Harmine - Moligand™, analytical standard, ≥98% , CAS No.442-51-3

CAS: 442-51-3 Cat. No.: H107068 Molecular Weight: 212.25 Beilstein Registry Number: 178813 EC Number: 207-131-4

GRADE & PURITY Analytical standard, Moligand™, ≥98%

Synonyms

7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole | HARMINE | HMS3885E10 | Spectrum5_001914 | 9H-Pyrido(3,4-b)indole, 7-methoxy-1-methyl- | HY-N0737A | Spectrum_001128 | 5-23-12-00237 (Beilstein Handbook Reference) | NCGC00016435-01 | NCGC00016435-03 | SMR0012332

Storage

Room temperature

Shipped In

Normal

Specifications

Synonyms

7-Methoxy-1-methyl-9H-pyrido[3, 4-b]indole | HARMINE | HMS3885E10 | Spectrum5_001914 | 9H-Pyrido(3, 4-b)indole, 7-methoxy-1-methyl- | HY-N0737A | Spectrum_001128 | 5-23-12-00237 (Beilstein Handbook Reference) | NCGC00016435-01 | NCGC00016435-03 | SMR0012332

Specifications & Purity

Moligand™, analytical standard, ≥98%

Storage

Room temperature

Shipped In

Normal

Grade

Analytical standard, Moligand™

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC1=NC=CC2=C1NC3=C2C=CC(=C3)OC
• IUPAC Name: 7-methoxy-1-methyl-9H-pyrido[3,4-b]indole
• InChIKey: BXNJHAXVSOCGBA-UHFFFAOYSA-N
• 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
• 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=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Class Harmala alkaloids

• 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.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CYP1A2 Tchem Cytochrome P450 1A2 (1 Activities)

Discover Target: CYP1A2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

DYRK1B Tchem Dual specificity tyrosine-phosphorylation-regulated kinase 1B (2 Activities)

Discover Target: DYRK1B

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

DYRK1A Tchem Dual specificity tyrosine-phosphorylation-regulated kinase 1A (6 Activities)

Discover Target: DYRK1A

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

MAOA Tclin Amine oxidase [flavin-containing] A (3 Activities)

Discover Target: MAOA

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CLK1 Tchem Dual specificity protein kinase CLK1 (4 Activities)

Discover Target: CLK1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

NISCH Tclin Nischarin (1 Activities)

Discover Target: NISCH

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

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

References

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,      [PMID:37822156] [10.1039/D3TB01509B]

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).  [PMID:36903298] [10.3390/molecules28052052]

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,      [PMID:33536926] [10.3389/fphar.2020.626065]

4. Gaofeng Cui, Haiqi Yuan, Zhiyan Jiang, Jing Zhang, Zhipeng Sun, Guohua Zhong.  (2019)  Natural harmine negatively regulates the developmental signaling network of Drosophila melanogaster (Drosophilidae: Diptera) in vivo.  ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY,      [PMID:31901541] [10.1016/j.ecoenv.2019.110134]

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).  [PMID:31723029] [10.1074/jbc.RA119.010809]

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).  [PMID:] [10.1007/s10337-012-2216-6]