂和水彻底清洁皮肤。儿童和成人的癫痫管理使用的是安定或苯巴比妥。呼吸抑制甚至呼吸停止可能会发生，特别是在儿童同时使用安定和苯巴比妥的情况下。这些药物最好只在可以进行紧急气管插管的重症监护区域使用。/建议/在有机氯中毒的患者中不使用肾上腺素，因为有机氯化物会引起心肌兴奋性和室性心律失常。然而，在液体管理无反应的低血压情况下，可能需要使用多巴胺，在心肺停止的情况下，可能需要使用肾上腺素。/有机氯杀虫剂/

Treatment is symptomatic and supportive. Oils should not be used as either cathartics or dermal cleansing agents, as they increase absorption. Gastric lavage and use of activated charcoal and sodium sulfate are indicated for ingestion. If dermal exposure occurred, contaminated clothes should be removed, and the skin should be thoroughly cleansed with soap and water. Management of seizures in both children and adults is with valium or phenobarbital. Respiratory depression and even respiratory arrest, especially with concomitant use of valium and phenobarbital in children, may occur. These drugs preferably should be used only in critical care areas where emergency endotracheal intubation can be performed. /It is recommended/ that epinephrine not be utilized in patients with organochlorine poisoning, as the organochlorines induce myocardial irritability and ventricular arrhythmias may occur. However, dopamine may be necessary in the event of hypotension unresponsive to fluid administration, and epinephrine may be necessary in the event of cardiopulmonary arrest. /Organochlorine insecticides/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

如果摄入，除非患者昏迷、抽搐或已给予活性炭和盐水泻药，否则应进行催吐。应避免使用基于油的泻药，如蓖麻油或其他包括脂肪或油的物质，因为这些化合物可能会增强氯化烃从胃肠道的吸收。肾上腺素是禁忌的，因为它可能由于氯化烃对心肌的刺激而诱发心室颤动。可以用安定（地西泮）以0.1毫克/公斤的剂量静脉给药，最大不超过10毫克，来治疗抽搐。除了作为肝肾功能衰竭的支持性措施外，增强消除的方法尚未成功。/氯化烃类杀虫剂/

In cases of ingestion, emesis is indicated unless the patient is comatose, is convulsing, or has administration of activated charcoal and saline cathartics. Oil-based cathartics such as castor oil or other substances including fats or oils should be avoided since these compounds may tend to enhance the absorption of the chlorinated hydrocarbon from the gastrointestinal tract. Epinephrine is contraindicated since it may induce ventricular fibrillation due to the sensition of the myocardium by the chlorinated hydrocarbons. Convulsions may be treated with diazepam in a dose of 0.1 mg/kg, administered intravenously, to a maximum of 10 mg. Methods to enhance elimination have not been successful other than as a supportive measure for hepatic and renal failure. /Chlorinated hydrocarbon insecticides/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

癫痫、低氧血症以及由此引起的酸中毒是直接危及生命的紧急情况。地西泮是首选的抗惊厥药。中度到重度中毒的患者应该建立静脉通道并使用心脏监护仪。在接触后最初的几小时内，建议采取通常的胃肠道净化措施（催吐/洗胃、活性炭、泻药）。实验动物研究表明，活性炭对氯化烃类杀虫剂的吸收非常不稳定。大多数有机氯杀虫剂含有有机溶剂，这些都是严重的吸入危险。皮肤去污（移除被污染的衣物，用水和绿色或温和肥皂清洗区域）是必要的，以防止持续的皮肤吸收。小心不要交叉污染健康人员。使用考来烯胺（每天四次，每次3-8克）可以使氯丹的粪便排泄量增加七倍，并将平均血半衰期从165天减少到80天。在有机氯化合物暴露且有大量肠肝循环的情况下，活性炭也可以减少半衰期，并应考虑在中度到重度急性中毒的连续剂量中使用。由于组织结合广泛和分布量大，透析、利尿和血液灌流无效。/有机氯/

