2,3,4,9-四氢-1H-beta-咔啉-3-甲酸 | 6052-68-2

• 物质功能分类: 医药中间体 - 杂环化合物
• 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: 2,3,4,9-四氢-1H-beta-咔啉-3-甲酸
• 中文别名: 2,3,4,9-四氢-1H-beta-咔啉-3-羧酸
• 英文名称: 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid
• 英文别名: 2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid；1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-3-carboxylic acid；tetrahydro-β-carboline-3-carboxylic acid；2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid；1,2,3,4-Tetrahydro-β-carbolin-3-carbonsaeure；2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-ium-3-carboxylate
• CAS: 6052-68-2
• 化学式: C₁₂H₁₂N₂O₂
• mdl: MFCD00204332
• 分子量: 216.239
• InChiKey: FSNCEEGOMTYXKY-UHFFFAOYSA-N

物化性质

• 熔点：
  289 °C (dec.)(lit.)
• 沸点：
  485.0±45.0 °C(Predicted)
• 密度：
  1.377±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65.1
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P301+P312,P302+P352,P304+P340,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：2-8°C，避光保存，并置于惰性气体环境中。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : (S)-(-)-2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole-3-
carboxylic acid
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 6052-68-2
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Skin irritation (Category 2), H315
Eye irritation (Category 2), H319
Specific target organ toxicity - single exposure (Category 3), H335
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xi Irritant R36/37/38
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Formula : C12H12N2O2
Molecular Weight : 216,24 g/mol
CAS-No. : 6052-68-2
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
(S)-(-)-2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid
Skin Irrit. 2; Eye Irrit. 2; STOT -
SE 3; H315, H319, H335
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
(S)-(-)-2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid
Xi, R36/37/38 -
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

---

SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

---

SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material. Dissolve or mix the material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

---

SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15: Regulatory information
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
For this product a chemical safety assessment was not carried out

---

SECTION 16: Other information
Full text of H-Statements referred to under sections 2 and 3.
Eye Irrit. Eye irritation
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Skin Irrit. Skin irritation
STOT SE Specific target organ toxicity - single exposure
Full text of R-phrases referred to under sections 2 and 3
Xi Irritant
R36/37/38 Irritating to eyes, respiratory system and skin.
Further information
Copyright 2013 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  2,3,4,9-四氢-1H-beta-咔啉-3-甲酸 在 盐酸 、 氯化亚砜 、 三氯异氰尿酸 、 水 、 一水合肼 、 溶剂黄146 、 三乙胺 、 potassium hydroxide 、 sodium nitrite 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 戊醇 、 邻二甲苯 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 55.5h， 生成 2-methyl-3-benzylamino-β-carbolinium trifluoromethanesulfonate
  参考文献：
  名称：

  3-Benzylamino-β-carboline derivatives induce apoptosis through G2/M arrest in human carcinoma cells HeLa S-3

  摘要：

  beta-Carboline derivatives are known as the lead compounds for anti-tumor agents. To examine an optimal structure for anti-tumor activity, we synthesized a variety of beta-carboline derivatives, possessing a variety of substituents on the nitrogen atom of the amino group of 3-amino-beta-carboline, and evaluated their anti-tumor activity for HeLa S-3 cell line. 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MU) assay showed that an optimal structure for anti-tumor activity was 3-cyclohexylmethylamino (le) or 3-benzylamino-beta-carboline (le. An optimal counter anion of 2-methyl-3-benzylamino-beta-carbolinium salts was a triflate anion 2c. In addition, the introduction of a hydroxyl group on the meta-position of the benzyl group of 3-benzylamino-beta-carboline (3e) enhanced its anti-tumor activity. Hoechst 33342 staining and DNA fragmentation assay suggested that 1f, 2c and 3e induced cell death by apoptosis unlike le. Flow cytometry analysis showed that if, 2c and 3e induced cell apoptosis through arrest of the cell cycle in the G(2)/M phase. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.044
• 作为产物：
  描述：

  L-色氨酸 在 盐酸 作用下， 以 聚合甲醛 、 水 为溶剂， 生成 2,3,4,9-四氢-1H-beta-咔啉-3-甲酸
  参考文献：
  名称：

  .beta.-Carbolin-3-carboxylic acid derivatives

  摘要：

  当给予患者，例如人类作为药物时，具有有价值的药理特性的一种公式为##STR1##的β-咔啉-3-羧酸衍生物已被证明具有有趣的镇静活性。

  公开号：

  US04371536A1

文献信息

• [EN] COMPOSITIONS AND METHODS FOR THE TREATMENT OF BACTERIAL INFECTIONS<br/>[FR] COMPOSÉS ET MÉTHODES POUR LE TRAITEMENT D'INFECTIONS BACTÉRIENNES
  申请人：CIDARA THERAPEUTICS INC

  公开号：WO2018006063A1

  公开（公告）日：2018-01-04

  Compositions and methods for the treatment of bacterial infections include compounds containing dimers of cyclic heptapeptides conjugated to one or more monosaccharide or oligosaccharide moieties. In particular, compounds can be used in the treatment of bacterial infections caused by Gram-negative bacteria.

