顺-九氯 | 3734-49-4

• 物质功能分类: 分析化学 - 标准品 - 挥发性有机化合物(VOCs)
• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 中文名称: 顺-九氯
• 中文别名: (1alpha,2beta,3alpha,3aalpha,4beta,7beta,7aalpha)-1,2,3,4,5,6,7,8,8-九氯-2,3,3a,4,7,7a-六氢-4,7-甲桥-1H-茚
• 英文名称: Nonachlor
• 英文别名: (1S,7R)-1,3,4,5,7,8,9,10,10-nonachlorotricyclo[5.2.1.02,6]dec-8-ene
• CAS: 3734-49-4；39765-80-5
• 化学式: C₁₀H₅Cl₉
• 分子量: 444.2
• InChiKey: OCHOKXCPKDPNQU-VAWIPOKJSA-N

物化性质

• 熔点：
  148℃
• 沸点：
  522.25°C (rough estimate)
• 密度：
  1.7470 (rough estimate)
• 闪点：
  -26 °C
• 溶解度：
  In water, 8.2X10-3 mg/L at 25 °C /Estimated/
• 蒸汽压力：
  1.00X10-6 mm Hg at 25 °C /Extrapolated/
• 亨利常数：
  Henry's Law constant = 2.5X10-5 atm-cu m/mol at 25 °C /Estimated/

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

代谢

(14)C-反式-非氯代烷，占技术级氯丹的大约7%，以玉米油单次给药给大鼠。收集粪便和尿液。大部分放射性出现在粪便中，并鉴定为：1,2-二羟基二氢氯代烯（17.9%），1-羟基-2-氯代烯（15.4%），氯丹氯醇（13.5%），氧化氯丹（4.1%），反式-氯丹（0.8%），以及1-羟基-2-氯代-2,3-环氧氯代烯。还有两个未鉴定的化合物和未改变的九氯。

(14)C-trans-nonachlor, which comprises about 7% of technical chlordane, was administered to rats in corn oil as a single dose. Feces and urine were collected. The bulk of the radioactivity appeared in the feces and was identified as: 1,2-dihydroxydihydrochlordene (17.9%), 1-hydroxy-2-chlordene (15.4%), chlordene chlorohydrin (13.5%), oxychlordane (4.1%), trans-chlordane (0.8%), and 1-hydroxy-2-chloro-2,3-epoxychlordene. There were two unidentified compounds and unchanged nonachlor ... .

来源:Hazardous Substances Data Bank (HSDB)

代谢

体外研究中，使用人和大鼠肝脏微粒体制备物，发现了反式氯丹、氧化氯丹、氯丹烯氯醇和1,2-二羟基二氢氯丹。在使用人肝脏制备物时，代谢物的水平非常低。这与在人组织中发现的反式九氯作为主要的氯丹残留物相一致...。

In vitro studies with human and rat liver microsomal preparations showed the presence of trans-chlordane, oxychlordane, chlordene chlorohydrin, and 1,2-dihydroxydihydrochlordene. With human liver preparations, the level of metabolites was very low. This correlates with the finding of trans-nonachlor as the major chlordane residue found in human tissues ... .

来源:Hazardous Substances Data Bank (HSDB)

代谢

河流鱼类，如斑节对虾（Leiostomus xanthurus），暴露在工业级七氯中24天。七氯、t-氯丹、顺式氯丹和非氯丹在工业级七氯中存在，并在可食用鱼组织中积累。七氯环氧化物形成并也被积累...。

The estuarine fish, spot (Leiostomus xanthurus), was exposed to technical heptachlor for 24 days. Heptachlor, t-chlordane, cis-chlordane, and nonachlor, which were present in the technical grade heptachlor, accumulated in edible fish tissue. Heptachlor epoxide formed and was also accumulated ... .

