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(1S,2R,3R,6R,7S,8S)-1,8,9,10,11,11-hexachlorotetracyclo[6.2.1.13,6.02,7]dodeca-4,9-diene | 309-00-2

中文名称
——
中文别名
——
英文名称
(1S,2R,3R,6R,7S,8S)-1,8,9,10,11,11-hexachlorotetracyclo[6.2.1.13,6.02,7]dodeca-4,9-diene
英文别名
——
(1S,2R,3R,6R,7S,8S)-1,8,9,10,11,11-hexachlorotetracyclo[6.2.1.13,6.02,7]dodeca-4,9-diene化学式
CAS
309-00-2
化学式
C12H8Cl6
mdl
——
分子量
364.9
InChiKey
QBYJBZPUGVGKQQ-VFBQXPTHSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 物理描述:
    Aldrin, liquid appears as a solution in oil of aldrin, a noncombustible water-insoluble solid. Used as an insecticide. Mixed with a flammable carrier solvent.
  • 颜色/状态:
    Colorless needles
  • 气味:
    ... Mild chemical odor ...
  • 沸点:
    145 °C at 2 mm Hg
  • 熔点:
    104 °C
  • 闪点:
    Approximately 150F or higher (EPA, 1998)
  • 溶解度:
    In water, 170 mg/l @ 25 °C
  • 密度:
    1.6 at 20 °C/4 °C (solid)
  • 蒸汽压力:
    1.20X10-4 mm Hg @ 25 °C
  • 亨利常数:
    4.40e-05 atm-m3/mole
  • 稳定性/保质期:

    Thermally stable up to 200 °C. Stable between pH 4 and 8.

  • 分解:
    When heated to decomposition it emits toxic fumes of /hydrogen chloride/.
  • 腐蚀性:
    NONCORROSIVE TO STEEL, BRASS, MONEL, COPPER, NICKEL, ALUMINUM

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
阿德林的主要反应是在双键处进行环氧化,形成6,7-环氧桥二阿德林。这种氧化可以是光化学的或生物学的(混合功能氧化酶),并且发生在土壤、植物组织和所有被研究的动物中。阿德林在植物和动物中也会降解为六氯-六氢-1,4-内亚甲基-茚-5,7-二羧酸和阿德林-反式二醇。在动物中,5-羟基二阿德林、9-酮二阿德林和酮-光二阿德林作为排泄代谢物形成。在排泄之前,羟基代谢物大部分进行了共轭反应。
DOMINANT REACTION OF ALDRIN IS EPOXIDATION AT DOUBLE BOND TO FORM 6,7-EPOXIDE B DIELDRIN. ... /SRP: THIS OXIDN CAN BE PHOTOCHEMICAL OR BIOLOGICAL (MIXED-FUNCTION OXIDASES) & OCCURS/ IN SOILS, PLANT TISSUES, & IN ALL ANIMALS STUDIED. ... ALDRIN IS ALSO DEGRADED IN PLANTS & ANIMALS TO HEXACHLORO-HEXAHYDRO-1,4-ENDO-METHYLENE-INDENE-5,7-DICARBOXYLIC ACID & TO ALDRIN-TRANS-DIOL. IN ANIMALS 5-HYDROXYDIELDRIN, 9-KETO-DIELDRIN & KETO-PHOTODIELDRIN ARE ... FORMED AS EXCRETORY METABOLITES. BEFORE EXCRETION THE HYDROXY METABOLITES ARE LARGELY CONJUGATED.
来源:Hazardous Substances Data Bank (HSDB)
代谢
最广泛报道的艾氏剂和狄氏剂降解排泄产物是一种六氯代二羧酸(4,5-开环艾氏剂-4,5-二羧酸),人们普遍认为这是一种终末哺乳动物代谢物。这一假设被以下发现所否定:在大鼠静脉注射(3.5毫克/千克)...4,5-开环艾氏剂-4,5-二羧酸后,在其尿液中识别出两种五氯代二羧酸(占22%)。
THE MOST EXTENSIVELY DEGRADED EXCRETION PRODUCT OF ALDRIN & DIELDRIN REPORTED ... IS A HEXACHLORINATED DICARBOXYLIC ACID /4,5-SECO-ALDRIN-4,5-DICARBOXYLIC ACID/, & IT HAS BEEN WIDELY ASSUMED THAT THIS IS A TERMINAL MAMMALIAN METABOLITE. THIS ASSUMPTION ... /IS/ DISCREDITED BY IDENTIFICATION OF TWO PENTACHLORINATED DICARBOXYLIC ACIDS (22%) IN URINE OF RATS DOSED IV (3.5 MG/KG) WITH ... /4,5-SECO-ALDRIN-4,5-DICARBOXYLIC ACID/.