Seizures, hypoxemia, and resultant acidosis are the immediate life-threatening emergencies. Diazepam is the anticonvulsant of choice. Moderately to severely poisoned patients should have intravenous lines and a cardiac monitor. The usual measures of gut decontamination (ipecac/lavage, charcoal, cathartics) are recommended within the first several hours after exposure. Experimental animal studies suggest that chlorinated hydrocarbon pesticide absorption by charcoal is highly variable. Most organochlorine inseticides contain organic solvents, which are severe aspiration hazards. Skin decontamination (removal of contaminated clothes, washing of area with water and green or mild soap) is necessary to prevent continued dermal absorption. Be careful not to cross-contaminate health personnel. The use of cholestyramine(3-8 g four times a day) increased fecal excretion of chlordecone by seven times and reduced the mean blood half-life from 165 to 80 days. In organochlorine exposures to compounds that have substantial enterohepatic recirculation, activated charcoal also may reduce the half-life and should be considered in serial doses for moderate to severe acute poisonings. Dialysis, diuresis, and hemoperfusion are ineffective because of extensive tissue binding and large volumes of distribution. /Organochlorines/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

1. 用肥皂和水清洗受污染的皮肤。2. 用大量清水冲洗受污染的眼睛15分钟。3. 摄入少量（小于10毫克/千克体重）发生在治疗前不到一小时的情况，最好通过以下方式处理：A. 服用吐根糖浆，随后喝1-2杯水。成人及12岁以上儿童的剂量：30毫升。12岁以下儿童的剂量：15毫升。B. 活性炭：/建议剂量：儿童用30克活性炭混合3-4盎司水，成人用100克混合8-10盎司水/...在呕吐停止后。C. 硫酸钠或硫酸镁，0.25克/千克，用自来水作为泻药。/低毒或中等到毒性的杀虫剂/

1. WASH CONTAMINATED SKIN WITH SOAP & WATER. 2. FLUSH CONTAMINATED EYES WITH COPIOUS AMOUNTS OF FRESH WATER FOR 15 MINUTES. 3. INGESTIONS OF SMALL AMOUNTS (LESS THAN 10 MG/KG BODY WEIGHT) OCCURRING LESS THAN AN HOUR BEFORE TREATMENT, ARE PROBABLY BEST TREATED BY: A. SYRUP OF IPECAC, FOLLOWED BY 1-2 GLASSES OF WATER. DOSE FOR ADULTS & CHILDREN OVER 12 YEARS: 30 ML. DOSE FOR CHILDREN UNDER 12 YEARS: 15 ML. B. ACTIVATED CHARCOAL: /SRP: 30 G ACTIVATED CHARCOAL IN 3-4 OZ WATER (CHILDREN), 100 G IN 8-10 OZ WATER (ADULT)/ ... AFTER VOMITING STOPS. C. SODIUM OR MAGNESIUM SULFATE, 0.25 G/KG IN TAP WATER, AS A CATHARTIC. /PESTICIDES OF LOW OR MODERATE TOXICITY/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

4. 在治疗开始前不到1小时内摄入大量（超过10毫克/千克）的，应通过洗胃进行治疗：A. 插管至胃部并吸出内容物。B. 用活性炭悬浮液洗胃……并在拔管前在胃中留下30-50克活性炭。C. 作为泻药使用，将硫酸钠0.25克/千克溶解在自来水中。注意：这些化学品的一些配方中包含了烃类（煤油、石油馏分）。摄入非常大的量可能会导致中枢神经系统抑制。在这种情况下，使用催吐剂是禁忌的。此外，胃插管存在吸入性烃类肺炎的风险。因此，请遵守以下预防措施：(1) 如果受害者昏迷或反应迟钝且具备条件，在进行胃插管之前插入一个气管内导管（如果有的话，带气囊的）。(2) 在插管和洗胃过程中，保持受害者的头部低于胃部水平（采用特伦德伦堡位，或左侧卧位，并让床头向下倾斜）。保持受害者头部向左转。(3) 尽可能经常吸出咽部，以移除呛入或呕吐的胃内容物。/低或中毒性农药/