来源:Hazardous Substances Data Bank (HSDB)

代谢

老鼠被喂食了含有10 ppm技术级氯丹的饮食，持续28天。然后对各种氯丹化合物的排泄进行了32天的跟踪。使用电子捕获、负离子化质谱法，结合毛细管气相色谱，测量了21只老鼠脂肪组织中技术级氯丹的14种成分或代谢物的浓度。两种主要八氯异构体，即伽马-氯丹和阿尔法-氯丹的半衰期分别确定为7.1天和5.9天。非氯代的半衰期为9.7天（顺式-非氯代）、14.3天（反式-非氯代）和54.1天（非氯代III）。排泄速率似乎受到分子三个结构特征的控制；环1上氯的总数和构型以及碳2上的氯数目。

Rats were fed a diet containing 10 ppm of technical chlordane for 28 days. The depuration of the various chlordane compounds was then followed for 32 days. The concn of 14 components or metabolites of technical chlordane were measured in the adipose tissues of 21 rats, using electron capture, negative ionization mass spectrometry, coupled with capillary gas chromatography. The half-lives of the two major octachloro isomers, gamma- and alpha-chlordane, were determined to be 7.1 and 5.9 d respectively. The half-lives of the nonachlors were 9.7 (cis-nonachlor), 14.3 (trans-nonachlor), and 54.1 days (nonachlor III). The depuration rates seem to be controlled by three structural features of the molecules; the total number and configuration of the chlorines on ring 1 and the number of chlorines on carbon 2.

来源:Hazardous Substances Data Bank (HSDB)

代谢

有机氯杀虫剂氯丹对人体的毒性影响进行了比较...。对血液中氯丹代谢物进行分析，发现它们的存在按以下顺序递减：顺式-非氯丹、氧氯丹、对氯丹环氧和反式-非氯丹。工人体内氯丹及其代谢物的总范围在9.84 : 4.47 ng/g之间。还发现，害虫控制操作员的血清甘油三酯、肌酸磷酸激酶和乳酸脱氢酶活性也较高...

The toxic effects of the organochlorine insecticide chlordane were compared in man... . Analysis of blood for chlordane metabolites showed their presence in the descending order of trans-nonachlor, oxychlordane, hepatachlorepoxide and cis-nonachlor. The total range of chlordane and its metabolites in the sera of workers was 9.84 : 4.47 ng/g. Serum levels of triglycerides, creatine phosphokinase and lactate dehydrogenase activities were also found to be higher in pest control operators ...

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。不应使用油作为泻药或皮肤清洁剂，因为它们会增加吸收。对于摄入情况，建议进行胃灌洗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。尤其是在儿童中同时使用安定和苯巴比妥时，可能会出现呼吸抑制甚至呼吸停止。这些药物最好只在能够进行紧急气管插管的危重病区使用。/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，在液体治疗无反应的低血压情况下，可能需要使用多巴胺，在心肺骤停的情况下，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

癫痫、低氧血症以及由此导致的酸中毒是立即威胁生命的紧急情况。地西泮是首选的抗惊厥药。中到重度中毒的患者应该建立静脉通道并使用心脏监护仪。大多数有机氯杀虫剂含有有机溶剂，这些溶剂是严重的吸入危险物。皮肤去污染（去除污染衣物，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。小心不要交叉污染医疗人员。使用考来烯胺（每天四次，每次3-8克）可以增加氯苯酮通过粪便的排泄量七倍，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中，对于那些有大量肠肝循环的化合物，活性炭也可以减少半衰期，并且在中到重度急性中毒时应该考虑连续剂量。由于广泛的组织结合和大量的分布容积，透析、利尿和血液灌注无效。/有机氯化物/

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. ...Most organochlorine insecticdes 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

治疗：快速作用的巴比妥类药物或地西泮可能有助于控制抽搐，但必须小心，不要加重任何呼吸抑制。可能需要进行氧疗和人工通气。避免使用肾上腺素。由于没有已知的特定解毒剂，对症治疗必须伴随完全休息。使用适量的肥皂和水清洗皮肤上溢出的任何化合物。如果溅入眼睛，请用水反复冲洗。/氯丹/

Treatment: A rapidly acting barbiturate or diazepam may aid in controlling convulsions, but care must be taken not to augment any respiratory depression. Oxygen therapy and artificial ventilation may be necessary. Avoid epinephrine. Since no specific antidotes are known, symptomatic therapy must be accompanied by complete rest. Use soap and water in adequate quantities to wash off any compound spilled on the skin. If spilled in eyes, wash repeatedly with water. /Chlordane/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

