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thiomersal | 878791-13-0

中文名称
——
中文别名
——
英文名称
thiomersal
英文别名
Thimerosal;thiomerosal;merthiolate;ethylmercurithiosalicylic acid sodium salt;Thiomersalate; Mercurothiolate
thiomersal化学式
CAS
878791-13-0
化学式
C9H9HgNaO2S
mdl
——
分子量
404.815
InChiKey
RTKIYNMVFMVABJ-UHFFFAOYSA-L
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):
    -2.07
  • 重原子数:
    14
  • 可旋转键数:
    1
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.22
  • 拓扑面积:
    41.1
  • 氢给体数:
    0
  • 氢受体数:
    3

ADMET

代谢
乙基汞(etHg)来源于硫柳汞(邻羧基苯硫基乙基钠盐)的代谢,硫柳汞是有机汞最广泛使用的形式[A32125]。
Ethylmercury (etHg) is derived from the metabolism of thimerosal (o-carboxyphenyl-thio-ethyl-sodium salt), which is the most widely used form of organic mercury [A32125].
来源:DrugBank
毒理性
  • 毒性总结
口服LD50:75 mg/kg(小鼠),91 mg/kg(小鼠)[L1694]。尽管甲基汞(meHg)被认为是一种有害物质,即使在通过食物如海鲜和大米(在亚洲)摄入的微量中也应避免,但世界卫生组织认为,无论多次/重复接触主要在怀孕或婴儿期接种的疫苗,小剂量的硫柳汞都是安全的[L1685,L1686,L1689]。
Ld50 Oral: 75 mg/kg (mouse), 91 mg/kg (mouse) [L1694] Although methylmercury (meHg) is considered a hazardous substance that is to be avoided even at small levels when consumed in foods such as seafood and rice (in Asia), the World Health Organization considers small doses of thimerosal safe regardless of multiple/repetitive exposures to vaccines that are predominantly taken during pregnancy or infancy [L1685, L1686, L1689].
来源:DrugBank
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,如有必要,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……。预见并治疗癫痫发作……。对于眼睛污染,立即用可用水冲洗眼睛。在转运过程中,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,则用生理盐水冲洗口腔,并给予5毫升/千克,最多200毫升的水进行稀释。给予活性炭……。/汞及其相关化合物/
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and teat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with available 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. Administer activated charcoal ... . /Mercury and related compounds/
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 解毒与急救
高级治疗:对于患有严重肺水肿或呼吸骤停的患者,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5%葡萄糖水。如果出现低血容量的迹象,使用乳酸钠林格液。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。如果血容量正常但仍然低血压,考虑使用血管加压药。注意液体过载的迹象。 ... 使用地西泮(安定)治疗癫痫。 ... 使用丙美卡因氢氯化物协助眼部冲洗。 /汞及其相关化合物/
Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient with severe pulmonary edema or respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W. 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. Consider vasopressors if hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Mercury and related compounds/
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 人类毒性摘录
人类暴露研究/在13名接受0.1%硫柳汞酊剂外用治疗脐膨出的婴儿中,有10名婴儿死亡。应用的次数在9到48次之间。从6名婴儿的各种组织中测定了汞的浓度。新鲜样本的肝脏、肾脏、脾脏和心脏的平均组织浓度从5152到11,330 ppb不等,这表明重复外用可能导致经皮吸收。
/HUMAN EXPOSURE STUDIES/ Ten of 13 infants exposed to topical applications of a thimerosal tincture 0.1% for the treatment of exomphalos died. The total number of applications ranged from 9 to 48. Mercury concentrations were determined in various tissues from 6 of the infants. Mean tissue concentrations in fresh samples of liver, kidney, spleen, and heart ranged from 5152 to 11,330 ppb, suggesting percutaneous absorption from repeated topical applications.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 人类毒性摘录
人类暴露研究/汞衍生物是常见的接触性过敏原,它们的交叉反应性并不是恒定的。硫柳汞是一种有机汞化合物,用作防腐剂,也用于大多数疫苗中作为保存剂。/研究的目的是/评估对汞衍生物过敏的患者对含有硫柳汞的疫苗的交叉反应性、暴露因素和耐受性。共招募了125名患者进行研究,其中72名女性和女孩,53名男孩和男性,平均年龄18.7岁,年龄范围3到65岁,对汞衍生物和/或硫柳汞的斑贴测试呈阳性;干预措施:对所有患者进行询问、斑贴测试、皮内测试和硫柳汞的肌肉内挑战。57名患者观察到对硫柳汞的敏感化。这125名患者中有24名表现出皮内反应阳性。氨化汞似乎是汞过敏的一个良好标记,在所有患者中引起了78%的阳性反应,而溴化汞引起了66%的阳性反应。在大多数情况下(125名中的100名),在汞衍生物之间发现了交叉反应性。硫柳汞的肌肉内注射仅在5名患者中引起了轻微的局部反应(总数的4%,硫柳汞阳性反应的9%)。儿童疫苗接种、用作防腐剂的溴化汞、破损的温度计和滴眼液的使用是主要的暴露源。大多数患者对有机汞和无机汞衍生物的测试呈阳性。即使对于对这种化学物质有迟发型超敏反应的个体,硫柳汞疫苗也是相对安全的,因为超过90%的过敏患者对硫柳汞的肌肉内挑战测试表现出了耐受性。提出了一种简化研究汞衍生物的斑贴测试方案。建议限制使用汞基防腐剂和汞温度计。
