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retronecine | 16662-45-6

中文名称
——
中文别名
——
英文名称
retronecine
英文别名
Retronecin;Heliotridin;1H-Pyrrolizine-7-methanol, 2,3,5,7a-tetrahydro-1-hydroxy-, (1S-cis)-;7-(hydroxymethyl)-2,3,5,8-tetrahydro-1H-pyrrolizin-1-ol
retronecine化学式
CAS
16662-45-6
化学式
C8H13NO2
mdl
——
分子量
155.197
InChiKey
HJSJELVDQOXCHO-UHFFFAOYSA-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

计算性质

  • 辛醇/水分配系数(LogP):
    -1.3
  • 重原子数:
    11
  • 可旋转键数:
    1
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.75
  • 拓扑面积:
    43.7
  • 氢给体数:
    2
  • 氢受体数:
    3

ADMET

代谢
向大鼠给药这些生物碱后,次裂碱和毛果芸香碱的水解产物——赫尔利奥特里丁,以N-氧化物形式被大量排出。
Heliotridine, the hydrolysis product from heliotrine and lasiocarpine, was excreted in the form of the N-oxide in larger quantities after the administration of each of these alkaloids /to rats/.
来源:Hazardous Substances Data Bank (HSDB)
代谢
.../和/ 海里奥特里丁,40% ...
The pa /pyrrolizidine alkaloids/, like many other foreign substances, undergo metab changes in animal body by more than one pathway. ... The known metabolites represent products of n-oxidation and dehydrogenation of pyrrolizidine moiety, of o-demethylation of methoxy groups when these are present in acidic moiety, and products of hydrolysis of ester linkages. ... The part of the administered dose that is excreted in the urine as the unchanged parent alkaloid depends mainly on its basic properties and water solubility. Lasiocarpine is excreted in trace quantities.../and/ heliotridine, 40%...
来源:Hazardous Substances Data Bank (HSDB)
代谢
动物研究的证据表明,肝毒性是由于肝细胞中的混合功能氧化酶形成有毒的吡咯代谢物所致。
Evidence from animal studies suggests that the hepatotoxicity is due to the formation of toxic pyrrolic metabolites by the mixed function oxidases of liver cells.
来源:Hazardous Substances Data Bank (HSDB)
代谢
在给予一些吡咯里西啶生物碱和半合成衍生物的大鼠肝脏中测量了吡咯代谢物的水平。基于海绿碱的生物碱产生的吡咯比类似的 retronecine 酯多,海绿碱二酯化物产生的吡咯比 retronecine 二酯化物少,因为前者更容易受到水解攻击。
Levels of pyrrolic metabolites were measured in the livers of rats given some pyrrolizidine alkaloids and semisynthetic derivatives. ... Heliotridine-based alkaloids gave more pyrrole than similar retronecine esters, heliotridine ditiglate gave less pyrrole than retronecine ditiglate because the former was more open to hydrolytic attack.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 副作用
职业性肝毒素 - 第二性肝毒素:在职业环境中的毒性效应潜力是基于人类摄入或动物实验的中毒案例。
Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
毒理性
  • 解毒与急救
基本治疗:建立专利气道。如有必要,进行吸痰。观察呼吸不足的迹象,如有需要,协助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿,如有必要进行治疗……。监测休克,如有必要进行治疗……。预见并处理癫痫发作……。对于眼睛污染,立即用水冲洗眼睛。在运输过程中,用生理盐水连续冲洗每只眼睛……。不要使用催吐剂。对于摄入,如果患者能吞咽、有强烈的干呕反射且不流口水,则用水冲洗口腔,并给予5毫升/千克,最多200毫升的水进行稀释……。在去污后,用干燥的无菌敷料覆盖皮肤烧伤……。/毒药A和B/
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 解毒与急救
高级治疗:对于无意识、严重肺水肿或呼吸停止的患者,考虑进行口咽或鼻咽气管插管以控制气道。使用气囊面罩装置的正压通气技术可能有益。监测心率和必要时治疗心律失常。 ... 开始静脉输液,使用D5W/SRP:“保持开放”,最低流量/。如果出现低血容量的迹象,使用乳酸钠林格氏液。注意液体过载的迹象。考虑使用药物治疗肺水肿。对于伴有低血容量迹象的低血压,谨慎给予液体。注意液体过载的迹象。用地西泮(安定)治疗癫痫。使用丙美卡因氢氯化物协助眼部冲洗。/毒药A和B/
Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 解毒与急救
表现取决于活跃的有毒成分。在大多数情况下,大量摄入后60到90分钟内会出现呕吐、腹痛和腹泻。某些毒素可能会导致严重的胃肠炎,进而导致大量的液体和电解质流失。...保持气道畅通,必要时协助呼吸。给予补充氧气。如果出现昏迷、癫痫、心律失常和低血压,则进行治疗。用静脉晶体液替换由胃肠炎引起的液体流失。...如果有的话,给予活性炭。如果及时给予活性炭,则不需要进行胃排空。 /植物和草药药物:第1组/
