盐酸四咪唑 | 5086-74-8

• 物质功能分类: 原料药 - 抗寄生虫病药 - 驱肠虫药
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并噻唑类
• 中文名称: 盐酸四咪唑
• 中文别名: 四咪唑盐酸盐；盐酸驱虫净；驱虫净盐酸盐；DL-2,3,5,6-四氢-6-苯基咪唑并[2,1-b]噻唑盐酸盐；盐酸左旋咪唑；四咪唑盐酸；盐酸噻咪唑；四咪唑,驱虫净；(R,S)-2,3,5,6-四氢-6-苯基咪唑异(2,1,6)噻唑盐酸盐
• 英文名称: tetramisole hydrochloride
• 英文别名: levamisole hydrochloride；(±)-tetramisole hydrochloride；l-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride；Anthelvet；Hydron;6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole;chloride
• CAS: 5086-74-8
• 化学式: C₁₁H₁₃N₂S*Cl
• 分子量: 240.757
• InChiKey: LAZPBGZRMVRFKY-UHFFFAOYSA-N

物化性质

• 熔点：
  266-267 °C(lit.)
• 溶解度：
  轻微溶于甲醇、加热微溶于水
• 稳定性/保质期：
  在常温常压下稳定，该物质呈现为白色或微黄色的针状结晶，无特殊气味，味道略带苦涩。它能够溶于水（21克/100毫升，20℃）、甲醇、丙二醇，并且能在乙醇、氯仿、己烷和丙酮中微溶。注意，该物质具有一定的刺激性。

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  40.9
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R22,R36/37/38
• WGK Germany：
  3
• 海关编码：
  2934999090
• 危险品运输编号：
  NONH for all modes of transport
• RTECS号：
  NJ5950000
• 危险标志：
  GHS07
• 危险性描述：
  H302,H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338
• 储存条件：
  常温下避光存放，置于阴凉干燥处并密封保存。

SDS

Name:	Tetramisole hydrochloride 99+% Material Safety Data Sheet
Synonym:	DL-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole hydrochloride; (+-)-2,3,5,6-Tetrahycro-6-phenylimidazo (2,1-b)thiazole monohydrochloride; Tatramisole; DL-Tetramisole hydrochloride; Tetramisol hydrochlorid
CAS:	5086-74-8

Section 1 - Chemical Product MSDS Name:Tetramisole hydrochloride 99+% Material Safety Data Sheet
Synonym:DL-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole hydrochloride; (+-)-2,3,5,6-Tetrahycro-6-phenylimidazo (2,1-b)thiazole monohydrochloride; Tatramisole; DL-Tetramisole hydrochloride; Tetramisol hydrochlorid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5086-74-8	Tetramisole hydrochloride	99+	225-799-5

Hazard Symbols: XN
Risk Phrases: 22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed.Toxic.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. The toxicological properties of this material have not been fully investigated.
Ingestion:
Harmful if swallowed. The toxicological properties of this substance have not been fully investigated. Causes gastrointestinal tract irritation.
Inhalation:
The toxicological properties of this substance have not been fully investigated. Causes irritation of the mucous membrane and upper respiratory tract.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid immediately. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Wash area with soap and water. Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Do not get in eyes, on skin, or on clothing. Do not ingest or inhale. Use only in a chemical fume hood.
Storage:
Keep containers tightly closed. Store in a cool, dry area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 5086-74-8: Personal Protective Equipment Eyes: Wear safety glasses and chemical goggles if splashing is possible.
Skin:
Wear appropriate protective gloves and clothing to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystals
Color: white
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 266.00 - 267.00 deg C
Autoignition Temperature: 500 deg C ( 932.00 deg F)
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: 210 g/l (20C)
Specific Gravity/Density: Not available.
Molecular Formula: C11H12N2S.HCl
Molecular Weight: 240.76

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 5086-74-8: NJ5950000 LD50/LC50:
CAS# 5086-74-8: Oral, mouse: LD50 = 210 mg/kg; Oral, rat: LD50 = 480 mg/kg.
Oral, Human: TDLo=2 mg/kg Carcinogenicity:
Tetramisole hydrochloride - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION
Other No information available.

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 22 Harmful if swallowed.
Safety Phrases:
S 28B After contact with skin, wash immediately with
plenty of water and soap.
S 38 In case of insufficient ventilation, wear
suitable respiratory equipment.
WGK (Water Danger/Protection)
CAS# 5086-74-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 5086-74-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5086-74-8 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

理化性质

盐酸四咪唑又名 DL-2,3,5,6-四氢-6-苯基咪唑并[2,1-b]噻唑盐酸盐，为白色结晶性粉末，味苦带涩。它易溶于水和甲醇，略溶于乙醇，不溶于丙酮。这是一种高效、低毒的广谱兽用驱虫药。

用途

盐酸四咪唑是一种具有驱虫剂活性的生物反应调节剂，可用作打虫药（针对线虫）、免疫调制剂等。

生物活性

Tetramisole 是右旋和左旋异构体的混合物，并被用作驱虫剂。体内研究显示，口服 Tetramisole 无毒，以有效低剂量注射给药后，在14个不同宿主中对所有成年和幼年的胃肠道及肺线虫进行了测试。