/HUMAN EXPOSURE STUDIES/ Mercury derivatives are frequent contact allergens and their cross-reactivity is not constant. Thimerosal is an organic mercurial used as an antiseptic and as a preservative in most vaccines. /The purpose of the study was / to evaluate cross-reactivity, exposure factors, and tolerance to vaccines containing thimerosal in patients sensitized to mercury derivatives.125 patients were recruited for the study, 72 women and girls and 53 boys and men, average age 18.7 years old, range 3 to 65, with positive patch tests to mercury derivatives and/or thimerosal; Interventions: All patients were studied by means of enquiry, patch tests, intradermal tests, and intramuscular challenge with thimerosal. A sensitization to thimerosal was observed in 57 patients. Twenty-four of these 125 patients presented a positive intradermal reaction. Ammoniated mercury seems to be a good marker of mercury sensitization eliciting positive reaction in 78% of all patients and merbromin in 66%. In most cases, (100/125) cross-reactivity was found among mercury derivatives. The intramuscular injection of thimerosal induced a mild local reaction in only 5 patients (4% of the total, 9% of thimerosal positive reactions). Childhood vaccinations, merbromin used as an antiseptic, broken thermometers, and the use of drops were the main sources of exposure. The majority of the patients showed positive tests to both organic and inorganic mercury derivatives. Vaccination with thimerosal is relatively safe, even for individuals with delayed type hypersensitivity to this chemical, since more than 90% of allergic patients tolerated intramuscular challenge tests with thimerosal. A simplified protocol of patch tests to study mercury derivatives is proposed. It would be advisable to restrict the use of mercurial antiseptics and mercury thermometers.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
  • 吸收
从胃肠道吸收的剂量小于0.01%(大鼠研究)[L1687]。
Less than 0.01% of an ingested dose is absorbed from the GI tract (rat study) [L1687].
来源:DrugBank
吸收、分配和排泄
  • 消除途径
消化道 [L1675]。
Gastrointestinal tract [L1675].
来源:DrugBank
吸收、分配和排泄
  • 分布容积
在266 L在一项研究中[第1678页]
266 L in one study [L1678]
来源:DrugBank
吸收、分配和排泄
  • 清除
粪便样本中检测到的高浓度汞表明,乙基汞可能通过胃肠道排出 [L1675]。
The high concentrations of mercury identified in stool samples suggest that ethylmercury may be eliminated through the gastrointestinal tract [L1675].
来源:DrugBank
吸收、分配和排泄
水银浓度在九名接受角膜移植手术的患者的房水和切除的角膜瓣中被测量。一种在含有硫柳汞的溶液中存放了几周的隐形眼镜被应用于一只眼睛4小时。4小时后,取出隐形眼镜并测定房水、角膜瓣和隐形眼镜本身的水银浓度。与对照组相比,受试者房水和角膜瓣中的水银含量显著升高;然而,4小时后隐形眼镜上残留的水银很少。受试者角膜瓣中的水银含量从每组织0.6到14纳克不等。受试者房水样本中的水银含量从20到46纳克/毫升不等。
Mercury concentrations were measured in the aqueous humor and excised corneal buttons of nine patients undergoing keratoplasty. A contact lens stored for several weeks in a solution containing thimerosal was applied to one eye for 4 hours. After 4 hours the lens was removed and mercury concentrations were determined in aqueous humor, corneal buttons, and the contact lens itself. Markedly elevated levels of mercury were determined in both aqueous humor and corneal buttons of subjects as compared to controls; however, there was little residual mercury on the contact lens after 4 hours.The mercury content in the corneal buttons of subjects ranged from 0.6 to 14 ng per tissue. The mercury content in samples of aqueous humor from subjects ranged from 20 to 46 ng/mL.