来源:Hazardous Substances Data Bank (HSDB)
代谢
在0-100天的时间过程中,将艾氏剂和狄氏剂添加到从菜豆(法国豆)根、茎和马铃薯块茎悬浮培养物中进行亚培养,其吸收和代谢过程相似,狄氏剂快速产生,其他代谢产物的出现则有所延迟。当艾氏剂和狄氏剂在亚培养后的第10天或第20天添加到菜豆培养物中时,艾氏剂转化为狄氏剂的通常程度发生了,但其他代谢产物的产生减少了。狄氏剂的产生在快速生长期间达到最大,并且可能与其他转化过程无关。
TIME COURSES (0-100 DAYS) OF UPTAKE & METABOLISM OF ALDRIN & DIELDRIN ADDED AT SUBCULTURE TO SUSPENSION CULTURES FROM PHASEOLUS VULGARIS (FRENCH BEAN) ROOT & SHOOT & SOLANUM TUBEROSUM (POTATO) TUBER WERE COMPARABLE, WITH RAPID DIELDRIN PRODN & DELAYED APPEARANCE OF OTHER METABOLITES. WHEN ALDRIN & DIELDRIN WERE ADDED TO PHASEOLUS CULTURES AT 10 OR 20 DAYS AFTER SUBCULTURE, USUAL EXTENT OF CONVERSION OF ALDRIN TO DIELDRIN OCCURRED, BUT WITH REDUCED PRODN OF OTHER METABOLITES. DIELDRIN PRODN WAS MAXIMUM DURING RAPID GROWTH PHASE & PROBABLY INDEPENDENT OF OTHER CONVERSIONS.
来源:Hazardous Substances Data Bank (HSDB)
代谢
在大鼠肝脏的微囊体中,通过还原型烟酰胺腺嘌呤二核苷酸刺激了艾氏剂向狄氏剂的环氧化。在精囊和肉芽组织的微囊体中,还原型烟酰胺腺嘌呤二核苷酸对艾氏剂的环氧化没有影响。显然,在肝脏中,艾氏剂是通过单加氧酶途径进行环氧化,在肉芽组织和精囊中是通过前列腺素合酶介导的途径,而在肺中则是通过这两种途径。
In microsomes from rat liver, aldrin epoxidation into dieldrin was stimulated by reduced nicotinamide adenine dinucleotide . ... In microsomes from seminal vesicles and granulation tissue, reduced nicotinamide adenine dinucleotide had no effect on aldrin epoxidation. ... Apparently, in the liver, aldrin is epoxidized by monooxygenase pathway, in granulation tissue and seminal vesicles by prostaglandin synthase-mediated pathway, and in the lung by both pathways.
来源:Hazardous Substances Data Bank (HSDB)
代谢
阿德林通过胃肠道的吸收,肺和皮肤。吸收后,阿德林主要通过淋巴系统转运到脂肪。一旦进入体内,阿德林主要在肝脏中通过细胞色素P-450系统的混合功能氧化酶转化为狄尔德林,在肺部和皮肤的转化程度较小。阿德林还可能通过前列腺素合酶介导的途径在外部组织中环氧化为狄尔德林。狄尔德林通过肝微粒体单加氧酶和环氧化酶水合酶进行代谢。其代谢物,其中主要的一种是9-羟基狄尔德林,在粪便中排出。(L87)
Aldrin is absorbed throught the gastrointestinal tract, lungs and skin. Following absorption, aldrin is redistributed primarily to fat via the lymphatic system. Once in the body, aldrin is readily converted to dieldrin, primarily in the liver by mixed-function oxidases of the cytochrome P-450 system, and to a lesser extent in the lung and skin. Aldrin may also be epoxidized to dieldrin by a prostaglandin synthetase-mediated pathway inextrahepatic tissues. Dieldrin is metabolized by liver microsomal monooxygenases and epoxide hydratases. Its metabolites, of which the primary one is 9-hydroxydieldrin, are excreted in the faeces. (L87)
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 毒性总结
识别:Aldrin是一种氯化环二烯杀虫剂。纯净的Aldrln是一种白色结晶固体。技术等级的Aldrin呈棕色。Aldrin已被用于各种制剂,包括可乳化浓缩物、可湿性粉剂、颗粒剂、灰尘和碳氢液体中的溶液。Aldrin具有轻微的化学气味,在大多数有机溶剂中(芳香族化合物、酯、酮、石蜡和卤化溶剂)中非常可溶。Aldrin的杂质包括八氯环戊烯、六氯丁二烯、甲苯和由Aldrin反应期间聚合形成的化合物混合物以及碳基化合物。Aldrin是一种非常有效的土壤杀虫剂,曾被用于处理种子。它曾被用来控制白蚁、玉米根虫、种子玉米甲虫和蛆虫、铁线虫、水稻水象甲、蚱蜢和日本甲虫。人体接触:中枢神经系统似乎是主要部位,结果出现癫痫。有毒暴露产生震颤、眩晕、过度兴奋、癫痫和昏迷。中毒主要通过皮肤吸收发生。流行病学研究没有显示任何致癌风险。吸收可以通过吸入、皮肤和胃肠道的途径发生。Aldrin在体内的临床毒性实际上是由于其迅速代谢为dieldrin。症状反映了由于GABA神经传递抑制的中枢神经系统毒性。头痛、震颤、过度兴奋、癫痫和昏迷已有报道。发生呼吸道吸收,呼出的Aldrin浓度较吸入浓度降低。Aldrin主要在肝脏迅速转化为dieldrin。因此,在血液或组织中几乎没有发现Aldrin。尸检病例显示大脑、肝脏和脂肪组织中存在dieldrin水平。在慢性口服给药后,血液中dieldrin浓度呈指数下降,估计半衰期为369天。消除主要通过胆汁经粪便发生。9-羟基二噁烷似乎是被排泄的主要代谢物。二噁烷也通过母乳排出。在局部或iv给药后,少量二噁烷代谢物通过尿液排出。在摄入后,尿液中也可能发现二噁烷代谢物。