N4-(6-chloro-2-methoxyacridin-9-yl)-N1,N1-diethylpentane-1,4-diamine dihydrochloride dihydrate | 6151-30-0

• 物质功能分类: 原料药 - 抗寄生虫病药 - 抗疟药
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N4-(6-chloro-2-methoxyacridin-9-yl)-N1,N1-diethylpentane-1,4-diamine dihydrochloride dihydrate
• 英文别名: quinacrine dihydrochloride dihydrate；quinacrine dihydrochloride；Erion；4-N-(6-chloro-2-methoxyacridin-9-yl)-1-N,1-N-diethylpentane-1,4-diamine;hydrate;hydrochloride
• CAS: 6151-30-0
• 化学式: C₂₃H₃₀ClN₃O*2ClH*2H₂O
• 分子量: 508.916
• InChiKey: SHUFTPHVWKTNFH-UHFFFAOYSA-N

物化性质

• 熔点：
  247 °C
• 溶解度：
  DMSO：10mg/mL（19.65mM）；；
• 稳定性/保质期：
  在常温常压下稳定，但对光照敏感，并且会吸收湿空气和空气中的水分。

计算性质

• 辛醇/水分配系数(LogP)：
  5.57
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  38.4
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S37/39
• 危险类别码：
  R22,R36/37/38

SDS

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Section 1. Chemical Product and Company Identification
Quinacrine hydrochloride dihydrate Catalog
Common Name/
Number(s).
Trade Name
CAS# 6151-30-0
Manufacturer
RTECS AR7876000
SPECTRUM CHEMICAL MFG. CORP.
TSCA TSCA 8(b) inventory:
Quinacrine hydrochloride
dihydrate
Commercial Name(s) Not available.
CI# Not available.
Synonym 6-Chloro-9=[[44-(diethylamino-1-methylbutyl]amino]-2-methoxyacridine
IN CASE OF EMERGENCY
hydrochloride
Chemical Name Not available.
Not available. CALL [phone]
Chemical Family
Chemical Formula C23H30ClN3O.2HCl.2H2O
SPECTRUM CHEMICAL MFG. CORP.

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Section 2.Composition and Information on Ingredients
Exposure Limits
TWA (mg/m3) STEL (mg/m3) CEIL (mg/m3)
Name CAS # % by Weight
1) Quinacrine hydrochloride dihydrate 6151-30-0 100
Toxicological Data Quinacrine hydrochloride dihydrate:
on Ingredients ORAL (LD50): Acute: 660 mg/kg [Rat]. 433 mg/kg [Rabbit].

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Section 3. Hazards Identification
Potential Acute Health Effects Very hazardous in case of ingestion. Hazardous in case of skin contact (irritant), of eye contact (irritant), of
inhalation. Slightly hazardous in case of skin contact (permeator).
Potential Chronic Health CARCINOGENIC EFFECTS: Not available.
Effects MUTAGENIC EFFECTS: Not available.
TERATOGENIC EFFECTS: Not available.
DEVELOPMENTAL TOXICITY: PROVEN
The substance is toxic to blood, the nervous system, the reproductive system, liver, heart.
Repeated or prolonged exposure to the substance can produce target organs damage.
Quinacrine hydrochloride dihydrate

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Section 4. First Aid Measures
Eye Contact Check for and remove any contact lenses. Immediately flush eyes with running water for at least 15 minutes,
keeping eyelids open. Cold water may be used. Do not use an eye ointment. Seek medical attention.
Skin Contact After contact with skin, wash immediately with plenty of water. Gently and thoroughly wash the contaminated skin
with running water and non-abrasive soap. Be particularly careful to clean folds, crevices, creases and groin.
Cold water may be used. Cover the irritated skin with an emollient. If irritation persists, seek medical attention.
Wash contaminated clothing before reusing.
Serious Skin Contact Wash with a disinfectant soap and cover the contaminated skin with an anti-bacterial cream. Seek immediate
medical attention.
Inhalation Allow the victim to rest in a well ventilated area. Seek immediate medical attention.
Serious Inhalation Not available.
Ingestion Do not induce vomiting. Examine the lips and mouth to ascertain whether the tissues are damaged, a possible
indication that the toxic material was ingested; the absence of such signs, however, is not conclusive. Loosen
tight clothing such as a collar, tie, belt or waistband. If the victim is not breathing, perform mouth-to-mouth
resuscitation. Seek immediate medical attention.
Serious Ingestion Not available.