来源:Hazardous Substances Data Bank (HSDB)

反应信息

  • 作为反应物:
    描述:
    参考文献:
    名称:
    READER, M. J.;LINES, C. B., J. PHARM. SCI., 1983, 72, N 12, 1406-1409
    摘要:
    DOI:
  • 作为产物:
    描述:
    sodium hydroxide 、 o-ethylmercurithio-benzoic acid重水 为溶剂, 生成 thiomersal
    参考文献:
    名称:
    硫柳汞的质子化和汞化衍生物的分子结构。
    摘要:
    硫柳汞的羧酸氧[[Ar(CO(2)))SHgEt] Na易受H(+)和[HgEt](+)的亲电子攻击而生成(Ar(CO(2)H)) SHgEt和[(Ar(CO(2(2)HgEt))SHgEt](2)。X射线衍射表明,(Ar(CO(2)H))SHgEt以氢键二聚体的形式存在,而[(Ar(CO(2)HgEt))SHgEt](2)是四核的,且有汞中心通过桥接羧酸根基团连接。(1)H NMR光谱研究表明(Ar(CO(2)H))SHgEt乙基的(199)Hg卫星的形式取决于磁场,因此内部的CH(2 )和CH(3)卫星在400 MHz处显示为单峰,
    DOI:
    10.1039/b823467a
  • 作为试剂:
    描述:
    碘苷thiomersal 作用下, 以 为溶剂, 反应 2.0h, 生成 2-脱氧-beta-D-赤式-呋喃戊糖5-碘尿嘧啶尿嘧啶
    参考文献:
    名称:
    Szepes; Gazdag; Meizei, Pharmazie, 1980, vol. 35, # 10, p. 602 - 604
    摘要:
    DOI:
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文献信息

  • Platinum(II) thiosalicylate and related complexes as ligands towards mercury(II) halides; X-ray crystal structure of the tetrametallic complex {[P2)(PPh3)2]·HgI2}2
    作者:Louise J. McCaffrey、William Henderson、Brian K. Nicholson
    DOI:10.1016/s0277-5387(97)00342-2
    日期:1998.1
    are discussed in terms of coordination to the various metal halide moieties. Reactions of the organomercury(II) thiosalicylate complex Thiomersal (EtHgSC 6 H 4 CO 2 Na) with cis -[PtCl 2 (PPh 3 ) 2 ], cis -[MCl 2 (dppe)] (MNi or Pd) leads to complete transfer of the thiosalicylate ligand from the mercury, and isolation of the previously reported thiosalicylate complexes [P t(SC 6 H 4 CO 2 )(PPh 3
    摘要硫代水杨酸铂(II)络合物[P t(SC 6 H 4 CO 2)(PPh 3)2] 1a与HgI 2反应形成包含IHg(μ-I)2 HgI中心核与硫醇盐的四金属配合物与每个汞中心配位的1a硫,形成了扭曲的四面体配位环境。总体而言,通过X射线衍射研究确定的配合物的结构特征与母体硫代水杨酸酯配合物1a相似,但相对于铂配位,硫代水杨酸酯配体的折叠角(与46°相比增加了59°)飞机。使用31 P NMR光谱研究了相关的五元环硫醇盐络合物[P t(SCHRCO 2)(PPh 3)2](RH或Me)与1a与一系列金属阳离子的反应。根据与各种金属卤化物部分的配位,讨论了1 J(PtP)耦合常数的变化。硫代水杨酸有机汞(II)硫柳汞(EtHgSC 6 H 4 CO 2 Na)与顺式-[PtCl 2(PPh 3)2],顺式-[MCl 2(dppe)](MNi或Pd)的反应导致从汞中完全转移出硫代水杨
  • Hg–C bond protonolysis by a functional model of bacterial enzyme organomercurial lyase MerB
    作者:Ramesh Karri、Ranajit Das、Rakesh Kumar Rai、Anaswara Gopalakrishnan、Gouriprasanna Roy
    DOI:10.1039/d0cc02232b
    日期:——
    Herein, we report a novel synthetic compound 1, having a highly nucleophilic selenolate (Se−) moiety and a thiol (–SH) functional group, which showed efficient Hg–C bond protonolysis of various R–Hg–X molecules including neurotoxic methylmercury and thimerosal, via direct –SH proton transfer to the highly activated C-atom of a departed R group with low activation energy barrier at room temperature