有机氯杀虫剂通过任何途径高度暴露的人员应被观察是否有感觉异常、协调性障碍、言语不清、精神异常和不自主的 motor 活动等警告性癫痫即将发作的症状。如果发生癫痫，将受害者置于左侧卧位，头部向下。移开可能造成伤害的家具或其他固体物品。如果下巴动作剧烈，将衬垫的压舌板放在牙齿之间以保护舌头。尽可能取下假牙和其他可移动的牙齿修复物。吸出口腔和咽喉分泌物，并在可能的情况下，插入一个口咽气道以保持舌头不被阻塞的开放通道。尽量减少噪音和任何可能触发癫痫活动的患者操作。通过面罩给予氧气。在呼吸受到抑制时，通过机械辅助通气来维持肺气体交换。/固体有机氯杀虫剂/

Persons exceptionally exposed to organochlorine pesticides by any route should be observed for sensory disturbances, incoordination, speech slurring, mental aberrations, and involuntary motor activity that would warn of imminent convulsions. If convulsions occur, place the victim in the left lateral decubitus position with the head down. Move away furniture or other solid objects that may be a source of injury. If jaw movements are violent, place padded tongue blades between the teeth to protect the tongue. Whenever possible, remove dentures and other removable dental work. Aspirate oral and pharyngeal secretions, and, when possible, insert an oropharyngeal airway to maintain an open passage unobstructed by the tongue. Minimize noise and any manipulation of the patient that may trigger seizure activity. Administer oxygen by mask. Maintain pulmonary gas exchange by mechanically assisted ventilation whenever respiratin is depressed. /Solid organochlorine insecticides/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 医疗监测

氯化炭（Chlordane）已广泛用于保护土壤和房屋基础免受白蚁侵害。害虫控制操作人员在工作中会暴露于氯化炭。研究了害虫控制操作人员血液中氯化炭及其代谢物与喷洒条件的关系。在一些暴露于氯化炭的害虫控制操作人员的血液中检测到了氯化炭及其代谢物，但在对照组中没有检测到。在害虫控制操作人员的血液中检测到了反式九氯（trans-nonachlor）及其代谢物氧化氯丹（oxychlordane）和环氧七氯（heptachlor epoxide）。血液中氯化炭及其代谢物的总浓度（反式九氯 + 氧化氯丹 + 环氧七氯）小于5.6 ppb（平均值：0.89 ppb）。氯化炭暴露的害虫控制操作人员血液中氯化炭及其代谢物的浓度与喷洒天数和喷洒的氯化炭量显著相关，尤其是在医学检查前的三个月内，与喷洒天数的关联系数很大（r=0.81，p<0.001）。血液中氯化炭及其代谢物的浓度被认为是氯化炭暴露工作人员生物监测的有用指标。

Chlordane has been widely used to protect soil and house foundations against termite infestation. Pest control operators are occupationally exposed to chlordane. The relationship between chlordane and its metabolites in blood of pest control operators and spraying conditions were investigated. Chlordane and its metabolites were detected in the blood of some chlordane-exposed pest control operators, but not in that of the controls. Trans-nonachlor and the metabolites oxychlordane and heptachlor epoxide were detected in the blood of pest control operators. Total concentrations of chlordane and its metabolites in blood (trans-nonachlor + oxychlordane + heptachlor epoxide) was less than 5.6 ppb (mean: 0.89 ppb). The concentration of chlordane and its metabolites in blood of chlodane-exposed pest control operators was significantly correlated with the number of spraying days and the amount of chlordane sprayed, particularly with a large correlation coefficient (r= 0.81, p< 0.001) with the spraying days in the three months prior to the medical examination. The concentration of chlordane and its metabolites in blood is considered to be a useful indicator of biological monitoring for chlordane exposed workers.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

非对称九氯，作为技术级氯丹的主要成分之一，是一个重要的化合物，因为它已知会在人体内累积……。/非对称九氯/

Trans-nonachlor, one of the major constituents of technical chlordane, is an important compound, since it is known to accumulate in humans ... . /trans- Nonachlor/

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, gastrointestinal tract, and skin. /Organochlorines/

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, although 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)

吸收、分配和排泄

有机氯杀虫剂确实会出现在母乳中。

Organochlorine insecticides ... do appear in breast milk. /Organochlorines/

来源:Hazardous Substances Data Bank (HSDB)

制备方法与用途

用途

反式九氯是一种有机氯杀虫剂，主要应用于农业生产中防治农作物病虫害。

类别

农药

毒性分级

中毒

急性毒性

口服-大鼠 LD50: 500毫克/公斤

可燃性危险特性

燃烧会产生有毒的氯化物气体

储运特性

应存放在通风、低温和干燥的地方，并与食品原料分开储运

灭火剂

干粉、泡沫或砂土