487-03-6

Basic information

• Product Name: HARMOL
• Synonyms: 1-Methyl-9H-beta-carbolin-7-ol;beta-Carboline, 7-hydroxy-1-methyl-;7-HYDROXY-1-METHYL-9H-PYRIDO[3,4-B]INDOLE;1-METHYL-9H-PYRIDO[3,4-B]INDOL-7-OL;HARMOL;TIMTEC-BB SBB005349;METHYLPYRIDOINDOLOL;1-Methyl-β-carboline-7-ol
• CAS NO: 487-03-6
• Molecular Formula: C₁₂H₁₀N₂O
• Molecular Weight: 198.22
• EINECS: 207-645-9
• Mol File: 487-03-6.mol
• Article Data: 18

Chemical Properties

• Melting Point: 231°C
• Boiling Point: 552.7°Cat760mmHg
• Flash Point: 255°C
• Appearance: /
• Density: 1.33g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.794
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly)
• PKA: pKa 7.90(H2O) (Uncertain);9.47 (Uncertain);15.75 (Uncertain)
• CAS DataBase Reference: HARMOL(CAS DataBase Reference)
• NIST Chemistry Reference: HARMOL(487-03-6)
• EPA Substance Registry System: HARMOL(487-03-6)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• Hazardous Substances Data: 487-03-6(Hazardous Substances Data)

Usage

General Description

Harmol, also known as 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, is a chemical compound that belongs to the class of isoquinoline alkaloids. It is found in various plants and has been isolated from the seeds of Peganum harmala. Harmol has been studied for its potential pharmacological properties, including its ability to act as a neurotransmitter and enzyme inhibitor. Additionally, harmol has been investigated for its potential use in treating various medical conditions, such as diabetes and cancer. However, further research is needed to fully understand the potential benefits and risks of harmol for medical and therapeutic purposes.

InChI:InChI=1/C12H10N2O/c1-7-12-10(4-5-13-7)9-3-2-8(15)6-11(9)14-12/h2-6,14-15H,1H3

Upstream product

• 442-51-3 harmine 
• 7647-01-0 hydrogenchloride 
• 257938-78-6 7-acetyloxy-1-methyl-9H-pyrido[3,4-b]indole 
• 17952-75-9 Tetrahydroharmol 
• 443-31-2 6-hydroxytryptamine 
• 1362736-69-3 C₁₀H₈N₂O₃ 
• 304-21-2 harmaline 

Downstream Products

• 486-84-0 harmane 
• 17952-75-9 Tetrahydroharmol 
• 1216704-96-9 7-deuteromethoxy-1-methyl-9H-pyrido[3,4-b]indole 
• 769966-41-8 1-methyl-7-benzoyloxy-9H-β-carboline 
• 1263295-59-5 7-(phenethoxy)-1-methyl-β-carboline 
• 241809-31-4 7-(cyclohexylmethoxy)-1-methyl-β-carboline 
• 1353182-56-5 1-methyl-7-(4-fluorobenzyloxy)-9-(4-fluorobenzyl)-β-carboline 

Relevant articles and documents

Contribution of individual cytochrome P450 isozymes to the O-demethylation of the psychotropic β-carboline alkaloids harmaline and harmine

The psychotropic β-carboline alkaloids, showing high affinity for 5-hydroxytryptamine, dopamine, benzodiazepine, and imidazoline receptors and the stimulation of locus coeruleus neurons, are formed endogenously from tryptophan-derived indolealkylamines through the Pictet-Spengler condensation with aldehydes in both plants and mammals. Cytochromes P450 1A1 (18.5), 1A2 (20), and 2D6 (100) catalyzed the O-demethylation of harmaline, and CYP1A1 (98.5), CYP1A2 (35), CYP2C9 (16), CYP2C19 (30), and CYP2D6 (115) catalyzed that of harmine (relative activities). The dehydrogenation/aromatization of harmaline to harmine was not carried out by aromatase (CYP19), CYP1A2, CYP2C9, CYP2D6, CYP3A4, pooled recombinant cytochromes P450, or human liver microsomes (HLMs). Kinetic parameters were calculated for the O-demethylations mediated by each isozyme and by pooled HLMs. Kcat (min-1) and Km (μM) values for harmaline were: CYP1A1, 10.8 and 11.8; CYP1A2, 12.3 and 13.3; CYP2C9, 5.3 and 175; CYP2C19, 10.3 and 160; and CYP2D6, 39.9 and 1.4. Values for harmine were: CYP1A1, 45.2 and 52.2; CYP1A2, 9.2 and 14.7; CYP2C9, 11.9 and 117; CYP2C19, 21.4 and 121; and CYP2D6, 29.7 and 7.4. Inhibition studies using monoclonal antibodies confirmed that CYP1A2 and CYP2D6 were the major isozymes contributing to both harmaline (20% and 50%, respectively) and harmine (20% and 30%) O-demethylations in pooled HLMS. The turnover numbers for CYP2D6 are among the highest ever reported for a CYP2D6 substrate. Finally, CYP2D6-transgenic mice were found to have increased harmaline and harmine O-demethylase activities as compared with wild-type mice. These findings suggest a role for polymorphic CYP2D6 in the pharmacology and toxicology of harmine and harmaline.

Antitumor agents 201. Cytotoxicity of harmine and β-carboline analogs

Twenty-six β-carbolines were evaluated for in vitro cytotoxicity in a human tumor cell line panel. Harmine (3) showed significant activity against several cell lines including three drug-resistant KB sublines with various resistance mechanisms. α-(4-Nitrobenzylidine) harmine (16) had a broad cytotoxicity spectrum (ED50 values from 0.3-1.2 μg/mL against 1A9, KB, SaOS-2, A549, SK-MEL-2, U-87-MG, and MCF-7 cells).

KINASE INHIBITOR COMPOUNDS AND COMPOSITIONS AND METHODS OF USE

Described herein are compounds having the following structure: formula (I) or a stereoisomer, pharmaceutically acceptable salt, oxide, or solvate thereof. Also disclosed are compositions containing the compounds, methods of inhibiting activity of DYRKl A in a cell, methods of increasing cell proliferation in a population of pancreatic beta cells, methods of treating a subject for a condition associated with insufficient insulin secretion, and methods of treating a subject for a neurological disorder.

Β dephosphorizing compd. carbocation-screw, its manufacturing method, and use a pharmaceutical composition

Disclosed in the present invention are a bis-2-carboline compound and a preparation method, a pharmaceutical composition and the use thereof. In particular, the bis-2-carboline compound and a pharmaceutical salt thereof are described as general formula I, and the bis-2-carboline compound is prepared through the condensation of 2-carboline intermediate and dihaloalkane. Also disclosed in the present invention are a pharmaceutical composition comprising an effective dose of the bis-2-carboline compound as shown in formula I and a pharmaceutically acceptable carrier, and the use of the bis-2-carboline compound in preparing drugs resistant to tumours such as melanoma, stomach cancer, lung cancer, breast cancer, kidney cancer, liver cancer, oral epidermoid carcinoma, cervical cancer, ovarian cancer, pancreatic cancer, prostate cancer, and colon cancer.