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Section 5. Fire and Explosion Data
Flammability of the Product May be combustible at high temperature.
Auto-Ignition Temperature Not available.
Flash Points Not available.
Flammable Limits Not available.
Products of Combustion These products are carbon oxides (CO, CO2), nitrogen oxides (NO, NO2...), halogenated compounds.
Fire Hazards in Presence of Not available.
Various Substances
Explosion Hazards in Presence Risks of explosion of the product in presence of mechanical impact: Not available.
of Various Substances Risks of explosion of the product in presence of static discharge: Not available.
Fire Fighting Media SMALL FIRE: Use DRY chemical powder.
and Instructions LARGE FIRE: Use water spray, fog or foam. Do not use water jet.
Special Remarks on Not available.
Fire Hazards
Special Remarks on Explosion Not available.
Hazards

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Section 6. Accidental Release Measures
Small Spill Use appropriate tools to put the spilled solid in a convenient waste disposal container. Finish cleaning by
spreading water on the contaminated surface and dispose of according to local and regional authority
requirements.
Large Spill Use a shovel to put the material into a convenient waste disposal container. Finish cleaning by spreading water
on the contaminated surface and allow to evacuate through the sanitary system.
Quinacrine hydrochloride dihydrate

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Section 7. Handling and Storage
Precautions Keep away from heat. Keep away from sources of ignition. Empty containers pose a fire risk, evaporate the
residue under a fume hood. Ground all equipment containing material. Do not ingest. Do not breathe dust.
Wear suitable protective clothing In case of insufficient ventilation, wear suitable respiratory equipment If
ingested, seek medical advice immediately and show the container or the label. Avoid contact with skin and eyes
Storage Keep container dry. Keep in a cool place. Ground all equipment containing material. Keep container tightly
closed. Keep in a cool, well-ventilated place. Combustible materials should be stored away from extreme heat
and away from strong oxidizing agents.

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Section 8. Exposure Controls/Personal Protection
Engineering Controls Use process enclosures, local exhaust ventilation, or other engineering controls to keep airborne levels below
recommended exposure limits. If user operations generate dust, fume or mist, use ventilation to keep exposure to
airborne contaminants below the exposure limit.
Personal Protection Splash goggles. Lab coat. Dust respirator. Be sure to use an approved/certified respirator or equivalent.
Gloves.
Personal Protection in Case of Splash goggles. Full suit. Dust respirator. Boots. Gloves. A self contained breathing apparatus should be used
a Large Spill to avoid inhalation of the product. Suggested protective clothing might not be sufficient; consult a specialist
BEFORE handling this product.
Exposure Limits Not available.

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Section 9. Physical and Chemical Properties
Physical state and appearance Solid. Odor Not available.
Taste Not available.
508.91 g/mole
Molecular Weight
Color Yellow.
pH (1% soln/water) Not available.
Boiling Point Not available.
Melting Point Decomposes.
Critical Temperature Not available.
Specific Gravity Not available.
Not applicable.
Vapor Pressure
Vapor Density Not available.
Volatility Not available.
Odor Threshold Not available.
Water/Oil Dist. Coeff. Not available.
Not available.
Ionicity (in Water)
Dispersion Properties See solubility in water.
Soluble in cold water.
Solubility

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Section 10. Stability and Reactivity Data
The product is stable.
Stability
Instability Temperature Not available.
Not available.
Conditions of Instability
Incompatibility with various Not available.
substances
Quinacrine hydrochloride dihydrate
Corrosivity Non-corrosive in presence of glass.
Special Remarks on Not available.
Reactivity
Special Remarks on Not available.
Corrosivity
Polymerization No.

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Section 11. Toxicological Information
Routes of Entry Eye contact. Inhalation. Ingestion.
Toxicity to Animals Acute oral toxicity (LD50): 433 mg/kg [Rabbit].
Chronic Effects on Humans DEVELOPMENTAL TOXICITY: PROVEN
The substance is toxic to blood, the nervous system, the reproductive system, liver, heart.
Other Toxic Effects on Very hazardous in case of ingestion.
Humans Hazardous in case of skin contact (irritant), of inhalation.
Slightly hazardous in case of skin contact (permeator).
Special Remarks on Not available.
Toxicity to Animals
Special Remarks on Not available.
Chronic Effects on Humans
Special Remarks on other Not available.
Toxic Effects on Humans

