304-21-2

Basic information

• Product Name: HARMALINE
• Synonyms: 1-METHYL-7-METHOXY-3,4-DIHYDRO-BETA-CARBOLINE;TIMTEC-BB SBB003407;1-Methyl-7-methoxy-3,4-dihydroxy-beta-carboline;1-methyl-7-methoxy-3,4-dihydro-β-carboline;HARMALINE(EXTRACTFORMPEGANUMHARMALAROOTS);PYRIDE(3,4-B)INDOLE,4,9-DIHYDRO-7-METHOXY-1-METHYL-;1-Methyl-7-methoxy-3,4-dihydro-β-carboline, Dihydroharmine, Harmalol methyl ether, 4,9-Dihydro-7-methoxy-1-methyl-3H-pyrido[3,4-b]indole;7-Methoxy-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole
• CAS NO: 304-21-2
• Molecular Formula: C₁₃H₁₄N₂O
• Molecular Weight: 214.26
• EINECS: 206-152-6
• Product Categories: Indoles and derivatives;Heterocyclic Compounds;Inhibitors
• Mol File: 304-21-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: 232-234 °C(lit.)
• Boiling Point: 354.4°C (rough estimate)
• Flash Point: 211.688 °C
• Appearance: /
• Density: 1.0850 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6450 (estimate)
• PKA: 4.2(at 25℃)
• Water Solubility: Slightly soluble in water
• Merck: 14,4613
• BRN: 207310
• CAS DataBase Reference: HARMALINE(CAS DataBase Reference)
• NIST Chemistry Reference: HARMALINE(304-21-2)
• EPA Substance Registry System: HARMALINE(304-21-2)

Safety Data

• Hazard Codes: Xn
• Statements: 25-20/21/22
• Safety Statements: 22-24/25-36
• RIDADR: 1544
• WGK Germany: 3
• RTECS: UU9800000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 304-21-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 304-21-2 differently. You can refer to the following data:
1. CNS stimulant, antiparkinsonian agent
2. CNS stimulant; may act through NMDA receptors. Reversible inhibitor of MAO-A

Definition

ChEBI: A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7 and has been reduced across the 3,4 bond.

Synthesis Reference(s)

Canadian Journal of Chemistry, 37, p. 1851, 1959 DOI: 10.1139/v59-272

Purification Methods

Recrystallise harmaline from MeOH and sublime it at high vacuum. It has UV in MeOH a

InChI:InChI=1/C13H14N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-4,7,15H,5-6H2,1-2H3

Upstream product

• 442-51-3 harmine 
• 106275-52-9 (7-methoxy-2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-methanol 
• 64-17-5 ethanol 
• 7803-57-8 hydrazine hydrate 
• 56-23-5 tetrachloromethane 
• 22375-73-1 N-(2-(6-methoxy-1H-indol-3-yl)ethyl)acetamide 
• 7732-18-5 water 
• 3610-36-4 2-(6-methoxy-1H-indol-3-yl)ethanamine 

Downstream Products

• 77784-76-0 2-benzyl-1,2,3,4-tetrahydro-7-methoxy-1-methylene-β-carboline 
• 77784-77-1 2-benzyl-1,2,3,4-tetrahydro-1-phenethylidene-β-carboline 
• 110815-49-1 2-acetyl-3-(2-benzenesulfonamidoethyl)-6-methoxyindole 
• 77784-80-6 1,2,3,4-tetrahydro-7-methoxy-2-(3-methoxybenzyl)-1-methylene-β-carboline 
• 105740-52-1 1-dibromomethyl-3,4-dihydro-7-methoxy-β-carboline 
• 1167055-45-9 7-methyl-1H-pyrrolo[2,3-c]pyridine-3-carboxylic acid 
• 89-41-8 4-methoxy-3-nitrobenzoic acid 
• 81589-53-9 11,16-dimethoxy-14-(13-methoxybenzyl)-16-de(methoxycarboxyl)gambirtannine 
• 153514-78-4 (CH₃OC₁₁H₇N₂CH₃)AuP(C₆H₅)3 
• 153514-76-2 (CH₃OC₁₁H₈N₂CH₃)*Au⁽¹⁺⁾*P(C₆H₅)3*{BF₄}^(1-)={(CH₃OC₁₁H₈N₂CH₃)AuP(C₆H₅)3}{BF₄} 
• 442-51-3 harmine 
• 26579-69-1 7-methoxy-2,3,4,9-tetrahydro-1H-pyrido<3,4-b>indol-1-one 
• 487-03-6 harmol 

Relevant articles and documents

Harmaline Analogs as Substrate-Selective Cyclooxygenase-2 Inhibitors

We report the design, synthesis, and evaluation of a series of harmaline analogs as selective inhibitors of 2-arachidonylglycerol (2-AG) oxygenation over arachidonic acid (AA) oxygenation by purified cyclooxygenase-2 (COX-2). A fused tricyclic harmaline analog containing a CH3O substituent at C-6 and a CH3 group at the C-1 position of 4,9-dihydro-3H-pyrido[3,4-b]indole (compound 3) was the best substrate-selective COX-2 inhibitor of those evaluated, exhibiting a 2AG-selective COX-2 inhibitory IC50 of 0.022 μM as compared to >1 μM for AA. The 2.66 ? resolution crystal complex of COX-2 with compound 3 revealed that this series of tricyclic indoles binds in the cyclooxygenase channel by flipping the side chain of L531 toward the dimer interface. This novel tricyclic indole series provides the foundation for the development of promising substrate-selective molecules capable of increasing endocannabinoid (EC) levels in the brain to offer new treatments for a variety of diseases, from pain and inflammation to stress and anxiety disorders.