儿童中有几例Aldrin中毒的病例,其表现出的中枢神经系统兴奋症状与成人相似。急性摄入后发生死亡。胎儿集中二噁烷,污染的母乳摄入增加了非常年轻的人中枢系统效应的风险。在花农接触包括Aldrin在内的多种杀虫剂后,观察到姐妹染色单体交换和交换型染色体畸变增加。心血管并发症包括在过量服用后血压波动和心动过速。在急性过量服用后的几天里,血液尿素氮水平、明显血尿和白蛋白尿均有升高。在杀虫剂制造工人中没有发现皮炎。在至少四年的随访中,杀虫剂制造工人的正常血液学参数有所记录。动物/细菌/病毒/细胞研究:几种动物吸入Aldrin后死亡。在二甲苯中单次皮肤应用Aldrin导致试验动物死亡。给大鼠口服Aldrin会导致惊厥。Aldrin在SV-40转化的人成纤维细胞(VA-4)中诱导非计划DNA合成,在存在和不存在大鼠肝微体的情况下。在用Aldrin或dieldrin处理后,大肠杆菌质粒的DNA断裂率与未处理的质粒DNA的DNA断裂率没有差异,这表明,至少在这些研究中,这些化合物没有直接与DNA发生作用。在不同的实验条件下测试了Aldrin和dieldrin对培养的大鼠胸腺细胞和人类淋巴细胞的胸腺嘧啶摄取的影响。两种化合物似乎对胸腺嘧啶摄取有边际效应,提示DNA合成受到抑制。Aldrin和dieldrin未在Fischer 344大鼠肝细胞原代培养中诱导非计划DNA合成。在肝细胞原代培养/DNA修复试验中使用高代谢能力的新鲜分离肝细胞监测DNA损伤的产生,通过测量DNA修复合成。Aldrin和dieldrin关于DNA修复的结果是模棱两可的,但DNA没有损伤。Aldrin在大鼠肝细胞碱性洗脱试验中诱导DNA链断裂。Aldrin和dieldrin抑制了6-硫鸟嘌呤敏感和6-硫鸟嘌呤抗性人畸胎瘤细胞间的间隙连接细胞间通讯。在几项研究中没有发现恶性肿瘤发病率的增加。在动物实验中,发现肝脏肿瘤包括肝细胞腺瘤的发生率增加。在动物研究中,Aldrin确实增加了胎儿死亡率,增加了腭裂和蹼足的发生率,并降低了出生后存活率。
IDENTIFICATION: Aldrin is a chlorinated cyclodiene insecticide. Pure aldrin is a white crystalline solid. Technical grade aldrin is tan in color. Aldrin has been used in various formulations which include emulsifiable concentrates, wettable powders, granules, dusts and solutions in hydrocarbon liquids. Aldrin has a mild chemical odor, and is very soluble in most organic solvents (aromatics, esters, ketones, paraffins and halogenated solvents. Impurities of aldrin include octachlorocyclopentene, hexachlorobutadiene, toluene and a mixture of compounds formed by polymerization during the aldrin reaction along with carbonyl compounds. Aldrin is very effective soil insecticide and has been used to treat seeds. It has been used to control termites, corn root worms, seed corn beetle and maggot, wire worms, rice water weevil, grasshoppers and Japanese beetles. HUMAN EXPOSURE: The CNS seems to be the primary site with resultant seizures. Toxic exposures produce tremors, giddiness, hyperexcitability, seizures and comas. Poisoning occurs mainly through absorption through the skin. Epidemiological studies do not show any carcinogenic risk. Absorption can occur by inhalation, dermal and gastrointestinal routes. Clinical toxicity from aldrin actually is due to its rapid metabolism in the body to dieldrin. Symptoms reflect CNS toxicity due to GABA neurotransmission inhibition. Headache, tremors, hyperexcitability, seizures and comas have been noted. Respiratory absorption occurs, expiratory aldrin concentrations are decreased compared to inspired concentrations. Aldrin is rapidly converted to dieldrin primarily in the liver. Consequently little aldrin is found in the blood or tissues. Autopsy cases show dieldrin levels in the brain, liver and adipose tissue. After chronic oral human administration, blood dieldrin concentrations decreases exponentially following first order kinetics with an estimated half life of 369 days. Elimination occurs primarily through the feces via the bile. 9-Hydroxydieldrin seems to be the major metabolite excreted. Dieldrin is also excreted in the breast milk. Small amounts of dieldrin metabolites are excreted in the urine after either topical or iv administration. Dieldrin metabolites