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Section 12. Ecological Information
Not available.
Ecotoxicity
Not available.
BOD5 and COD
Products of Biodegradation Possibly hazardous short term degradation products are not likely. However, long term degradation products may
arise.
Toxicity of the Products The products of degradation are more toxic.
of Biodegradation
Not available.
Special Remarks on the
Products of Biodegradation

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Section 13. Disposal Considerations
Waste Disposal

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Section 14. Transport Information
DOT Classification Not a DOT controlled material (United States).
Not applicable.
Identification
Special Provisions for Not applicable.
Transport
Quinacrine hydrochloride dihydrate
DOT (Pictograms)

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Section 15. Other Regulatory Information and Pictograms
TSCA 8(b) inventory: Quinacrine hydrochloride dihydrate
Federal and State
Regulations
California
Proposition 65
Warnings
Other Regulations OSHA: Hazardous by definition of Hazard Communication Standard (29 CFR 1910.1200).
CLASS D-1B: Material causing immediate and serious toxic effects (TOXIC).
Other Classifications WHMIS (Canada)
CLASS D-2A: Material causing other toxic effects (VERY TOXIC).
DSCL (EEC) R36/38- Irritating to eyes and skin.
R48/22- Harmful: danger of serious
damage to health by prolonged
exposure if swallowed.
Health Hazard
HMIS (U.S.A.) 2 National Fire Protection
1 Flammability
1 Association (U.S.A.)
Fire Hazard
2 0 Reactivity
Health
Reactivity
0
Specific hazard
Personal Protection
E
WHMIS (Canada)
(Pictograms)
DSCL (Europe)
(Pictograms)
TDG (Canada)
(Pictograms)
ADR (Europe)
(Pictograms)
Protective Equipment
Gloves.
Lab coat.
Quinacrine hydrochloride dihydrate
Dust respirator. Be sure to use an
approved/certified respirator or
equivalent. Wear appropriate respirator
when ventilation is inadequate.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性

Quinacrine hydrochloride hydrate（美酚喹盐·水合物）是一种抗疟药，同时在体内外均具有抗肿瘤作用。该药物通过抑制 NF-κB 并激活 p53 信号转导途径，诱导肿瘤细胞凋亡。

体外研究

Quinacrine 在浓度为 5-20 μM（24 小时）时能抑制 SGC-7901 细胞的生长。在浓度分别为 7.5 和 15 μM（24 小时）的情况下，Quinacrine 能诱导 SGC-7901 细胞凋亡，与线粒体依赖信号通路有关，并涉及 p53 表达上调和 caspase-3 激活途径。治疗 24 小时后，Quinacrine（15 μM）显著增加了促凋亡蛋白的水平，包括细胞色素 c、Bax 和 p53，同时降低了抗凋亡蛋白 Bcl-2 的水平，从而使得 Bax/Bcl-2 比例向有利于凋亡的方向转变。

细胞活力检测

• 细胞系：SGC-7901 细胞
• 浓度：0, 5, 10, 15 和 20 μM
• 培养时间：24 小时
• 结果：随着浓度增加，细胞活力呈剂量依赖性下降。平均 IC₅₀ 值为 16.18 μM。

凋亡分析

• 细胞系：SGC-7901 细胞
• 浓度：7.5 和 15 μM
• 培养时间：24 小时
• 结果：治疗后早期和晚期凋亡细胞百分比显著增加至 26.30%，而对照组仅为 3.37%。

Western Blot 分析

• 细胞系：SGC-7901 细胞
• 浓度：15 μM
• 培养时间：24 小时
• 结果：细胞色素 c 蛋白相对量上调，从 0.10 升高至 0.24。p53 蛋白相对量显著增加，从 0.06 上升到 0.19。Bax/Bcl-2 比例显著升高，从 1.21 增加至 2.59。

体内研究

Quinacrine（每公斤体重 100 mg，每周三次连续两周）在第 30/31 天时能明显抑制循环白血病细胞，并增加中位生存时间 (MST)。该药物在测试剂量下未减少动物的体重。

结果

• 动物模型：带有急性髓性白血病（AML）PS 模型的雌性 SCID 小鼠
• 剂量：100 mg/kg
• 给药方式：口服灌胃 (po)；每周三次，连续两周
• 结果：
  • 第一只 AML 小鼠体内研究中，在第 30/31 天的血液样本（占白细胞百分比）检测中，对照组小鼠中有 72% 的人源肿瘤细胞，而 Quinacrine 治疗的小鼠中仅剩 2.2%。
  • 对照组小鼠的中位生存时间为 34 天，而 Quinacrine 治疗组为 46 天。