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Harmine - 10mM in DMSO, high purity , CAS No.442-51-3, Inhibitor of dual specificity tyrosine phosphorylation regulated kinase 1A;Inhibitor of dual specificity tyrosine phosphorylation regulated kinase 1B
Potent and selective inhibitor of DYRK1A
Basic Description
Synonyms
HARMINE | 442-51-3 | 7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole | Banisterine | Telepathine | Leucoharmine | Yageine | Yajeine | 9H-Pyrido[3,4-b]indole, 7-methoxy-1-methyl- | 7-Methoxy-1-methyl-9H-beta-carboline | Harmin | Harmine (Telepathine) | Banisterin | Telepathin | 7-Methoxy-1
Specifications & Purity
Moligand™, 10mM in DMSO
Biochemical and Physiological Mechanisms
Potent and selective inhibitor of DYRK1A (dual specificity tyrosine-phosphorylated and -regulated kinase). (IC 50 values are 0.08 (DYRK1A), 0.9 (DYRK2), 0.8 (DYRK3), 4.3 (PIM3) and 1.5 μM (CK1)). 5-HT antagonist and MAO inhibitor.
Storage Temp
Store at -80°C
Shipped In
Ice chest + Ice pads
This product requires cold chain shipping. Ground and other economy services are not available.
Grade
Moligand™
Action Type
INHIBITOR
Mechanism of action
Inhibitor of dual specificity tyrosine phosphorylation regulated kinase 1A;Inhibitor of dual specificity tyrosine phosphorylation regulated kinase 1B
Taxonomic Classification
Kingdom
Organic compounds
Superclass
Alkaloids and derivatives
Class
Harmala alkaloids
Subclass
Not available
Intermediate Tree Nodes
Not available
Direct Parent
Harmala alkaloids
Alternative Parents
Beta carbolines Indoles Anisoles Methylpyridines Alkyl aryl ethers Pyrroles Heteroaromatic compounds Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Hydrocarbon derivatives
Molecular Framework
Aromatic heteropolycyclic compounds
Substituents
Harman - Beta-carboline - Pyridoindole - Indole - Indole or derivatives - Anisole - Methylpyridine - Alkyl aryl ether - Benzenoid - Pyridine - Heteroaromatic compound - Pyrrole - Ether - Azacycle - Organoheterocyclic compound - Organopnictogen compound - Organic nitrogen compound - Organic oxygen compound - Hydrocarbon derivative - Organonitrogen compound - Organooxygen compound - Aromatic heteropolycyclic compound
Description
This compound belongs to the class of organic compounds known as harmala alkaloids. These are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.
External Descriptors
an alkaloid
Data sources
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Associated Targets(Human)
Names and Identifiers
IUPAC Name
7-methoxy-1-methyl-9H-pyrido[3,4-b]indole
INCHI
InChI=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
InChIKey
BXNJHAXVSOCGBA-UHFFFAOYSA-N
Smiles
CC1=NC=CC2=C1NC3=C2C=CC(=C3)OC
Isomeric SMILES
CC1=NC=CC2=C1NC3=C2C=CC(=C3)OC
WGK Germany
3
RTECS
UV0175000
Alternate CAS
442-51-3
MeSH Entry Terms
9H-Pyrido(3,4-b)indole, 7-methoxy-1-methyl-;Banisterine;Harmine;Leucoharmine;Telepathine;Yageine
Molecular Weight
212.25
Beilstein
178813
Reaxy-Rn
178813
Reaxys-RN_link_address
https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=178813&ln=
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
Chemical and Physical Properties
Melt Point(°C)
262-264°C
Molecular Weight
212.250 g/mol
XLogP3
3.600
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Exact Mass
212.095 Da
Monoisotopic Mass
212.095 Da
Topological Polar Surface Area
37.900 Ų
Heavy Atom Count
16
Formal Charge
0
Complexity
258.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
Citations of This Product
1.
Yuanyuan Li, Guangmei Yang, Yuting Wang, Yahong Li, Shu Zhang, Ruyi Li, Linxin Yang, Jian Wang, Xibo Pei, Qianbing Wan, Junyu Chen.
(2023)
Osteoimmunity-regulating nanosilicate-reinforced hydrogel for enhancing osseointegration. Journal of Materials Chemistry B,
2.
Peijian Sun, Yipeng Wang, Song Yang, Xuehui Sun, Bin Peng, Lining Pan, Yunzhen Jia, Xiaobing Zhang, Cong Nie.
(2023)
Molecularly Imprinted Polymer Nanospheres with Hydrophilic Shells for Efficient Molecular Recognition of Heterocyclic Aromatic Amines in Aqueous Solution. MOLECULES,
28
(5):
(2052).
3.
Miao Jiefei, Meng Chi, Wu Hongmei, Shan Wenpei, Wang Haoran, Ling Changchun, Zhang Jinlin, Yang Tao.
(2021)
Novel Hybrid CHC from β-carboline and N-Hydroxyacrylamide Overcomes Drug-Resistant Hepatocellular Carcinoma by Promoting Apoptosis, DNA Damage, and Cell Cycle Arrest. Frontiers in Pharmacology,
11
(2389).
4.
Gaofeng Cui, Haiqi Yuan, Zhiyan Jiang, Jing Zhang, Zhipeng Sun, Guohua Zhong.
(2020)
Natural harmine negatively regulates the developmental signaling network of Drosophila melanogaster (Drosophilidae: Diptera) in vivo. ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY,
190
(110134).
5.
Shijiao Tian, Wenming Jia, Mei Lu, Juan Zhao, Xiulian Sun.
(2019)
Dual-specificity tyrosine phosphorylation-regulated kinase 1A ameliorates insulin resistance in neurons by up-regulating IRS-1 expression. JOURNAL OF BIOLOGICAL CHEMISTRY,
294
(52):
(20164-20176).
6.
Zhang Chunhua, Wu Huiqin, Huang Xiaolan, Zhu Zhixin, Luo Huitai, Huang Fang, Lin Xiaoshan.
(2012)
Simultaneous Determination of Toxic Alkaloids in Blood and Urine by HPLC–ESI–MS/MS. CHROMATOGRAPHIA,
75
(9):
(499-511).
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6 Citations