99011-02-6

• 常用中文名：咪喹莫特
• 常用英文名：imiquimod
• CAS号：99011-02-6
• 分子式：C₁₄H₁₆N₄
• 分子量：240.304
• 相关类别： 原料药 影响免疫功能药 免疫调节药
• 发布时间：2018-08-31 19:43:30
• 更新时间：2024-01-02 18:43:22
• Imiquimod是免疫应答调节剂和 toll样受体7激动剂。

名称

• 中文名: 咪喹莫特
• 英文名: imiquimod
• 中文别名: 咪喹莫德; 1-异丁基-4-氨基-1H-咪唑并[4,5-C]喹啉; 1-异丁基-1H-咪唑[4.5-C]喹啉-4-胺基; 1-(2-甲基丙基)-4-氨基-1H-咪唑并[4,5-c]喹啉
• 英文别名: imiquimod; ALDARA; MFCD00866946

物化性质

• 密度: 1.3±0.1 g/cm3
• 沸点: 456.7±48.0 °C at 760 mmHg
• 熔点: 292-294°C
• 分子式: C₁₄H₁₆N₄
• 分子量: 240.304
• 闪点: 230.0±29.6 °C
• 精确质量: 240.137497
• PSA: 56.73000
• LogP: 3.46
• 外观性状: 白色至灰白色结晶粉末
• 蒸汽压: 0.0±1.1 mmHg at 25°C
• 折射率: 1.681
• 储存条件: Store at +4°C
• 稳定性: Incompatible with strong oxidizing agents.
• 水溶解性: 水溶性：实际上不溶
• 分子结构:

  1、 摩尔折射率：71.02

  2、 摩尔体积（cm³/mol）：187.7

  3、 等张比容（90.2K）：496.2

  4、 表面张力（dyne/cm）：48.8

  5、 极化率（10-24cm3）：28.15

• 更多:

  1.性状：白色结晶粉末。

  2.熔点（ºC）：292～294

生物活性

• 描述: Imiquimod是免疫应答调节剂和 toll样受体7激动剂。
• 相关类别:
  信号通路 >> 自噬 >> 自噬
  信号通路 >> 免疫及炎症 >> Toll样受体(TLR)
  研究领域 >> 炎症/免疫
• 靶点:

  toll-like receptor 7[1]

• 体内研究: 在动物模型中,咪喹莫特通过增加NK细胞活性,激活巨噬细胞分泌细胞因子和一氧化氮,并诱导B淋巴细胞的增殖和分化来刺激先天免疫应答。咪喹莫特通过诱导,合成和释放细胞因子刺激先天免疫反应,包括干扰素-α(IFN-α),白细胞介素(IL)-6和肿瘤坏死因子(TNF)-α[1]。
• 参考文献:

  [1]. Bilu D, et al. Imiquimod: modes of action. Br J Dermatol. 2003 Nov;149 Suppl 66:5-8.