  用于治疗细菌感染的组合物和方法包括含有环七肽二聚体与一个或多个单糖或寡糖基团结合的化合物。特别是，这些化合物可用于治疗由革兰氏阴性细菌引起的细菌感染。
• Cytotoxic and Insecticidal Activities of Derivatives of Harmine, a Natural Insecticidal Component Isolated from Peganum harmala
  作者：Yong Zeng、Yaomou Zhang、Qunfang Weng、Meiying Hu、Guohua Zhong

  DOI：10.3390/molecules15117775

  日期：——

  develop novel β-carbolines endowed with better insecticidal activity, a simple high-yielding method for the synthesis of harmine compounds starting from L-tryptophan has been developed and a series of 1,3-substituted β-carboline derivatives have been synthesized and evaluated for their cytotoxicity against insect cultured Sf9 cell line in vitro and insecticidal activities against 4th instar larvae of mosquitos

  在不断努力开发具有更好杀虫活性的新型 β-咔啉的过程中，开发了一种以 L-色氨酸为原料合成有害化合物的简单高产方法，并开发了一系列 1,3-取代的 β-咔啉衍生物合成并评估了它们对昆虫培养的 Sf9 细胞系的体外细胞毒性和对蚊子 4 龄幼虫库蚊和芥子蚜虫 Lipaphis erysimi 的杀虫活性。结果表明，1-苯基-1,2,3,4-四氢-β-咔啉-3-羧酸（化合物2）和1-苯基-β-咔啉-3-羧酸甲酯（化合物13）代表最佳潜在的化合物，在 50-200 mg/L 的浓度下处理 24 小时后，Sf9 细胞的抑制率分别为 71.55% 和 60.21%。化合物2和13对蚊子4龄幼虫也表现出较强的杀虫活性，LC(50)值为20.82 mg/L和23.98 mg/L，LC(90)值为88.29 mg/L和295.13 mg/L ， 分别。此外，化合物2和13对芥菜蚜虫的LC(50)值为53.16
• [EN] AZASULFURYLPEPTIDE-BASED CD36 MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS CD36 À BASE D'AZASULFURYLPEPTIDES ET UTILISATIONS DE CEUX-CI
  申请人：RSEM LTD PARTNERSHIP

  公开号：WO2016029324A1

  公开（公告）日：2016-03-03

  Novel azasulfuryl-containing peptidomimetics capable of inhibiting CD36 activity are disclosed. Use of these azasulfuryl-containing peptidomimetics for the treatment of CD36-related diseases, disorders or conditions, including TLR2-mediated inflammatory disease, disorder or condition, and methods of obtaining such azasulfuryl-containing peptidomimetics, are also disclosed.

  揭示了能够抑制CD36活性的新型含氮硫酰基的肽类模拟物。还揭示了利用这些含氮硫酰基的肽类模拟物治疗与CD36相关的疾病、紊乱或状况，包括TLR2介导的炎症性疾病、紊乱或状况的用途，以及获取这种含氮硫酰基的肽类模拟物的方法。
• [EN] COMPOSITIONS AND METHODS FOR THE TREATMENT OF FUNGAL INFECTIONS<br/>[FR] COMPOSITIONS ET MÉTHODES DE TRAITEMENT D'INFECTIONS FONGIQUES
  申请人：CIDARA THERAPEUTICS INC

  公开号：WO2015164289A1

  公开（公告）日：2015-10-29

  Compositions and methods for the treatment of fungal infections including compounds containing a chemotaxis receptor ligand moiety and a polyene antifungal agent moiety are disclosed. In particular, compounds containing a polyene antifungal agent and a formyl peptide receptor ligand can be used in the treatment of fungal infections caused by a fungus of the genus Aspergillus or Candida.

  揭示了用于治疗真菌感染的化合物和方法，包括含有趋化受体配体基团和聚烯抗真菌剂基团的化合物。具体来说，含有聚烯抗真菌剂和甲酰肽受体配体的化合物可用于治疗由曲霉属或白念珠菌属真菌引起的真菌感染。
• Lipid probes and uses thereof
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：US10168342B2

  公开（公告）日：2019-01-01

  Disclosed herein are methods, compositions, probes, assays and kits for identifying a lipid binding protein as a drug binding target. Also disclosed herein are methods, compositions, and probes for mapping a ligand binding site on a lipid binding protein, identification of lipid binding proteins, generating drug-lipid binding protein profiles, high throughput drug screening, and identification of drugs as potential lipid binding protein ligands.

  披露了用于识别脂质结合蛋白作为药物结合靶点的方法、组合物、探针、检测和试剂盒。此外，还披露了用于绘制脂质结合蛋白上的配体结合位点、识别脂质结合蛋白、生成药物-脂质结合蛋白轮廓、高通量药物筛选以及识别作为潜在脂质结合蛋白配体的药物的方法、组合物和探针。

表征谱图