1,2,3,3-四甲基-3H-吲哚鎓碘化物 | 5418-63-3

• 物质功能分类: 医药中间体 - 杂环化合物 - 吲哚类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 1,2,3,3-四甲基-3H-吲哚鎓碘化物
• 中文别名: 1,2,3,3-四甲基-3H-吲哚碘化物；1,2,3,3-四甲基-3H-碘代吲哚
• 英文名称: 1,2,3,3-tetramethyl-3H-indolium iodide
• 英文别名: 1,2,3,3-tetramethyl-3H-indol-1-ium iodide；1,2,3,3-tetramethylindolium iodide；1,2,3,3-tetramethylindolenium iodide；N-methyl-2,3,3-trimethylindolium iodide；1-methyl-2,3,3-trimethyl-3H-indolium iodide；1,2,3,3-tetramethyl-3H-indolium iodide salt；N-methyl-2,3,3-trimethylindolenine iodide；N-methyl-2,3,3-trimethylindolenium iodide；1,2,3,3-tetramethyl-3H-indole iodide；tetramethyl indolium iodide；1,2,3,3-tetramethylindol-1-ium;iodide
• CAS: 5418-63-3
• 化学式: C₁₂H₁₆N*I
• 分子量: 301.17
• InChiKey: HCYIOKVZAATOEW-UHFFFAOYSA-M

物化性质

• 熔点：
  258 °C (dec.)(lit.)
• 稳定性/保质期：
  如果按照规定使用和储存，则不会发生分解，目前没有已知的危险情况。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.28
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36
• 危险类别码：
  R22,R36/37/38
• 海关编码：
  2933990090
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  请将药品存放在密闭、阴凉干燥的地方保存。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 1,2,3,3-Tetramethyl-3H-indolium iodide
CAS-No. : 5418-63-3
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Acute toxicity, Oral (Category 4)
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful if swallowed. Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R22 Harmful if swallowed.
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36 Wear suitable protective clothing.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C12H16IN
Molecular Weight : 301,17 g/mol
Component Concentration
1,2,3,3-Tetramethyl-3H-indolium iodide
CAS-No. 5418-63-3 -
EC-No. 226-526-2

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx), Hydrogen iodide
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Light sensitive.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: crystalline
Colour: pink
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 258 °C - dec.
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
Light.
Incompatible materials
Oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
LD50 Oral - rat - 707 mg/kg
Remarks: Behavioral:Tremor. Behavioral:Muscle weakness. Behavioral:Ataxia.
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion Harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: NM2251250

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material. Dissolve or mix the material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  1,2,3,3-四甲基-3H-吲哚鎓碘化物 在 sodium hydroxide 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 2.25h， 生成 费舍尔氏醛
  参考文献：
  名称：

  인돌계 화합물, 이를 포함하는 색재 조성물 및 이를 포함하는 수지 조성물

  摘要：

  这份规范包括新型印度制药化合物，包括这些化合物的颜料配方和包含它们的树脂配方。

  公开号：

  KR20160022280A
• 作为产物：
  描述：

  3-甲基-2-丁酮 在 溶剂黄146 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 12.0h， 生成 1,2,3,3-四甲基-3H-吲哚鎓碘化物
  参考文献：
  名称：

  A mitochondria-targeted fluorescent dye naphthalimide-thioether-cyanine for NIR-activated photodynamic treatment of cancer cells

  摘要：

  这项工作中NPSCY对半胱氨酸的特异识别以及对癌细胞的光动力治疗。

  DOI：

  10.1039/d0tb02851g

文献信息

• Divergent synthesis of 5′,7′-difluorinated dihydroxanthene-hemicyanine fused near-infrared fluorophores
  作者：Shasha Zheng、Gu Lingyue、Michelle Jui Hsien Ong、Denis Jacquemin、Anthony Romieu、Jean-Alexandre Richard、Rajavel Srinivasan

  DOI：10.1039/c9ob00568d

  日期：——

  dihydroxanthene-hemicyanine fused scaffold in 2 steps and 54% overall yield from the corresponding salicylic aldehyde. A 6′-regioselective nucleophilic aromatic substitution (SNAr) reaction with a wide range of nitrogen, sulfur or selenium nucleophiles then gives access to 16 near-infrared (NIR) fluorophores emitting in the 710–750 nm range. We also report the experimental and theoretical photophysical

  我们描述了方便地访问5'，6'，7'-三氟二氢黄嘌呤-半花菁融合支架的2个步骤，并从相应的水杨醛中获得了54％的总收率。然后，与多种氮，硫或硒亲核试剂进行6'-区域选择性亲核芳香取代（S N Ar）反应，即可获得16种在710-750 nm范围内发射的近红外（NIR）荧光团。我们还报告了这些独特的光学试剂的实验和理论光物理研究，包括第一批6'-重原子取代的二氢黄嘌呤系列，扩展了用于生物医学和材料应用的多氟化标记物的范围。
• Erlotinib-Guided Self-Assembled Trifunctional Click Nanotheranostics for Distinguishing Druggable Mutations and Synergistic Therapy of Nonsmall Cell Lung Cancer
  作者：Yu Gao、Huijuan Zhang、Yingying Zhang、Tingting Lv、Lu Zhang、Ziying Li、Xiaodong Xie、Fengqiao Li、Haijun Chen、Lee Jia

  DOI：10.1021/acs.molpharmaceut.8b00561

  日期：2018.11.5

  outcome of molecular targeted therapies is restricted by the ambiguous molecular subtypes of nonsmall cell lung cancer (NSCLC), which are difficult to be defined with druggable mutations, and the inevitable emergence of drug-resistance. Here we used the Cu-catalyzed click chemistry to synthesize a chitosan-based self-assembled nanotheranostics (CE7Ns) composed of a near-infrared (NIR) fluorescent photosensitizer