Presentation depends on the active toxic agent. In most cases, vomiting, abdominal pain, and diarrhea occur within 60 to 90 minutes of significant ingestion. With some toxins, severe gastroenteritis may result in massive fluid and electrolyte loss. ... Maintain open airway and assist ventilation if necessary. Administer supplemental oxygen. Treat coma, seizures, arrhythmias, and hypotension if they occur. Replace fluid loss caused by gastroenteritis with intravenous crystalloid solutions. ... Administer activated charcoal if available ... Gastric emptying is not necessary if activated charcoal is given promptly. /Plants and Herbal Medicines: Group 1/
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 人类毒性摘录
人类暴露研究/迄今为止报告的最大爆发发生在阿富汗西北部赫拉特省的古兰区,靠近苏联边境。...据估计,疫情影响了大约35,000人,分布在98个村庄。对受影响村庄的7,200名居民进行检查,发现22.6%的人有疾病证据,其中15%的人病情较重。因此,估计大约有8,000人患有这种疾病,包括5,000人严重受影响。所有年龄组的人都受到影响,但46%的研究对象年龄在14岁以下。然而,在2岁以下的儿童中没有发现疾病的迹象。关于从14个肝活检和8个尸检中获得的病理材料的详细报告已经完成.../尽管/没有指出症状出现和活检/尸检之间的时间间隔。病理发现具有特征性,范围从具有特征性静脉阻塞的急性疾病到非门脉性肝硬化,这在上述22例中有5例观察到。疫情被归因于小麦的大规模污染,小麦是主要粮食作物,在连续两年干旱之后,与Heliotropium popovii H. Riedl亚种gillianum H. Riedl的种子混合,这种植物在小麦作物中大量生长。这些种子含有吡咯烷生物碱,据两个实验室报告,其浓度分别为7.2和13.2-14.9 g/kg,主要被识别为heliotrine的N-氧化物(74%)...,还有一两种与lasiocarpine性质相似的化合物。来自几个村庄的小麦样本平均含有40粒种子/公斤,即重量的0.03%。据估计,成年人每天至少消耗700克面粉,含有大约2毫克生物碱(基于种子分析的平均值)。/吡咯烷生物碱/
/HUMAN EXPOSURE STUDIES/ The largest outbreak reported to date occurred in the Gulran district of Herat Province in northwest Afghanistan, close to the border of the USSR. ...The outbreak, was estimated to have affected a population of approximately 35,000 in 98 villages. Examination of 7,200 inhabitants of the affected villages showed evidence of disease in 22.6%, which was more serious in 15%. Thus, it was estimated that approximately 8,000 subjects suffered from the disease including 5,000 who were seriously affected. All age groups were affected, but 46% of subjects were below 14 years of age. However, no sign of disease was found in children below 2 years of age. A detailed report concerning the pathological material obtained from 14 liver biopsies and 8 autopsies was made... /although/ the time interval between the onset of symptoms and the biopsy/autopsy was not indicated. Pathological findings were characteristic, ranging from acute disease with characteristic veno-occlusion to non-portal cirrhosis, which was observed in 5 of the above 22 cases. The outbreak was ascribed to massive contamination of wheat, the staple food crop, following 2 years of drought, with the seeds of Heliotropium popovii H. Riedl subsp. gillianum H. Riedl, which had been growing profusely among the wheat crop. The seeds contained pyrrolizidine alkaloids at concentrations reported by 2 laboratories to be 7.2 and 13.2-14.9 g/kg, identified mainly as the N-oxide of heliotrine (74%)..., and one or two other compounds similar in character to lasiocarpine. Samples of wheat from several villages contained an average of 40 seeds/kg, i.e., 0.03% by weight. It was estimated that an adult consumed at least 700 g flour/day, containing approximately 2 mg alkaloid (based on a mean of the seed analyses). /Pyrrolizidine alkaloids/
来源:Hazardous Substances Data Bank (HSDB)