may also be found in the urine after ingestion. There have been a few cases of aldrin toxicity in children with resulting signs of CNS stimulation similar to adults. Death has resulted after acute ingestion. The fetus concentrates dieldrin, and the possibility of contaminated breast milk consumption increase the risk of CNS effects in the very young. Increased sister chromatid exchanges and exchange type chromosome aberrations were noted in floriculturists after exposure to several pesticides including aldrin. Cardiovascular complications include blood pressure fluctuations and tachycardia after overdose. Blood urea nitrogen levels, gross hematuria and albuminuria for several days after an acute overdose was noted. No dermatitis was seen in pesticide manufacturing workers. Normal hematological parameters were noted in pesticide manufacturing workers during at least a four years of follow up. ANIMAL/BACTERIAL/VIRAL/CELL STUDIES: Inhalation exposure to aldrin in several species resulted in death. Single dermal applications of aldrin in xylene produced death in test animals. Oral administration of aldrin to rats causes convulsions. Aldrin induced unscheduled DNA synthesis in SV-40 transformed human fibroblast cells (VA-4) both in the presence and absence of rat liver microsomes, The DNA breakage rates in Escherichia coli plasmid after treatment with aldrin or dieldrin did not differ from those in untreated plasma DNA suggesting that, at least in these studies, the compounds did not interact directly with DNA. The effects of aldrin and dieldrin on the uptake of tritiated thymidine by cultured rat thymocytes and human lymphocytes were tested under different experimental conditions. Both compounds appeared to have marginal effects on thymidine uptake, suggesting inhibition of DNA synthesis. Aldrin and dieldrin did not induce unscheduled DNA synthesis in primary cultures of Fischer 344 rat hepatocytes. In the hepatocyte primary culture/DNA repair test using freshly isolated hepatocytes of high metabolic capability to monitor the production of DNA damage by measuring DNA repair synthesis. Aldrin and dieldrin gave equivocal results concerning DNA repair, but there was no damage to DNA. Aldrin induced DNA strand breaks in an alkaline elution rat hepatocyte assay. Both aldrin and dieldrin inhibited gap junctional intercellular communication between 6-thioguanine sensitive and 6-thioguanine resistant human teratocarcinoma cells in culture. No increased incidence of malignant neoplasms have been found in several studies. In animal assays there was an increased incidence of hepatic tumors including hepatocellular adenomas. In animal studies, aldrin did cause an increase in fetal mortality, increased incidence of cleft palate and webbed foot and a decreased postnatal survival have been reported.[
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 毒性总结
Aldrin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。Aldrin还抑制了Na+ K+ ATPase和Ca2+和Mg2+ ATPase,这些对于钙跨膜转运至关重要。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。这导致过度兴奋和全身性癫痫发作。