MSDS

Imiquimod SAFETY DATA SHEET Section1. IDENTIFICATION Product name:Imiquimod Section2. HAZARDS IDENTIFICATION GHS classification PHYSICAL HAZARDSNot classified HEALTH HAZARDS Acute toxicity (Oral)Category 3 Category 2 Skin corrosion/irritation Serious eye damage/eye irritationCategory 2A Not classified ENVIRONMENTAL HAZARDS GHS label elements, including precautionary statements Pictograms or hazard symbols Signal wordDanger Hazard statementsToxic if swallowed Causes skin irritation Causes serious eye irritation Precautionary statements: Do not eat, drink or smoke when using this product. [Prevention] Wash hands thoroughly after handling. Wear protective gloves/eye protection/face protection. [Response]IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. Rinse mouth. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. If eye irritation persists: Get medical advice/attention. IF ON SKIN: Gently wash with plenty of soap and water. If skin irritation occurs: Get medical advice/attention. Take off contaminated clothing and wash before reuse. [Storage]Store locked up. [Disposal]Dispose of contents/container through a waste management company authorized by the local government. Section3. COMPOSITION/INFORMATION ON INGREDIENTS Substance/mixture:Substance Imiquimod Components: Imiquimod Section3. COMPOSITION/INFORMATION ON INGREDIENTS Percent:>98.0%(LC)(T) CAS Number:99011-02-6 Synonyms:1-Isobutyl-1H-imidazo[4,5-c]quinolin-4-amine , 4-Amino-1-isobutyl-1H-imidazo[4,5- c]quinoline Chemical Formula:C14H16N4 Section4. FIRST AID MEASURES Inhalation:Remove victim to fresh air and keep at rest in a position comfortable for breathing. Get medical advice/attention if you feel unwell. Skin contact:Remove/Take off immediately all contaminated clothing. Gently wash with plenty of soap and water. If skin irritation or rash occurs: Get medical advice/attention. Eye contact:Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. If eye irritation persists: Get medical advice/attention. Ingestion:Immediately call a POISON CENTER or doctor/physician. Rinse mouth. A rescuer should wear personal protective equipment, such as rubber gloves and air- Protection of first-aiders: tight goggles. Section5. FIRE-FIGHTING MEASURES Suitable extinguishingDry chemical, foam, water spray, carbon dioxide. media: Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to from the chemical:generate poisonous fume. Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing method according to the surrounding situation is used. Uninvolved persons should evacuate to a safe place. In case of fire in the surroundings: Remove movable containers if safe to do so. Special protectiveWhen extinguishing fire, be sure to wear personal protective equipment. equipment for firefighters: Section6. ACCIDENTAL RELEASE MEASURES Personal precautions,Use extra personal protective equipment (P3 filter respirator for toxic particles). Keep protective equipment and people away from and upwind of spill/leak. Entry to non-involved personnel should emergency procedures: be controlled around the leakage area by roping off, etc. Environmental precautions: Prevent product from entering drains. Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it. containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with up: appropriate laws and regulations. Section7. HANDLING AND STORAGE Precautions for safe handling Technical measures:Handling is performed in a well ventilated place. Wear suitable protective equipment. Prevent dispersion of dust. Wash hands and face thoroughly after handling. Use a closed system if possible. Use a local exhaust if dust or aerosol will be generated. Advice on safe handling: Avoid contact with skin, eyes and clothing. Conditions for safe storage, including any incompatibilities Storage conditions:Keep container tightly closed. Store in a cool and dark place. Store locked up. Store away from incompatible materials such as oxidizing agents. Packaging material:Comply with laws. Section8. EXPOSURE CONTROLS / PERSONAL PROTECTION Engineering controls:Install a closed system or local exhaust. Also install safety shower and eye bath. Personal protective equipment Imiquimod Section8. EXPOSURE CONTROLS / PERSONAL PROTECTION Respiratory protection: Dust respirator, self-contained breathing apparatus(SCBA), supplied air respirator, etc. Use respirators approved under appropriate government standards and follow local and national regulations. Hand protection:Impervious gloves. Eye protection:Safety goggles. A face-shield, if the situation requires. Skin and body protection: Impervious protective clothing. Protective boots, if the situation requires. Section9. PHYSICAL AND CHEMICAL PROPERTIES Solid Physical state (20°C): Form:Crystal- Powder Colour:White - Very pale yellow Odour:No data available pH: No data available Melting point/freezing point:294°C Boiling point/range:No data available Flash point:No data available Flammability or explosive limits: Lower:No data available Upper:No data available Relative density:No data available Solubility(ies): [Water]Very slightly soluble [Other solvents]No data available Log Pow:2.91 Section10. STABILITY AND REACTIVITY Stable under proper conditions. Chemical stability: Possibility of hazardous No special reactivity has been reported. reactions: Incompatible materials: Oxidizing agents Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx) products: Section11. TOXICOLOGICAL INFORMATION Acute Toxicity:No data available Skin corrosion/irritation: No data available Serious eyeNo data available damage/irritation: Germ cell mutagenicity: No data available Carcinogenicity: IARC =No data available NTP =No data available Reproductive toxicity:No data available RTECS Number:NJ5903450 Section12. ECOLOGICAL INFORMATION Ecotoxicity: No data available Fish: Crustacea:No data available No data available Algae: Persistence / degradability: No data available No data available Bioaccumulative potential(BCF): Mobility in soil Log Pow:2.91 Imiquimod Section12. ECOLOGICAL INFORMATION Soil adsorption (Koc): No data available Henry's LawNo data available constant(PaM3/mol): Section13. DISPOSAL CONSIDERATIONS Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system. Observe all federal, state and local regulations when disposing of the substance. Section14. TRANSPORT INFORMATION 6.1: Toxic substance. Hazards Class: UN-No:2811 Proper shipping name:Toxic solid, organic, n.o.s. Packing group:III Section15. REGULATORY INFORMATION Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002 and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport, loading and unloading were prescribed. SECTION 16 - ADDITIONAL INFORMATION N/A

安全

• 符号: GHS06
• 信号词: Danger
• 危害声明: H300-H315-H319-H335
• 警示性声明: P261-P264-P301 + P310-P305 + P351 + P338
• 个人防护装备: Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
• 危害码 (欧洲): T: Toxic;Xi: Irritant;
• 风险声明 (欧洲): R25;R36/37/38
• 安全声明 (欧洲): S26-S45
• 危险品运输编码: UN 2811 6.1/PG 3
• 海关编码: 2933990090

合成路线

上下游产品

上游产品  6
99010-63-6 99010-64-7 132206-92-9 1040136-68-2
99010-09-0 99009-85-5
下游产品  0

制备

4-羟基-2-(1H)-喹啉酮和冰乙酸混合，冷却后，滴加发烟硝酸。将反应液倒入到冰中，搅拌。过滤，滤饼水洗至近中性，干燥，二甲基甲酰胺重结晶，得3-硝基-4-羟基-2-(1H)-喹啉酮。将其和三氯氧磷混合，滴加吡啶反应，倒入到冰中，该混合液用氯仿提取，提取液用水和盐水洗、干燥、过滤、浓缩至固体析出。过滤，干燥，氯仿重结晶，得3-硝基-2,4-二氯喹啉。将其溶于乙醇，加入三乙胺，滴加异丁胺，反应完毕后，反应液倒入冰水中，搅拌2h。过滤，干燥，得2-氯-3-硝基-4-异丁氨基喹啉。将其溶于无水乙醇，加入Raney镍进行氢化反应。经过滤、乙醇重结晶，得2-氯-3-硝基-4-异丁氨基喹啉。该物质和原甲酸三乙酯反应得1-(2-甲基丙基)-4-氯-1H-咪唑并[4,5-c]喹啉。将其和甲氧基乙醇、氨水混合后密闭在高压釜中反应，过滤，用溶剂洗滤饼、干燥、重结晶，得咪喹莫特。

海关

海关编码	2933990090
中文概述	2933990090. 其他仅含氮杂原子的杂环化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%
申报要素	品名, 成分含量, 用途, 乌洛托品请注明外观, 6－己内酰胺请注明外观, 签约日期
Summary	2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%