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    苯酐retronecine吡啶 作用下, 生成
    参考文献:
    名称:
    西番莲提炼油的工艺开发:监测蔷薇科植物种子油中的吡咯烷核生物碱
    摘要:
    初生植物的特征在于高含量的多不饱和脂肪酸,并显示出高比例的ω-3/ω-6脂肪酸。此外,西番莲(Boraginaceae)还显示出高水平的十八碳四烯酸含量(ω-3; 18:4; 6,9,12,15-十八碳二烯酸),具有令人关注的促进医学和健康的特性。另一方面,紫花科植物含有具有遗传毒性和致癌性的吡咯烷核生物碱(PA)。开发了HPLC-ESI-MS / MS和参数方法来监控种子油中1,2-不饱和PA的总和。该方法用于使用实验室模型实验和中型L. squarrosa进行中试炼油,以监测炼油的不同步骤籽油。检出限和定量限(LOQ)分别达到0.02μg逆转录酶当量(RE)/ kg和0.05μgRE / kg。在pH 2.2下进行多个洗涤步骤可以将PA含量显着降低至起始值的0.07%。此外,结合与洗涤中和,漂白和脱臭可减少的PA含量L.草油低于LOQ(0.05微克RE /千克)。新近建立的方法还用于分析市售的香菜籽油(Echium
    DOI:
    10.1007/s11746-014-2426-1
  • 作为产物:
    描述:
    grantaline 在 barium dihydroxide 作用下, 反应 2.0h, 生成 retronecine
    参考文献:
    名称:
    Grantianine 和 grantaline,Crotalaria virgulata subsp. 的生物碱。格兰蒂亚娜
    摘要:
    摘要 提供了 Crotalaria virgulata subsp. 的生物碱 Grantianine 和 Grantaline 的表征数据。格兰蒂亚纳 生长在澳大利亚的植物还含有1-羟甲基-1β,2β-环氧-8αH-吡咯里西啶。
    DOI:
    10.1016/s0031-9422(00)80361-1
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文献信息

  • Method And Assay Kit For Detection Of Toxicity Induced By Pyrrolizidine Alkaloids
    申请人:Lin Ge
    公开号:US20130189710A1
    公开(公告)日:2013-07-25
    An antibody, which specifically recognizes adducts between pyrrole and cellular macromolecules. Such adducts are likely to occur in mammals suffering an incident of pyrrolizidine alkaloid poisoning. The antibody can be produced using a synthetic immunogen conjugated with a pyrrole as a hapten and it can be used, for example in an assay kit and/or by itself, as a novel means for detecting or diagnosing pyrrolizidine alkaloid poisoning both clinics and research laboratories.
    一种抗体,特异性识别吡咯与细胞大分子之间的加合物。这种加合物很可能在哺乳动物遭受吡咯啉生物碱中毒事件时发生。该抗体可以使用与吡咯偶联的合成免疫原作为半抗原来生产,并且可以用作检测或诊断吡咯啉生物碱中毒的新方法,例如在检测试剂盒和/或单独使用,无论是在临床还是研究实验室中。
  • PROCÉDÉ D'EXTRACTION DES ALCALOÏDES PYRROLIZIDINIQUES
    申请人:Robertet S.A.
    公开号:EP3922633A1
    公开(公告)日:2021-12-15
    L'invention se rapporte à un procédé d'extraction des alcaloïdes pyrrolizidiniques présents dans un extrait végétal d'intérêt, comprenant au moins une étape d'hydrodistillation ou de distillation dudit extrait.
    本发明涉及一种提取相关植物提取物中吡咯里西啶生物碱的工艺,该工艺至少包括一个对所述提取物进行水蒸馏或蒸馏的步骤。
  • Pre-analysis treatment method for sample containing plurality of components with greatly different concentrations
    申请人:AiSTI SCIENCE CO., Ltd.
    公开号:US10656126B2
    公开(公告)日:2020-05-19
    A pre-analysis treatment method includes: a first retaining step of supplying, to a solid phase, each predetermined amount of the sample and a first solvent, and allowing a component at low concentration to be retained in the solid phase; a first washing step of supplying the first solvent to the solid phase and removing a component at high concentration from the solid phase; a second retaining step of supplying the sample in a smaller amount than the predetermined amount supplied in the first retaining step, and a second solvent to the solid phase, and allowing the component at high concentration to be retained in the solid phase; and an elution step of simultaneously extruding the components retained in the solid phase with an extrusion solvent.
    一种分析前处理方法包括第一保留步骤:向固相提供各预定量的样品和第一溶剂,并允许低浓度成分保留在固相中; 第一洗涤步骤:向固相提供第一溶剂,并从固相中去除高浓度成分;第二保留步骤:向固相中提供小于第一保留步骤中预定量的样品和第二溶剂,并允许高浓度组分保留在固相中;以及洗脱步骤:同时用挤出溶剂挤出保留在固相中的组分。
  • Jizba, Josef; Budesinsky, Milos; Vanek, Tomas, Collection of Czechoslovak Chemical Communications, 1982, vol. 47, # 2, p. 664 - 669
    作者:Jizba, Josef、Budesinsky, Milos、Vanek, Tomas、Boeva, A.、Dimitrova, Kalinka、et al.
    DOI:——
    日期:——
  • REPRESENTATIVE DIAGNOSTICS
    申请人:Ventana Medical Systems, Inc.
    公开号:EP3371594A1
    公开(公告)日:2018-09-12
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