Aldrin 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. Aldrin 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 CNS. This results in hyperexcitation and generalized seizures. (T10, L87)
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 致癌性证据
人类致癌性证据不足。动物致癌性证据有限。总体评估:第3组:该物质对人类致癌性无法分类。
Inadequate evidence of carcinogenicity in humans. Limited evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 致癌性证据
癌症分类:B2组可能的人类致癌物
Cancer Classification: Group B2 Probable Human Carcinogen
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 致癌性证据
分类:B2;可能的人类致癌物。分类依据:经口给予的艾氏剂在三种不同品系的小鼠中,无论雄性还是雌性,都显著增加了肿瘤反应。结构上相关的化学品,包括代谢物狄氏剂,已经观察到肿瘤诱导。人类致癌性数据:不足。动物致癌性数据:充分。
CLASSIFICATION: B2; probable human carcinogen. BASIS FOR CLASSIFICATION: Orally administered aldrin produced significant increases in tumor responses in three different strains of mice in both males and females. Tumor induction has been observed for structurally related chemicals, including dieldrin, a metabolite. HUMAN CARCINOGENICITY DATA: Inadequate. ANIMAL CARCINOGENICITY DATA: Sufficient.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
母血、胎盘和脐带血来自同一母亲/儿童对进行分析,以确定在100名妇女研究中有机氯杀虫剂从母亲到胎儿的转移。在所有分析的样本中均检测到艾氏剂,表明存在胎盘转移。发现杀虫剂浓度与孕妇年龄、饮食习性和居住地区之间存在相关性。
MATERNAL BLOOD, PLACENTA, & UMBILICAL CORD BLOOD OF SAME MOTHER/CHILD PAIR WERE ANALYZED TO DETERMINE ORGANOCHLORINE PESTICIDE TRANSFER FROM MOTHER TO FETUS IN STUDY OF 100 WOMEN. ALDRIN WAS DETECTED IN ALL SAMPLES ANALYZED, INDICATING PLACENTAL TRANSFER. CORRELATION WAS FOUND BETWEEN PESTICIDE CONCN & AGE, DIETETIC HABITS & AREA OF RESIDENCE OF PREGNANT WOMEN.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
在血浆中,阿德林和狄尔德林主要与α-和β-脂蛋白组分相关联。
IN PLASMA, BOTH ALDRIN & DIELDRIN ARE ASSOCIATED MAINLY WITH ALPHA- & BETA-LIPOPROTEIN FRACTIONS ... .
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
ALDRIN尚未在...普通人群中发现,也未曾发现于...从事生产它的男性的体脂中;只在这些男性的血液中发现了微量。急性中毒的人...会迅速转化为/狄尔德林/...。
ALDRIN HAS NOT BEEN FOUND IN ... GENERAL POPULATION OR ... IN BODY FAT OF MEN ENGAGED IN MANUFACTURING IT; ONLY TRACES ARE FOUND IN BLOOD OF SUCH MEN. PERSONS ACUTELY POISONED ... MAKE THE CONVERSION /TO DIELDRIN/ ... RAPIDLY.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
(36)CL Aldrin...在口服给大鼠和断奶仔猪后迅速吸收,并集中在肝脏和脂肪储存处,从这些地方...它仅缓慢排出。(14)C Aldrin喂给大鼠后排泄在粪便中(12周内剂量的90%)和尿液中(10%),作为亲水性代谢物与少量未改变的Aldrin和Dieldrin的混合物。
(36)CL ALDRIN ... IS RAPIDLY ABSORBED AFTER ORAL ADMIN TO RATS & WEANLING PIGS & BECOME LOCALIZED IN LIVER & FAT DEPOTS, FROM WHICH ... IT IS ONLY SLOWLY EXCRETED. (14)C ALDRIN FED TO RATS IS EXCRETED IN FECES (90% OF DOSE IN TWELVE WK) & URINE (10%), AS MIXT OF HYDROPHILIC METABOLITES TOGETHER WITH SMALL AMT OF UNCHANGED ALDRIN & DIELDRIN.
来源:Hazardous Substances Data Bank (HSDB)

安全信息

  • 危险品标志:
    N,T,Xn,F,Xi
  • 安全说明:
    S16,S22,S26,S33,S36,S36/37,S45,S60,S61,S62,S7
  • 危险类别码:
    R67,R20/21/22,R38,R40,R36,R36/37/38,R24/25,R65,R50/53,R11,R39/23/24/25,R48/24/25
  • RTECS号:
    IO2100000
  • 海关编码:
    2903820010
  • 包装等级:
    II
  • 危险类别:
    6.1(a)
  • 危险品运输编号:
    2761

SDS

SDS:8b676ef524f4cd7f9ab1913c18bd7e5c
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