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

• 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: (2S,6R,7R,8R)-1,8,9,10,11,11-hexachlorotetracyclo[6.2.1.13,6.02,7]dodeca-4,9-diene
• CAS: 309-00-2
• 化学式: C₁₂H₈Cl₆
• 分子量: 364.9
• InChiKey: QBYJBZPUGVGKQQ-SUFXPJIHSA-N

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DOMINANT反应是在双键处进行环氧化以形成6,7-环氧B二氯。这种氧化反应可以是光化学的或生物学的(混合功能氧化酶)并且在土壤、植物组织和所有研究过的动物中发生。阿德林在植物和动物中也被降解为六氯六氢-1,4-内亚甲基-茚-5,7-二羧酸和顺式-阿德林二醇。在动物中，5-羟基二氯、9-酮二氯和酮-光二氯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

最广泛降解的艾氏剂和狄氏剂排泄产物报道是一种六氯代二羧酸（4,5-开环艾氏剂-4,5-二羧酸），并且人们普遍认为这是一种终末哺乳动物代谢物。这种假设被两种五氯代二羧酸（占22%）的鉴定所驳斥，这些酸在大鼠静脉注射（3.5毫克/千克）... 4,5-开环艾氏剂-4,5-二羧酸后的尿液中被发现。

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

在添加到从菜豆（法国豆）根和茎以及马铃薯块茎的悬浮培养物中的时候，农药阿德林和狄艾德林（滴滴涕）的吸收和代谢过程（0-100天）是相似的，其中狄艾德林的产生迅速，而其他代谢产物的出现则有所延迟。当阿德林和狄艾德林在子培养后的10天或20天添加到菜豆培养物中时，阿德林通常转化为狄艾德林的过程发生了，但其他代谢产物的产生减少了。狄艾德林的产生在快速生长期达到最大，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通过前列腺素合酶介导途径，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

动物将阿德林转化为狄尔德林的能力已经得到证实。……这种转化也发生在较低等的动物、植物和微生物中。

The conversion of aldrin to dieldrin by mammals has been demonstrated ... . ... The conversion occurs also in lower animals, plants, and microorganisms.

来源:Hazardous Substances Data Bank (HSDB)

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作用。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)

毒理性

• 致癌性证据

在美国环保局(EPA)的《致癌物风险评估指南(拟议)框架》内，建议与小鼠肝脏肿瘤反应相关的艾氏剂/狄氏剂的最合适的癌症风险描述符是“不太可能是一种人类致癌物”，这个描述符与EPA引用的苯巴比妥的例子一致。

Within the framework of EPA's Proposed Guidelines for Carcinogen Risk Assessment, it is proposed that the most appropriate cancer risk descriptor for aldrin/dieldrin, relating to the mouse liver tumor response, is 'not likely a human carcinogen', a descriptor consistent with the example of phenobarbital cited by EPA.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

A3：已确认的动物致癌物，对人类的相关性未知。

A3: Confirmed animal carcinogen with unknown relevance to humans.

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/儿童对被分析，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、饮食习性及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...从事其制造的男性的体脂中；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/狄尔特林/...。

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