四氢维洛林 | 4747-99-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 中文名称: 四氢维洛林
• 英文名称: Norlaudanosolin
• 英文别名: (+/-)-Tetrahydropapaveroline；(R,S)-norlaudanosoline；Norlaudanosoline；Tetrahydropapaveroline；1-[(3,4-dihydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol
• CAS: 4747-99-3
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: ABXZOXDTHTTZJW-UHFFFAOYSA-N

物化性质

• 沸点：
  573.2±50.0 °C(Predicted)
• 密度：
  1.406±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  93
• 氢给体数：
  5
• 氢受体数：
  5

SDS

Name:	(+/-)-Tetrahydropapaveroline Hydrobromide 98% Material Safety Data Sheet
Synonym:	Norlaudanosoline Hydrobromide
CAS:	4747-99-3

Section 1 - Chemical Product MSDS Name:(+/-)-Tetrahydropapaveroline Hydrobromide 98% Material Safety Data Sheet
Synonym:Norlaudanosoline Hydrobromide

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
4747-99-3	(+/-)-Tetrahydropapaveroline Hydrobrom	98%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. 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. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use agent most appropriate to extinguish fire. 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:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated 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 process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 4747-99-3: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: slightly gray
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 277 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C16H17NO4.HBr
Molecular Weight: 368.23

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 4747-99-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(+/-)-Tetrahydropapaveroline Hydrobromide - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 4747-99-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 4747-99-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 4747-99-3 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

反应信息

• 作为反应物：
  描述：

  四氢维洛林 在 吡啶 作用下， 反应 1.33h， 生成 benzopyrrocoline tetraacetate
  参考文献：
  名称：

  Electrochemical and enzyme-mediated oxidations of tetrahydropapaveroline

  摘要：

  DOI：

  10.1021/jo00025a030
• 作为产物：
  描述：

  羟基酪醇 在 potassium phosphate 、 三氧化硫吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 13.0h， 生成 四氢维洛林
  参考文献：
  名称：

  One-pot triangular chemoenzymatic cascades for the syntheses of chiral alkaloids from dopamine

  摘要：

  一锅法、一底物、三角形化酶级联反应，包括转氨酶（TAm）和诺可克洛啉合酶（NCS），可实现（S）-苄基异喹啉和（S）-四氢原咱呱啶生物碱的形成。

  DOI：

  10.1039/c4gc02325k
• 作为试剂：
  描述：

  docosyl 4-methybenzoate 在 samarium diiodide 、 水 、 氯化铵 作用下， 以 四氢维洛林 为溶剂， 以63%的产率得到二十二烷
  参考文献：
  名称：

  Using Toluates as Simple and Versatile Radical Precursors

  摘要：

  The viability of the toluate moiety as a radical precursor has been examined by studying deoxygenation and cyclization reactions.

  DOI：

  10.1021/ol800944p

文献信息

• Methods for treating an inflammatory condition or inhibiting JNK
  申请人：——

  公开号：US20040127536A1

  公开（公告）日：2004-07-01

  This invention is generally directed to Indazole Derivatives having the following structure: 1 or pharmaceutically acceptable salt thereof, wherein R 1 , R 2 and A are as defined herein. Such compounds have utility in the treatment of a wide range of diseases and disorders that are responsive to JNK inhibition, such as an inflammatory disease or disorder. Thus, methods of treating such diseases and disorders are also disclosed, as are pharmaceutical compositions containing one or more compounds of the above compounds.

  这项发明通常涉及吲唑衍生物，具有以下结构： 1 或药用可接受的盐，其中R 1 ，R 2 和A如本文所述定义。这类化合物在治疗对JNK抑制剂有响应的广泛疾病和障碍，如炎症性疾病或障碍中具有用途。因此，还披露了治疗这些疾病和障碍的方法，以及包含一个或多个上述化合物的药物组合物。
• Indazole compounds, compositions thereof and methods of treatment therewith
  申请人：Bhagwat S. Shripad

  公开号：US20050009876A1

  公开（公告）日：2005-01-13

  This invention is generally directed to the use of Indazole Compounds for treating or preventing diseases associated with protein kinases, including tyrosine kinases, such as proliferative diseases, inflammatory diseases, abnormal angiogenesis and diseases related thereto, atherosclerosis, macular degeneration, diabetes, obesity, pain and others. The methods comprise the administration to a patient in need thereof of an effective amount of an indazole compound that inhibits, modulates or regulates tyrosine kinase signal transduction. Novel indazole compounds or pharmaceutically acceptable salt thereof are presented herein.