• 体外研究：Tetramisole（10 μg/mL）作用于蠕虫病毒，导致离体肌肉持续性收缩。它还使蛔虫肌肉的静息电位从34 mV 降至10 mV，并引起之前用高K Tetramisole (0.1 mM) 作用过的猫肌肉产生更强的抽搐反应。
• 增强效应：Tetramisole（0.1 mM）增强了鸡肌肉抽搐反应的准备状态并逆转了 Tubocurarine 的抑制效果，从而产生了可逆性的神经肌肉阻滞和肌肉挛缩。

体内研究

体内实验显示：

• Tetramisole (2 mg/kg, i.v.) 作用于猫后，在20秒延迟后引起了瞬膜强烈收缩，并伴随着短暂的血压下降，随后持续上升长达20分钟。与未使用利血平治疗的猫相比，其收缩反应更大。
• Tetramisole (5-10 mg/kg, i.v.) 在兔子身上造成短暂的血压急剧下降，部分与阿托品作用相反。
• 经过三周处理后，Tetramisole (15 mg/kg) 处理的羊群中粪便线虫虫卵数开始增长，并持续升高到12周。

用途

盐酸四咪唑用作左旋咪唑中间体及抗蠕虫药。

反应信息

• 作为反应物：
  描述：

  盐酸四咪唑 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 (E)-1-nitroso-2-oxo-3-(2-nitrosothioethyl)-5-phenylimidazolidine
  参考文献：
  名称：

  Gouesnard, Jean-Paul, Journal of the Chemical Society. Perkin transactions I, 1986, p. 1901 - 1904

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(2-Methoxyethyl)-4-phenyl-2-imidazolidon 生成 盐酸四咪唑
  参考文献：
  名称：

  RAGHU, S.;HOFFMANN, A. K.;SINGH, B.

  摘要：

  DOI：

文献信息

• [EN] PRODRUG COMPOSITIONS AND METHODS OF TREATMENT<br/>[FR] COMPOSITIONS DE PROMÉDICAMENT ET PROCÉDÉS DE TRAITEMENT
  申请人：AQUESTIVE THERAPEUTICS INC

  公开号：WO2021087359A1

  公开（公告）日：2021-05-06

  Pharmaceutical compositions include a prodrug of epinephrine are described.

  药物组合物包括表述的肾上腺素前药。
• Multi-functional ionic liquid compositions for overcoming polymorphism and imparting improved properties for active pharmaceutical, biological, nutritional, and energetic ingredients
  申请人：Rogers D. Robin

  公开号：US20070093462A1

  公开（公告）日：2007-04-26

  Disclosed are ionic liquids and methods of preparing ionic liquid compositions of active pharmaceutical, biological, nutritional, and energetic ingredients. Also disclosed are methods of using the compositions described herein to overcome polymorphism, overcome solubility and delivery problems, to control release rates, add functionality, enhance efficacy (synergy), and improve ease of use and manufacture.

  揭示了离子液体及制备活性药物、生物、营养和能量成分的离子液体组合物的方法。还揭示了利用本文描述的组合物的方法，以克服多型性、克服溶解度和输送问题、控制释放速率、增加功能性、增强功效（协同作用）以及改善易用性和制造工艺。
• [EN] COMPOUNDS AND USES FOR THE TREATMENT AND PREVENTION OF DISEASES AND CONDITIONS ASSOCIATE WITH OR AGGRAVATED BY IMPARED MITOPHAGY<br/>[FR] COMPOSÉS ET UTILISATIONS POUR LE TRAITEMENT ET LA PRÉVENTION DE MALADIES ET D'ÉTATS ASSOCIÉS À UNE MITOPHAGIE DÉFICIENTE OU AGGRAVÉS PAR CELLE-CI
  申请人：YISSUM RES DEV CO OF HEBREW UNIV JERUSALEM LTD

  公开号：WO2019175873A1

  公开（公告）日：2019-09-19

  The present invention provides compounds and methods for the treatment and prevention of diseases and conditions associate with or aggravated by impaired mitophagy.

  本发明提供了用于治疗和预防与受损线粒体自噬有关或由其恶化的疾病和病况的化合物和方法。
• METHODS AND COMPOSITIONS FOR TREATING INFECTION
  申请人：UNIVERSITY OF ROCHESTER

  公开号：US20150238473A1

  公开（公告）日：2015-08-27

  Provided herein are compositions and methods for treating or preventing infection.

  本文提供了用于治疗或预防感染的组合物和方法。
• [EN] DUAL FUNCTIONING IONIC LIQUIDS AND SALTS THEREOF<br/>[FR] LIQUIDES IONIQUES À DOUBLE FONCTION ET SELS DE CEUX-CI
  申请人：UNIV ALABAMA

  公开号：WO2010078300A1

  公开（公告）日：2010-07-08

  Disclosed herein are ionic liquid compositions comprising active pharmaceutical, biological, and nutritional compounds, and methods of use. Further disclosed are compositions of matter including liquid ion pairs alone or in solution and their use; compositions of ionic liquids that are 'solvated,' for example, 'hydrated' and their uses.

  本文揭示了包括活性药物、生物学和营养化合物的离子液体组合物，以及其使用方法。进一步揭示了包括液态离子对的物质组合物，单独或溶解后使用；以及离子液体的“溶剂化”组合物，例如“水合”的组合物及其用途。

表征谱图