  非小细胞肺癌（NSCLC）的分子亚型模棱两可，难以针对药物突变进行定义，并且不可避免地出现了耐药性，这限制了分子靶向疗法的结果。在这里，我们使用铜催化的点击化学合成由近红外（NIR）荧光光敏剂Cy7和分子靶向药物厄洛替尼组成的基于壳聚糖的自组装纳米热力学（CE7Ns）。特征明确的CE7Ns可以在酸性条件下在溶菌酶的存在下快速释放厄洛替尼和Cy7，区分NSCLC的三种分子亚型，并特异性结合厄洛替尼敏感的表皮生长因子受体（EGFR）突变的PC-9细胞。与其他NSCLC细胞相比，PC-9细胞对CE7Ns的吸收更多，因此在PC-9细胞中产生明显的荧光信号。NIR照射后，CE7Ns中的Cy7在PC-9细胞中产生高活性氧。厄洛替尼靶向治疗和光动力治疗之间的协同作用显着上调了癌症抑制因子p53并抑制Survivin，从而导致更多的细胞凋亡和细胞周期停滞。静脉内给药后，厄洛替尼引导的CE7Ns在PC-9接
• [EN] THERANOSTIC CONJUGATES<br/>[FR] CONJUGUÉS THÉRANOSTIQUES
  申请人：ARIEL SCIENT INNOVATIONS LTD

  公开号：WO2021009759A1

  公开（公告）日：2021-01-21

  Provided herein is a drug delivery (DD) system for ratiometric luminescence determination of drug release degree in drug delivery monitoring, which includes a drug, a switchable reporter and non-switchable reporter providing two distinguishable signals for detection; or a single switchable reporter providing two distinguishable signals for detection, and a cleavable linker connecting a drug to a switchable reporter, as well as a method for ratiometric luminescence determination of drug release in a target in vivo or in vitro), which is effected by administering the DD system provided herein that is capable of releasing a drug from the DD system, measuring two luminescent signals provided by the switchable reporter and the non-switchable reporter, or the single switchable reporter, determining the ratio between these two luminescence signals, and determining the drug release degree through the ratio between the two luminescence signals.

  本文提供了一种药物递送（DD）系统，用于药物递送监测中药物释放程度的比例荧光测定，该系统包括一种药物、一种可切换的报告物和一种不可切换的报告物，用于提供两种可区分的信号以进行检测；或者一种单一可切换的报告物，用于提供两种可区分的信号以进行检测，以及一种可切割的连接剂，连接药物和可切换的报告物，以及一种比例荧光测定方法，用于在目标（体内或体外）中测定药物释放，通过给予本文提供的能够从DD系统中释放药物的DD系统，测量可切换的报告物和不可切换的报告物提供的两个发光信号，或者单一可切换的报告物，确定这两个发光信号之间的比例，并通过这两个发光信号之间的比例确定药物释放程度。
• On-Resin Strategy to Label α-Conotoxins: Cy5-RgIA, a Potent α9α10 Nicotinic Acetylcholine Receptor Imaging Probe
  作者：Markus Muttenthaler、Simon T. Nevin、Marco Inserra、Richard J. Lewis、David J. Adams、Paul F. Alewood

  DOI：10.1071/ch19456

  日期：——

  solid phase peptide synthesis (Boc-SPPS), and coupled Cy5 to the N-terminus of α-conotoxin RgIA while still attached to the resin. Folding of the two-disulfide containing Cy5-RgIA benefitted from the hydrophobic nature of Cy5, resulting in only the globular disulfide bond isomer. In contrast, wild-type α-RgIA folded into the inactive ribbon and bioactive globular isomer under the same conditions.

  溶液内缀合是用荧光团标记肽和蛋白质的最常用策略。然而，缺乏位点特异性控制和荧光团的高成本被认为是这种方法的局限性。在这里，我们通过两步合成路线轻松获得了克 Cy5-COOH，证明了 Cy5 对 HF 处理稳定，因此与叔丁氧羰基固相肽合成 (Boc-SPPS) 兼容，并将 Cy5 与α-芋螺毒素 RgIA 的 N 末端仍附着在树脂上。含有双二硫键的 Cy5-RgIA 的折叠受益于 Cy5 的疏水性，仅产生球状二硫键异构体。相比之下，野生型 α-RgIA 在相同条件下折叠成无活性带状和生物活性球状异构体。标记的 α-RgIA 保留了其可逆抑制乙酰胆碱 (100 µM) 诱发电流的能力，Cy5-RgIA 的 IC 50为 5.0 nM（希尔系数 = 1.7），α-RgIA 的 IC 50为 1.6（希尔系数 = 1.2）。非洲爪蟾卵母细胞中异源表达的 α9α10 烟碱乙酰胆碱受体 (nAChR)
• MII-tt-DTT及其在制备抗结直肠癌药物中的应用
  申请人：河南大学

  公开号：CN113648307B

  公开（公告）日：2022-09-30

  本发明属于化工医药技术领域，具体涉及MII‑tt‑DTT在制备抗癌药物中的应用，所述MII‑tt‑DTT的化学结构如下所示：MTT结果显示：MII‑tt‑DTT能显著抑制结直肠肿瘤细胞的增殖，并定位到线粒体。Annexin V and PI双染凋亡检测结果显示：MII‑tt‑DTT能诱导细胞凋亡；Western Blot结果显示：MII‑tt‑DTT能诱导细胞铁死亡。本发明的小分子化合物MII‑tt‑DTT作为新的抗结直肠肿瘤药物或者其辅助成分进行开发，抑制肿瘤效果显著，将为治疗和治愈结直肠肿瘤提供新的途径和手段。