    在此,我们提出一个新的合成化合物1,具有高度亲核的selenolate(硒- )部分和一个巯基(-SH)的官能团,其显示各种R-汞-X分子的高效汞-C键的质子分解,包括神经毒性和甲基汞在没有任何外部质子源的情况下,硫柳汞通过直接–SH质子转移到离去的R基团的高活化C原子上而在室温(21°C)下具有较低的活化能垒,因此具有一定的功能MerB的模型。
  • Exploring the Lewis basicity of the metalloligand [Pt2(µ-Se)2(PPh3)4] on metal substrates by electrospray mass spectrometry. Synthesis, characterization and structural studies of new platinum selenido phosphine complexes containing the {Pt2Se2} core
    作者:Jeremy S. L. Yeo、Jagadese J. Vittal、William Henderson、T. S. Andy Hor
    DOI:10.1039/b104996h
    日期:2002.1.23
    basic metalloligand leads to the identification and isolation of the doubly-protonated species, [Pt2(μ-SeH)2(PPh3)4]2+, whose sulfide analogue cannot be isolated. A three-step strategy is employed in the use of ESMS as a probe: (i) preliminary screening of the metalloligand with an array of acidic main group and transition group metal compounds, (ii) identification of potentially stable and isolable
    电喷雾质谱法(ESMS)已被用来作为一种工具来探测metalloligand的反应性[PT 2(μ-Se)的2(PPH 3)4 ]与金属基片,它们导致带电的配位络合物的形成通过的损失卤化物或其他不稳定的配体。在置换反应中使用的众多金属基材中,有Au(anpy)Cl 2(anpy =环金属化的2-苯胺基吡啶基),HgPhCl和Pb(NO 3)2。在路易斯碱性金属配体上进行酸滴定导致鉴定和分离双质子化物质[Pt 2(μ-SeH)2(PPh 3)4 ] 2+,其硫化物类似物无法分离。在使用ESMS作为探针时,采用了三步策略:(i)用一系列酸性主族和过渡族金属化合物初步筛选金属配体,(ii)鉴定就地形成的潜在稳定和可分离的产物(iii)在实验室规模上重复有希望的反应,并分离和表征目标产物。对[Pt 2(μ-SeH) 2(PPh 3) 4 ] [ClO 4 ] 2,[Pt 2(μ3 -Se) 2(PPH
  • Method and kit for detecting, or determining the quantity of, metabolites of fentanyl and metabolites of fentanyl analogs
    申请人:Randox Laboratories Limited
    公开号:US20030170728A1
    公开(公告)日:2003-09-11
    The invention provides an immunogen comprising a hapten coupled to an antigenicity-conferring carrier material, a conjugate comprising the aforementioned hapten coupled to a labelling agent, as well as, antibodies raised against the aforementioned immunogen and capable of binding with at least one structural epitope of metabolites of fentanyl and of metabolites of fentanyl analogs.
    本发明提供了一种免疫原,包括偶联到赋予抗原性的载体材料上的半抗原,以及偶联到标记试剂上的上述半抗原的共轭物,以及针对上述免疫原产生的抗体,能够结合芬太尼代谢物和芬太尼类似物代谢物的至少一个结构表位。
  • Method and kit for detecting, or determining, 3,4-methylenedioxymethamphetamine
    申请人:——
    公开号:US20040121400A1
    公开(公告)日:2004-06-24
    The invention provides a hapten, an immunogen comprising the hapten coupled to an antigenicity-conferring carrier material, a conjugate comprising the hapten coupled to a labelling agent, as well as, antibodies raised against the aforementioned immunogen and capable of binding with MDMA.