  这项发明通常涉及使用吲唑化合物来治疗或预防与蛋白激酶相关的疾病，包括酪氨酸激酶，诸如增殖性疾病、炎症性疾病、异常血管生成及其相关疾病、动脉硬化、黄斑变性、糖尿病、肥胖、疼痛等。这些方法包括向有需要的患者施用有效量的吲唑化合物，以抑制、调节或控制酪氨酸激酶信号转导。本文中提供了一种新型的吲唑化合物或其药用可接受的盐。
• PHOSPHONIUM ION CHANNEL BLOCKERS AND METHODS FOR USE
  申请人：Nocion Therapeutics, Inc.

  公开号：US20210128589A1

  公开（公告）日：2021-05-06

  The invention provides compounds of Formula (I), or pharmaceutically acceptable salts thereof: The compounds, compositions, methods and kits of the invention are useful for the treatment of pain, itch, and neurogenic inflammation.

  本发明提供了式(I)的化合物，或其药用可接受的盐： 本发明的化合物、组合物、方法和试剂盒可用于治疗疼痛、瘙痒和神经性炎症。
• The Catalytic Potential of<i>Coptis japonica</i>NCS2 Revealed - Development and Utilisation of a Fluorescamine-Based Assay
  作者：Thomas Pesnot、Markus C. Gershater、John M. Ward、Helen C. Hailes

  DOI：10.1002/adsc.201200641

  日期：2012.11.12

  The versatility and potential of a norcoclaurine synthase (NCS) from Coptis japonica NCS2 has been investigated, together with the development and application of a novel fluorescence-based high-throughput assay using nearly forty amines/aldehydes. The stereocontrol exerted by CjNCS2 on selected non-natural substrates has been determined, where the tetrahydroisoquinolines (THIAs) were formed as the

  研究了来自黄连NCS2的正月桂氨酸合成酶（NCS）的多功能性和潜力，以及使用近四十种胺/醛的新型荧光高通量测定方法的开发和应用。已经确定了Cj NCS2对选定的非天然底物施加的立体控制，其中天然氢去甲可可碱在> 95％ee中形成了四氢异喹啉（THIAs）作为（1 S）异构体。利用报告的黄藻NCS X射线晶体结构对涉及THIA机制中间体的对接计算，并与Cj结合NCS2筛选结果可进一步了解NCS的作用方式。这些发现表明，除了关键的活性位点残基K122和E110，D141对于酶促转化在机械上也是必不可少的。我们提出的机理进一步支持了NCS对醛底物的超强耐受性，其中醛从酶口袋中伸出。
• Purification and characterization of coclaurine N-methyltransferase from cultured Coptis japonica cells
  作者：Kum-Boo Choi、Takashi Morishige、Fumihiko Sato

  DOI：10.1016/s0031-9422(00)00481-7

  日期：2001.4

  S-Adenosyl-L-methionine (SAM): coclaurine N-methyltransferase (CNMT), which catalyzes the transfer of a methyl group from S-adenosyl-L-methionine to the amino group of the tetrahydrobenzylisoquinoline alkaloid coclaurine. was purified 340-fold from Coptis japonica cells in 1% yield to give an almost homogeneous protein. The purified enzyme, which occurred as a homotetramer with a native Mr of 160 kDa

  S-腺苷-L-甲硫氨酸 (SAM)：椰油碱 N-甲基转移酶 (CNMT)，催化甲基从 S-腺苷-L-甲硫氨酸转移到四氢苄基异喹啉生物碱椰油碱的氨基。以 1% 的产率从日本黄连细胞中纯化 340 倍，得到几乎均质的蛋白质。纯化的酶以同源四聚体形式出现，天然 Mr 为 160 kDa（凝胶过滤色谱），亚基 Mr 为 45 kDa（SDS-聚丙烯酰胺凝胶电泳），其最适 pH 值为 7.0，pI 为 4.2。而 (R)-coclaurine 是酶活性的最佳底物，Coptis CNMT 具有广泛的底物特异性，没有立体特异性 CNMT 甲基化去甲月桂醇内酯、6,7-二甲氧基-1,2,3,4-四氢异喹啉和 1-甲基-6,7 -二羟基-1,2,3,4-四氢异喹啉。该酶不需要任何金属离子。对氯汞苯甲酸盐和碘乙酰胺不抑制 CNMT 活性，但添加 5 mM 的 Co2+、Cu2+ 或 Mn2+ 分别严重抑制了 75%、47%