5-甲基色胺盐酸盐 | 1010-95-3

• 物质功能分类: 医药中间体 - 原料药中间体
• 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: 5-甲基色胺盐酸盐
• 中文别名: 3-(2-氨乙基)-5-甲基吲哚盐酸盐
• 英文名称: 5-methyltryptamine hydrochloride
• 英文别名: 2-(5-methyl-1H-indol-3-yl)ethan-1-amine hydrochloride；5-methyltryptammonium chloride；hydron;2-(5-methyl-1H-indol-3-yl)ethanamine;chloride
• CAS: 1010-95-3
• 化学式: C₁₁H₁₄N₂*ClH
• mdl: MFCD00012683
• 分子量: 210.706
• InChiKey: RBHDFGBPJGEYCK-UHFFFAOYSA-N

物化性质

• 熔点：
  290-292 °C
• 溶解度：
  DMSO（少许）、甲醇（少许）、水（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.0
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  41.8
• 氢给体数：
  3
• 氢受体数：
  1

安全信息

• 危险等级：
  6.1
• 危险品标志：
  T+
• WGK Germany：
  3
• 海关编码：
  2942000000
• 安全说明：
  S24/25
• 危险类别码：
  R26/27/28
• 储存条件：
  2～8℃

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Methyltryptamine, HCl
Synonyms: 3-(2-Aminoethyl)-5-methylindole hydrochloride

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 5-Methyltryptamine, HCl
CAS number: 1010-95-3

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C11H14N2.ClH
Molecular weight: 210.7

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen chloride.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

制备方法

医药中间体。

用途简介

反应信息

• 作为反应物：
  描述：

  5-甲基色胺盐酸盐 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 12.5h， 生成 5-methyl-N-tosyl-N’-methyltryptamine
  参考文献：
  名称：

  直接构建双吡咯烷并[2,3-b]二氢吲哚和（+）-WIN 6421的全合成的KI催化氧化系统的探索。

  摘要：

  一种简便和对环境无害的KI（催化量）/ NABO 3 ·4H 2 O型氧化系统已被开发用于串联氧化aminocyclization /耦合色胺，得到一系列3一，3一'-bispyrrolidino [2,3- b高效率的二氢吲哚（产率高达94％）。该反应具有亲电性“ I + ”机理，这一机理与典型的自由基引发过程有很大不同，并且温和得多，可以很容易地被放大以合成（+）-WIN 6482。

  DOI：

  10.1039/c9cc08646c
• 作为产物：
  描述：

  1-Oxo-6-methyl-1,2,3,4-tetrahydro-norharman 在 盐酸 、 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 5-甲基色胺盐酸盐
  参考文献：
  名称：

  N6-取代的腺苷受体激动剂。合成和药理活性为有效的抗伤害感受药。

  摘要：

  合成了腺苷的新型N6-（吲哚-3-基）烷基衍生物。在结合研究和苯基苯醌诱导的扭体试验中评估了这些化合物的腺苷受体亲和力和抗伤害感受活性。这些类似物中的大多数表现出有效的镇痛活性而没有副作用。其中，化合物3c（UP 202-32）以特定方式与A1（Ki = 110 nM）和A2（Ki = 350 nM）腺苷受体结合，因为它不与许多其他受体（尤其是阿片样物质结合位点）相互作用。苯基苯醌试验（ED50 = 3.3 mg / kg口服）中的抗伤害感受活性被8-环戊基茶碱拮抗，表明腺苷能机制是该化合物观察到的镇痛作用的基础。

  DOI：

  10.1021/jm00051a007

文献信息

• NOVEL COMPOUNDS FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES
  申请人：Griffioen Gerard

  公开号：US20130289033A1

  公开（公告）日：2013-10-31

  This invention provides novel compounds and the novel compounds for use as a medicine, more in particular for the prevention or treatment of neurodegenerative disorders, more specifically certain neurological disorders, such as disorders collectively known as tauopathies, and disorders characterised by cytotoxic α-synuclein amyloidogenesis. The present invention also relates to the use of said novel compounds for the manufacture of medicaments useful for treating such neurodegenerative disorders. The present invention further relates to pharmaceutical compositions including said novel compounds and to methods for the preparation of said novel compounds. The compounds have the formula (A1), wherein R 1 , R 2 , R 4 , R 5 , R 6 , E, n, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , B, R 8 , and m are as defined in the claims.