    本发明提供了一个半抗原(hapten),一个将该半抗原偶联到具有抗原性的载体材料上的免疫原(immunogen),一个将该半抗原偶联到标记试剂上的结合物(conjugate),以及针对上述免疫原所产生并能够与MDMA结合的抗体。
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表征谱图

  • 氢谱
    1HNMR
  • 质谱
    MS
  • 碳谱
    13CNMR
  • 红外
    IR
  • 拉曼
    Raman
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ir
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  • 峰位数据
  • 峰位匹配
  • 表征信息
Shift(ppm)
Intensity
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Assign
Shift(ppm)
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测试频率
样品用量
溶剂
溶剂用量
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同类化合物

(βS)-β-氨基-4-(4-羟基苯氧基)-3,5-二碘苯甲丙醇 (S)-(-)-7'-〔4(S)-(苄基)恶唑-2-基]-7-二(3,5-二-叔丁基苯基)膦基-2,2',3,3'-四氢-1,1-螺二氢茚 (S)-盐酸沙丁胺醇 (S)-3-(叔丁基)-4-(2,6-二甲氧基苯基)-2,3-二氢苯并[d][1,3]氧磷杂环戊二烯 (S)-2,2'-双[双(3,5-三氟甲基苯基)膦基]-4,4',6,6'-四甲氧基联苯 (S)-1-[3,5-双(三氟甲基)苯基]-3-[1-(二甲基氨基)-3-甲基丁烷-2-基]硫脲 (R)富马酸托特罗定 (R)-(-)-盐酸尼古地平 (R)-(+)-7-双(3,5-二叔丁基苯基)膦基7''-[((6-甲基吡啶-2-基甲基)氨基]-2,2'',3,3''-四氢-1,1''-螺双茚满 (R)-3-(叔丁基)-4-(2,6-二苯氧基苯基)-2,3-二氢苯并[d][1,3]氧杂磷杂环戊烯 (R)-2-[((二苯基膦基)甲基]吡咯烷 (N-(4-甲氧基苯基)-N-甲基-3-(1-哌啶基)丙-2-烯酰胺) (5-溴-2-羟基苯基)-4-氯苯甲酮 (5-溴-2-氯苯基)(4-羟基苯基)甲酮 (5-氧代-3-苯基-2,5-二氢-1,2,3,4-oxatriazol-3-鎓) (4S,5R)-4-甲基-5-苯基-1,2,3-氧代噻唑烷-2,2-二氧化物-3-羧酸叔丁酯 (4-溴苯基)-[2-氟-4-[6-[甲基(丙-2-烯基)氨基]己氧基]苯基]甲酮 (4-丁氧基苯甲基)三苯基溴化磷 (3aR,8aR)-(-)-4,4,8,8-四(3,5-二甲基苯基)四氢-2,2-二甲基-6-苯基-1,3-二氧戊环[4,5-e]二恶唑磷 (2Z)-3-[[(4-氯苯基)氨基]-2-氰基丙烯酸乙酯 (2S,3S,5S)-5-(叔丁氧基甲酰氨基)-2-(N-5-噻唑基-甲氧羰基)氨基-1,6-二苯基-3-羟基己烷 (2S,2''S,3S,3''S)-3,3''-二叔丁基-4,4''-双(2,6-二甲氧基苯基)-2,2'',3,3''-四氢-2,2''-联苯并[d][1,3]氧杂磷杂戊环 (2S)-(-)-2-{[[[[3,5-双(氟代甲基)苯基]氨基]硫代甲基]氨基}-N-(二苯基甲基)-N,3,3-三甲基丁酰胺 (2S)-2-[[[[[[((1R,2R)-2-氨基环己基]氨基]硫代甲基]氨基]-N-(二苯甲基)-N,3,3-三甲基丁酰胺 (2-硝基苯基)磷酸三酰胺 (2,6-二氯苯基)乙酰氯 (2,3-二甲氧基-5-甲基苯基)硼酸 (1S,2S,3S,5S)-5-叠氮基-3-(苯基甲氧基)-2-[(苯基甲氧基)甲基]环戊醇 (1-(4-氟苯基)环丙基)甲胺盐酸盐 (1-(3-溴苯基)环丁基)甲胺盐酸盐 (1-(2-氯苯基)环丁基)甲胺盐酸盐 (1-(2-氟苯基)环丙基)甲胺盐酸盐 (-)-去甲基西布曲明 龙胆酸钠 龙胆酸叔丁酯 龙胆酸 龙胆紫 龙胆紫 齐达帕胺 齐诺康唑 齐洛呋胺 齐墩果-12-烯[2,3-c][1,2,5]恶二唑-28-酸苯甲酯 齐培丙醇 齐咪苯 齐仑太尔 黑染料 黄酮,5-氨基-6-羟基-(5CI) 黄酮,6-氨基-3-羟基-(6CI) 黄蜡,合成物 黄草灵钾盐