4. INGESTIONS OF LARGE AMOUNTS (MORE THAN 10 MG/KG) OCCURRING LESS THAN AN HR BEFORE TREATMENT, SHOULD PROBABLY BE TREATED BY GASTRIC LAVAGE: A. INTUBATE STOMACH & ASPIRATE CONTENTS. B. LAVAGE STOMACH WITH SLURRY OF ACTIVATED CHARCOAL ... /&/ LEAVE 30-50 G ACTIVATED CHARCOAL IN THE STOMACH BEFORE WITHDRAWING TUBE. C. SODIUM SULFATE, 0.25 G/KG IN TAP WATER, AS A CATHARTIC. CAUTION: HYDROCARBONS (KEROSENE, PETROLEUM DISTILLATES) ARE INCLUDED IN SOME FORMULATIONS OF THESE CHEMICALS. INGESTION OF VERY LARGE AMOUNTS MAY CAUSE CNS DEPRESSION. IN THIS CASE, IPECAC IS CONTRAINDICATED. ALSO, GASTRIC INTUBATION INCURS A RISK OF HYDROCARBON PNEUMONITIS. FOR THIS REASON OBSERVE THE FOLLOWING PRECAUTIONS: (1) IF THE VICTIM IF UNCONSCIOUS OR OBTUNDED & FACILITIES ARE AT HAND, INSERT AN ENDOTRACHEAL TUBE (CUFFED, IF AVAILABLE) PRIOR TO GASTRIC INTUBATION. (2) KEEP VICTIM'S HEAD BELOW LEVEL OF STOMACH DURING INTUBATION & LAVAGE /SRP: TAP WATER IN CHILDREN, ISOTONIC SALINE IN ADULTS/ (TRENDELENBURG, OR LEFT LATERAL DECUBITUS, WITH HEAD OF TABLE TIPPED DOWNWARD). KEEP VICTIM'S HEAD TURNED TO THE LEFT. (3) ASPIRATE PHARYNX AS REGULARLY AS POSSIBLE TO REMOVE GAGGED OR VOMITED STOMACH CONTENTS. /PESTICIDES OF LOW OR MODERATE TOXICITY/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

有机氯化物从肺部、胃肠道和皮肤被很好地吸收。

Organochlorines are well absorbed from the lung, GI tract, and skin. /Organochlorines/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

滴滴涕的两个异构体（包括其代谢物氧氯丹）在动物体内脂肪中积累。储存的倾向性较低。在30天的滴滴涕喂养试验中，脂肪中储存水平与喂养水平的比例约为0.1，在大约2年的慢性喂养过程中，这个比例逐渐接近1。

The two isomers of chlordane (including its metabolite oxychlordane) accumulate in body fat of animals. The propensity for storage is low. Ratio of storage level in fat to feeding level is about 0.1 in a 30 day feeding trial of chlordane and roughly approaches unity for a chronic 2 year feeding ... .

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

一个重要的观察结果是，美洲大蠊能够轻易地排出氧氯丹，与此相反，老鼠则会储存它。

One important observation made was that the American cockroach readily excretes oxychlordane, in contrast to the rat, which stores it.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

主要排泄途径是胆汁，尽管几乎所有有机氯化合物都会产生可测量的尿液代谢物。许多未经代谢的杀虫剂被肠道有效重吸收（肠肝循环），从而大大减缓了粪便排泄。/固体有机氯杀虫剂/

The chief route of excretion is biliary, althugh nearly all organochlorines yield measurable urinary metabolites. ... Many of the unmetabolized pesticides are efficiently reabsorbed by the intestine (enterohepatic circulation) substantially retarding fecal excretion. /Solid organochlorine insecticides/

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  6.1(b)
• 危险品标志：
  Xn
• 危险类别码：
  R22
• 包装等级：
  III
• 危险类别：
  6.1(b)
• WGK Germany：
  3