  本发明提供了新型化合物，以及这些新型化合物作为药物的使用，特别是用于预防或治疗神经退行性疾病，更具体地是一些神经系统疾病，例如统称为tauopathies的疾病，以及以细胞毒性α-突触核蛋白淀粉样生成特征的疾病。本发明还涉及将所述新型化合物用于制造用于治疗此类神经退行性疾病的药物。本发明进一步涉及包括所述新型化合物的药物组合物以及制备所述新型化合物的方法。这些化合物的公式为(A1)，其中R1、R2、R4、R5、R6、E、n、Y1、Y2、Y3、Y4、Y5、B、R8和m如权利要求中所定义。
• Scope of the Reactions of Indolyl- and Pyrrolyl-Tethered <i>N</i>-Sulfonyl-1,2,3-triazoles: Rhodium(II)-Catalyzed Synthesis of Indole- and Pyrrole-Fused Polycyclic Compounds
  作者：Liangbing Fu、Huw M. L. Davies

  DOI：10.1021/acs.orglett.7b00180

  日期：2017.4.7

  An efficient synthesis of tetrahydrocarboline-type products and polycyclic spiroindolines has been achieved. The transformation proceeds via rhodium(II)-catalyzed intramolecular annulations of indolyl- and pyrrolyl-tethered N-sulfonyl-1,2,3-triazoles. The reaction could be tuned toward either the formal [3 + 2] cycloaddition or the C–H functionalization reaction depending on the electronic and structural

  已经实现了四烃型产物和多环螺二吲哚的有效合成。该转化通过铑（II）催化的吲哚基和吡咯基连接的N-磺酰基-1，2，3-三唑的分子内环化而进行。根据底物的电子和结构特征，可将反应调整为正式的[3 + 2]环加成反应或CH–H官能化反应，从而产生各种结构相关的杂环化合物。
• DNA Methyltransferase inhibitors
  申请人：The Penn State Research Foundation

  公开号：EP1420021A1

  公开（公告）日：2004-05-19

  A compound of the formula or a pharmaceutically acceptable salt thereof, whereinR1, R2, and R3 are the same or different and are independently hydrogen, lower alkyl, aryl or substituted aryl, lower alkoxy, lower alkoxyalkyl, or cycloalkyl or cycloalkyl alkoxy, where each cycloalkyl group has from 3-7 members, where up to two of the cycloalkyl members are optionally hetero atoms selected from oxygen and nitrogen, and where any member of the alkyl, aryl or cycloalkyl group is optionally substituted with halogen, lower alkyl or lower alkoxy, aryl or substituted aryl, and whereR3 can be ribose, deoxyribose or phosphorylated derivatives thereof, whereinR1, R2, and R3 are not all hydrogen and whereinwhen R3 is ribose, deoxyribose or phosphorylated derivatives thereof, one of R1 or R2 is not hydrogen.

  该化合物的结构式为 或其药用可接受盐， 其中R1、R2和R3相同或不同，且独立地为氢、较低烷基、芳基或取代芳基、较低烷氧基、较低烷氧基烷基、环烷基或环烷基烷氧基，其中每个环烷基团具有3-7个成员，其中最多两个环烷基成员可选择为氧和氮，且烷基、芳基或环烷基团的任何成员可选择地取代有卤素、较低烷基或较低烷氧基、芳基或取代芳基，以及 其中R3可以是核糖、脱氧核糖或其磷酸化衍生物， 其中R1、R2和R3不全为氢， 当R3为核糖、脱氧核糖或其磷酸化衍生物时，R1或R2中的一个不是氢。
• Treatment of bacterial induced diseases using DNA methyl transferase inhibitors
  申请人：Benkovic J. Stephen

  公开号：US20050227933A1

  公开（公告）日：2005-10-13

  Methods for treating and/or preventing disease conditions caused or induced or aggravated by microbes, especially bacteria, by inhibiting DNA methyltransferase activity, such as by administering to an animal a DNA methyltransferase inhibitor, are disclosed, along with methods of reducing or ablating virulence in bacteria by inhibiting DNA methyltransferase activity.

  通过抑制DNA甲基转移酶活性，例如通过向动物施用DNA甲基转移酶抑制剂，来治疗和/或预防由微生物，特别是细菌引起、诱导或加重的疾病状况的方法被揭示，同时还揭示了通过抑制DNA甲基转移酶活性来减少或消除细菌的毒力的方法。
• Asymmetric Dearomatization of Indoles through a Michael/Friedel-Crafts-Type Cascade To Construct Polycyclic Spiroindolines
  作者：Xiaohu Zhao、Xiaohua Liu、Hongjiang Mei、Jing Guo、Lili Lin、Xiaoming Feng

  DOI：10.1002/anie.201410814

  日期：2015.3.23

  through a cascade reaction between 2‐isocyanoethylindole and alkylidene malonates catalyzed by a chiral N,N′‐dioxide/MgII catalyst. Fused polycyclic indolines containing three stereocenters were afforded in good yields with excellent diastereo‐ and enantioselectivities through a Michael/Friedel–Crafts/Mannich cascade. When 2‐substituted 2‐isocyanoethylindoles were used, spiroindoline derivatives were obtained

  通过手性N，N'-二氧化物/ Mg II催化剂催化2-异氰基乙基吲哚和亚烷基丙二酸酯之间的级联反应，实现了吲哚的高效不对称脱芳香化。通过Michael / Friedel-Crafts / Mannich级联反应，可以很好地获得具有三个立体中心的熔融多环二氢吲哚，并具有出色的非对映异构和对映选择性。当使用2-取代的2-异氰基乙基吲哚时，螺二氢吲哚衍生物是通过Michael / Friedel-Crafts反应获得的。