Harmine 7-甲氧基-1-甲基-9H-吡啶[3,4-b]吲哚

CAS 442-51-3 MFCD00004958

化学结构图

442-51-3
SMILES: COc1ccc2c(c1)[nH]c1c(C)nccc12

化学属性

Mol. FormulaC13 H12 N2 O
Mol. Weight212.25
Melting Point>164ºC (dec.)
TSCANo
Density1.252
Boiling Point

别名和识别编码

Chemical NameHarmine
CAS Number442-51-3
Synonym 1-Methyl-7-methoxy-?-carboline 6-Methoxyharmane 7-Methoxy-1-methyl-9H-pyrido(3,4-b)indole 7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole 7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole, 1-Methyl-7-methoxy-β-carboline, Banisterin 7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole; 7-Methoxy-1-methyl-9H-beta-carboline 7-methoxy-1-methyl-9H-β-carboline 7-甲氧基-1-甲基-9H-吡啶并[3,4-b]吲哚 9H-Pyrido(3,4-b)indole, 7-methoxy-1-methyl- 9H-Pyrido[3,4-b]indole, 7-methoxy-1-methyl- Banisterin Banisterine Harmin Harmine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
MDL NumberMFCD00004958
Beilstein Registry Number178813
EC Number207-131-4
PubChem Substance ID5280953
Merck Number4616
Reaxys-RN178813
Chemical Name Translation7-甲氧基-1-甲基-9H-吡啶[3,4-b]吲哚
Wiswesser Line NotationT B656 EN HMJ F1 KO1
LabNetwork Molecule IDLN01307236
InChIInChI=1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3
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分类

  • {SNA} Bioactive Small Molecules, Building Blocks, Carbazoles, Chemical Synthesis, H, Heterocyclic Building Blocks, 细胞生物学
  • Neurochemicals
  • Indole Derivatives
  • Pharmaceuticals
  • {SNA} Bioactive Small Molecules, Building Blocks, Carbazoles, Cell Biology, Chemical Synthesis, H, Heterocyclic Building Blocks
  • {SNA} Bioactive Small Molecules, Building Blocks, C13 to C27, Cell Biology, Chemical Synthesis, H, Heterocyclic Building Blocks, Indoles
  • Intermediates & Fine Chemicals
  • {uni_hamburg} no charge; nitrogen heterocycle; carbocycle; aromatic; large ring; fused rings; 5ring; 6ring; 9ring; 13ring; ether; 1fragment

产品应用

  • 中枢神经系统兴奋剂。

相关文献及参考

  • [2]. Neumann F, et al. DYRK1A inhibition and cognitive rescue in a Down syndrome mouse model are induced by new fluoro-DANDY derivatives. Sci Rep. 2018 Feb 12;8(1):2859.
  • [3]. Zhang L, et al. Harmine suppresses homologous recombination repair and inhibits proliferation of hepatoma cells. Cancer Biol Ther. 2015;16(11):1585-92.
  • [4]. Zhong Z, et al. Treatment with harmine ameliorates functional impairment and neuronal death following traumatic brain injury. Mol Med Rep. 2015 Dec;12(6):7985-91.
  • Chen, K.K., et al.: J. Pharmacol. Exp. Ther., 79, 127 (1943),
  • DiStefano, S., et al.: J. Pharmacol. Exp. Ther., 174, 456 (1970),
  • Merck: 14,4616
  • Merck: 14,4616 Beilstein:23(2)348
  • Short: EINECS
  • Short: III/5a
  • [1]. Glennon RA, et al. Binding of beta-carbolines and related agents at serotonin (5-HT(2) and 5-HT(1A)), dopamine (D(2)) and benzodiazepine receptors. Drug Alcohol Depend. 2000 Aug 1;60(2):121-32.

安全信息

WGK Germany3
RTECSUV0175000
GHS Symbol
Precautionary statements
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西，喝水或吸烟。
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P301+P312+P330
  • P304+P340+P312
  • P305+P351+P338
  • P308+P311
  • P321 Specific treatment (see … on this label). 具体治疗（见本标签上的）。
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • H332 Harmful if inhaled 吸入有害
  • H302 Harmful if swallowed 吞食有害
  • H312 Harmful in contact with skin 皮肤接触有害
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H302+H312+H332
Signal word Danger
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
Safety Statements
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套；
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
  • S9 Keep container in a well-ventilated place 保持容器在通风良好的场所；
  • S60 This material and its container must be disposed of as hazardous waste 该物质及其容器必须作为危险废物处置；
  • S36 Wear suitable protective clothing 穿戴适当的防护服；
Risk Statements
  • R20/21/22 Harmful by inhalation, in contact with skin and if swallowed 吸入、皮肤接触和不慎吞咽有害
  • R36 Irritating to eyes 刺激眼睛
  • R20/22 Harmful by inhalation and if swallowed 吸入和不慎吞咽有害
Hazard Codes Xn 
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intramuscular
SPECIES OBSERVED        : Human - man
DOSE/DURATION           : 3 mg/kg
TOXIC EFFECTS :
   Behavioral - sleep
   Behavioral - tremor
   Gastrointestinal - nausea or vomiting
REFERENCE :
   AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und
   Pharmakologie.  (Berlin, Ger.) V.110-253, 1925-66.  For publisher
   information, see NSAPCC.  Volume(issue)/page/year: 129,133,1928

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : 60 mg/kg
TOXIC EFFECTS :
   Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation)
   Behavioral - excitement
   Behavioral - ataxia
REFERENCE :
   NEPHBW Neuropharmacology.  (Pergamon Press Ltd., Headington Hill Hall,
   Oxford OX3 OBW, UK) V.9-    1970-  Volume(issue)/page/year: 10,15,1971

TY

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Amphibian - frog
DOSE/DURATION           : 300 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   QJPPAL Quarterly Journal of Pharmacy & Pharmacology.  (London, UK)  V.2-21,
   1929-48.  For publisher information, see JPPMAB.  Volume(issue)/page/year:
   9,37,1936

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - guinea pig
DOSE/DURATION           : 100 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und
   Pharmakologie.  (Berlin, Ger.) V.110-253, 1925-66.  For publisher
   inform

TYPE OF TEST

Storage condition +4°C 4 4℃

其他信息

  • 不溶于水。

系列性分类

  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Heterocyclic Building Blocks 杂环合成砌块
  4. Carbazoles 咔唑
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Heterocyclic Building Blocks 杂环合成砌块
  4. Indoles 吲哚
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Heterocyclic Building Blocks 杂环合成砌块
  4. Indolines 吲哚啉
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Heterocyclic Building Blocks 杂环合成砌块
  4. Indoles 吲哚
  5. C13 to C27 - Indoles
  1. Life Science 生命科学
  2. Biochemistry / Glyco-Chemistry
  3. Alkaloids
  1. Medical Research Areas
  2. GPCR & G Protein
  3. 5-HT Receptor  (5-羟色胺受体)

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